Target Companies and Evaluate Roles

2 hours, 18 links

You’re reading an excerpt of Ask Me This Instead: Flip the Interview to Land Your Dream Job, a book by Kendra Haberkorn. This powerful work is written by a veteran recruiter for job-seekers who want to find their dream job—not just the next job. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, worksheets and a question database, commentary and future updates, and a high-quality PDF download.

At many points throughout our lives, we decide that it’s time to find a new job and we begin to search, evaluate, and take steps to pursue specific companies and positions. The search often starts with Google or LinkedIn and a specific current or aspirational job title. There are geographic, industry or functional job boards that curate a more tailored list of roles and there are professional and personal networks too. Jobs and opportunities are more discoverable than ever. In fact, they find you! If you start searching online, you’ll begin to see ads or postings pop up wherever you go. Then, if you look at recruiters representing a particular discipline or company, you might see their name pop up in your inbox asking to connect. With so much information it should be easy to find the right opportunity. It’s not, and that’s not for lack of information or access.

The more information and choices you have in front of you, the harder it is to narrow your focus on the right opportunities. Pair information overload, inbound requests from recruiters, and jobs ads that find you with the sales and marketing messaging built into the recruiting process, and there is the chance that you’ll end up applying to, interviewing for and accepting a job that sounded great all along but is not what you’re interested in doing. I’ve seen this play out time and time again and even had it happen to me.

I thought that I was good at making decisions about my career. But as I reflected on the last couple of years, I realized I had trusted the companies and teams to do the evaluation for me. As they became more excited about my candidacy for their position and my ability to fit their needs, I became more excited. I ended up not asking the tough questions and did not orient my decision around the things that truly mattered most to me at that particular time in my life and career.

If you’re reading this, there is a good chance you’re looking for a new job or starting to interview with companies. Interviews are exciting, time-consuming, and stressful for many people. With the impact of the decisions resulting from these conversations, that’s not surprising. A significant portion of the stress is tied to the end outcome. When we put ourselves out there and find a role or company where we can see ourselves working, succeeding, and thriving, we get attached to that future version of ourselves. We start to daydream about what the new role will do for our careers, bank account, and reputation. We begin to spend time reviewing our resume, pulling up old performance reviews (“What are my strengths, really?”), and practicing responses to interview questions in front of the mirror, on our commute, or with a trusted friend or family member. As the process progresses, so does the investment we’re making in that outcome. We might start telling our friends, shopping for a new work wardrobe, even apartment hunting.

important The cost (personal, financial and otherwise) of accepting the wrong job is high. And, the prospect of finding a new job is daunting. We shouldn’t have to rely on other people’s excitement or on our own imperfect instincts—with all our blind spots and gaps in self-awareness—when making choices in our careers. Luckily, with thoughtful and diligent preparation, you won’t have to, and the entire process will be more manageable and productive. My preparation strategy will take you through a variety of specific activities and actions that build upon one another.

You’ll begin by reflecting on and designating your top priorities for your next role. Then, you’ll research roles that align with your priorities, starting with those titles and positions you’re most familiar with.

Next, you’ll broaden your search through an activity that will enable you to find roles with unexpected or unique titles that are tied to your priorities, so that you understand the full landscape of opportunities you can pursue.

Moving beyond research, you’ll analyze the job descriptions to determine which roles and companies most closely match your objectives and excite you.

Once you are familiar with the opportunities, you’ll work through a chapter and some exercises that will help you tell your career story, refine your resume, and solidify or update your priorities before you apply.

Together, these activities will help you understand how your past experiences, interests, and aspirations are connected. You’ll reconfirm the type of environments and teams that led to your most fulfilling, fun, rewarding work, as well as those experiences that you’d prefer not to encounter again. With this preparation as the foundation, you’ll be ready to articulate your accomplishments throughout the interviews and have a targeted list of questions you’ll want the interviewer to answer.

Determine Your Job Priorities

You can’t optimize for everything. It is incredibly rare for a particular job to meet or exceed all of your expectations. There are many aspects of the work experience that you will have to understand and evaluate while you are looking for a new job. Some, such as the role, your pay and benefits, and the people you’ll collaborate with on a daily basis, are easy to connect to your personal experience right away. Others, including broader company context and long-term career opportunities, may not be as tangible from the start, but may be among the most important criteria for you.

As you pursue the application and interview process, you will receive a lot of information about each of these topics. Most of the time, the messages will be subtle and embedded into a larger conversation. This is why a clear understanding of what you want to prioritize will enable you to proactively listen for signals and ask specific questions to get a comprehensive picture of how a particular opportunity aligns with what matters most to you. When your core priorities and actual work experience complement one another, you can focus on your achievement and fulfillment. However, if aspects of your work experience don’t match the factors you know are most important to your satisfaction and success, problems will emerge. Initially, the problems might be subtle frustrations. Over time, those annoyances will build and the cumulative impact of an ongoing, growing issue can become intolerable.

As you read through the priorities outlined in this section, reflect on your past experiences and take the time to complete the activity, Rank Your Top Priorities. By doing so, you’ll have clarity about what priorities you should focus on as you interview for jobs. Later, in the Ask Me This Instead section, you’ll have the chance to select questions tied to your priorities that will help you get to the heart of these matters in each of your conversations.


The combination of responsibilities and expectations that fill your days at work are what constitute the role. For many people, the role is, without a doubt, one of their top priorities in the job search. Choosing to focus on the tangible foundation of what work represents, particularly as we spend many hours of most days focused on those activities, makes sense.

So, what are the indicators that the role might be one of your top priorities?

  • This role is a critical stepping stone on a longer-term career path.

  • You are pursuing an educational certificate, degree, or training program to gain access to a specific type of role (e.g. a coding bootcamp, MBA or apprenticeship program).

  • The position represents a meaningful promotion or acceleration of your professional trajectory.

  • The way you spend your days—the activities, tools and interactions—is key to your satisfaction, productivity, or fulfillment.

  • You are making an intentional shift or pivot in a new direction.

If the bullets above resonate, focus on the following aspects of the role in your interview preparation and conversations.

First, people often think the job description is an accurate representation of the role. I’ll go into more details about job descriptions later, but for now, know that they are not as indicative of the work or experience as they should be. You will need to push to get a real, tangible view into what the day-to-day looks like. For example, it’s incredibly helpful to understand which meetings you will attend, the cadence of deadlines and how much of your time is spent in various activities. You’ll want to make sure the team can articulate these elements of the job in more depth than what is on the job description. You’ll need to ask them to show you the day-to-day experience via a glimpse into weekly calendars, reviewing agendas or letting you audit meetings. The title section of this book, Ask Me This Instead, will help you develop a list of questions to do this! If you don’t know what you’ll actually be doing, it’s hard to know if you’ll enjoy it or be successful.

important Job responsibilities are distinct from expectations, though they often get bundled together. To understand the role, you need to get clarity on the responsibilities as well as the expectations. Responsibilities are the tasks, activities, and meetings that fill your day. Expectations are the more subtle measures of success, the “how” you get the work done, the way the team wants you to show up. You could be an expert in the execution of the tasks and still not meet expectations.

Responsibilities may be metrics—quantifiable, demonstrable outcomes you need to achieve or projects and documents you need to deliver. While there might be subjectivity associated with the approach, quality, value, or impact when it comes to responsibilities, there is also a binary element that is more easy to discern. Did you reach the target numbers or submit the report on time or not?

You often find out there was an expectation when you fail to meet it. It’s the nuance—the unsaid beliefs about what really matters that will ultimately shape your experience and how people perceive your performance. These underlying expectations might include whether you answer emails or Slacks “on time,” whether you work “enough” hours, whether your attitude and presence in meetings “mesh” with the team’s, or whether you adeptly navigate office politics without ruffling feathers. The quotes are intentional. Most of the time, leaders know what they mean when they say “on time,” “enough,” and “mesh,” but they don’t communicate their expectations properly. It’s frustrating and can be the result of intentional manipulation or poor management. Either way, it’s hard to recover.

Your references can also be extremely helpful when evaluating a role and throughout the rest of the interview process. While preparing your application, ask them to review the job description and highlight examples of why they think you’ll be a strong candidate (or if they think it’s not the right next move). They will likely share insights and examples that you wouldn’t have come up with otherwise. It’s also possible that they’ll point out areas where you will need to grow and learn to fulfill the responsibilities of the position. These tips can help you proactively consider a learning plan and prioritize where you might want to proactively prepare to address questions that will come your way during interviews. The added bonus of this exercise? You’re prepping your references to have examples ready to share with hiring managers or recruiters as you get to the final stages of the process!

Spend extra effort on the questions database later in the book to hone in on getting the answers you need to these questions! If you know the responsibilities, understand the expectations and are excited to step in, work hard and live up to all those “asks,” your success will follow.

Inclusion and Belonging

Many companies are focusing more on diversity, equity, inclusion, and belonging. For individuals, the existence or absence of a feeling of belonging can transform their work experience, performance, and satisfaction. When you belong, and when you can show up as your authentic self, you are more likely to not only survive at work, but thrive. An exclusionary environment, one that denies you the opportunity to be yourself, or expects you to withhold certain parts of yourself, can chip away at your confidence, relationships, and commitment in meaningful and often painful ways. We all want to be accepted for who we are, including those aspects of our identity that are visible as well as those parts of ourselves that we hold more closely or that are not visible.

important This conversation is evolving, and thankfully, becoming one that is top of mind for leaders and businesses everywhere. As this book is being written, dynamic discussions and debates are influencing the “what”, “when” and “how,” but also the “who” and “why” for initiatives and actions tied to diversity, equity, inclusion, and belonging. The language and priorities are shifting while leaders react, respond, and commit to a path forward. In this section and throughout the book, I’ll use the abbreviation DEI for diversity, equity, and inclusion. Belonging and justice are part of the equation, though not as familiar as part of an acronym at this time. On the note of acronyms and language, different terms are used or preferred in different contexts and awareness about the nuance and significance of these terms is beneficial (find out more about exclusionary words you might come across in the hiring process here and culturally conscious identifiers here). The landscape will change by tomorrow and your own perspective may be very different from that which is presented here or elsewhere—and that’s the point! As you approach your career and find the opportunities that are right for you, your own experience and opinions and how they relate to the company and team you’re considering joining, matter.

In a contrived structure like a hiring process, it can be difficult to know when to bring your full self into the conversation and to anticipate how others will respond to what is uniquely you. Though the topic is nuanced and conversations can be difficult to initiate, it is important that you realize you have permission to ask questions and advocate for yourself. Before you’d make a decision about accepting a role, you need to understand whether or not the work environment will build you up or break you down. Your happiness and health, not to mention your success, will depend on it.

For some, belonging is not something that is a conscious, daily effort. Perhaps you’ve always felt like you belonged at work, or have been part of the majority and never had an experience where you were excluded or treated differently because of who you are. If this is you, this section is as important for you as it is for those who have had dramatically different experiences. Gaining empathy and understanding about the lives of others is valuable as the implications of these realizations about your similarities and differences can have meaningful impacts on your work and life experience. As we become more connected and spend more time at work and with our colleagues, the need for community and belonging has become more present, visible, and urgent. Understanding whether or not this potential work environment values diversity and takes tangible steps to bring everyone along can be a key decision criteria as you think about how the work environment and team will shape you, your experience and knowledge, and your understanding of the world around you. Diversity in leadership significantly improves a company’s chances of success, in startups and established companies, and contributes toward the long-term culture and experience of the team as well.

There are many people, and perhaps even you, who know first hand the impact of being the only team member who is a person of color, who has a disability, who is LGBTQIA+, from a particular generation or the only woman in a room. For individuals who claim one or more of these identities or who bring yet another point of view and lived experience onto the team, a desire for belonging, as well as physical and psychological safety, are an omnipresent reality and priority. On top of the day-to-day stress of work, people with these visible or unseen aspects of identity are also subject to more microaggressions, discrimination, harassment, and violence.

No one wants to inadvertently join a company where they, or other team members, will be subject to unacceptable treatment and a lack of respect for their humanity. If we all seek out and demand environments that prioritize DEI, teams will become more representative, we’ll see the benefit of increasing innovation, and both businesses and individuals will thrive.

If you want to…

  • show up as your authentic self without having to assimilate, code switch, change or adjust parts of yourself;

  • work with team members who will embrace and respect your experiences (even if they do not or cannot understand them!), bring you along, and amplify your voice and talent; and

  • work for a company that supports the values, social movements and causes you believe in

…then take a proactive approach to understand how a company and team support diversity, equity, inclusion, and belonging in the following dimensions.

Evaluate the Company’s Efforts

Are a company’s efforts integral and genuine, or superficial and performative? As you research, prepare questions to ask your interviewers, and go through conversations, you will need to probe into the details about the company’s philosophy and tangible actions to understand where a particular organization and team are on their DEI journey.

  • Are the company’s efforts proactive—taking steps toward a more inclusive environment on an ongoing basis—or reactive—responding to issues or pressure only when they arise?

  • Does the company make statements or social posts but neglect to take specific internal actions that would lead to measurable change?

  • Do different team members, and specifically those in leadership positions, share contrary or inconsistent information about what the company believes or does to support diversity, equity, inclusion, and belonging?

  • Does the topic come up frequently on their website, in external press or profiles, in job descriptions and interviews, or only if you ask questions about it?

A company where this work is integral to the business and their values will be well-poised to respond to the events happening in the world. Companies in this position can proactively adapt their employee experience and culture while referencing and improving existing programs and practices. These companies will have existing infrastructure that enable them to support employees, and to take timely, thoughtful, and genuine action—whether a statement, donation, or policy change—in a consistent and sustainable manner. The response to these actions (e.g. on review sites like Glassdoor or in comments below the social or blog posts) from current and former employees will demonstrate enthusiasm and support for the efforts.

On the other hand, if a company’s commitment is superficial or performative, you’ll see spotty or inconsistent responses to the events impacting the world or members of their team. An email, social post or statement might be released without the underlying structures or support to drive real, tangible change. In other cases, companies may quickly join a viral social trend without fully understanding the origins of the post or the implications of their use of a hashtag, as was apparent during the summer of 2020 when black squares filled social feeds and #BlackoutTuesday began to trend and disrupt the actual goals of the campaign. A superficial approach is one that may have good intentions accompanied by a lack of follow-through and the absence of resources, time, money, and dedicated roles to support the effort. Performative displays or actions are often for the sake of optics or attention and to get through a moment, rather than support a movement. It is hard for companies to respond to every local, national, or international cause with the same level of attention or action. The absence of a response in a particular situation might be grounded in a targeted strategy of supporting a specific type of cause or a preference for behind-the-scenes donations, among many other possible scenarios. As you explore, remember that things are usually more complicated than they appear.

Evaluate the Company’s Track Record and Roadmap

At the foundation, DEI work exists because individuals and leaders want to create and sustain positive change. To envision and create purposeful programs is difficult. To implement, maintain, and improve them is even more challenging. Some companies might be new to this work and “all in”; others have been at it for years and have barely tapped the surface of what is possible or necessary to make their workplace more representative, equitable, and inclusive.

Understanding where a company is coming from, as well as the plan for what they will do in the months or years that follow will illuminate aspects of their intentions and dedication to these efforts. To get to these insights, ask questions during your interviews that will help you examine the following:

  • Does the company have programs or existing metrics and data available that highlight the work that has been done and indicates a sustained, ongoing commitment to future endeavors?

  • Even if you would take a different approach, choose another way of framing or start with another initiative, do you feel comfortable and aligned with the progress, tactics and momentum you discover?

  • Does the company have a prioritization or decision-making structure in place to determine which specific issues or opportunities they will address in their DEI efforts? Can the interviewers speak to how DEI efforts are chosen or sequenced? For example, is the team going to focus first on internal training programs about unconscious bias or update their recruiting process to be more inclusive?

  • Are you able to find information about their partnerships, advertising spend, or investors to evaluate if there is consistency on the implied or stated values with that data or those decisions and outcomes?

  • Can interviewers provide information about progress and failures in order to demonstrate an iterative and learning-focused approach to DEI efforts?

No company has a perfect track record and there isn’t a formula for the roadmap of activities, investment, or changes to create a diverse, equitable, and inclusive workplace. Each company’s strengths and opportunities will be unique given the evolving needs of their workforce. This is true even within a company. Individuals on the same team or with the same title might have dramatically different experiences, relationships, and outcomes. It’s also true that departments or teams may have location-specific challenges based on the unique attributes of their environment and population. A one-size-fits-all approach is not sufficient, and could do more damage than good.

The process that a company uses to determine what investment and activities they dedicate time toward can indicate if they intend to solve the obvious or underlying problems as well as if they know who to bring into the conversation and how to make progress. Finding out what gets measured in surveys or employee data and how it gets presented to the team will also reinforce or invalidate the messages you hear throughout the hiring process.

As you go through the hiring process, from application through interviews and offer negotiations, ask revealing questions (the Ask Me This Instead section will equip you with some good ones!) and listen. In companies where this work is integral, you’ll hear evidence and find examples of momentum and also come across reflection and humility around the missteps and failures. There should be both. No journey is without detours and roadblocks and these insights will help you choose whether or not this is the place where you will want to contribute your energy, expertise, and experience.

Determine if You Want To and Can Be Part of the Journey

important Once you understand where a company is at, as well as where it is going, you may choose to see how you can be involved. Or not. You may care deeply about how DEI manifests at an organization and choose not to invest your personal attention, emotional labor, and action to the work. It’s also possible that you’ll decide to weave in and out depending on where you are at work and in life and what you want to dedicate your energy to in that period. For some, this results in feelings of guilt or the perception that others are judging you for your choices. Stay true to your purpose and choose your commitments—this is work you can contribute to if you want to. Underrepresented individuals or groups should not do all the work—it must be an opt-in, remunerated effort that is collaborative with allies.

Regardless of how you may choose to participate, it is helpful to be aware of what the team, committee, or related community structures look like at a particular company. Select questions that will help you understand the answers to the following as you move through the interview process.

  • Is this an “initiative” vs. a commitment or ongoing business priority?

  • Is this a HR program? Does the work depend on or sit solely within that function? This is important because the role of a HR team as it supports the business and mitigates risk may conflict with the interests of those trying to transform the team and experience with regard to DEI from the inside. It’s valuable to have someone in a leadership position who can partner with HR while advocating for these initiatives from a different perspective.

  • Does it have the support of the CEO and other C-level leadership?

  • Are the efforts tied to one person or a small group of people?

  • Does the company have employee resource groups (ERGs), affinity organizations, or similar groups in place? What is the frequency and nature of their interactions? What programs are in motion and how are they progressing? What budget do they have to work with? Do the groups have organizational support?

  • Does the company have a team or role dedicated to this work or is it something individuals do above and beyond their jobs?

  • Do you have information that there is empowerment and support (e.g. budget) for those who participate?

  • Are those involved open to new and even contrary points of view and will they respond to conflict and debate productively?

  • How do participants feel their contributions are viewed and valued?

If you decide to dedicate your time and effort to this work, you’ll want to know what you’re getting into and how it will complement or contrast with other aspects of your role and experience. If the work belongs to a certain team, or if there is a dedicated role, there may be a particular focus and limits to what you can influence or contribute. In other instances, companies will have grassroots efforts, where anyone can contribute (likely in a volunteer capacity) and help shape the agenda, but your resources may be limited and your contributions may not be viewed with the same weight or impact as those critical to your role. Be aware that in some companies, if your participation in DEI efforts is viewed as distracting from your contributions in your role, or if you are viewed as part of the push for change, it may undermine how your job performance is viewed.

You’ll have to make choices as you learn more in the interview process and once you’ve joined a company. As with other aspects of work, it’s unlikely you’ll find everything you’re looking for. By asking questions and exploring how the companies you interview with are approaching this work, you’re demonstrating the importance of these efforts. If every candidate asked about DEI in their interviews, the expectations and accountability to have a point of view and tangible evidence of a commitment would be reinforced. When you do this work and ask these questions, you’re helping to pave the way for the team members and candidates who will follow. If this is something that matters to you, ask every interviewer a question about it. What they say, or what they are unable to share, will tell you everything.

In working on this section, and on broader, related themes throughout the book, I partnered with Megan Abman, Karyn Lu, and Regina Motarjeme from Strata RMK Consulting to help expand my perspectives beyond the work environments I’ve been closest to in my career. With their deep passion, innate curiosity, data-driven and human-centric approach, the Strata team consults, educates, and leads teams and companies toward a resilient foundation and enduring commitment to diversity, equity, and inclusion. I am grateful for their partnership and wisdom and inspired by their work.


There is a reason why “people are our greatest asset” or “the people are the best thing about working here” are quotes you often hear about the work experience. Who we spend our long days with, and how we interact, communicate and collaborate with them, are meaningful elements of our jobs. Later in the book, we’ll take a deep dive on specific people you’re likely to meet in the interview process to help you think through the importance of different relationships. This section will focus on a broader spectrum of relationship-oriented criteria, including team dynamics and leadership influence.

How do you know if people, and specifically the team dynamics and leadership influence tied to those relationships, are one of your top priorities?

  • You value and emphasize work relationships over work responsibilities.

  • Work is a primary source of connection and community in your life.

  • You prefer collaborative and interactive work environments and activities over solo, independent efforts.

  • This is a network-building stage of your career that will help unlock doors in the future.

If relationships are one of your top priorities, make sure you get to know your interviewers! Throughout the interviews, you’ll get information from and about them that you will be able to logically analyze. You’ll also gain insights that will lead you to form intuitive impressions about each person and the group as a collective. It’s unlikely that you’ll be able to meet with every single person who works at the company, so these interviewers are also a proxy for the full team. If you believe that meeting with someone in a particular role or on a specific team would be critical to your ability to make a decision about joining the team, ask to have that conversation if the opportunity isn’t offered.

Interviewers are unlikely to dish on the drama or politics, so let’s explore how you get more information about the team dynamics. When you meet with people one on one, it’s hard to judge how collaboration comes to life on a team and at a company. Yet, understanding individual perspectives as well as what the collective interaction looks like is key to the work experience.

storyI recall a team that I was part of where, if you met each of us individually, you might have been impressed by our qualifications. We would have appeared to be smart, capable, passionate individuals who could thoughtfully articulate elements of the business, a role’s value proposition, and engage in a responsive, credible and personal way. At the same time, if you had observed all of us in a team meeting discussing a complicated or controversial decision, the differences in our styles and approaches would have been apparent. It’s not that we didn’t respect one another, or recognize each other’s expertise, we just didn’t have an effective approach to collaboration. We hadn’t found our rhythm or invested in making the outcomes, as well as the journey to getting there together, more enjoyable.

To narrow the focus on what aspects of the team dynamics you will want to examine, focus on these four “Cs”: communication, collaboration, competition, and community.

  • Communication. How you like to share and receive updates

    • What are the methods or tools you find most effective when communicating with team members?

    • How frequently do you want or need to be in touch with others on your team?

    • How do you like to participate in or receive updates about important decisions?

  • Collaboration. How you like to work with others on your team

    • Do you prefer group or independent work?

    • What makes collaborative meetings or activities most effective or enjoyable for you?

    • Do you like clear roles and responsibilities or a more open and evolving structure to projects?

    • Do you want to start a meeting with a detailed agenda or blank whiteboard?

  • Competition. How you view individual and collective achievement

    • Are you motivated to ascend and focused on your own outcomes?

    • Do you enjoy roles or teams where individual performance drives rewards?

    • Are you comfortable with a hierarchy that impacts how people interact?

  • Community. How you view your colleagues

    • Are you looking for interaction beyond and outside the workplace?

    • Do you see team members as prospective friends or prefer to keep your personal and professional lives separate?

It would be incredibly valuable if you could spend the day with a prospective team member shadowing meetings, observing the tools and technology that facilitates their work and gathering information about the pace and intensity of the role. Unfortunately, that experience is rare. Toward the end of the interview process, or after an offer, you can request the opportunity to audit a team meeting or follow a team member for all or a portion of one of their days. It’s possible the company will give you the chance, which could meaningfully impact your understanding and perception about the role. If you get the chance to see a day in the life, take advantage of the opportunity to observe and ask more detailed questions! If not, leveraging the strategies outlined throughout this book will get you as close to an insider’s view as possible.

Next, let’s look at leadership. Whether you report to someone in the C-Suite or are starting out at the entry level, the influence of the leadership team will contribute to your experience. There are many types of leaders that you’ll encounter along the way. Understanding what you value in their experience and approach will enable you to ascertain whether or not the company’s leadership is what you’re looking for in your next role.

In order to evaluate or probe in a relevant direction with your interviewers about the influence of leadership, take some time to consider the profiles of leaders you’ve worked with in the past. Identify the aspects of their approach that you admired and want to see replicated in future leaders and pinpoint the styles of leadership that will not support your current career objectives.

Here is a list of reflection questions to help you define what you’re looking for from leadership as you refine your list of priorities:

  • Do you value a leader’s previous experience and prefer to work with those individuals who have solved similar problems in previous roles? Or, can you get excited about someone who has ascended into the leadership position quickly based on their intellect, ideas or expertise?

  • Do you want the leadership team to have breadth and depth of experience or are you comfortable with a team that has a narrow focus and set of expertise from a functional or industry point of view?

  • Would you like to have leaders who lead from afar, trusting their teams to fulfill their roles, or are you someone who values a hands-on, involved leader?

  • What about various leaders' communication styles did you appreciate in the past? What types of communication—or lack thereof—frustrated you and impeded your success?

  • Would you prefer your leader trust best practices and industry standards or lean on experimentation, testing and exploration?

You will have to determine what styles of leadership resonate with you. This is particularly important for those you’ll interact with the most—your manager—as well as those who will indirectly impact your experience from the top (like you’re manager’s manager). In conversations with your prospective manager, department executive and peers, listen for clues and ask specific questions to get more clarity on what leadership looks like at the company.

In evaluating the people aspect of a prospective opportunity, pay close attention to the words your interviewers say (as well as what they might leave out), their body language, inability or unwillingness to address certain topics, or a lack of enthusiasm and attention paid to the conversation overall. Monitor your reactions as well, specifically those that might yield insights that you will need to look into further. Take notes after the conversations about what you liked about the interaction and how you think it will contribute to a positive work experience. If you have lingering questions, add comments about what you might need to explore further with a particular member of the team. These reactions are fleeting but telling. Capturing reflections soon after the conversation so you can follow-up is worthwhile, especially if you are interviewing at multiple companies where experiences have the tendency to blend together. As you respond to interviewers’ questions and listen to their responses to yours, assess whether or not you believe they are genuine and telling the truth.

Your goal is to find people who you will be able to collaborate with effectively; learn from and potentially teach things to; and who you can communicate with productively in order to accomplish required objectives. At certain stages of your career, you might be looking for even more out of these working relationships, for example, some team members eventually become dear friends. Knowing what you want out of these relationships and approaching the conversations with those priorities in mind will help you determine if you can see yourself in the team room, pushing toward deadlines and celebrating big wins with this particular group. As I stated above, in People and Power in the Interview Process, we’ll dive deep into the specific people you’re likely to meet to help you understand more about how they could influence your interview or working experience. The titular section, Ask Me This Instead, also includes questions for each of the core profiles so that you take advantage of the opportunity to understand their particular points of view on the topics that matter most to you.

Offer Package

The components and value of the offer package—the salary, benefits, bonus program, stock options, vacation time, volunteer opportunities, and more—are parts of the work experience that most people can’t ignore. These are the factors that help us determine whether a particular job will enable us to live our lives. What you focus on within the offer package is highly dependent on your needs and desires.

Within the key aspects of an offer package, you might prioritize with the following in mind:

  • Are you responsible for financially supporting yourself and/or others?

  • Are focused on specific financial goals or obligations?

  • Are health and wellbeing priorities for you, or for those you support?

  • Do you want to balance the short vs. long-term rewards?

  • Do you prefer stability and consistency or can you tolerate variability and risk?

  • Is it important to you that the company provide volunteer days, donation matching, or other ways to support causes you believe in?

An entire book can be written about the offer and negotiation process. This is not one of those books, but highlighting this component of the employment experience as an important aspect of what you need to reflect upon to codify your personal priorities and address during the hiring process is worthwhile. There are a few areas I want to emphasize as you prepare to interview and ask focused questions.

In recent years, the conversation has shifted and new laws have emerged to address pay inequity. As someone who has talked to thousands of people about salary and seen offers and payroll files, I am glad there are great minds, brave voices, and admirable organizations working to address these gaps—because there is a lot of work left to do. Each of us can contribute to a more equitable future if we take steps to ask informed questions and gather inputs from credible sources that will help us advocate confidently to earn what our work is worth. And, by taking these steps for yourself, you pave the way for others like you. Some companies have taken bold steps to address the issues, adjust pay, and even publish the salaries of all their employees in an abundance of transparency, but most have not.

State and national laws, guidelines, and regulations vary about when, if, and how employers can ask about or share information regarding pay, benefits, and other elements of an offer. These may be dependent on the level of a role. For example, executives may have access to different types of compensation or contracts outlining what they are entitled to throughout and at the conclusion of their employment. In other cases, there may be a union that negotiates on behalf of everyone. Pay is an important (OK, absolutely critical) aspect of employment for most people, and it’s also very personal. What defines a satisfactory salary or hourly rate will depend on the person, their experience, the role and location, as well as their perception of the value of the contributions they make and the personal responsibilities they have to manage.

How can you take steps to get the rewards you deserve? First, start with publicly available information on various websites (including, PayScale and Glassdoor) that highlight salary information for roles and by geography or other criteria. Consider this information directional. The inputs used to generate the average ranges are often anonymous, which means they may be accurate (after all, there isn’t a motivation to misrepresent) but they are absent of meaningful context used to determine pay rates. For example, it can be hard to decipher the size of an organization, the breadth of the pay band (is that salary at the top end or bottom for that company and role), whether or not that person is a top performer or barely scraping by, if they’ve had raises and progression tied to market or individual results, and if their offer was determined or influenced by their past salaries, experience, or other factors. Take these numbers and start to formulate your floor, the base level of a yearly salary or hourly wage that you’d be able (and ideally excited) to accept. Do your best to make that floor a realistic, achievable one for the roles you’re targeting.

Once you have your target number or range—one that will cover your bills, enable you to save and enjoy life, and that will motivate you—I recommend you check it with a neutral and informed person (yes, a human being, not a website). Ask a recruiter or HR colleague from a former employer, or a former manager, peer, or executive who has visibility into recruiting and or internal pay bands in the field or function. You’ll need to describe the role and responsibilities and the company size and stage to help them frame their response. Share an open range and ask them if they believe it’s on point. This information and framing enables them to give you a more targeted and honest answer. They may adjust the range up or down or share other considerations that will help you feel more confident or lead you to do more research.

important A lot of people won’t take the steps to vet their compensation expectations. They’ll make the determination on their own or with a close friend, partner, or spouse, because it can be awkward to talk about compensation. That’s why it’s so important. The more we talk about it, the better prepared and informed we’ll all be. We won’t have to wonder where we stand or if we could have asked for more. The more we talk about it, the less awkward it becomes, the more comfortable you’ll be in conversations with hiring managers or recruiters about the salary of a job you want.

It’s important to remember that base pay is not the only factor that matters in the offer. There are also benefit programs, paid time off or vacation time, parental leave, bonuses, stock awards, and other components that some companies will be able to offer their employees. The collective aspects of an offer, often called “compensation” or ”total rewards,” matter, and individual pieces will rank in a different order for different people. For example, if you have planned or ongoing health care needs, or if you are providing health care for a spouse or dependent, you will want to look at your current health insurance offering. What does it cost you each pay period or month; how much do you spend toward prescriptions, office visits, or other healthcare obligations; do you like the way the plan and access to providers is structured? If you plan to start a family in the next few years, you’ll want to get an idea of what parental leave, childcare, and flexible schedule options are available.

As you kick off your job search, research what companies you’re interested in offer across their different benefit programs—many have highlights listed on their careers page. Google unfamiliar terms or reach back out to the recruiter or HR professional in your network to get more information about anticipated costs and how these programs are implemented. Then, if you receive an offer, take the time to read up about their programs and policies and look into the associated eligibility and costs. If you have questions, or want more information, ask for it! An informed decision is in your best interest and, while you may or may not be able to negotiate for everything you want, you will be able to put the advantages and tradeoffs of an offer into perspective.

Work-Life Balance

Work, whether we want it to or not, often crosses over and impacts the rest of our life. Understanding how a prospective opportunity complements or disrupts your personal priorities and interests is necessary. The language and conversation around “work-life balance” is evolving. Depending on the path you pursue and your personal preferences, how work plays into the rest of your life—and vise versa—varies significantly. It’s also likely that what “balance” means to you will change throughout your career. At its core, work-life balance is about whether or not this particular role provides the space and flexibility for you to enjoy your life outside the office or bring parts of yourself into the office, for example, establishing friendships, celebrating holidays and heritage months, or sharing more about your weekends than commentary about the weather. Because I touch on relationships, community, and inclusion in the people, employee experience, and inclusion belonging sections, I’ll hone in on schedules, boundaries, and how to evaluate the time commitment you’re willing to give to a role.

What signals in your personal life might indicate that you’d want to focus on work-life balance in your next opportunity?

  • You have personal or family obligations.

  • External hobbies, passions or activities are important to you.

  • Work is just that—work, and you want to be able to compartmentalize and contain its impact on the rest of your life.

  • You are at a stage of your career where more time spent at work will pay off—perhaps because you believe in the mission or are working toward a promotion.

  • You’re coming off a period of intensity and want the pendulum to swing back toward balance.

  • A remote role or flexible schedule will enable you to manage your work and personal commitments more effectively.

As your life changes, your priorities will change too. It’s important to note that you can ask questions to clarify your understanding of a particular company’s approach to balance without disclosing details about your “why” if you prefer to keep your personal life and considerations more private.

One of the most important places to start is tied to the schedule and hours you’re required or expected to work. Some roles, depending on their classification, will have specific schedules and will be eligible for overtime. Often, there is more clarity with those positions about when you work, when you’re off, and what responsibilities you have. For other roles, including those that do not have specific shifts, assigned schedules, or the need to track your time to calculate overtime pay, you’ll have to spend more time figuring out what the real “schedule” is. While the reference to a 9-to-5 is common, the reality is that many people work many more hours than the so-called 40 hour work week. Sometimes, you’ll see these signals in the job descriptions (“work hard/play hard,” “you want to work hard on the toughest problems,” “our team chooses to go above and beyond….always,” “we do more, with less”) or in Glassdoor reviews, but other times you’ll have to push for answers.

Sometimes these extra hours are pushes to get key projects across the line, and staying late or coming early is manageable. In other scenarios, the role, team or even company consistently and continuously operate at a pace and intensity that requires long hours 5, 6 or even 7 days a week. Because work is on our phones, as well as in the office or on a laptop at many companies, the boundary between the office and home, as well as the workweek and weekend, is less clear. Technology can mean that you’re always “accessible” via email, phone, text or chat. This means that, even if you commonly work from the office, you might also work from home too—on evenings and weekends. As you learn more about the team, seek to understand their definition of “accessible” and how it differs from “available.” In those non-working hours, are you expected to respond within a certain timeframe (or is there a precedent or preference in place on the team) or can you respond if you choose to and leave until the next work day if you have other plans?

There might be a time in your life where you are willing to have a job that requires a significant time commitment. Perhaps you’re particularly passionate about the work you’re doing or there are meaningful financial rewards tied to your contributions. Those factors may make the extra work worth it. In many cases, those incentives are not present, and if you want more boundaries or the chance to live your life outside of work too, you’ll have to ask for clarity about how committed and connected the team or company will expect you to be (including when and how you take time off) from those you meet in interviews. Knowing whether or not you’re in one of those phases of life where you can over-contribute to work relative to the number of hours in a day and whether or not this job might require it will be important to clarify. You’ll also need to assess how the team establishes and maintains boundaries between work and life so that you understand what space you’ll have to do the things you want to do to rest, recover, and re-energize.

Career Path

Some people know early on what they hope their long-term career path will look like, or even the culminating role or accomplishment they aim to achieve. Others will find their path as they go or even explore multiple different paths while searching for the work that inspires, fulfills, or compensates them. There are many ways to move through your career. Some individuals might be focused on ascending through a particular promotion track, others might take lateral moves through different functions or departments, and some might find the role that will carry them throughout their career and stick with it. Whether you are looking to climb that career mountain, happy at the plateau, or seeking to find a role to build a home around, figuring out if your expectations are likely to be met by a particular role is beneficial.

Here are some questions to consider that might lead you to prioritize the career path available in your next role:

  • Are you intentionally looking for career advancement?

  • Is now the right time for you to focus on work?

  • Does the role you take next need to confer value or signal specific skills or achievements to others?

  • Is there a clear direction within your chosen discipline that requires or allows for a particular progression and/or timeline?

  • Are you confident in the industry and/or company—that it has staying power, relevancy and prominence now, and over the next ten years?

  • Is this the function you want to focus on long-term—will this role and the skills you develop serve as stepping stones to ongoing career opportunities?

  • Is the ability to advance through roles in this company connected to career milestones you have identified and are working toward?

  • Is having opportunities to learn and grow in your next role important to you?

Questions about career path or promotion opportunities come up frequently with candidates during the interview process. It makes sense in many regards. Candidates want to find out about future roles, growth, and rewards, as well as if the roles will provide the title, prestige, and learning they want in their career. To be able to effectively understand the potential career path at a particular organization, you’ll need to evaluate it from various angles.

The average tenure at companies has decreased relative to prior generations. It also takes time, often multiple years, to develop the skills and operational familiarity that will result in a promotion. With that frame of reference, there’s a good chance you won’t be at the company to take them up on their career path progressions. Instead, you’ll probably take new positions elsewhere to optimize your trajectory and total rewards. And, you’ll make those moves on your own timeline, for the reasons and opportunities that matter most to you.

In reality, there may not be enough information for an interviewer to talk about career paths during the hiring process. Unless you’re stepping into a role on a team where there is history and evidence of growth, advancement and acceleration for others, they may not have a clear perspective on what’s next for someone like you. If you’re joining a large team, where many people fulfill the same position and have for years, there is a better chance your interviewers can more accurately tell you what the potential pathways look like as well as what factors contribute to making those moves possible. If you are the first person to have this role, one of a small cohort, or if you are stepping into a new team, an interviewer can give you an answer, but you won’t be able to know if it’ll be true. If there is not an established process in place, are they giving you credible information or generic indicators to move the conversation along? It’s hard to tell.

Additionally, it is unclear if your potential will equate to high performance. During the interview process, the company is assessing if they believe you have the potential to succeed. Can you effectively fulfill the responsibilities? Do you have the capabilities and skills? Will you approach the work with engagement, passion, and performance that differentiates you relative to peers?

And finally, it is also uncertain if you will like “it” (the job, the team, the city, the work, etc.) enough or care long enough to perform, stay, and succeed in progressive roles to get that desired promotion, or if you’ll even want it when it’s offered. The grass is always greener…

There are fields in which a clear career trajectory still exists, but there are many more where the thing to focus on in a new role is whether the skills you learn are applicable to a wide number of future opportunities. Careers, jobs, companies, and industries are changing fast, and one of the best things you can do for your career “path” is to treat it flexibly. The most important factor in having a long-term career path is deciding that the job you are interviewing for is the job you want and then succeeding throughout the interview process so that you get the job. This book is one of the tools that will help ensure you pursue and have access to the career path, whatever that might be, that best suits your aspirations and goals.

Company Mission

Why a company exists, the problems the team is focused on solving, and the steps they’ll take to get there represent aspects of the company’s mission and goals. A company’s mission is its reason for existing. Some companies treat their mission statements like inspirational quotes about changing lives, or the world. Others are more straightforward: to provide a product or service that people need. The work that the team does, as well as the goals the business is focused on, is tied to that purpose, that reason for being. The mission, and the underlying goals and values that the company has will drive decision making, influence team structure and role design, and help shape the culture. In mission-driven organizations, the pull to participate and make a difference is a leading factor why people choose to work there and the resulting camaraderie and commitment can create a unique environment.

To determine whether or not a company’s mission and goals will rise to the top of your priority list, consider the following:

  • Are you purpose-driven when it comes to your career?

  • Is there a cause that you want to commit to working on professionally?

  • Do you need to believe in the underlying “why” to commit to a company?

  • Is it important for you to be able to connect your work to higher-level company initiatives and outcomes?

  • Does the company’s mission resonate with you?

Most companies will highlight information about their mission on their website. Finding the “About Us” or “Mission” sections will help you gather information. Spend some time reviewing this content. A connection to the mission, or the absence of one, can have a significant impact on your experience. If you are passionate about a cause, being around people who are working toward related goals can be energizing. On the other hand, if you are not deeply committed to the work or end outcome, it can be isolating, even demoralizing.

Throughout the course of the interviews, listen for clues about how the mission influences the experience and work. Consider how often the topic comes up in interviews and how the team members talk about what it means. Are the signals that you hear and see in line with your level of attachment and interest in supporting the end goal of the company? Would you feel comfortable if you were a contrarian or apathetic participant in company meetings or initiatives?

important It’s also important to learn how the team works toward the company mission as well. If you are excited about their “why,” but disagree with how the company is tackling the problems and opportunities or have concerns about who they are partnering with to achieve results, the mismatch could be disheartening or troublesome. It’s worthwhile to determine who “wins,” when the company succeeds (investors, executives, employees or customers). Are those who have the potential to benefit the most the people you’d be excited to support and cheer on along the way?

Company Goals

Once you understand and assess the company’s mission, it’s time to understand how the organization’s goals are structured. Some companies can plan effectively multiple years out and cascade relevant information, goals, and responsibilities throughout the organization. When you’re interviewing with a company with that level of sophistication into their multi-year planning, you’ll be able to ask about their objectives and get reliable information in return. Many companies, especially early-stage startups, are still working on next week or tomorrow and the ability to pinpoint specific initiatives or outcomes multiple months or years out is… out of the question. There may be ideas or aspirations, visions, and dreams, you should explore with your interviewers, but you can’t put too much weight into information that falls into one of those categories.

The sophistication of a company’s goal-setting process, communications, and ability to cascade and distribute that information effectively throughout the organization will vary significantly. A scrappy, small company might do this well with a refined approach, accurate data, and synchronized responsibilities and cross-functional efforts. Some of the world’s top companies might be successful despite a broken or overly complicated and slow goal-setting process that is disconnected from most employees' experience. It’s valuable, if not imperative, to care about the purpose the team is working toward and understand the categories of goals they will focus on in the near term (often tied to revenue, growth, margin, client, or customer satisfaction). The “what,” “how,” “how fast” and “with whom” are the type of details that you’ll have to push to learn more about during the interview process.

With that in mind, prioritize getting a very clear picture of what’s going on right now concerning how the team operates and what they view as their organizational strengths or weaknesses during the interviews. The more you know now, if “now” sounds exciting and aligned with your aspirations, the better you can feel about “later.” If you can get behind the current initiatives and see yourself working well with the people who are on the team and find yourself curious about how a particular project might turn out, those are good signals. Perhaps that company is a place where, regardless of where they or you end up in 5–10 years, you’ll have benefited from the experience.

When it comes down to the position specifically, the professional goals you’ll be working toward and measured against are likely to be fluid, dynamic, and subject to evolving conditions. Hiring managers know the pain they are currently experiencing and the desired immediate solutions. If it’s an established company they might also have a general idea of the rhythm of work, how it plays out throughout the year and over time. If that’s the case, then they can probably share a realistic goal, but the problem there is that they could be resistant to change. The work may trend toward evolution rather than revolution—you might not be part of building something new, innovative, or challenging to the status quo.

Conversely, if it’s a new position at a startup or rapidly changing company, there is a good chance they haven’t thought that far out—they don’t have time. They are solving to survive and it’s better to understand if you’re excited by the current problems, pain points, and people, and open to the unknown, uncertain shifts that are likely to occur. Are you comfortable with ambiguity, changes, and risk or do you prefer stability and certainty? If the value proposition changes, how will you respond? If the role is on the dynamic, uncertain end of the spectrum, the good news is that you might have the chance to influence the path forward. By the time you get oriented to the existing expectations and make progress toward the known goals, you’ll have insight about what else needs to be done and how your background and expertise could contribute to the long-term impact. For this to be true, you have to find out how open your future manager and organization are to individuals driving the process.

And if we haven’t all figured this out yet, the world can throw curveballs into any company’s plans. Long-standing companies can fail, previously unknown products can quickly change our lives, and economic, political, or other global influences can impact how companies adapt and respond. It’s impossible to pick the winners, but you can pick your team.

Company Operations

As you search for opportunities and pick roles to pursue, another important factor to consider is where a particular company is on their journey as well as how that stage impacts the way the organization operates. The way work gets done, and the philosophy and technology that drive a company’s operations, can impact not only your day-to-day, but your overall experience and success.

In order to determine if a company’s operations supports your ability to do your best work and if that is something you want to focus on in your job search, think about these questions:

  • Is the company a brand new startup or established player?

  • How comfortable are you with change and ambiguity?

  • Is the company launching the minimum viable product, a new product or iterating and improving upon existing products?

  • What does the organizational hierarchy look like and will it impact decision making, approvals, or access to information?

The way a company operates will influence how work, collaboration, communication, and outcomes are experienced and achieved. I’ve found that the size, revenue, or maturity of a company are not always the best indicators of where they are on their journey. I have another way of thinking about it, which is easier to get at during interviews. When calibrating across different opportunities, the metric I find most helpful is about “process.”

  • Teams (or companies) with no process. There are teams and companies at all stages with no process in place for good, dubious, or concerning reasons. As you interview, you will get hints about lacking or absent processes associated with the work you would do. Stepping into a role where this is the case will require hustle, creativity, research, and problem solving, and a lot of hard work. These opportunities are great for those with a builder’s mindset, who aren’t flustered by ambiguity and who can be resilient through changes over and over (and over) again.

  • Teams with emerging processes. These are teams where they have initial and functioning processes mapped out and operational. The primary challenge is about scale or efficiency. Stepping into a role where this is the case will require systems thinking, the ability to connect the dots, and a commitment to collaboration and compromise. These opportunities are great for those who thrive on enabling human processes with technology, and who get excited by transforming spotty or chaotic processes into highly reliable, high performing ones.

  • Teams with established processes. These are teams where they have working, scaled, and distributed processes in place. Stepping into a role where this is the case will require a precision mindset and a commitment to optimizing and refining on the margins. These opportunities are great for those who like to be part of broader initiatives and play a more defined role, and who prefer a more steady cadence to the rhythm of work.

  • Teams with outdated and cumbersome processes. These are teams where the processes have been in place for so long and are so embedded in the way the company operates and delivered that they are both critical to success and a primary source of complaints. Stepping into a role where this is the case will require a patient mindset and the ability to mobilize across teams, leverage distributed resources and move forward in incremental and often slow steps. These opportunities are great for those who can see the chance to innovate in anything, and who are comfortable with longer-term time horizons to see change along with a more consistent state for their role and responsibilities.

storyI’ve had the chance to operate on teams and in companies with processes at each of the stages outlined above, and there are positive aspects and challenges to each situation. At this point in my career, I’m more of a “no process” or “emerging process” kind of person, but someday that could change, and it wasn’t always the case. I realize that my time spent with “established” and “outdated and cumbersome” processes has also been beneficial. It accelerated my ability to build, adapt, and transform in environments with “no” or “emerging” processes because I had models to work from and incorporate into my work. In anticipation of interviews, start to think about where you prefer to be in the journey of a particular team or company. Then during the interviews, ask questions of the hiring manager, direct reports, and cross-functional colleagues about the process to gain more context about how your preferences would align with their circumstances.

Company Reputation

Choosing a new role and working at a specific company has implications now, and later. There are certain companies that inspire trust, others that are recognized for their innovation, social impact, or growth, and some that are known for developing exceptional leaders across a number of disciplines. On the other hand, some companies rise and fall, are known for toxic leaders and internal strife, terrible customer experiences, or failed products, and are the subject of editorials and exposés. Some companies that have amassed billions in funding or revenue can be the same companies with bad reputations in other arenas.

The surprising reality is that companies on either end of the spectrum can offer valuable learning, growth, and opportunities, so it’s up to you to decide how the company’s reputation on different fronts will impact your decision. As you reflect, consider:

  • Do you need this role/company to be a launchpad for future opportunities?

  • What aspects of a company’s reputation matter to you?

  • How have previous experiences shaped your ability to respond to issues or take part in change and transformation?

In order to determine if this stop on your career journey will be worthwhile, think about the “dirt” you might discover and how significant it will be to you and your success.

If you’re wondering, “dirt” is what everyone on the outside loves to talk about and what those on the inside hope to hide, especially during the interview process. It’s the information you find when you go looking—employee reviews, rankings on top employer lists, podcasts, press releases, and product placements. Sometimes it’s as simple as broken tools, outdated technology, or cumbersome processes; other times it’s more complicated—toxic personalities, manipulation, lack of strategy, too much or too little on the roadmap, a vision without substance, systemic racism, harassment, or unclear and unachievable goals. The “what” may be unique to each company, but there is dirt, somewhere, everywhere, under… there. It’s important to know what that dirt is before you make a decision. Because the existence of dirt is universal when it comes to companies, it’s mostly about awareness and a conscious decision to choose the dirt in one place over the dirt in another. The dirt you know vs. the dirt you’ll come to find hiding in places you hadn’t had access to or anticipated during the hiring process.

You will need to get under the surface. The canned answers that someone shares as part of the standard interview process might be far from the truth. As an experienced interviewer and hiring manager, I had polished, positive answers reframing anything “tough” ready to go, including answers to the questions about my own failures and choices. Every now and then, someone would ask me a question that would make me pause, look up, and then back at them and say what actually came to my mind, abandoning the words I’d carefully prepared in case that line of questioning came up.

If you begin to ask tough questions and get to the end of an interview process without insight into the dirt, it’s a chance to reflect. No dirt? Nothing wrong? Not possible! Try to ask another question or come at it from a different angle. On the other hand, if someone offers flags or if there is an issue or concern that emerges out of every conversation, a hint of something that just isn’t right, listen, push, and probe. Don’t worry, this can be tough, which is why I’ve prepared a list of questions in the Ask Me This Instead section to help you get the information you need. The proactive slips, misses, and gaffes are very telling. Sometimes it’s sabotage, other times it’s evidence that, even in a context where people are supposed to be polite, diplomatic, and restrained salespeople, there is enough of something going wrong that they just can’t hide it.

Once you know the dirt, weigh the magnitude of the flags and flaws you discovered. Chances are, they will seem worse and more complicated than they are to those inside. Are they the problems you might enjoy solving? Are you OK with conflict, complexity, or chaos? There are good problems for every type of person. The problems I love to solve would make someone else run away! It’s about finding and balancing the problems and potential that are best for you.

Employee Reviews

Before interviews, one of your primary sources for learning about employees’ experiences working at a particular company is the internet. There are endless websites with content and information including The Muse and city-focused Built In sites as well as sources for employee reviews and rankings such as Glassdoor, which can provide interesting tidbits and candid feedback. As you read through the information, try to balance it with your own real-life experience as you go through interviews as many of the inputs are anonymous and thus hard to qualify. What didn’t work for someone else, could work well for you—no two employees will have the same experience even given similar circumstances or timing at a company.

Beyond the sites we might seek out when we’re doing research, we’re inundated by messages about work everywhere we go. While scrolling through your LinkedIn feed you see updates from your network about the exciting jobs someone’s just started or the company milestones that they’re “so lucky” to be around for. Sometimes, you’ll see an intriguing headline about great perks or high salaries and click into it. It’s hard to escape. Those messages, particularly the constant flow of them, can be helpful or disruptive at different periods during our career. Those messages can also be very persuasive. When targeted by messages with positive “filters,” we’re likely to fall prey. Especially on those hard days, the days when we’re down or disappointed. The days when our boss or co-workers frustrate and exasperate us. The days when someone else gives notice, and excitedly talks about their new opportunity and we wonder, “What do they know that I don’t?” Spoiler alert—they don’t necessarily know anything more than you do.

important It’s important to read reviews and social posts with a thoughtful and objective perspective. Think about when people write reviews or share content to their social feeds. Actually, no, don’t think about people, think about yourself. When have you been moved to share your thoughts or opinions with people who you don’t know and likely won’t meet? My experience has led me to think of three primary situations when people post work-related content:

  1. When they were bragging, inspired, or excited—these are the new jobs, company milestones, and heartfelt messages.

  2. When they were raging, ruminating, or shocked—these moments are prime fodder for anonymous review sites.

  3. When they’ve been asked or incentivized to do so—perhaps to push a big announcement or balance out something negative.

It’s those polarizing experiences that compel us to seek reactions, validation, and camaraderie or commiseration. Read reviews and social posts with those frames in mind and with the recognition that you don’t know the context behind the narrative they are sharing. These precautions do not invalidate the experiences or feelings shared by the person behind the screen, but help remind you that these are but one input in a long list that can be used to shape your thoughts about a particular role or company.

If during the interview process you want to ask about something you read on these sites or in an article, do it! Especially about those tough reviews—give an interviewer who you think is in a position to respond to the feedback the chance to provide their own or the company’s point of view. You might appreciate their insight and you’ll certainly learn something about how they respond to challenges and feedback as part of the broader experience and reputation associated with the company.

One final note, a significant portion of the content you’ll find on sites is paid for and promoted. It doesn’t mean it’s untrue, but it is placed, polished, and a bit of theater, which means that there is a layer of authenticity missing. Perhaps the company is building its employment brand and took advantage of a content pitch for a piece that’s part of a package, or it might be a promotion to pair with a strategic launch or announcement. It could also be damage control. In general, it’s contrived and strategic messaging and you can consider it an advertisement of sorts. Take it, along with all information you receive, and use your critical reading, processing, and personal experience to assess the truth.

Employee Experience

One of my least favorite questions to be asked by candidates during the interview process was some version of, “What’s the culture like at [COMPANY]?” Because I was asked this question so often, I had many handy responses to rotate through or customize to the candidate I was speaking with, but those answers were never really that great. Culture, for me, is a living, breathing experience made up of and dependent on the behaviors, words, and actions of individuals, team, and the company collectively. There can be dominant themes, and also micro-patterns, present in different pockets of the organization.

And what matters most about culture is a special combination for each and every person. I knew my answers about culture didn’t stack up to reality, but with such a generic question, I often couldn’t do much more. Eventually, I started asking a follow-up question of the candidate to ask them to specify a particular aspect of the culture that they wanted me to talk about so that I could give them information that they might actually find useful rather than a pre-packaged blurb that could have been copied/pasted at one of many different companies.

Because culture is so hard to grasp, I now focus on and emphasize the “employee experience” working somewhere rather than the culture. You can get at “an experience” in much more tangible ways through questions, conversations, and observations throughout the hiring process. They are the foundation of what you might choose to label as culture, and since that’s what I know hundreds of people have asked me about, they are the topics I want you to diligently investigate at each step of the hiring process.

When it comes to employee experience, consider the following:

  • How does the company present itself on the careers page? Are there video games or volunteer days? Pictures of a beautiful office or an overview of benefits? Does the company’s “personality” come through?

  • Do you get a glimpse of the makeup of the team? Is it inclusive or homogeneous?

  • Do you see evidence that people bring their full selves to work? For example, personal photos on their desks, Pride or Black History Month posters, or a dress code that lets people freely show their personality and style?

The actual office or work environment often gets bundled into the employee experience or marketed as a key element of the value proposition. It makes sense, the office is easy to photograph and is something that is generally consistent for the onsite team. If you’re interviewing for a role where you’d be in an office, take in what you see and consider how the environment will work for you. For example, if you know an open workspace is a distracting and unproductive environment for you and that is how their space is set up, ask about the availability of private or quiet workspaces for when you need to focus or if you have the ability to work from home to get a key project complete.

For individuals who have accessibility or health needs for a specific type of space or workstation, ask those questions to the person who is most likely to be informed or able to share accurate information and partner internally to get to the desired outcome. In some cases, you will be able to see their commitment—do they include accessibility information in their interview materials; are there all-gender restrooms available; is there a functional and comfortable lactation room; do the desks and office chairs adjust to different sizes or ergonomic needs, etc.? These questions are best directed to someone in HR who can work through a dialogue about reasonable accommodations for a specific position or worksite while maintaining the appropriate level of privacy and confidentiality. Though it can be difficult to raise these questions during the interview process, understanding whether or not the company not only fulfills the legal obligations but meets your needs is important.

Although many companies and teams were already working remotely in some capacity, the pandemic of 2020 ushered in a new point of view for many on the importance of remote and flexible work arrangements for roles where it is possible to do the work from home and on distributed teams. In the past, some companies prioritized the in-office experience for a variety of reasons including collaboration, community building, perceived productivity, and tradition. With the sudden and extended requirement to work remotely, teams adapted in ways they hadn’t previously thought possible, incorporating new tools and tactics to get the work done, collaborate under a new context, and continue to move the business forward.

If the role you are interviewing for is going to be remote, understanding how the team approaches distributed work, whether or not they have been doing this successfully for a long or short period of time, the tools and technologies the team uses and how they cultivate community and collaboration at a distance is important. As for the “office,” which may now be in your bedroom or kitchen, ask about the budget or equipment provided to set up your workspace.

The pandemic experience will transform the way many companies approach their office space and the way they expect their team members to show up, but even out of that context, confirming that the way the team operates and how it’s evolved will help you make sure it’s an environment that works for you.

Activity: Rank Your Top Priorities

Thinking about your priorities is only the first step. To pursue them requires an extra layer of attention and intention. Putting your priorities at the foundation of your job search enables and empowers you to focus your efforts and target the roles and companies where you’re most likely to find your match.

If you do not put yourself at the center of the search, the company’s priorities will take precedence throughout your conversations and in the final outcome.

Use this section to proactively articulate what you’re prioritizing at this stage in your career. Once you write it out, you’ll find yourself evaluating everything—a job post, a benefits package, a prospective team dynamic—more confidently.

Find the activity in this Google Doc!

A Job Title Is Just a Starting Point

important Titles matter so much and also not at all. During the job search, titles help you align your understanding of how your experience, career stage, and existing leveling might transition into an open role. Similarly, the titles on your resume will help others understand how they might work with you. Some companies will use industry or functional standards for their titles and others will have bespoke titles because the job doesn’t exist somewhere else. Companies may also label the same or similar work in distinct, unique, or seemingly contrary ways, even within their organization! A director at a Fortune 100 is quite senior within the organization and often deep into their career, whereas a director at a startup might run a function and have seniority within the company early on. Their experience and expertise is unlikely to be the same, though the value that each brings to their organization can be significant.

Occasionally during the recruiting process a title evolves or changes because the team learns more about what they are actually looking for and makes a more precise commitment to a level or framing. Perhaps the original title wasn’t attracting the right talent or the right talent changed the context for the role, and subsequently the best way to label it. In other scenarios, the team is testing titles—putting out the same or similar job descriptions under separate titles to see what attracts the people they’re looking to hire.

The variability, the evolution, the testing are all possible scenarios. What’s most important is for you to understand what the label represents and determine if it matches your expectations and aspirations. If the title doesn’t, but everything else lines up, it might be worth doing some research on how comparable organizations title similar roles in order to start a dialogue with the hiring team about whether a change is possible (note, I’d only do this at the late to final stages—it could be too disruptive to the process early on).

How should you think about titles? Titles are chapter labels in the career story but not indicative of the identity or value of the person who has them. After all, we don’t normally get to pick our titles, someone else does or some structure sets them for us. Titles are signals, but we still have to help others cut through the noise. Find ways to understand the “what,” “how” and “to what impact” when you’re learning more about a particular role and calibrate your experience to their frame of reference. Through it all, don’t let titles, your own or those on the job description, limit you. As you do your research and preparation, expanding your search criteria and focusing on what is highlighted within the responsibilities and qualifications section will open up new roles that may be a match for what you’re looking for. Your current title, or the one at the top of the posting, should not be limiting factors into the positions you consider applying to. Working with the right people, on the right problems, toward a meaningful purpose at an appropriate pay rate will mean more now, and over time, than a word or two on your resume or LinkedIn profile.

Activity: Assess the Landscape

In order to find the right opportunities to pursue, you need to expand your search and become aware of the broader landscape of opportunities that could be available to you. This exercise will bring you from the starting point of a single title to a more comprehensive view of the type of roles that encompass the type of skills and abilities you possess (with any number of different titles!).

Find the activity in this Google Doc!

Activity: Create a Personal CRM

Don’t just search for jobs, look for people and keep track of them!

Find the activity in this Google Doc!

Break Down a Job Description

The truth behind most job descriptions is that they are lightly edited, kind of plagiarized, branded marketing documents with a lot of words that often don’t say that much. Once hiring managers know they have an opening, they think of the most common label that exists that represents the position they have in mind and put it into a search engine. This results in a bunch of job descriptions from other companies. With all these examples, they begin to skim them and pull out the “best parts,” copying them into a document before massaging them into a more coherent and relevant version to post (or simply doing a “find and replace” for the other company and substituting their own). Oh, and they try to make it sound fun and compelling (you’ll learn, you’ll make a difference, we’re changing the world, and free beer on Fridays!). They do their best to make this job, this work, this grind, sound appealing or at least more appealing than the grind that you know or that other companies might be offering.

It’s almost impossible to encapsulate the experience of a job in a short list of bullets, even if you start from scratch. Because of that, most job descriptions are also too long—both in the list of responsibilities you’ll have and the qualifications you’re supposed to bring. And yet, when we’re searching for a job we tend to believe them. It’s magical thinking. One way to ground yourself in this reality is to stop everything you are doing right now and look at your company’s careers page. Do the job descriptions sound like they represent the work and environment that you experience every day?

Although job descriptions might try to make it seem otherwise, there are few truly original jobs. You might have had this realization while searching and comparing titles. Because the job description as a “tool” is so broken, you have to look beyond, dig deeper, and discover what is actually going on for this position and within this company. To do this, you need to break down a couple job descriptions.

Activity: Break Down a Job Description

Once you have found several postings that you’re drawn to, pick two to break down. This will help on multiple fronts. First, it’ll help you more quickly and critically evaluate job descriptions. It will also help you tailor your application materials and will kickstart your reflection on your experience in anticipation of interviews. Remember, you may not be able to check off every line of the job description, and that’s OK!

Find the activity in this Google Doc!

Write a Resume That Tells Your Career Story24 minutes, 4 links

Once you think you’ve found the job you want, it’s time to move to the next step—preparing to apply and interview. Yes, preparing. If you have really found the job you want, don’t send off a resume on an impulse! Time is of the essence, but sending off an incomplete or rushed resume or application could shut the door now, and for future opportunities. Once you have your target roles and companies, it’s time to build your collateral. For now, a resume and LinkedIn profile are still part of that solution. The flaws of the job description are mirrored by those we all put into our own marketing documents—our resumes. Truthfully, the resume is a relic that definitely needs to be innovated. We spend countless hours writing bullets that make sense to us but that might not connect with anyone else. We curate a document that highlights what we think are our top or most impressive accomplishments, but that might not reflect our real capabilities or our interests. We edit the statements over and over for space, change the vocabulary so much so that often what we end up with is a list of generic jargon.

important Just because the resume structure is outdated doesn’t mean your experience isn’t compelling, or that your passions and what you want to learn aren’t important when seeking a new opportunity. My approach to building out your resume will help you see your experience holistically to bring out the best of what you’ve accomplished. It’ll take extra work—more than dusting off the last version and adding some new bullets. In fact, you’re going to start thinking about your resume as a story. Perhaps you haven’t thought about your resume as a story before. But if you take a storytelling approach to reflecting on your experience before you craft a document, you will unlock a more interesting and comprehensive version of your experience. As an added benefit, thinking through the events, people, and context is valuable interview prep as it enables you to add more nuance and depth to your responses.

To start, you’re going to begin to view yourself as the central character on a journey with heroes and villains, struggles and successes, learnings and legacies. This exercise will help make this process less of a task… you might actually enjoy it (maybe just a little bit).

You’re reading a preview of an online book. Buy it now for lifetime access to expert knowledge, including future updates.
If you found this post worthwhile, please share!