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.
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important Just because the resume structure is outdated doesn’t mean your experience isn’t compelling, or that your passions and what you want to learn aren’t important when seeking a new opportunity.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).
I urge you not to skip this exercise! Remember that resumes get only a few seconds of attention at key decision points in the hiring process. The reader skims the highlights—employers, titles, progression—and quickly determines if the remaining bullets are worth reading. Relevant, compelling, well-written bullets keep the reader focused and engaged. Unfortunately most resumes are full of the same kind of meaningless jargon and exaggerations as a typical job description and show very little of the person behind them. Remember, you’re not just trying to get any job, you want to get the right job, and you can only do that by showing up as who you really are. This activity will help your resume stand out from the pack, keep the attention of your reader, and increase the likelihood of your getting an interview with a company you’ll actually want to work at. It will require a mindset shift to share your experience in a new way. It’ll be worth it.
Identify Your Main Characters
The Protagonist. You! This story is about what you want and need—a new job. Your resume needs to include the information that puts you on the best path to get to your end destination. Think through the moments you’re most proud of, the feedback you’ve received, the contributions, and impact you’ve made in each of your roles, and what you’ve learned.
Other Primary Characters. Along the way, you’ve worked with and met people who have influenced your story and success. Understanding their influence as well as thinking about the context of your relationships will unlock plot points you might not have previously considered adding to your resume. What type of characters should you think about?
The Heroes. There are surely people who have inspired you, pulled you along and served as role models throughout your career. You may envy their abilities at the start, until you realize the hero will help you see your potential and achieve it. Whom have you admired, who shined the light on your capabilities and cleared the path for you?
The Villains. Every now and then, you encounter someone who makes work harder, frustrates and exasperates you and seems to find joy in crushing your spirit, productivity, or results. There are important insights to be garnered from your experience with villains that may represent some huge lesson, impact, and growth in your career. We often tend to put these experiences aside, but I recommend you evaluate them closely to see what positive results came out of them (especially as there will be a lot of interview questions that you can connect back to these experiences!).
The Crew, Squad, or Posse. When have you been better because you were together? Thinking about the people who were by your side during periods of peak performance or intense creative collaboration as well as the day-to-day will lead you to remember moments and challenges that you wouldn’t recall if you were only thinking about yourself.
The Teacher. Hopefully you’ve had a manager, mentor, or colleague who took you under their wing and accelerated your ability to be effective in a given role. Think about people from across the companies you worked with who opened your mind about new ways to solve problems or who pushed you to gain the skills you needed to progress and advance.
The Protégés. As you have developed expertise and experience, who did you support along the way? How have you built stronger peers or direct reports by stepping in and stepping up to support collective outcomes? When did your insight or contribution change the way others approached a problem or project?
Like in any good story, characters may switch between roles as they learn, grow, and evolve … or devolve. I’ve had villains become valuable members of my crew and heroes fall to the dark side. Those can be particularly engaging stories to consider as you think about what interactions created the most growth or led to the most important professional relationships and experiences. You’ll have the chance to workshop your resume at the end of this section and in the workbook.
Consider the Place and Time
The setting, or place and time, are often included on a resume without much extra thought—this role was at that company, located in this city. Seems simple enough, right? In the most basic sense, that is the setting. However, now is the time to start to think about setting more broadly, specifically where the companies you worked at were in time and place, that influenced your experience. How you operate in a well-established company with hundreds of people is dramatically different than a high-growth startup. The distance the company traveled while you were there impacts your role and responsibilities and contextualizes why you might have pursued a specific path or hit certain roadblocks during your tenure. The more you can connect dots and make your experience come to life in relevant and specific ways, the more the hiring team will be able to assess if your skills and capabilities will be effective in their environment.
As you consider the setting, ask yourself about the situations below to reflect on how they might have evolved during your time in a particular position. This will surface new awareness about how you changed and grew in response to the world around you. With the context fresh in your mind, you might see the events and accomplishments through a new lens and with more clarity about the impact, reasoning behind, or significance of a particular experience.
Examples of Place or Time
Prompts to Consider How the Setting Impacted You
Strong economy vs. recession
Were you able to choose the job you wanted, or did you have to take the job that was available? Did you have part-time or contract roles rather than a full-time, regular position? Did your trajectory (title or pay) flatten or slow down? Did you have to take a role outside your preferred industry or function? Did the company have layoffs or did your compensation and/or benefits decrease?
Were you in a role at a company’s headquarters or a smaller satellite? Were you in a city where there was a density of talent to hire and a strong team to work with and learn from? Were you in a larger city or market with diverse industries and opportunities that you could access or were there limits? How did a remote-first or distributed team structure impact your experience in previous roles?
Company success or failure
Were there periods of rapid growth (hiring) or contraction (layoffs, turnover) that impacted you? Did the company raise venture capital or go through a merger or acquisition? Did the company have a competitive advantage, was it disrupting an industry or fading out of relevancy? Were there news stories or features about the company, its leadership or products? Were these stories positive or negative? Was the company meeting or exceeding goals or missing expectations? Was there steady and consistent leadership or new executives stepping in and changing the course?
Your own place and time
Did you have a well-defined role or did you “wear many hats?”Were there training programs available or did you have to drive your own development? Were you just starting out in your career, hitting your stride, or angling for the next step? Was work a priority or were you more focused on other aspects of your life?
Map Out Pivotal Moments
Your career, like a plot, is made up of a series of events. There are events of a more significant magnitude—new jobs and promotions, for example. Then there are those that may seem small, but that are, upon reflection, deeply meaningful and important—perhaps that first tough conversation with a direct report or turning a bad relationship around.
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Though time facilitates a natural sequence and order of the events that take place, it may not always be the most compelling way to tell your story, specifically within the context of a particular role or period of time. The moments that are most relevant, impactful, and indicative of the journey you’ve been on as the protagonist might need to be put into a structure that will catch attention, build suspense (OK, probably more like interest in this scenario) and keep the reader curious and wondering about what they will read next.
Start to think about events, accomplishments, and activities that were important to you at the various stages and steps of your career and that would be interesting to the reader (like a recruiter assessing your potential, a hiring manager wondering if you’ve got the capabilities, or a future direct report trying to see if you’re someone they think they’ll learn a lot from).
To refresh your memory about events that are important to your plot, ask yourself the questions below. These questions are not only helpful for crafting your resume, but also for practicing your answers to interviewers’ questions.
What were specific, high-impact initiatives that you contributed to?
When did you take a bold or controversial stance?
When did you achieve something unexpected under tight deadlines, or despite other obstacles and constraints?
How did you change the outcome of a key decision or important project?
When have you changed someone’s perspective or challenged the status quo?
When did you lack confidence, but persevere and achieve the desired outcome?
If you were able to share your best work with a future colleague, what would you share?
What would others consider your greatest success, and would you highlight the same thing?
When has someone recognized you for an accomplishment, large or small?
When did you adapt to surprises or change successfully?
As you take this new lens, you might change whether or not you include a specific accomplishment and how you combine and sequence as part of a larger whole. You’ll start to see how the story comes together once you consider the relationship between the events, the characters who helped shape them, and the setting that influenced why things transpired the way they did. Your job is to thread all these points in time together so that they don’t come across as random occurrences but a strategically threaded and cohesive progression of discovery, growth, and impact.
This will help them move through your resume and keep reading to understand not just what you can do but more about your progression and your potential. Who you are is more than what you’ve done!
Include Tension and Conflict
The desire to move beyond and even forget particular conflicts we have throughout our careers is natural. However, conflict in your career, like the tension in a story, is where some of the most interesting and important moments occur. In fact, these moments often represent the catalyst for characters to transform. Being able to articulate how these tests impacted you will add depth, interest, and a dose of reality to your resume. Without realizing it, you’re also preparing for the interviews by thinking about the experiences that pushed you and those that you might want to avoid in the future. These memories can be helpful in building the list of questions you’ll ask certain interviewers.
Consider a broader lens
Relationships that got off to a bad start that ultimately turned around
External factors that shifted timelines, product design, or even internal operations
The dynamics in meetings during periods of stress or high stakes
When a customer backed out of a deal or a colleague unexpectedly left the team
Trust, or rather the lack thereof, within a team or organization
Hard moments, unexpected changes, or big surprises
Failure that led you to quit, change course, fire someone
Times when you made a mistake or intentionally disrupted progress
The times you cried or lost your temper
A moment or experience that was embarrassing
A period when you were bored or unengaged in your work
New hire or new manager changing the status quo
When you didn’t believe in the company, its product, or people
Moments that made you look for another role
Lack of a feeling of belonging, being “othered,” or needing to assimilate
As you reflect, acknowledge the frustration, pain, and problems, and the context that surrounded them. Then, think about what positive growth, lesson, or change happened as a result. That is where the magic lies and what will be most helpful as you craft your resume, prepare to respond to interview questions, and evaluate if you’d encounter similar challenges in a new role.
Connect Your Story to Their Needs
One of the reasons I recommend taking the storytelling approach to updating your resume is that it helps you think about your journey and accomplishments in a new light. When confronted with a blank document, the pressure to put the “right” examples down is real and there is a tendency to fall into self-doubt. This can result in bullets that are bland (when you’re writing something to fill space) or even untruthful (when you don’t think a particular bullet is strong enough so you modify the details to sound more impressive). Then, because many people write resumes in isolation without feedback from those who worked with them or know them well in a professional capacity, resumes often fail to capture the reader’s attention—and that’s the entire point! Recruiters and hiring teams want to connect dots quickly between candidates and their role. Think about what they are looking for and how you can specifically and clearly connect your experience to their needs.
important If time and capacity were unlimited, resumes should be customized to a specific company and role. Because that level of tailoring often requires more time than you have available, consider developing one or two versions, each emphasizing a unique angle on a potential company’s needs. For example, you might be open to manager and individual contributor roles. Consider framing one resume about management and leadership, going deep into your ability to get results through others via coaching, delegation and feedback. For the other version, you could focus on the depth of your expertise, technical or functional accomplishments, and examples of your ability to collaborate.
Or, let’s say you are applying to a Fortune 500 company and a Series A startup. For the Fortune 500 company, you might choose to include more information about your cross-functional talents, project management capabilities, and communication skills. For the version you’d submit to the startup, you’d highlight examples of your flexibility and resilience, when you delivered results under pressure, and your ability to take on new and diverse challenges.
As you review job descriptions and begin to think about how your experience either directly or indirectly contributes to your ability to fulfill the different roles, remember it’s rare for anyone to have a line for line match with a job description’s “requirements”—do not let this deter you. For example:
If the role you’re pursuing has different goals than what your prior experience can speak to, take the chance to highlight the “how” more than the “what.” Include details on the way you approached setting a goal and breaking down the milestones, along with indicators of how you tracked and measured success.
If there is a new system or technology required that you don’t have experience with, share details about similar technologies or your experience learning a new tool to get results.
If the role is a management position and you’ve never led a team, incorporate information about your experience mentoring colleagues, leadership experience outside of work (in academic or volunteer contexts), or examples of when you made decisions or delegated work as a peer or project manager.
If the role has an expanded scope over a workstream or team that you have not led before, reference your cross-functional collaboration, shared initiatives, or instances where you influenced the work product or outcomes for that function.
When you are connecting your experience with the responsibilities and requirements listed in job descriptions, make sure you expand your brainstorming. Your experience in academic programs or community organizations could demonstrate the skills needed. It’s also a good time to reflect on feedback you’ve received. There, you might rediscover insights about learning and growth that are transferable. It is critical in these instances to give specific examples of curiosity, learning, impact or expertise that you believe is indicative of your ability to take on the responsibilities of this role. Simply saying you have a growth mindset or are a life-long learner is not enough! Take the opportunity to show the hiring team what you have to offer rather than just telling them.
Activity: Translate Your Story Into a Compelling Resume
Activity: Connect Your Story to the Roles You Want
It’s time to bring together all the previous activities, align your experience to key themes, and then select the most compelling examples of your experience to highlight under each role as you pull everything together into a resume.
Cover letters are one of the aspects of the application process that cause a lot of angst, confusion, and frustration. Candidates wonder if the hiring team even reads them or if the time they spent is wasted. While I cannot vouch for every company’s application review process or every hiring manager’s approach, when I’m recruiting I open the cover letters attached to applications as often as possible. I find they give new insight and add breadth and depth to the resume bullets, which are often generic. Though I cannot guarantee that everyone, or even someone, at the company will read your cover letter, refining your thinking and how you articulate your experience, readiness, and alignment with the requirements of the role is additional practice and preparation for you.
A well-written cover letter is a short, to-the-point pitch about why you are the candidate for this job. It should add something new about your experience and abilities to the application—building upon rather than restating what is in your resume. If you cannot customize your resume to every position, you must tailor your cover letter! To miss the chance to bridge your list of accomplishments and skills with their opportunity and highlight why you chose this position over others out there might mean you don’t get to interview.
You don’t have to overthink or spend hours crafting your cover letter. Building upon the framework below enables you to complement the information presented on your resume, customize the application to the company, and highlight some of what makes you a great candidate.
As a customer of COMPANY, I know firsthand how effective the targeting and messaging of your marketing campaigns are and I want to join your team as the Director of Digital Marketing to play a role in your ongoing success.
From the earliest days of my career, I knew data-driven marketing was my passion. I followed my instincts through progressive roles starting with a stint as a Digital Marketing Specialist at a small startup where I focused on SEM and Analytics and then took on email, paid social, and display efforts. After several years, my former manager recruited me into a Digital Advertising Campaign Manager role at Amazon where I led a high-performing team responsible for >100 campaigns a month before being promoted to Senior Manager of Advertising Performance and Optimization.*
I build programs that get results across channels, whether starting from scratch or scaling and adapting existing efforts. As a leader, I partner cross-functionally to ensure our marketing strategy and metrics tie to business objectives and am a hands-on manager who believes that coaching and feedback empower individuals to succeed in their roles. I’m curious too—I follow industry leaders, research the latest tools and tactics, and continually analyze campaign performance to ensure we’re testing, iterating, and executing the most effective campaigns possible.
I’ve spent years refining my expertise so that when my dream role came around, I’d be ready. The right role is COMPANY’s Senior Director of Marketing. My resume highlights my accomplishments and quantitative examples that demonstrate how I can help COMPANY continue to drive customer acquisition and retention toward sustainable revenue growth. I look forward to exploring this opportunity with you soon.
The interview process is often just a few hours spread over several days or weeks. That is not a lot of time to get to know the company, responsibilities, and expectations, let alone all the people. You’re going to spend 40+ hours a week over the course of many months or years working with these individuals. It’s important to recognize each person’s unique contribution to the process, work, and your experience. The people you spend your days with can transform the mundane into meaningful or turn a dream job into a toxic, miserable slog. Your interviewees are a small representation of the company in most cases (unless you’re interviewing at a tiny company or new startup) and your time with them is your primary chance to get a window into the broader employee and team experience.
Throughout a standard interview process, you’ll encounter a handful of prospective colleagues. Some of these interviewers could play a key role in your experience and others you will just know in passing, but they are all valuable guides to your future work experience. Each person brings a different lens to the company, role, and team and can unlock new perspectives and information that others wouldn’t be able to share. Crafting a targeted set of questions for each interviewer profile that addresses specific areas of interest based on your established priorities will help ensure you efficiently and effectively gather information.
To get the best 360° view of the company, you’ll need to take advantage of the opportunity to ask a tailored set of questions to each person. In this section, I’ll explore the roles, personas and priorities of the people commonly involved in the interview process so that you can incorporate them into the plan you create later in this book. Some sections are more expansive than others—these are people who are more pivotal and influential in the recruiting process. For example, the recruiter is someone you’ll almost always interact with, and the hiring manager is probably the most important person for you to get to know. In some cases, a single person can play more than one of the roles outlined, which is why it’s so important for you to know who you are interviewing with, why, and what their role will be in the process. Remember that titles or roles do not always equate to influence or trust within the hiring team—anyone participating in the process could be the key vote or veto in interviews. Make sure you take an inclusive approach to engage with each one of your interviewers. Later, in the question section of the book, you’ll see questions designed for each of these personas so that you can create your specific interview plan.
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