Ask Me This Instead Question Database

Common Candidate Question: What are the current focus areas for the company as a whole?

Who to Ask: CEO / Founder

Why You Shouldn’t Ask That Question: Generally speaking, the focus areas are often around specific products and services, customers, and an internal team initiative or two. By the time you get to speak with a CEO you should have an understanding of these high-level topics. This is your chance to understand something only the CEO could share and highlight your own talent more specifically.

Ask This Instead: Let say the team I’d join accomplishes the current list of priorities earlier than expected and has capacity to take on one new, high-impact initiative—what would you ask the team to do and why would this be at the top of your list?

Why: This question is specific to the team and gives you insight into what is on the CEO mind as well as insight into the “why” behind the “what.”

Common Candidate Question: How has the company changed since you joined?

Who to Ask: Cross-Functional

Why You Shouldn’t Ask That Question: Asking about change and evolution at a company is important, but if the question is asked this way, they might select a change that isn’t relevant or interesting to you.

Ask This Instead: With regard to the team I join, how have the cross-functional collaboration and achievements changed since you joined?

Why: Here, you focus on an element that is relevant to the team you join and specific enough to give you insight into this particular team member, collaboration, and progress toward goals.

Common Candidate Question: What can you tell me about your new products or plans for growth?

Who to Ask: Executive / Boss’ Boss

Why You Shouldn’t Ask That Question: Asking this question might indicate a lack of preparation or research. In many cases, there will be news articles or publicly available information about products and plans. If there is not information accessible online, this is the type of insight to suss out in earlier conversations so that you can listen, learn and do research to more effectively ask questions of senior leaders at the later stages of the interview process.

Ask This Instead: While researching online, I noticed that you plan to launch [INSERT PRODUCT OR SERVICE] in Q3. That exciting. How did you prioritize this path relative to others that might have also been worthwhile to pursue?

Why: This indicates that you have been paying attention and are working to connect dots and learn more about the company. Their answer might unlock information about how the company prioritizes goals and sets a roadmap, as well as give you hints about other products or services that could come into play at some point and how the company evaluates the landscape and makes strategic decisions.

Common Candidate Question: What are the current goals that the company is focused on, and how does this team work to support hitting those goals?

Who to Ask: Executive / Boss’ Boss

Why You Shouldn’t Ask That Question: By the time you’re speaking with an executive in the interview process, it’s best if you can demonstrate an understanding of the company goals as well as the team’s role in supporting those initiatives.

Ask This Instead: Based on earlier conversations, I know that [INSERT INFORMATION ABOUT A SPECIFIC GOAL] is on the roadmap for this team in the upcoming months. If I were to join the team, where do you think I could step in and add the most value to help others achieve this goal?

Why: This demonstrates that you are aware of certain priorities and eager to contribute. The response will give you a heads-up on expectations or current pain points that will be relevant to your role.

Common Candidate Question: Is there a formal mission or company values?

Who to Ask: Executive / Boss’ Boss

Why You Shouldn’t Ask That Question: It’s a closed question. An interviewer could simply respond “Yes,” which doesn’t give you any more information. Additionally, this is information that is often available on “Careers” or the “About Us” pages on the website.

Ask This Instead: While reading over your values, I found [INSERT A VALUE] really resonated with me personally because [TELL THEM SOMETHING ABOUT YOU THAT CONNECTS YOU TO THEIR CULTURE]. Can you tell me about an example where you or another team member brought this value to life?

Why: It less about whether they have a mission, values, or similar structure, but how those words or phrases actually come to life in a company. Asking a more specific question will demonstrate thoughtfulness and their answer will illuminate if those words are truly a part of the company’s culture.

Common Candidate Question: How does the company take an idea from inception to completion?

Who to Ask: Executive / Boss’ Boss

Why You Shouldn’t Ask That Question: This question has potential. It shows you’re trying to understand more about how they operationalize their ideas, but it falls a little short because it might lead an interviewer to describe a generic workflow or go in an entirely different direction than you expected.

Ask This Instead: Can you describe the process that brought [INSERT PRODUCT, PROCESS OR SERVICE] to life from an idea to generating revenue? What were the key learnings, and is that how products are typically launched?

Why: When possible, get specific. It forces your interviewers to respond with real vs. hypothetical information. This question shows that you’re paying attention and are curious about how the team works. It also provides the chance to learn about another launch because you ask for a comparison in the follow-up question. You might get a two-for-one here and learn a lot in the process.

Common Candidate Question: What’s the biggest change/challenge the department/company/industry has had to face recently?

Who to Ask: Executive / Boss’ Boss

Why You Shouldn’t Ask That Question: This can be a good question as-is, but it’s a better question when you focus in on a very specific change or challenge.

Ask This Instead: I’ve observed that the industry landscape is changing [INSERT IN WHAT WAYS]. How is the company positioned to maintain competitive advantage or seize the opportunity to capture increased market share?

Why: Here is a chance for you to show you’re curious and aware of the landscape beyond your specific role, and ask a targeted question about the company’s readiness to respond. This will help you understand whether or not they are well positioned and get insight into work or company priorities that might be ahead.

Common Candidate Question: How transparent is the company about operations/revenue/future plans?

Who to Ask: Executive / Boss’ Boss

Why You Shouldn’t Ask That Question: When posed with this question, an interviewer might just respond with a generic answer such as “The company is very transparent, it’s one of our core values,” and leave it at that. If there is an area of transparency that is important to you or that you feel will be key to your ability to be successful in the role, it’s best to target the question on that topic specifically.

Ask This Instead: In my current role, I have regular updates from leadership regarding [INSERT TOPIC REVENUE, PROGRESS TOWARD GOALS, ETC.], which helps me to do [SOMETHING] better. How is this information shared with the team I might join?

Why: This question is targeted on what matters to you within the context of the job. Once you have the first part of the question answered, you could also do a follow-up to get even more insight. For example, “What other types of information do you share with this team to enable them to achieve their goals?”

Common Candidate Question: What is the single largest problem facing the company today?

Who to Ask: Executive / Boss’ Boss

Why You Shouldn’t Ask That Question: I think this is a valuable question that can become even more valuable with a small addition or two!

Ask This Instead: What is the single largest problem facing the company today and why do you think it a problem worth solving? What steps are being taken to address it right now?

Why: A question like this gives you insight into a problem as well as why, in the mind of the interviewer, it is critically important to address. Then, the follow-up question lets you know if the company is proactive about addressing problems or if their efforts are stuck at “awareness” and stop short of “action.”

Common Candidate Question: What has been the top accomplishments of the organization over the past year?

Who to Ask: Executive / Boss’ Boss

Why You Shouldn’t Ask That Question: Getting the answer to this question is worthwhile, and if you can get the interviewer to go a layer or two beneath the initial response, it’ll yield valuable information.

Ask This Instead: When you’re had the chance to highlight specific accomplishments to the board or shareholders, what were the top few things you chose to share? How did they respond? What did you share back with the team?

Why: Here, you’ll get information about the top accomplishments, and you’ll also understand the impact of each accomplishment (e.g. it was worthy of board awareness), the feedback the executive received and, hopefully, evidence that the executive provides context and updates back to their team.

Common Candidate Question: What did your company do in response to a world event (for example, Black Lives Matter)?

Who to Ask: CEO / Founder

Why You Shouldn’t Ask That Question: While you will receive information about the company’s response, this question will not necessarily lead the interviewer to share more about how their response informs ongoing actions and how integrated their external responses may be with internal efforts.

Ask This Instead: What comes after any statement or actions that you make in response to a world event (for example, Black Lives Matter)?

Why: This question is aimed at understanding whether statements or responses are performative and reactive, rather than proactive and sustaining.

Common Candidate Question: Who’s leading your DEI program?

Who to Ask: Cross-Functional

Why You Shouldn’t Ask That Question: This question will yield an answer about “who” but not necessarily how, what, and toward what outcomes.

Ask This Instead: Who is holding the organization accountable when it comes to DEI efforts (e.g., executive leadership, board, committee, public, no one)? Is DEI led solely by HR/People Ops?

Why: This question is aimed at understanding the structure, sustainability, and accountability of DEI efforts as well as open up insights that will enable you to determine if the company approach is in line with your expectations and values.

Common Candidate Question: Tell me more about [THIS] value.

Who to Ask: Executive / Boss’ Boss

Why You Shouldn’t Ask That Question: If a company has a value tied to DEI efforts (for example, inclusivity), asking this question is a great place to start, but it might not be specific enough to yield the insights you’re looking for.

Ask This Instead: I noticed you had the value [NAME VALUE]. I curious about how the team brings this value to life. What other rituals, beliefs, or activities celebrate DEI within the company?

Why: This question gets the interviewer thinking specifically about practices that resonate with them on a personal level and opens the door for a more in-depth response about how the company values and DEI come to life within the organization.

Common Candidate Question: What does mentorship and career development look like here?

Who to Ask: HR

Why You Shouldn’t Ask That Question: This question positions mentorship and career development as ideals, and does not specifically call out how these programs are run, who participates, and how they ensure that underrepresented team members have the same access and opportunities.

Ask This Instead: How structured is the company approach to mentorship? How does the company support these formal/informal relationships for all team members, including those from underrepresented groups (in particular if the leadership team is homogeneous)? How has mentorship impacted your experience here (whether as a mentor or mentee)?

Why: These questions ask the interviewer to speak on a personal level as well as about systems that are in place for mentorship. It also touches on whether DEI is baked into those programs to mitigate affinity bias.

Common Candidate Question: Tell me about some of your recent projects.

Who to Ask: Manager

Why You Shouldn’t Ask That Question: This question will yield insights about the nature of work being completed, but will stop short of the outcomes and how those were perceived.

Ask This Instead: When was the last time your team failed to achieve the desired outcomes of a particular project? How did other teams or leadership respond? What were your main takeaways?

Why: This question is aimed at understanding if the company/team is open about failures and, more importantly, practices a growth mindset.

Common Candidate Question: Is everyone able to contribute ideas or feedback on their experience?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: With this question, you might get a yes or no (and likely yes, of course!) answer rather than insight into how employees provide feedback and share ideas.

Ask This Instead: Are all feedback mechanisms anonymous? If so, why is that the case? How are engagement surveys or other results shared with the team?

Why: These questions will give you insight into a company approach to transparency and feedback. Companies that are working toward true inclusion generally aim to make it safe for employees to voice their feedback.

Common Candidate Question: What does your DEI program’s budget look like?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: Although this is a good place to start, you may have a hard time creating an equivalency between multiple organizations that you’re interviewing with.

Ask This Instead: Do you know how much money is allocated to your DEI efforts? If so, how much is that per employee?

Why: Do the math. Does the DEI funding equate to more than the cost of a burrito ($7) per employee? While it’s not everything, funding can be a good indicator (or a warning sign) of how important DEI efforts are to the organization.

Common Candidate Question: Who’s participating in your DEI program?

Who to Ask: Peer / Teammate

Why You Shouldn’t Ask That Question: This question may provide helpful insights into who, how many, and the representation (both with regard to identity and role within the company) of the individuals who are doing this work, but does not give you any insight into the sustainability of the DEI program.

Ask This Instead: Are your DEI efforts being driven by one person or a small group of people? What would happen if they left the company? Are there succession plans in place?

Why: These questions will indicate if the efforts can endure as business, team, or individual context changes.

Common Candidate Question: Tell me about your benefit offerings.

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: Asking about the benefit offerings will yield information that is top of mind or readily available and common.

Ask This Instead: Can you describe how your benefit offerings have evolved/are evolving to be more inclusive of individuals and families with unique needs?

Why: Here, you indicate you are looking specifically for information on inclusive benefits and will get insights into understanding what that means—whether equitable parental leaves, transgender-inclusive healthcare plans, fertility support, or floating/open holidays to accommodate varied religious or cultural holidays without having to disclose personal information (if you don want to). You can see where the company is prioritizing investment as well as get a view into how deeply integrated their DEI efforts are within the strategy and operations of the organization.

Common Candidate Question: What does it take to be successful at this company?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: This question is problematic because it perpetuates a narrow definition of success, stifling the value of diverse perspectives. It also assumes that success is equally likely for everyone who takes the same steps, which is unlikely to be the case.

Ask This Instead: Do you feel you can bring your authentic self to work? Do you have to assimilate or code-switch to be successful at this company? Can you give me an example?

Why: This a specific, hard-hitting question aimed at understanding if the organization is seeking candidates for “culture fit” vs. “culture add.”

Common Candidate Question: Does the company have a DEI program?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: This question sets up for a yes/no answer, but having a program is not the full story.

Ask This Instead: What is the next level for the company with regard to your DEI efforts—what is the evolution and how will the organization continue to improve?

Why: This question forces the interviewer to get specific about where DEI efforts are going, and how transparent that is to any member of the organization.

Common Candidate Question: How do you measure the effectiveness of the DEI efforts?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: Understanding effectiveness is valuable but difficult. The interviewer or the organization itself may not have data-driven insights to refer to or an understanding of what success looks like in their current efforts. Further, data-driven DEI isn’t necessarily more “effective” than DEI approaches that value smaller accomplishments, specifically with the day to day belonging and inclusion felt by marginalized people. Focusing on data can sometimes be a downfall for companies when it leads them to: prioritize long-term results over short-term improvements; focus on hiring and promotion numbers; and/or not take an intersectional approach to data collection. It can also lead companies to give up too soon because it can take years to see numbers improve.

Ask This Instead: How does the company balance data (if there are specific metrics being used) and actual employee experiences and feelings when assessing the success of DEI efforts? Because progress can take time (even years) and certain aspects are hard to measure, how will the company assess progress if there aren always “results” to share?

Why: These questions will help you understand how the company approaches measuring it efforts. Whether metrics or less quantitative approaches are used, you will learn about what matters to the company with regard to DEI, whether or not they rely on numbers that tell an incomplete story, and if they are focused on external “wins” rather than sustained progress and change.

Common Candidate Question: What percentage of the organization is engaged with the DEI program?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: This is a good place to start, but you might want to know specifically who is involved and what roles they play within the organization and with regard to the DEI efforts.

Ask This Instead: Who leads your company DEI efforts? Are you aware of any patterns in participation (for example, do certain teams or levels opt in or out of these efforts)? Are DEI leaders at the company paid, or is the work done on top of their everyday work?

Why: The labor of DEI work often falls on people from underrepresented or underinvested groups, who are sometimes not paid for their work. This question is aimed at understanding the level of allyship within a company and who is actively participating in this work.

Common Candidate Question: Is [COMPANY] better than its competitors? Will it look better on my resume?

Who to Ask: Backchannel Reference

Why You Shouldn’t Ask That Question: Better is subjective and relative to the dimensions that matter to you.

Ask This Instead: As I consider [COMPANY] relative to [COMPETITOR] as the place I would go next in my career, I have outlined some advantages and questions I like to run by you to see if you’d have thoughts or recommendations about how I weigh the tradeoffs and differences.

Why: Focusing in on a specific aspect of why you would choose one company or the other will enable your contact to target their response.

Common Candidate Question: What gets you most excited about the company future?

Who to Ask: CEO / Founder

Why You Shouldn’t Ask That Question: This question helps you understand the mindset of the CEO, but might result in a canned answer about goals, the team, etc.

Ask This Instead: If [COMPANY] had the chance to be on the cover/front page of all the major business publications and websites this year, what would you want the headline to be? Why?

Why: This taps into something that would be exciting and pushes the CEO to take a moment to reflect, as it not just something they would be excited about but something that would matter beyond the company.

Common Candidate Question: Where do you see this company in the next few years?

Who to Ask: CEO / Founder

Why You Shouldn’t Ask That Question: This is a question that a CEO would surely have an answer prepared for. You’re also likely to find it on the website or in recent press articles, so try to find it and use your time to ask questions that might not be as readily available.

Ask This Instead: Two years from now, which teams at [COMPANY] will be the largest—what will they be focused on and why are they the teams that will need to grow to support long-term success?

Why: This question is more precise and will give you information that is not necessarily being talked about in articles or evident on the careers page. Itl also help you contextualize whether or not you’d be joining a team expecting growth (and thus, potentially opportunities) or if the company will be investing in other areas.

Common Candidate Question: What would you say is the time spent on creating new products/projects?

Who to Ask: CEO / Founder

Why You Shouldn’t Ask That Question: The time spent likely correlates to the scale and complexity of a project, so a generic question like this one may not get at what you’re looking to understand.

Ask This Instead: I was told it took 18 months to successfully launch [PROJECT, PRODUCT, PROCESS]. Is that a typical or targeted timeline or do projects often move faster? How are timelines agreed upon? What do you see that knocks things off course most often?

Why: Here, you connect the question to something you’ve learned in the process as well as posed a question about pace and intensity. This will help you understand if the company operates at a pace that you will like. Additionally, the follow-up questions get at decision making and pain points, which are helpful to understand.

Common Candidate Question: Which competitors/products/targets are you most worried about?

Who to Ask: CEO / Founder

Why You Shouldn’t Ask That Question: Depending on the role you are interviewing for, the CEO may not give you a specific answer here. There is a way to get at competition in a positive way by asking a different kind of question.

Ask This Instead: While [COMPANY] works to maintain competitive advantage and continue to grow, what other companies in this industry are doing work that you admire? How do you motivate the team to stay on top of innovation and progress relative to that company?

Why: While getting at competition, this question takes a positive frame, enabling the CEO to share insight on the landscape but then shift inward toward their leadership style.

Common Candidate Question: What goals do you have for the company, yourself, and employees over the next five years?

Who to Ask: CEO / Founder

Why You Shouldn’t Ask That Question: As written, this question is broad and the CEO will likely give a high-level answer. Learning more about their mindset around goals is important, so focusing in on a single aspect is beneficial.

Ask This Instead: As the CEO, what goals do you have for yourself and how do you share them with the team and get their feedback?

Why: Interviewers often ask you about feedback and growth. Asking them the same question can provide a lens into the way a company or individual approaches feedback as well as insight into who they are as a person.

Common Candidate Question: What can you tell me about your organization plans for new services, products, or plans for growth?

Who to Ask: Executive / Boss’ Boss

Why You Shouldn’t Ask That Question: These are all great things to learn more about, but it’s also a very broad question that an interviewer will likely give a pretty high-level and generic response to if asked.

Ask This Instead: What is the top priority for [COMPANY]—more revenue, new products, team growth, or something else? What changes or efforts are in motion to specifically support this objective? Why is it the most important vs. others?

Why: Here, you highlight those key elements of a business and offer the interviewer a choice about what to share, as well as push for more specific details about the status and importance of a particular topic.

Common Candidate Question: What the company’s biggest threat to success this year, and how will I be able to help overcome it in this role?

Who to Ask: Executive / Boss’ Boss

Why You Shouldn’t Ask That Question: Understanding the threats or risks to a business that you are considering joining is important. At the same time, if it’s the biggest threat to the business, it’s unlikely that it’ll be something that you independently will address.

Ask This Instead: If you wanted the team to take a critical business risk that would not impact [COMPANY] ability to succeed, what problem would you ask the team to solve?

Why: This is a question that a senior executive is in a position to address that will provide you with a better understanding of prospective risks.

Common Candidate Question: How many people have joined the company recently?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: In many cases, resources like the careers site can give you insight into hiring trends and LinkedIn has insights about company growth available. Understanding how many people have recently joined may not unlock anything that will specifically connect back to the role or team you’re looking to join.

Ask This Instead: In addition to [INSERT THE TEAM YOU’RE INTERVIEWING FOR], tell me a bit more about other teams that I might work with that have also been growing recently at [COMPANY]. What is driving the investment in new hires in those teams?

Why: Getting to a more specific and related aspect of team growth is beneficial. Furthermore, understanding how the company is investing in the groups that you will be working with may provide valuable information about the resources, complexity, and priority of the shared initiatives.

Common Candidate Question: I wanted to know if you base your innovation process more on the Silicon Valley style “move fast and break things,” or precision and artistry?

Who to Ask: CEO / Founder

Why You Shouldn’t Ask That Question: The root of this question is interesting, but it might feel a bit cliche to ask it this way.

Ask This Instead: If you think back to one of the company greatest breakthroughs, what were the factors that contributed to the team’s ability to innovate and how have those learnings been incorporated into other initiatives?

Why: Asking about a specific example will illustrate how the team collaborates to innovate and succeed as well as how those experiences influence future initiatives.

Common Candidate Question: What do you want the company to be known for among employees—past, present, and future?

Who to Ask: CEO / Founder

Why You Shouldn’t Ask That Question: Similar to other questions in the CEO section, this question is one that you might find evidence of in articles and on the website (for example, in the mission statement). Taking a slightly different angle will help you avoid a canned “PR” response.

Ask This Instead: If alumni were to say a couple short sentences about their time here after they leave to others in the community or prospective employees, how would you want them to describe their experience? Is this how you think people are currently describing their experience? If not, what would need to change/evolve for it to be true?

Why: This question requires that the CEO reflect on what they think someone (likely a particular person) would say after leaving as well as think about what people might currently be saying. It requires them to be open and honest because the candidate actually has the chance to ask current and former employees questions.

Common Candidate Question: How would you describe this company values?

Who to Ask: Cross-Functional

Why You Shouldn’t Ask That Question: Asking this question will get you a description, or perhaps a list, because that’s what you asked them to give you.

Ask This Instead: How do different teams live the company values in their own unique way?

Why: By asking the question this way, you get the benefit of their cross-functional perspective and an understanding of how different teams approach or live the values.

Common Candidate Question: How did you get your start with your career? How long have you been with the company?

Who to Ask: Cross-Functional

Why You Shouldn’t Ask That Question: Chances are they got their start just like you—by interviewing! Make the effort to ask a question that will tell you something more about your prospective colleague and the work environment.

Ask This Instead: Tell me about how your career journey brought you here. Why was this the best next step for you?

Why: This question turns your interviewer into a storyteller and also highlights a bit of the “why” they joined and what made that decision the right one for them, which could be interesting or helpful for you to know.

Common Candidate Question: What are the company senior leaders like? What do they care about and talk about most?

Who to Ask: Direct Report

Why You Shouldn’t Ask That Question: This question could go down multiple different paths. Most likely, the interviewer will respond with what first comes to mind, which may not be what is most important to you.

Ask This Instead: Tell me about what you think the leadership team says is most important—in company meetings or based upon the goals and priorities the team is working toward.

Why: With these questions, you will get insight into the priorities that are integral to the company success (for example, goals tied to user or revenue growth, the “what”) as well as information about other expectations or goals that the leadership team has (such as the timeline for achievement or preferences about what approaches should be taken, the “how”).

Common Candidate Question: What are some of your biggest worries or challenges these days? What keeps you up at night?

Who to Ask: Executive / Boss’ Boss

Why You Shouldn’t Ask That Question: This question could go down multiple different, and potentially irrelevant, paths or result in a canned “PR” answer.

Ask This Instead: What is a really important problem that the company needs to solve that is proving more difficult than expected? What are you testing or focused on right now to try to change the course?

Why: These questions keep the focus on the work to be done, highlighting a specific challenge and then bringing the focus back on how the company or team works to address issues.

Common Candidate Question: How do leaders set employees up for success?

Who to Ask: Executive / Boss’ Boss

Why You Shouldn’t Ask That Question: With this straightforward question, you’re likely to get a high-level answer.

Ask This Instead: Can you tell me about how you help support the onboarding and integration process with new team members in your department? How do you stay connected with them over time?

Why: The onboarding and integration period is critical and getting more information about the leaders‘ involvement as well as a view into the process at the start and over time will be interesting to learn more about.

Common Candidate Question: Is your leadership team diverse?

Who to Ask: Executive / Boss’ Boss

Why You Shouldn’t Ask That Question: There is too much wiggle room here for the interviewer to give generic answers rather than address your underlying question.

Ask This Instead: How is the company addressing the fact that the entire leadership team (and/or board) is white and predominantly male?

Why: This may be a fairly common scenario, and it important to investigate whether the company doesn’t see a problem, or if they’re making strides to change. The company should be able to give you a very specific answer to this question.

Common Candidate Question: How would you describe the overall style of management at the company?

Who to Ask: Peer / Teammate

Why You Shouldn’t Ask That Question: Asking about management styles is valuable as you evaluate who you might be interacting with and learning from in a new role. However, the overall style is probably hard to capture; a more focused question is more likely to get you what you need.

Ask This Instead: For the managers I’ll be working with most frequently, what do they have in common, and what is different about their leadership approaches?

Why: In this question, you focus in on the people you are going to interact with the most, and by asking a comparison question you will learn more about individuals and the collective group.

Common Candidate Question: How much exposure do we get to the top executives within the organization? Is there an open-door policy within the organization?

Who to Ask: Peer / Teammate

Why You Shouldn’t Ask That Question: A question about exposure might give an impression that you are prioritizing visibility or access specifically. Understanding how leaders participate in your work is important and reframing the question will get at similar insights from a different angle.

Ask This Instead: What aspects of this role are highly visible and important to the executive team? How do they weigh in, assess progress, and communicate expectations or changes?

Why: These questions get at oversight and exposure as well as intervention and/or support. The second question will likely provide valuable information and indicate that you are not just focused on visibility.

Common Candidate Question: Is [NAME] a good manager to work for?

Who to Ask: Backchannel Reference

Why You Shouldn’t Ask That Question: Depending on your back-channel’s relationship with the hiring manager, they may or may not be able to provide transparent or helpful information in response to a question like this.

Ask This Instead: Some of the most important things I looking for in my manager include [DESCRIBE], in your experience working with [NAME], how does their style and approach align with those priorities?

Why: With this framing, your contact will understand what you’re looking for and can frame stylistic aspects of the manager’s approach as well as layer in strengths and developments in a more productive way.

Common Candidate Question: Tell me about your best boss.

Who to Ask: Direct Report

Why You Shouldn’t Ask That Question: When building relationships with your prospective direct reports, it’s great to learn more about what has worked for them in the past. However, with this question they could also share examples that are nothing like your style or philosophy. What is best for them might be irrelevant to you.

Ask This Instead: When has a mentor or manager really transformed your working experience? What were the factors that led to their coaching or development, what tactics did they use? Why was this approach so impactful for you?

Why: This framing of the question opens the door to learning more about what works without anchoring a particular approach as the “best,” leaving room for you to share more about your style while keeping in mind their experience and preferences.

Common Candidate Question: How do you anticipate interacting with your new hire—do you have a weekly one-on-one meeting, or do you mostly rely on email, or something else?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: This question puts all the power in their preferences, when you could influence the structure of the working relationship.

Ask This Instead: I really appreciate the opportunity to have regular 1:1s as well as the chance to ask questions in the moment or Slack/email/texts when something pops up. What is your preferred cadence and structure for communicating with your team?

Why: This sets an expectation by indicating your experience and preferences before asking how the manager chooses to adapt, which opens the door for a more tailored response.

Common Candidate Question: Why did you choose this career and industry?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: There is nothing wrong with asking “why,” however, expanding the question slightly will give you much more insight into a person who could be very influential in your career.

Ask This Instead: I love to hear more about your career journey and the path that led you to where you are today at [COMPANY].

Why: This question enables the manager to tell their story, which most people love to do. And, if you are passionate about having a similar career path, you might get a window into the steps you could take and how they will help you be successful.

Common Candidate Question: What have been some of your biggest challenges during your career? How did you, or do you, deal with them?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: This is a great question to ask your manager in a mentorship session but might not be the right question to ask during interviews, unless you really believe it will help you make a decision about this position.

Ask This Instead: Ask this question in a career development conversation if this person becomes your manager!

Why: Focus your time during the interview process on the questions that will truly help you make your decision but tuck this one away for a conversation at a later date.

Common Candidate Question: How and when is feedback provided to employees?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: As is, this question will get you a response that is process—and timeline-based rather than customized to what your actual experience will be.

Ask This Instead: Without sharing explicit details, tell me about the last two to three times you gave feedback to one of your direct reports—what was the reason, what was the setting/format, and how did it change the outcome/behavior?

Why: This question takes it to another level! You’ll get specific insight into how and why your manager gives feedback (when not compelled to by a mandatory process) and how successful that coaching was for the people who received it.

Common Candidate Question: Could you tell me a little bit about the person I would report to directly?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: This question is too high-level to get at what might be most important to you because it opens the door for the interviewer to go in any direction that comes to mind.

Ask This Instead: When people talk about [NAME OF MANAGER]. what are the things that stand out about her/their/his leadership, expertise, and connections within the company?

Why: This question pushes the interviewer to really reflect on what others might say and how they would frame that in an interview context, but also suggests the possibility that you might be able to cross check their input, therefore requiring them to be more open and honest. Ask this question to everyone you meet in the interview process!

Common Candidate Question: How does your department fit into the organization overall?

Who to Ask: Cross-Functional

Why You Shouldn’t Ask That Question: A question asked around “overall” will often yield an answer that is similarly broad and won’t enhance your understanding of the context that could impact your work.

Ask This Instead: Which cross-functional teams does your team work with to achieve [INSERT specific goal] and how does that collaboration play out day to day (or in meetings, or in goal setting)?

Why: Here, you get more information about how the teams are organized within the company as well as more details about how they work together.

Common Candidate Question: What are the biggest rewards of the job and working for this company?

Who to Ask: Cross-Functional

Why You Shouldn’t Ask That Question: Rewards mean different things to different people, and in an interview, asking a question about rewards could go in a variety of directions that may not be helpful to you.

Ask This Instead: Why do you choose to do your role at [COMPANY] vs. a similar role at [COMPETITOR] or another company?

Why: In this question you will learn more about the value proposition the company offers employees, understand more about the interviewer and, potentially, get insight into rewards.

Common Candidate Question: What mistakes have people made in this position?

Who to Ask: Cross-Functional

Why You Shouldn’t Ask That Question: Understanding where there is room for improvement is helpful, but doing so by referencing mistakes may not land well as your interviewer may not feel comfortable pointing out their own or someone else’s shortcomings.

Ask This Instead: Could you share an example or two where the initial approach to do [SPECIFIC RESPONSIBILITY] didn’t work out as planned and what you or the team did in response to get to a better outcome?

Why: This question will open the door for the interviewer to share a mistake, but from a learning and growth oriented angle. You’ll gain insight into how mistakes are addressed and new solutions adopted.

Common Candidate Question: What do you feel has made you successful working here?

Who to Ask: Direct Report

Why You Shouldn’t Ask That Question: This question is a good starting point—you’ll get to know more about your prospective direct report, including whether certain support from their manager contributed to their success, but it misses an opportunity to connect their success to your ability to support them going forward.

Ask This Instead: What do you feel has made you successful working here so far?

Why: A couple follow-up questions can unlock even more valuable, and future-oriented, insights including their understanding of and perspective on what success looks like, and how you could play a role in supporting them as their manager.

Common Candidate Question: Do you expect the main responsibilities for this position to change in the next six months to a year?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: If the job description is used as the framework for the main responsibilities, there is a great likelihood they will change because the job description is a marketing asset with a short list of the top (or first) responsibilities that came to mind when the role needed to be posted.

Ask This Instead: If you consider the job description and responsibilities wee discussed so far in the process, which ones do you think will be the same 6–12 months from now and which ones will be new or different?

Why: This question enables you to bridge the gaps between the job description and reality now, and over time in a way that might unlock new responsibilities or clarify expectations for the role.

Common Candidate Question: Is there anything else I could tell you about myself that would help you with your decision?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: This question is both open—it isn’t clear what you want—and closed—the interviewer can simply respond “yes” or “no.”

Ask This Instead: If you were to tell other interviewers to push or probe further on an element of my experience, what can I prep or anticipate additional questioning about in future conversations?

Why: This question gets at what questions might be lingering, but with a proactive lens—that you are willing to listen to the feedback and provide more information about your experience to resolve any gaps.

Common Candidate Question: How does this position help your department achieve its goals?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: Asking this question might get you an answer that closely resembles the job description rather than new insights.

Ask This Instead: Describe the process you used to design this role and the associated responsibilities to make sure it effectively supported the key departmental or company goals?

Why: Reframing the question in this way will help you understand more of the context behind why the role was opened and how they determined which responsibilities were most important relative to broader priorities.

Common Candidate Question: What are the major metrics for the person in this position?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: This question will get you information that is beneficial to understand but, by asking simply “what,” it stops short of the next layer of information, which is really valuable.

Ask This Instead: Wee discussed metrics including [INSERT KEY METRICS]—what are the expectations around setting targets, and reporting and communicating progress or problems?

Why: In this format, you’ll demonstrate listening and awareness about the requirements of the role and get more information about how the metrics are developed and monitored.

Common Candidate Question: What are you hoping for your new hire to accomplish in the first three months on the job?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: There’s a good chance that the team is hoping you make progress toward a number of bullets on the job description, so this is a good time to make the question more specific so that you get more of what you’re looking to learn.

Ask This Instead: If I could make one clear, tangible impact in this role within the first three months, what would be your top priority for me to focus on?

Why: This question will highlight a top priority and give you a heads up on what you might need to focus on in subsequent interviews or should you join the team.

Common Candidate Question: How do you envision your new hire stepping into the role? Will they jump in and ask a lot of questions to learn the job, or do you expect them to follow a week-by-week or day-by-day training plan, or something else?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: The way a new hire steps into the job will be dependent on who that new hire is, so take advantage of the opportunity to tell the interviewer more about you while getting information about their preferences or process.

Ask This Instead: I tend to [ask lots of questions, follow my training plan, etc.] as I get up to speed—can you tell me more about how this would fit into our 1:1 meetings or other touch points so I can get your direction and coaching?

Why: By asking the question this way you can share more about your working style and get information about the relationship with the manager, including how they coach and direct work.

Common Candidate Question: How will the arrival of your new employee make your life easier?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: It can be a good idea to ask a question like this, and a more structured approach will open up even more valuable information.

Ask This Instead: Should I join and take on responsibilities that you might be owning right now, what are the new or different responsibilities or work you’ll be excited to focus on?

Why: Here you get to demonstrate interest in making their work experience better and also gain a view into what else the manager and team are prioritizing.

Common Candidate Question: What do you believe is the main reason someone could fail in this position?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: Asking this question will give you an idea of why you could miss the mark, but not much more, and it could lead the interviewer to wrap up their response with failure rather than recovery and growth, which could leave them with a negative feeling.

Ask This Instead: What are the mistakes you believe I’ll make and learn from while getting up to speed in this role? What types of mistakes are hard to recover from in this role or at the company? How do you coach your team to respond when they make mistakes?

Why: This acknowledges the fact that everyone makes mistakes but also includes the emphasis on learning and potential impact of making a misstep.

Common Candidate Question: What is the single largest problem facing your team today?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: It is helpful to know what the largest problem facing the team is and even more important to understand how it could impact your experience or workload should you take the position.

Ask This Instead: What project or problem is taking a disproportionate amount of effort or resources right now? How does this role contribute to making the situation better?

Why: This question focuses on what will really matter—how does a particular problem impact the way the team operates and how is the team adapting to the situation?

Common Candidate Question: Thinking back to people you’ve seen do this work previously, what differentiated the ones who were good from the ones who were really great at it?

Who to Ask: Peer / Teammate

Why You Shouldn’t Ask That Question: This is the start of a great question. Adding a little bit more before you send it to the interviewer to share their perspective will increase the value of their response.

Ask This Instead: Thinking about the people who have done this or similar work, what contributions of theirs stand out? What capabilities or actions do you think contributed to that success or impact?

Why: This reframing directs the interviewer to respond in a way that is more helpful to you by touching on the contributions and the underlying “what” and “how.”

Common Candidate Question: What are the common career paths in this department?

Who to Ask: Peer / Teammate

Why You Shouldn’t Ask That Question: Understanding what paths might be possible is important, but for many roles or in smaller companies and teams, there might not be a “common” career path, so the answer may be based on a narrow or hypothetical set of examples.

Ask This Instead: Tell me about your path of growth on this team and how it is similar or different to others who have ascended or moved laterally across multiple roles.

Why: Framing the question about their growth as well as asking them to compare their experience with the experiences of others will give you a better understanding of how these transitions practically play out.

Common Candidate Question: What are the prospects for growth?

Who to Ask: Peer / Teammate

Why You Shouldn’t Ask That Question: An interviewer who gets this question and is prepared will quickly tell you there are so many prospects for growth before going into a specific example that might be real or hypothetical, and that may or may not be reflective of the overall experience.

Ask This Instead: If I were to come in over the next 6–12 months and succeed in all the existing aspects of this role so that everything was running smoothly, what other new elements or responsibilities would you add into the mix?

Why: Taking this approach clarifies what you mean by growth, which otherwise was left open to interpretation, and asks for specific input on what would be next.

Common Candidate Question: Would you like a list of references?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: This is a “yes” or “no” question that doesn’t allow you to demonstrate that you can be proactive and prepared.

Ask This Instead: I have a list of references including [name/reference title/company/context]; let me know if and when you like me to provide their contact information.

Why: This approach demonstrates that you are confident, credible, and willing to have others back you up. It shows you’re ready and aware of the typical steps in the interview process.

Common Candidate Question: What types of volunteer work and community service does the organization encourage?

Who to Ask: HR

Why You Shouldn’t Ask That Question: Volunteering and community service are wonderful things to dedicate time to in life. However, unless volunteering is connected to the work you’d do (for example roles in corporate social responsibility), or if it will make or break your decision to join the team it might not be a valuable use of your time.

Ask This Instead: Take the time to ask another question that is more closely connected to the work experience. If you have an existing volunteer commitment that could impact your schedule or other work commitments, you can frame the question like this:

Why: These questions go deeper into what specifically matters to you, whether a specific commitment or broader indicators about how volunteering and civic engagement might be supported as part of the employee experience.

Common Candidate Question: What types of rewards do you offer employees? What types of achievements or traits are rewarded?

Who to Ask: HR

Why You Shouldn’t Ask That Question: Understanding total rewards is important! This question, however, enables the interviewer to respond with the “what” without having to tell you more about the “why,” “when,” “who,” and “how,” which will tell you much more.

Ask This Instead: What drives compensation changes—is it performance (effort or outcomes), cost of living/market, company performance, or something else? Is my manager the primary decision maker or is there a matrix or another level of decision makers involved? Beyond salary increases, are there other rewards (bonuses, perks, etc.) associated with this role?

Why: The devil is in the details. To get a comprehensive understanding of certain programs or processes will require a series of targeted questions. This is an example where the “who,” “what,” “where,” “when,” “why,” and “how” structure of questioning can give you a much more complete picture than a single, open-ended question.

Common Candidate Question: What is your preferred way of communication? Email, phone, in-person?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: If asked this question, a likely response will be “in person,” but the reality of work means that a preference or the best option might only be one of the options available.

Ask This Instead: There are so many channels for communication, what are your preferences for how your team uses email, Slack, texts, or in-person meetings to make each interaction as productive as possible?

Why: Here, you’ll get more insight into how the team communicates and interacts in different situations. It’s also an opportunity to respond and share some of your preferences or successful communication tactics.

Common Candidate Question: What’s your timeline for next steps?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: The truth is, timelines are fluid and do not always follow the desired plan, so this question will yield an answer, but not necessarily one that you can count on.

Ask This Instead: I am actively interviewing and anticipate onsite interviews the week of [DATE]—is that in line with your timeline? If not, can you share more specifics so I can be proactive in sharing my own timelines as I move forward?

Why: This question reminds the team that you have options, sets clear boundaries, and creates a specific timeline to follow up on if things are not progressing as communicated.

Common Candidate Question: If I were hired for the position, what would be the ideal starting date?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: Most often you’ll get an answer that is something like “as soon as possible” or “yesterday.” The team is hiring to fill a need and the sooner that person is in place, the better.

Ask This Instead: I available to start as soon as [YOUR DATE], would that align with what the team needs?

Why: This is an opportunity for you to set boundaries and protect personal or other commitments during the hiring process from the start. If you leave it up to the company, there is a chance they will ask or influence you to do everything on their timeline, which might not be the best for you.

Common Candidate Question: What sorts of technology will your new employee use in the job?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: If critically important, this information is usually included in the job description.

Ask This Instead: In my current role, I spend my day using [Slack, Salesforce, Zoom]—does your team use these technologies, and if not, what others are in place?

Why: If you work in a similar role or industry, there is a good chance you know the technologies. But if it important to you, or you like to prepare in advance, a specific question will help.

Common Candidate Question: How do people typically dress for work in your department? Does that vary depending on their level of customer contact, or other factors?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: Asking about the dress code can help you prepare for onsite interviews (where you’d observe it), and provide hints about the broader work experience. Taking it beyond the actual outfit might be even more revealing.

Ask This Instead: As I would prepare for a transition to your team, what are the expectations with regard to dress code if there are any? Has working from home impacted those guidelines? Do these guidelines indicate anything more broadly about the employee experience?

Why: This enables you to get a read on something practical and relatively straightforward—dress code—and also an angle into culture or other aspects of the employee experience.

Common Candidate Question: How many people work in this office/department?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: Ask for a number and you’ll get a number. The size of the team may be important to you, so package that ask with something else to get more.

Ask This Instead: My understanding is that the team has [NUMBER] people on it right now. Do you think that it is right-sized for the work to be done or will additional hires be made in the near term?

Why: If you start with a number that you’ve researched, the interviewer can confirm. Then, by asking about size relative to work, you might get a pulse on capacity and intensity as well as growth plans.

Common Candidate Question: Is relocation a possibility?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: This is a “yes” or “no” question rather than a question that will be answered based on your potential and the interview team’s enthusiasm about your ability to contribute. Relocation restrictions or limits are often listed in the job description and your application (with work locations, etc.) likely signals that you may not be in the location of the company.

Ask This Instead: As you know, I currently live in [PLACE] and would happily relocate for this position to [PLACE]. What type of relocation assistance is available?

Why: By taking this approach, you proactively frame it as a possibility, just one that needs to be addressed. This answer will help you understand if relocation or remote work is a possibility and assess what you might need to negotiate around should you receive an offer.

Common Candidate Question: What have you heard about working at [COMPANY]

Who to Ask: Backchannel Reference

Why You Shouldn’t Ask That Question: This is a very open-ended question, which could result in a response going down any number of relevant or random directions that are not helpful to you.

Ask This Instead: Here a few observations I have of [COMPANY] so far in the interview process X, Y, and Z, which lead me to believe that the work experience will be [DESCRIBE]. How does that align or contrast with your experience or knowledge of the team?

Why: When a back-channel contact is taking time to support your decision process, you need to provide them with as much specific context as possible so that they can recall and share the most relevant information.

Common Candidate Question: What could you tell me about the company that isn widely known?

Who to Ask: CEO / Founder

Why You Shouldn’t Ask That Question: This question could go in any direction, one that is helpful or many that have nothing to do with your experience, interests, prospective role, or decision-making process.

Ask This Instead: What do you wish the press or employee reviews about [COMPANY] covered that they most often ignore?

Why: This takes an open-ended question and gets at not just something that people may not know, but something that the CEO believes is important.

Common Candidate Question: Can you tell me how you respond to negative employee feedback?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: This is an important insight to garner about a particular company, especially if you have heard information about what employees want to change. This question will likely yield a generic response that may not unlock any new information for you.

Ask This Instead: Can you tell me about a time when employees shared negative feedback either internally or on a public review site? How did the company or leadership team respond and take steps to address it?

Why: This question gets to a level of specificity that will help you understand the nature of actual negative feedback provided by employees as well as how the company responds.

Common Candidate Question: Do you think that [JOB] would be a good move for me to make right now?

Who to Ask: Backchannel Reference

Why You Shouldn’t Ask That Question: With this question, there is the possibility that they say “no” even if you have your heart set on it. There are many factors that will influence what they would share about it being right for you, and you have to help them provide the feedback that is most targeted.

Ask This Instead: At a high level, my objectives for my next position are A, B, and C. The main responsibilities of this position include [DESCRIBE]. Based on your knowledge of my description and those attributes of the role, what would you suggest I prioritize or do to really assess if this move would help me accomplish my near-term goals?

Why: Again, providing context is key for the back-channel conversation. Ultimately, you are the only person who can determine what is right for you, but others can provide suggestions about what factors you should explore in more depth or consider.

Common Candidate Question: What can I clarify for you about my qualifications?

Who to Ask: Direct Report

Why You Shouldn’t Ask That Question: Offering to answer further questions is worthwhile, though this question might result in an answer of “nothing right now,” which is a missed opportunity to cover more about your background and experience.

Ask This Instead: I like to ask if you have anything you’d want to clarify about my qualifications, and if not, I have something else I’d like to share with the time remaining.

Why: This is a simple addition, it lets them direct what information you might share or gives you the chance to highlight something that you think they might want or need to know.

Common Candidate Question: Why do you think the team is hiring for this position?

Who to Ask: Direct Report

Why You Shouldn’t Ask That Question: Asking this question might result in a recitation of the bullets on the job description, the problems that need to be solved or the gaps in experience. You are probably already aware of each of those aspects.

Ask This Instead: What is the elevator pitch that you think adequately conveys the reasons why someone should be excited to take this role?

Why: You should ask this question to everyone you meet in the process as the selling points they share will either build your enthusiasm and increase your understanding or fall flat relative to your expectations and aspirations.

Common Candidate Question: What are the pain points you have to deal with day-to-day that the person in this role should remedy?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: This question is close, but not all the way to getting you the insight you need.

Ask This Instead: What emails, meetings, or lingering items on your to-do list shift when someone starts in this position?

Why: By framing it this way, you’re asking the interviewer to be more specific and giving yourself a valuable lens into some of the very granular aspects of the role that might not otherwise come up.

Common Candidate Question: What does a typical day look like?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: For many roles, there isn’t a typical day and so this question might get you a generic list of tasks or interactions that won’t help you assess the role more effectively.

Ask This Instead: If you were to start my onboarding plan if I were to join the team, what are the meetings you invite me to and why?

Why: This question requires the interviewer to think specifically about onboarding and start to share specific information that will help you understand more about the flow of a day or week on the team.

Common Candidate Question: What sort of budget would I be working with?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: This topic is important to cover but this question misses the opportunity for you to say more about yourself while also getting more information about the role.

Ask This Instead: In my current role (or in previous roles), Ie managed a budget of [DOLLARS]—how does that compare to the budget available for [SPECIFIC or OVERALL SCOPE OF ROLE]? How are those funds determined, approved, and spent?

Why: By asking the question in this way, you provide a helpful frame of reference to contrast or compare the roles and scope as well as learn more about the process for approving budgets at the company.

Common Candidate Question: What would you say is the most fun or creative part of the job?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: Depending on the role, creativity and fun might be hard for the interviewer to articulate.

Ask This Instead: Within the responsibilities of the role, where are the processes, systems, etc. already defined, and where is there a need to design, build, or create new ways of accomplishing the goals?

Why: Rather than focusing on fun, asking the question this way will provide information about where there might be creativity or flexibility in the role.

Common Candidate Question: What is the toughest time of the month or year for someone in this position?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: This question gets at the “what” and “when,” and taking it another step further will help you understand more about the actual working experience.

Ask This Instead: Every role has periods of intensity, pressure, or deadlines that require extra effort to get through—what are those periods for this position/team and how does the team prepare in order to get through those pushes?

Why: Adding the follow-up questions will push your interviewer to give you more complete picture of the periods of intensity and how the team responds.

Common Candidate Question: What job shadowing opportunities are available for an applicant before they accept an offer?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: Having the opportunity to shadow could be incredibly valuable, but if they don’t have an existing program, the interviewer might indicate that it’s not possible rather than thinking through how it could be done.

Ask This Instead: Ie found that observation is one of the best ways to really understand the work I’d be stepping into. Would it be possible to shadow a team member to meetings at a final stage of the interview process?

Why: Here you’ve asked a specific question and indicated the underlying “why.” Though the company may not have planned to do something like this, by asking it could become a possibility.

Common Candidate Question: Is this a new role that has been created?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: This is a “yes” or “no” question that might not get you any information about the “why.”

Ask This Instead: Tell me more about the context for why this role is open—would I be the first to take this on or am I stepping into a role previously filled by someone else to carry the work forward? If 1: What are the top 1–3 reasons why this role was created? If 2: What would the team like to see the next person do to keep up momentum or evolve the approach or outcomes?

Why: This framing takes a basic question and, via the follow-up questions, adds depth and breadth that will provide valuable insight for later stages of the interview process.

Common Candidate Question: Who will I report to directly?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: This is important information! But asking the question this way will likely get you a name and little more.

Ask This Instead: Based on our conversation, and the job description, it seems like I will report to [NAME/TITLE]—tell me more about how this role fits into their broader team.

Why: Here, you can demonstrate research or awareness about the role (and they will correct you if you have it wrong), and also learn more about the team and opportunity.

Common Candidate Question: Can you tell me what the team is like?

Who to Ask: Cross-Functional

Why You Shouldn’t Ask That Question: Getting a cross-functional team member’s perspective on the team will round out your understanding of who they are and how they work with others. Taking the chance to focus this question in a more specific direction will yield more interesting insights.

Ask This Instead: Tell me how your team and others describe the team I be working with:

Why: Using this structure, you could start with the first portion, asking the interviewer to share more about what others might think about the team, and then ask some follow-ups to get some of the strengths and gaps it would be helpful to understand should you join the team.

Common Candidate Question: How do leaders encourage employees to ask questions?

Who to Ask: Cross-Functional

Why You Shouldn’t Ask That Question: It’s really important to understand how the company responds to the feedback and questions employees have. Taking this question to a more specific structure will push the interviewer to share more information.

Ask This Instead: What are the channels available for employees to share feedback or ask questions to leaders about company strategy, goals, and the employee experience? How often and in what ways do leaders respond?

Why: This framing opens the door for information about how employees engage with leaders as well as how leaders respond.

Common Candidate Question: What do you/employees like most about working here?

Who to Ask: Direct Report

Why You Shouldn’t Ask That Question: What people like or do not like may or may not be relevant to what matters to you or your experience.

Ask This Instead: What part of the employee experience do you get the most positive feedback about? Why do you think this is?

Why: Rather than ask about what someone likes or what they think other people like, ask about what people think or the feedback they share and hear about as that is more likely to indicate broader aspects of the culture and experience.

Common Candidate Question: How did you get to the company, and to your current position?

Who to Ask: Direct Report

Why You Shouldn’t Ask That Question: This is a great place to start a question, but adding some specifics will expand upon what you’re able to garner from the interviewer’s response.

Ask This Instead: What brought you to [COMPANY], why did you think this was the place and role that was best for you at this point in your career? How is the experience living up to your expectations and what would you like to see in the future?

Why: You could ask this question of any of your interviewers, but taking a moment to understand a prospective direct report journey is a valuable relationship building opportunity.

Common Candidate Question: What your least favorite part of working here?

Who to Ask: Direct Report

Why You Shouldn’t Ask That Question: This question opens the door to a few things, including a possible rant or an answer that is not as authentic because the interviewer may not feel comfortable sharing negative thoughts or experiences with you.

Ask This Instead: I hoping you’ll be open with me and tell me what you don’t like about working here or what you would like to see change. What do you think I could do in this role to help make it better?

Why: This framing acknowledges that asking for the dirt requires trust. It also enables you to get a view into something that might be less positive about the work experience and what, if anything, a team member might expect you to do about it.

Common Candidate Question: Can you walk me through your typical work day?

Who to Ask: Direct Report

Why You Shouldn’t Ask That Question: Asking someone about their work day will likely get you an overview of the meetings, interactions, and obligations they spend their time on, but might not unlock the “so what” about those experiences.

Ask This Instead: If you were to consider your responsibilities within a pie chart, what is the overall percentage you spend on each type of activity [INSERT SOME EXAMPLES—meetings, reporting, administrative]. How would you re-allocate those percentages in an ideal world? What should be added or removed from the list?

Why: Here, you’ll get not only the what but an impression about how much time is allocated and whether or not the team member believes that this is the best use of their efforts, or if there is a different allotment that would be preferable.

Common Candidate Question: Who are the other members of the department (by position) and how would we all interact?

Who to Ask: Direct Report

Why You Shouldn’t Ask That Question: Using this structure will likely result in a list of names and roles and some context about meetings or projects, rather than any underlying insights that could make your experience better or worse.

Ask This Instead: Tell me more about how this department operates—what type of group meetings, goal setting, or communication practices are in place?

Why: Providing examples of what you want to know about operations will help the interviewer respond with more specific and illustrative examples.

Common Candidate Question: How does your department communicate? Do you meet as a group, or communicate another way?

Who to Ask: Direct Report

Why You Shouldn’t Ask That Question: This question will get you a description of communication practices, but not much more.

Ask This Instead: If you could change one to two things about how the team or department communicates to help everyone do their jobs better, what would you do?

Why: This is a positive framing that will also highlight potential issues or opportunities, as well as get your interviewer insights on what could make the situation better.

Common Candidate Question: Can you tell me about the last team event you did together?

Who to Ask: Direct Report

Why You Shouldn’t Ask That Question: Understanding what a team did in the past may be helpful, but if they went bowling or to happy hour, will that really give you information to help you understand if this is the team and role for you?

Ask This Instead: How does this team build community and get to know one another?

Why: Events are only one way that team building occurs, so broadening the question will help you understand their approach and if it is something you feel compatible with.

Common Candidate Question: Tell me about what teamwork looks like here.

Who to Ask: Executive / Boss’ Boss

Why You Shouldn’t Ask That Question: This question focuses on the concept of teamwork, rather than the behaviors and outcomes associated success.

Ask This Instead: What are the behaviors of successful teams here compared to less successful teams? Why might this be the case?

Why: These questions require the interviewer to reflect on team dynamics and to reveal insights into what collective success looks like at the company.

Common Candidate Question: What’s your favorite part about working here?

Who to Ask: Peer / Teammate

Why You Shouldn’t Ask That Question: It’s great to know what someone’s favorite part of working at a company is, but it’s even better if you know more about their experience with something that matters to you. For some, their favorite part could just be the paycheck, and that won’t necessarily help you make a decision.

Ask This Instead: If you were to leave [COMPANY] tomorrow, what are the 1–2 things that would stand out as top memories, accomplishments, or relationships that you take with you?

Why: This question captures a more authentic view into someone experience and also opens the door for a broader conversation about culture, team work, or other aspects of the employee experience.

Common Candidate Question: How would you describe the work environment here?

Who to Ask: Peer / Teammate

Why You Shouldn’t Ask That Question: Asking the interviewer to describe the experience will yield information but not necessarily reveal specific aspects of the company.

Ask This Instead: What is unique about the work experience and environment at [COMPANY]? Why do you think this is specific to this company?

Why: This question pushes the interviewer to get specific about the company and take their answer to the next level in a way that will tell you more about what your working experience could look like.

Common Candidate Question: Can you tell me a bit about the team I would be working with?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: Learning about the people is one of the most important parts of the interview process. This question helps get at that objective, though it provides the interviewer with the opportunity to go in the direction of their choosing rather than one that is most interesting for you.

Ask This Instead: What are a few keywords that come to mind when you think about the people or team I be working with?

Why: This is an unexpected question and will provide a new view into the characteristics of the team in a way that could be very interesting. If the interviewer is put on the spot, they might be more likely to give an intuitive, truthful response.

Common Candidate Question: Could you go into more detail about the company’s culture?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: This is one of the most popular questions that candidates ask and one of the questions that can lead to a superficial, canned, and cliché answer. If culture matters, you need to indicate what aspect of culture you want the interviewer to shed light upon so that you get what you’re looking for out of the conversation.

Ask This Instead: I thrive on teams that collaborate through … I most engaged when … I most productive when … in environments that … I achieve my goals when … I connect with my team and company by … I learn best if…

Why: After you think about what matters to you, frame the question around those specific elements to one or all the interviewers you meet, so that you get a deeper understanding of how culture comes to life at the company.

Common Candidate Question: What benefits are focused on work-life balance?

Who to Ask: HR

Why You Shouldn’t Ask That Question: What matters to you is very specific and asking an open-ended question like this one will not necessarily guide your interviewer to share the most relevant and detailed information you need.

Ask This Instead: At this point in my career, [INSERT BENEFIT: PTO, childcare, wellness stipend, remote/flexible work, 401(k), healthcare, etc.] is something I value as part of the total rewards package. Can you tell me about [COMPANY] offerings?

Why: Focusing on the program(s) that matter to you will ensure that you get specific information rather than a sales pitch on a particular benefit or perk.

Common Candidate Question: Tell me about work/life balance.

Who to Ask: HR

Why You Shouldn’t Ask That Question: Balance will mean something different to each person, so taking a more specific approach to this question will get you more clarity.

Ask This Instead: Take the opportunity to ask about work/life balance with the lens that matters to you, for example:

Why: This question provides the chance for the interviewer to comment on patterns and the team or organization response and protocol rather than making blanket statements.

Common Candidate Question: What are your thoughts on working from home—for example when there bad weather, or in general?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: Someone’s thoughts about working remotely or from home may not be indicative of the company policy.

Ask This Instead: While researching, I came across some comments on working from home [seems possible, not available], is there an official policy or general practice that the company or this team has adopted?

Why: Starting with a reference point either based in research or potentially your own experience as well as asking about policies or practices will get you a more accurate response.

Common Candidate Question: What is/was your work from home policy during COVID-19?

Who to Ask: Recruiter

Why You Shouldn’t Ask That Question: As long as the pandemic endures, it is likely that this information will be proactively shared. Take advantage of the opportunity to ask additional questions to learn more about how the company responded.

Ask This Instead: How did your leadership team respond to COVID-19 and the need to work from home? What specifically changed with regard to your policies or benefits (for example, budget for home office equipment or extended time off for caretakers)?

Why: With these questions, you will learn more about how the leadership team responds to unexpected challenges as well as get insight into how the company responded to changes.

Common Candidate Question: Do you plan to return to the office after COVID-19?

Who to Ask: HR

Why You Shouldn’t Ask That Question: Unless the company has made a public statement to the contrary, there is a likelihood that their plans are either TBD or that they plan to return and are awaiting the appropriate time.

Ask This Instead: What are your plans for an eventual return to the office? What are the factors (for example, a vaccine) that will influence the decision? How are you preparing for new health and safety guidelines?

Why: There remains a lot of uncertainty about the duration of the pandemic and when certain aspects of life will start to look like they did prior to COVID-19. Asking about decision criteria and the company preparation or readiness to return will give you valuable information about the pandemic and general operations/planning.

Common Candidate Question: Is it possible for this role to remain remote after COVID-19?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: Unless the company has established new guidelines or policies, there may not be an answer to the question and your interviewer may not have access to the evolving conversations.

Ask This Instead: Will the company consider long-term remote options for all or even specific roles? What will influence those decisions? Will there be specific limitations (e.g. remote but only from specific states, etc.)? Will benefits or pay change depending on an employee decision to be remote in certain geographies?

Why: Even if your interviewer does not know a final decision, asking these questions will yield insight into what considerations are being explored at the company for specific roles, or overall.

Common Candidate Question: How did your team adapt to working from home?

Who to Ask: Manager

Why You Shouldn’t Ask That Question: This is a valid question, but could result in a variety of different answers depending on how the interviewer interprets “adapt.” To get a more specific answer, clarify what you’re looking for.

Ask This Instead: When your team made the shift to remote work? What changes were made with regard to:

Why: With this framing, you can focus the interviewer on what matters most to you about team work, collaboration, and what the day-to-day looks like.