CEO / Founder
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.
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?
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.”
Cross-Functional
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.
With regard to the team I join, how have the cross-functional collaboration and achievements changed since you joined?
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.
Executive / Boss’ Boss
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.
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?
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.
Executive / Boss’ Boss
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.
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?
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.
Executive / Boss’ Boss
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.
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?
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.
Executive / Boss’ Boss
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.
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?
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.
Executive / Boss’ Boss
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.
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?
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.
Executive / Boss’ Boss
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.
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?
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?”
Executive / Boss’ Boss
I think this is a valuable question that can become even more valuable with a small addition or two!
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?
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.”
Executive / Boss’ Boss
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.
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?
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. Diversity & Inclusion
CEO / Founder
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.
What comes after any statement or actions that you make in response to a world event (for example, Black Lives Matter)?
This question is aimed at understanding whether statements or responses are performative and reactive, rather than proactive and sustaining.
Cross-Functional
This question will yield an answer about “who” but not necessarily how, what, and toward what outcomes.
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?
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.
Executive / Boss’ Boss
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.
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?
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.
HR
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.
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)?
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.
Manager
This question will yield insights about the nature of work being completed, but will stop short of the outcomes and how those were perceived.
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?
This question is aimed at understanding if the company/team is open about failures and, more importantly, practices a growth mindset.
Manager
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.
Are all feedback mechanisms anonymous? If so, why is that the case? How are engagement surveys or other results shared with the team?
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.
Manager
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.
Do you know how much money is allocated to your DEI efforts? If so, how much is that per employee?
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.
Peer / Teammate
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.
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?
These questions will indicate if the efforts can endure as business, team, or individual context changes.
Recruiter
Asking about the benefit offerings will yield information that is top of mind or readily available and common.
Can you describe how your benefit offerings have evolved/are evolving to be more inclusive of individuals and families with unique needs?
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.
Recruiter
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.
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?
This a specific, hard-hitting question aimed at understanding if the organization is seeking candidates for “culture fit” vs. “culture add.”
Recruiter
This question sets up for a yes/no answer, but having a program is not the full story.
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?
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.
Recruiter
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.
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?
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.
Recruiter
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.
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?
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. Future of Company
Backchannel Reference
Better is subjective and relative to the dimensions that matter to you.
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.
Focusing in on a specific aspect of why you would choose one company or the other will enable your contact to target their response.
CEO / Founder
This question helps you understand the mindset of the CEO, but might result in a canned answer about goals, the team, etc.
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?
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.
CEO / Founder
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.
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?
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.
CEO / Founder
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.
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?
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.
CEO / Founder
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.
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?
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.
CEO / Founder
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.
As the CEO, what goals do you have for yourself and how do you share them with the team and get their feedback?
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.
Executive / Boss’ Boss
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.
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?
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.
Executive / Boss’ Boss
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.
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?
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.
Recruiter
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.
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?
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. Leadership
CEO / Founder
The root of this question is interesting, but it might feel a bit cliche to ask it this way.
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?
Asking about a specific example will illustrate how the team collaborates to innovate and succeed as well as how those experiences influence future initiatives.
CEO / Founder
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.
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?
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.
Cross-Functional
Asking this question will get you a description, or perhaps a list, because that’s what you asked them to give you.
How do different teams live the company values in their own unique way?
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.
Cross-Functional
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.
Tell me about how your career journey brought you here. Why was this the best next step for you?
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.
Direct Report
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.
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.
Is there anything else that you believe is important to them, but might be left unsaid, or gets less attention?
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”).
Executive / Boss’ Boss
This question could go down multiple different, and potentially irrelevant, paths or result in a canned “PR” answer.
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?
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.
Executive / Boss’ Boss
With this straightforward question, you’re likely to get a high-level answer.
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?
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.
Executive / Boss’ Boss
There is too much wiggle room here for the interviewer to give generic answers rather than address your underlying question.
How is the company addressing the fact that the entire leadership team (and/or board) is white and predominantly male?
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.
Peer / Teammate
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.
For the managers I’ll be working with most frequently, what do they have in common, and what is different about their leadership approaches?
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.
Peer / Teammate
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.
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?
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. Management
Backchannel Reference
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.
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?
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.
Direct Report
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.
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?
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.
Manager
This question puts all the power in their preferences, when you could influence the structure of the working relationship.
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?
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.
Manager
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.
I love to hear more about your career journey and the path that led you to where you are today at [COMPANY].
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.
Manager
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 question in a career development conversation if this person becomes your manager!
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.
Manager
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.
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?
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.
Recruiter
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.
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?
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! My Success
Cross-Functional
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.
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)?
Here, you get more information about how the teams are organized within the company as well as more details about how they work together.
What are the biggest rewards of the job and working for this company?
Cross-Functional
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.
Why do you choose to do your role at [COMPANY] vs. a similar role at [COMPETITOR] or another company?
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.
Cross-Functional
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.
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?
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.
Direct Report
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.
What do you feel has made you successful working here so far?
Tell me about your definition of success in your role and what support you might need to continue on that path toward your longer-term career goals?
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.
Manager
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.
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?
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.
Manager
This question is both open—it isn’t clear what you want—and closed—the interviewer can simply respond “yes” or “no.”
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?
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.
Manager
Asking this question might get you an answer that closely resembles the job description rather than new insights.
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?
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.
Manager
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.
Wee discussed metrics including [INSERT KEY METRICS]—what are the expectations around setting targets, and reporting and communicating progress or problems?
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.
Manager
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.
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?
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.
Manager
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.
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?
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.
Manager
It can be a good idea to ask a question like this, and a more structured approach will open up even more valuable information.
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?
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.
Manager
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.
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?
This acknowledges the fact that everyone makes mistakes but also includes the emphasis on learning and potential impact of making a misstep.
Manager
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.
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?
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?
Peer / Teammate
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.
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?
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.”
Peer / Teammate
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.
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.
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.
Peer / Teammate
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.
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?
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.
Recruiter
This is a “yes” or “no” question that doesn’t allow you to demonstrate that you can be proactive and prepared.
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.
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. Offer Package
HR
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.
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:
I am a board member at [insert organization] and am required to attend monthly meetings on the last Thursday of the month from 1–3 pm. Currently, I block this time on my calendar, communicate my anticipated absence to the team, and ensure that my work will not be impacted. Would that approach work here, or is there something else I would need to do?
Or, you can ask some follow-up questions to the initial question to get more insight:
Does the company time-off policy include time for volunteer days? Has the company ever sponsored team or company volunteer opportunities—if so, how did those opportunities get determined?
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.
HR
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.
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?
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.
Manager
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.
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?
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.
Recruiter
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.
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?
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.
Recruiter
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.
I available to start as soon as [YOUR DATE], would that align with what the team needs?
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.
Recruiter
If critically important, this information is usually included in the job description.
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?
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.
Recruiter
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.
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?
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.
Recruiter
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.
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?
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.
Recruiter
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.
As you know, I currently live in [PLACE] and would happily relocate for this position to [PLACE]. What type of relocation assistance is available?
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. Respond to Rumors / Press
Backchannel Reference
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.
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?
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.
CEO / Founder
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.
What do you wish the press or employee reviews about [COMPANY] covered that they most often ignore?
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.
Recruiter
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.
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?
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. Role Specifics
Backchannel Reference
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.
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?
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.
Direct Report
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.
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.
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.
Direct Report
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.
What is the elevator pitch that you think adequately conveys the reasons why someone should be excited to take this role?
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.
Manager
This question is close, but not all the way to getting you the insight you need.
What emails, meetings, or lingering items on your to-do list shift when someone starts in this position?
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.
Manager
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.
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?
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.
Manager
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.
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?
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.
Manager
Depending on the role, creativity and fun might be hard for the interviewer to articulate.
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?
Rather than focusing on fun, asking the question this way will provide information about where there might be creativity or flexibility in the role.
Manager
This question gets at the “what” and “when,” and taking it another step further will help you understand more about the actual working experience.
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?
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.
Manager
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.
I 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?
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.
Recruiter
This is a “yes” or “no” question that might not get you any information about the “why.”
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?
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.
Recruiter
This is important information! But asking the question this way will likely get you a name and little more.
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.
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. Team Dynamics
Cross-Functional
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.
Tell me how your team and others describe the team I be working with:
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.
Cross-Functional
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.
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?
This framing opens the door for information about how employees engage with leaders as well as how leaders respond.
Direct Report
What people like or do not like may or may not be relevant to what matters to you or your experience.
What part of the employee experience do you get the most positive feedback about? Why do you think this is?
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.
Direct Report
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.
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?
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.
Direct Report
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.
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?
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.
Direct Report
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.
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?
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.
Direct Report
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.
Tell me more about how this department operates—what type of group meetings, goal setting, or communication practices are in place?
Providing examples of what you want to know about operations will help the interviewer respond with more specific and illustrative examples.
Direct Report
This question will get you a description of communication practices, but not much more.
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?
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.
Direct Report
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?
How does this team build community and get to know one another?
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.
Executive / Boss’ Boss
This question focuses on the concept of teamwork, rather than the behaviors and outcomes associated success.
What are the behaviors of successful teams here compared to less successful teams? Why might this be the case?
These questions require the interviewer to reflect on team dynamics and to reveal insights into what collective success looks like at the company.
Peer / Teammate
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.
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?
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.
Peer / Teammate
Asking the interviewer to describe the experience will yield information but not necessarily reveal specific aspects of the company.
What is unique about the work experience and environment at [COMPANY]? Why do you think this is specific to this company?
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.
Recruiter
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.
What are a few keywords that come to mind when you think about the people or team I be working with?
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.
Recruiter
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.
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…
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. Work / Life Balance
HR
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.
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?
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.
HR
Balance will mean something different to each person, so taking a more specific approach to this question will get you more clarity.
Take the opportunity to ask about work/life balance with the lens that matters to you, for example:
When are the work peaks and valleys throughout the week? How do people manage and respond to requests in the evening, while on vacation, or during the weekend? How does the company take steps to protect employees from burnout (and how has this changed as a result of COVID-19)? How does the company support parents or caretakers (and how has this changed as a result of COVID-19)? How does this team respond if someone child walks into a Zoom meeting? Is the team/company open to a regular or recurring daytime commitment (for example, a mid-afternoon work out, volunteer, or family commitment like school drop off/pick up)? How do team members communicate about those commitments?
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.
Recruiter
Someone’s thoughts about working remotely or from home may not be indicative of the company policy.
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?
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.
Recruiter
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.
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)?
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.
HR
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.
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?
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.
Manager
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.
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?
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.
Manager
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.
When your team made the shift to remote work? What changes were made with regard to:
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.