10 questions I’d ask when interviewing for a new job
I've compiled this list over the years of interviewing many candidates
This is one of the topics that I receive questions about most often. Over the years at TestBox, I interviewed lots of candidates for a range of different roles. I always enjoyed the final part of the interview when we opened up the floor for the candidates to ask us anything, as the range of questions asked was quite wide.
Here is the list of questions that I plan to ask when I am next in the interviewee seat along with the reasoning for each. There is also a section for specific questions that I’d ask if considering a Chief of Staff role.
Leave me a comment with other questions you like to ask when interviewing for a new role. And don’t forget to go ahead and click ❤️ if you found this helpful!
Questions to ask regardless of role
1. What does success look like for this role? (Can you share a 30/60/90 day plan?)
Ideally, this has come up in the interview process already. However, so often hiring managers are so focused on assessing candidates that they may forget to proactively share this context.
Particularly for roles without clear cut career progression (especially Chief of Staff roles), this question can help you understand how your potential manager approaches career advancement. If they provide a thoughtful, clear answer then that means they’ve given time to crafting the career ladder. If the answer they provide is vague or doesn’t translate into a concrete understanding for you, this could be a warning sign that your career advancement might stall or be an uphill battle in which you’ll have to constantly prove / defend yourself.
2. What do you anticipate being the biggest challenge for this role?
This can sometimes be a throwaway question if the interviewer isn’t particularly candid, but if they are, you can learn a lot more about cross/intra-team dynamics or the macro-environment for the business. If you ask this to multiple interviewers – not just your potential manager – then you can also start to get a sense of how the team is feeling and potential different hot button issues.
3. Is this role a net new addition to the team or a backfill for someone? Can you share any context on the backfill situation?
I’ve seen a lot of wonky circumstances under which a new person is brought into a team. I have had friends who were interviewed by someone who didn’t know they themselves were being backfilled. I’ve heard of people who joined a new team only to find out all of the former team members had left. You never quite know what’s going on inside a team or company, and once again, this question may not reveal much if someone doesn’t open up, but if you start to get the sense that you’re getting a cagey response or something way too vague, that could be a warning sign in and of itself.
4. Is there anything else I should know about the business or team that we haven’t already discussed?
I was asked this once by a candidate and it took me by surprise, but I appreciated being asked this a lot. I don’t think the question is necessarily aimed at uncovering skeletons in the closet but instead to give the interviewer a chance to share additional context. Most of the time, interviews are on such tight schedules that interviewers are juggling sharing more context with giving the candidate time to prove themselves. This gave me a chance, as an interviewer, to go back to some context I wanted to share in more detail.
Chief of Staff specific questions
5. Do you consider this role to be part of the executive team or adjacent?
Chief of Staff is a very unique role and it can sometimes be an expectation that they are part of the executive team if the candidate is extremely experienced. On the other hand, if the candidate is less experienced, the Chief of Staff may listen in on executive team discussions and meetings or support with creating the agenda but not attend. There are all sorts of possible arrangements, but this question allows you to get on the same page as your potential manager. It helps ensure everyone has the same expectations of the role.
6. Who is part of your executive team and what does each person own currently?
On the surface, this question helps provide context on the leadership of the company. However, for a potential Chief of Staff, it also reveals a lot more about what the role may look like. Often in startups, the Chief of Staff fills in gaps. You can start to get a sense of what those gaps may be through understanding which executive team roles are filled vs not.
For example, if a company has a CEO and CTO but no COO, a Chief of Staff may end up doing more operations. If there’s no CFO, you may end up responsible for some company finance and working with accountants. In a company where the COO and CFO roles are filled but there isn’t a CPO, the Chief of Staff may end up focusing more on supporting Product.
This isn’t a perfect way to figure out what your responsibilities will be – you should always ask that directly, of course – but it can be a good way to figure out where scope creep may come from. Sometimes the CEO may not even realize these are gaps they need filled until after they have a super awesome, competent Chief of Staff available.
7. Do you want someone to be Chief of Staff for a year or two and rotate into a different position, or do you want someone in the role for longer?
The majority of Chief of Staff roles that I’ve encountered are intended to be rotational, lasting a year or two. However, there are some instances where this isn’t the expectation. Asking for clarity early on is important to make sure that your career goals align with the way in which a potential manager intends to invest in their new hire. If they want someone in the role for longer, the skills that you’ll need to build are different from if they are looking for someone to rotate out of the role after a while.
8. What are some recurring responsibilities you’d like your Chief of Staff to take on?
Along with the question below, this is a way you can start to understand what your day to day might look like. If the interviewer is at a loss for answers, a follow-up example you can provide is this:
A Product Manager may be expected to play some role in sprint/work planning, maintaining a task management system, and running related meetings with the engineering org. Are there parallel expectations for the Chief of Staff, whether it’s running OKR planning, annual/quarterly planning, or all hands meetings? Or are there recurring tasks such as payroll or team satisfaction surveys or planning onsites that might fall to the Chief of Staff?
This way, you can start to understand a bit of what the role would actually look like.
9. What is the percentage of time you’d like your Chief of Staff to spend on special projects vs recurring responsibilities?
Once you have a sense of the recurring responsibilities, you can try to better understand what portion of the job they’ll take up. Asking this question forces both a potential manager and you to understand the realities of what might fall to the Chief of Staff.
If the answer is something incredibly unrealistic – such as 10% on recurring responsibilities and the rest on special projects, but with a laundry list of recurring responsibilities that’s extremely time consuming, then this is a good warning sign. The role may need to be more tightly scoped, or at least you need to discuss prioritization and see how receptive your potential manager is.
10. What are some of the special projects you’d like a Chief of Staff to tackle this quarter?
Oftentimes, Chief of Staff job postings allude to “special projects” but don’t specify what those would look like. Asking this can push a potential manager to get more tactical and specific. If they’re not sure how to answer, you can also ask, “What are some of the hardest questions you’re facing right now that you’d like your Chief of Staff’s help with tackling?”
Tl;dr
The portion of the interview when your interviewer asks, “Any questions for us?” is invaluable. Here’s a list of questions I’d ask as an interviewee to better gauge if a potential role is a good fit for me. These questions will also provide more context that many interviewers may forget to share – or choose not to share, which may be a cause for concern.
Let me know what other questions you like to ask when interviewing for a new role.
This list has actually been really helpful for me. I asked the question "What does success look like in this role during x period" and for whatever reason the interviewers didn't give a concrete plan and their response was rather vague ("be willing to learn, enthusiastic, give it a try attitude"). That and other responses clued me into the fact that while career progression exists in the company, there wasn't really a clear cut idea of what that could look like. Thanks for doing these and the recent rubric was helpful as well!