3 questions to X-ray your future manager during the job interview

And how to pick the best ones for the occasion!

Krzysztof Przybylski
7 min readApr 26, 2021
No managers were harmed in the making of this article

It’s said that people don’t leave bad companies, they leave bad bosses. I doubt if this is entirely true but I’m sure, that given a choice, people won’t ever join a company to work for a bad manager. The only problem is — how to tell if your future leader is any good before you sign the contract? Well… read on!

In my previous article, I explained why it is so important to ask questions during the job interview. What I didn’t cover is how to create a list of interesting questions and select the best ones for a particular interview. The short answer is — you collect as much information about the company as you can and connect the dots. Every dot you can’t connect has a potential to be a great question.

How to come up with the right questions?

1. Listen to the company storytelling

Starting from the obvious — the company’s website and social media profiles. What kind of story company builds around itself? What are its employees proud of? How do they differentiate themselves from the competition?

2. Check out what people say

Ask Google. Search for opinions about the company — from clients, users, and employees. Especially insightful might be interviews with founders, executives, or top managers. What do they focus on? What goals and obstacles for the company they name?

3. Read carefully the job profile

Compare it with different job descriptions from the same company. What is unique for this role? How does it map in the organization? Look through similar roles’ descriptions in different companies. What stands out? Are there any surprising expectations? Any typical requirements missing?

4. Talk to insiders

This is by far the biggest leverage you can get before the interview. Use LinkedIn to find out if any of your contacts either works for the company or can introduce you to its employees. Even if you can’t get any introduction, reach out directly to the company’s employees. If you can’t find anyone in the role you’re applying for, aim for the same team or department. You’ve got nothing to lose and a lot to win.

It might be overkill to do it for every recruitment process, but if there’s one you are serious about, I recommend going through all the steps by the time you have a chance to speak with the hiring manager. If you ever get caught off guard, you can fall back to my top questions below.

Rodin, The Thinker in The Gates of Hell

I think that being busy is not the same as being effective. One needs to regularly hit the pause button to understand what’s really important and what’s merely disguising as urgent.

How much time at work can you dedicate to just thinking?

Nowadays, it’s all too easy to get on a hamster wheel of never-ending meetings, emails, or slack conversations. This question probes if your hiring manager has the will and power to get off it. If they can’t do it, it’s highly unlikely your fate will be any different.

What you typically get as an answer is a list of excuses — why generally it’s possible to stop and think in this organization… but the manager didn’t have a chance to do it lately. In that case, ask who is able to do it regularly. If the answer is not obvious then the situation is not so easy either.

Another common response is “It’s up to you, you design and control your work time”. This is a fair answer but begs to inquire further — at what cost? What are the consequences of cutting oneself off the grid? How other employees respond and how will they evaluate your behavior when you press pause to simply think?

Finally, when you get a straightforward answer, it is worth discussing if this is done on a regular basis and whether it is enough. It can lead to insightful discoveries about the work cycles or approach to plan and reflect, not only on the manager’s personal level but broader organization.

Follow-up: What do you use it for?

Strategic planning? Reflection? Problem solving? Learning & development? Creating new opportunities for your team? This can reveal what are managers’ priorities or preferences, what they naturally gravitate to.

Team diversity: any differences between classical fantasy and the modern workplace?

I believe that teams make things happen, not individuals. It’s important for me to understand what kind of team I’ll be joining.

What are the strengths and weaknesses of your team?

This question reveals if managers really lead a team or rather manage the work of a group of individuals. If they start to enumerate different team members’ attributes, then most likely don’t even think of their direct reports as a team. In this case, remind them that the question was about the whole team and see if this changes anything in the way they answer.

Answer to this question is especially important if you are to join a team that collaborates closely and everyone contributes to the final team’s result. However, there is a case where the hiring manager’s direct reports are autonomous contributors that do not share common goals, just work within the domain that the manager is responsible for. In this situation try to understand if you are getting hired to increase the diversity of competencies, experience, and perspectives or to fit the profile of other team members.

Follow-up: What kind of impact do you expect from me?

How does the team’s profile map to your capabilities? Are you hired to cover the team’s weakness or double down on their strength? There will be completely different expectations and interactions with teammates in both of those scenarios. Also, you might gauge if the hiring manager is assessing your strengths and weaknesses well.

“One meeting can enhance the quality of your subordinate’s work for two weeks” Andy Grove

The one-on-one meetings will be probably the richest interaction between us and form the cornerstone of our relationship. I’d like to know what to expect from them.

How your 1:1 meetings with direct reports look like?

There is no perfect answer to this question — effective 1:1s might be many different things. However, they can’t be all of those things at once! What the hiring manager focuses on, spends time on, and considers an uncompromisable core of these meetings will tell you a lot about his or her leadership style.

It’s less about things like frequency and length of the 1:1 meetings, and much more about their purpose, value, and subjects that are being discussed. Is it mainly a status meeting to let managers know if there are any new things they need to worry about? Or is there anything more it can be? Is there a time & place for personal and professional development, providing feedback about the organization, planning career development, or simply blowing off some steam when necessary?

I always pay attention to how deliberate managers are about 1:1s, if they have a clear sense of what is a valuable meeting for them and for their direct reports. It’s typically a warning signal when they seem to just go with the flow and grab any suggestion you make.

Follow-up: What I could do to get the most out of 1:1s with you?

This question uncovers the responsibility split, you can learn what will be given and what needs to be earned. Who is a driving force for your 1:1s? Are you behind the wheel or on the passenger seat? This often shows not only how your 1:1 meeting will look like, but the whole relationship with your future manager.

It won’t work unless you put it into practice!

I used these 3 questions in multiple recruitment processes to get a glimpse of the real person that the hiring manager was. You can do the same!

I hope you’ll find questions from this article useful… and with a little bit of luck, I might be the one being X-rayed. Please be kind! 😉

P.S. Let me know if this article was helpful for you — leave a like or a comment. I’ll be happy to share more recruitment tips & tricks if readers, like you, find them valuable.

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Krzysztof Przybylski

Connecting the dots, catalysing ideas, making things happen.