Questions to ask before taking up a new job

Nearly all interviewers expect you to ask questions at the end of the interview. 

While most of the advice is genuine, but they dont uncover as much information as you would need. Also some of them are cliche and the team is often prepped with the standard answers, having already rehearsed it with several candidates. 

Here are a few questions that could uncover a lot of more signal. Also the surprise element to this questions will help get the most signal for you as an interviewee

1. What could go wrong if I join the team in the first 90 days ?

In any role there will be a rampup time, this question ensures commitment to the rampup and guarantees the runway. Having said that, any org or team may have skeletons buried and burning fires. This question and the discussion henceforth will help build commitment to a leadership transition and support through that journey. It can also help you understand the resources(existing TLs, peer managers, XFN counterparts) you can leverage to rampup.

2. What does failure look like after 1 year ? 

These two questions are good because they distill the top 2-3 priorities of this role that are needed for success. It also helps extract and gives the opportunity to align on the right expectations. 

3. What is the hardest feedback you have given to a manager ? 

Everyone has strengths and weaknesses. This will give you a sense of style of how the manager helps people grow and develop on their weakness. Also there can be several followups like what makes the feedback hard. It could reveal not only about the manager's work style but also challenges in their terrain that another able manager is having a hard time resolving. It might expose structural flaws of the terrain that you are not likely to get otherwise. 

4. What was the hardest feedback you have received as a manager ? 

5. What is the relative weight of how people conduct their work and the output they generate ?

This might give you signals of how much psychological safety there is in the team and what kind of culture the manager promotes. 

6. How do you resolve conflicting priorities between projects across two different teams ? 

This will give you a sense about how neat the boundaries are, how the goals are structured, how principled/adhoc resolution approaches are, how people/project/collaboration tradeoffs are made in an org. As a manager, this is something you will have to deal with all the time. 

7. What will you do if your team suddenly starts missing the goals ? How would you debug it ?

This will tell you what phase of growth this manager is in as described here. Good managers also regress in these growth stages when they face pressure from the top. 

References

1. 40 interview questions to ask and how to go deeper than what's culture like ?
2. How to respond to the interview questions "what do you have for me" ?