Probe question to learn how new manager is going to handle failures?

Question

Context:

My team participates in delivering complex products that assumes commitments from multiple teams. Certain commitments ("deliver by" dates) are absolutely crucial for project success, yet due to complexity it is not uncommon to see that our sister teams are missing due dates.

Our sister teams have other commitments too and sometimes they have to prioritize. Sometimes prioritizing was not done in favor of the bigger project that our team is spearheading.

My team is in charge of defining execution plans, asking for commitments from the others and driving the project to completion. With lots of power comes lots of responsibilities and every failure during execution our project plan is getting attention and sometimes unpleasant questions from multiple senior managers across the company.

My senior managers did not do a great job surfacing real problems with the projects we delivered in the past, and I'm under the impression that all the bosses that came to lead my team were lacking depth and oftentimes were not fighting enough for getting enough budget / buffer (in terms of planning to spend more time and assign more people) that would increase chances of success for our project.

A few bosses quit or let go and now we have another one. I feel that new boss is going to shift the blame on us but I'm not 100% sure yet.

Question: I want to have honest conversation with my boss and my intention is to get clear understanding on how he is going to handle failures. If he is willing to shift the blame on us and needlessly restructure the team instead of addressing painpoints with the other teams, I'd rather find another job as this behavior would invite more problems. How can I be sure that new boss is going to address project issues in constructive matter? What questions I can ask on my 1:1 with them and what are the definitive markers of someone who does not intend to solve real problems?

Answer 1

It doesn't sound like you will be directly involved in interviewing candidates for your boss's role, so this may not be directly relevant, but one of my favorite interview questions is,

Can you describe a time you had one of your projects/assignments fail? And tell us what you did as a result, and how you learned from it?

Having someone describe a specific example often gets a more meaningful answer than just asking "how do you handle failures?" which pretty much always elicits a throwaway textbook response.

Since you (apparently) won't be involved in the actual interview or selection process, you can turn this tactic on it's head when you're speaking with your new boss, by describing to them, upfront, the types of failures you often see in your department, and asking for their thoughts on the best ways to respond. Even better, if you can also mention some ideas or suggestions you have for improvements, or responses you've seen as successful in your specific environment.

This way, you'll get the same benefit as my interview question - specific, meaningful discussion about actual issues instead of generic canned answers which you might get if you asked your new boss, "how do you handle failure?"

Answer 2

I would like to agree with jcmack about discussing the actual pain points as a conversation starter and assessing how adequately (to your judgment) your new manager responds to them. With this being the main purpose of your conversation, you can use previous failures as examples and try to gauge your manager's reaction and perception of these failures to try to determine how he is going to handle such failures in the future. You need to take care, however, to present these examples as objectively as you can so that your manager's perception is not influenced by your own.

All this is of course dependent on how much your new manager is open to such discussion, which may be an indicator in and of itself.