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There's a long text about context, so I will summarize with a direct question:

Question: I haven't been able to "extract" from my PI the help that I need about building confidence and persisting in the field. What are precise questions to ask? And what are the limits of what makes sense for me to ask the PI, in contrast to the fact that I might just need to seek therapy for something like imposter syndrome instead?

I elaborate on the question below, in bold, after some context. I also provide an answer below with what I attempted. However, I do not think I succeeded, hence the question.

Context: I have a satisfying postdoc position:

  • the group is active, diverse, people are likable.
  • The PI is experienced, renowned, and seemingly supportive.
  • I have better funding than I've ever had; probably hard to top.
  • I am supported to do the research that I want, I am free to collaborate, and I have more opportunities to pursue than I've ever had.
  • I live with my partner, who's working in a similar field.

Some of these points are more pronounced given that I've come from a place with a serious lack of opportunities in the field.

I am less than halfway through (~8 months) my contract at the moment, and I feel like I haven't accomplished much. I come from a rough PhD, with a "somewhat" supportive supervisor, but with questionable practices (e.g. discouraging collaborations, creating a feeling of anxiety about sharing ideas). I have left my PhD with a borderline feeling of failure: compared with more junior students in my current group, I don't have many publications, and they're arguably of lower quality. I only partially feel confident about the results, which were less about conceptual quality and steered (by the senior coauthor) to cater to publication metrics. Furthermore, I have moved to a neighbouring field; the younger members are ahead of me, so I feel like I need to catch up.

Overcoming the self-doubt I have about my own capacities as a researcher, some stemming from the PhD, has been difficult, and I feel like I have to build confidence, which is not happening.

The PI seems supportive, and although my self-doubt creeps in with feelings of being ostracized in favour of more promising members, I have no argument against the fact that the PI chose to hire me.

My PI is a "right questions" type of person. So in trying to be on the same page as them:

What are the good questions to ask, when asking about how productive or competent I need to be? How to get their opinion on my ability to persist in the field?

I think having the answers to this will put in perspective how I can be confident. An important assumption here is that I believe that confidence goes a long way. Surely there's no going forward with this career without the metrics, but I can only gather the metrics if I have confidence in my capacity. And I do not seek confidence from the approval of my PI, I seek confidence in knowing what the expectations are and where do I place myself before them.

Because of this situation, I am (and have been) asking the question of whether I should leave academia and pursue a job in industry. I do not want to do this, however. I like the idea of teaching, I want to have my own group, do my own research, and advise students. I don't mind in principle to grind for grants, but if doing this will be impossibly difficult because "I'm not good enough", then I have no other choice. And I know I might just not be as satisfied in industry given how it works.

More context: I am in a similar situation as the one described in Postdoc in good environment, but haven't accomplished anything on my own: How long is it reasonable to stick around?. However, I wanted to be more specific at some points, so I thought my question would be warranted. I will nevertheless try to make parallels with that Question.

I've also read How to effectively deal with Imposter Syndrome and feelings of inadequacy: "I've somehow convinced everyone that I'm actually good at this". But the statement "I've somehow convinced everyone that I'm actually good at this" doesn't resonate much with me, and neither did the replies there.

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It sounds like you have already spoken with your advisor to some degree about this, and you are not yet satisfied with the outcome. I don't believe that at this stage of your career it is your advisor's job to provide mental health help. It sounds like they are already providing a good and reinforcing work environment, and the persistent issues you are experiencing should really be dealt with by a mental health professional.

Ask yourself this, is there anything reasonable that your advisor can actually do to make these doubts go away? Would you like them to tell you how awesome you are doing every day? Wouldn't that feel a bit weird, you are both adults and you are training potentially to be a group leader?

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