Exactly! In the past I asked high level/generic questions and often got very little out of it. Shallow responses or no responses at all in some cases.

Nowadays I send the email I will paste below to every new hire after a couple of months in the team..

Some people never bother to schedule the conversation (less than 20%) and I leave it at that. For the other folks - the big majority - I had great conversations/results from this effort. Learned a ton of surprising things, found hidden talents within the team, found and then went to fix serious problems.

The email:

Subject: Talk.

Oi <Joe>, how are you doing?

I would like to establish a communication channel between us, and as a first step towards this have a conversation - can you please schedule a 30 minutes conversation with me using https://<my-own-url>.youcanbook.me/ ? Feel free to pick any available slot there - if it is open it means I will be available and working at this time. We can talk using <videoconferencingservice> (if we happen to be at the same building we can have the conversation personally).

Before the conversation I would like to ask you to please think carefully about the following questions, and be prepared to discuss what you understand as most important:

- How can I help you?

- Is there anything you would like to tell me?

- Is there anything you would like to ask me?

- What is your profile? What are your strenghts that you like to mention? What do you like doing the most? What motivates you?

- If you were in my place, is there anything you would change? What?

- Who are the 2 people you most admire within the company? Why?

- What information you assume I don't have that you can give me and will allow me to do my work better?

- Where do you inconsistencies between what we preach and what is in our culture document at <URL> and between day-to-day practice?

- Is there anything you would change in our culture document? Is there anything missing that you judge it is important?

- What are you current attributions? Do you judge you day-to-day challenging enough and do you see the company helping you grow or do you feel you need more space?

- Is there any self-managed project ( <URL-TO-EXPLANATION> ) that you would like to establish?

- What do you understand as key to grow in our company?

- Do you receive enough feedback to grow and improve performance?

- Do you consider your leadership micromanages you, stays pretty far, or typically can find right balance in each situation?

- Do you feel your leadership cares about you?

- In your view does your leadership communicate very clearly what are the objectives to be achieved? Does it support the team in staying focused on what is most important?

- How do you evaluate the quality of the company information you receive? Do you feel you regularly receive relevant information from senior leadership to understand where we are going? How do you evaluate your own participation in setting the company direction?

- Do you feel your leaders have the necessary technical skills to manage your work effectively?

- Would you recommend your leader to other people in the company?

- What feedbacks you have to give me? What concerns you the most in my work? What makes you happy and you want to make sure I continue doing?

Regards,