My current conversations look like:
However, I feel like a lot of conversation tends to be more surface-level and conversation tends to die down in the later half of the meeting. I'm not sure about how to
have deeper conversations
what kinds of questions I should be thinking about, and
what mindset should I keep to have deeper/meaningful conversations
Some hurdles I find:
In conversations in general, not just work related, it’s often helpful to take the first step going deeper yourself. Be comfortable and confident, and the other person will reciprocate if they want to. For instance instead of saying “Hey I’ve worked at xyz company for the last 2 years and I’ve been learning more about DevOps recently” try, “I’ve recently failed in this way …” or “I’m feeling like I’m struggling in this area …” and see how the other person opens up and relates.
Here are some counter thoughts to the hurdles you have:
Rahul always talks about the importance of empathy, so if you’re an engineer and they are a PM you could ask “What is something you want to tell every engineer you work with but can’t” or “What do you wish engineers did differently when working with product?”
If there is a big difference in seniority I believe that it is because your match is OK with that and they are there in a networking and growth platform as the mentor. Personally I bet it would be enjoyable then for them to answer your questions like “What led to your success” “What do you wish you knew sooner” and “What challenges did you overcome”
I believe Rozie was just posting about this and a great way to have honest, real, deep conversations would be to talk about failures (and of course what you can both learn from them).