One thing that I started doing at OpenAI is that I created a policy for myself to be *100% transparent* with my manager about everything. It seems obvious and weird to say aloud, but I bet most people don’t actually do this. But once I started doing it, I realized there are a lot of benefits. For example, when managers ask people “how is your week”, many people may say “good” and then dive into a report of what they did that week. Some people may be shy about any struggles they may be having. I’ll be fully transparent about everything—X is good, I’m blocked on Y because of Z, I like A and B but I wish C could be better. I tend to use my 1-1s to talk about bigger picture stuff instead of technical details since that’s where managers can help the most (I’m experienced enough to not require technical guidance most of the time). Another example is when managers ask “is there anything the team could do better for you.” It feels odd to critique the person in charge of your career, but I am very blunt about this, while being clear about the broader context (here are 5 things that I don’t like, but I’m so grateful to be here working with you). I also communicate that I have no expectation of them solving my problems—I’m simply giving them information so they can appropriately triage it into their priority list. My guess is that managers actually appreciate this; it’s much worse to learn that someone doesn’t like their role via a conversation after they announce that they’re leaving. For some people it’s also awkward to ask for things from your manager (e.g., can I spend some time on this, promotions, becoming a manager, etc). When I’m serious about something I bring it up very early with some hedging (e.g., I know it can be far off but I want to work towards X). This helps your manager give feedback early and help keep you on track. The biggest benefit for me, though, is that verbalizing this to another person forces honesty on myself—have I been working hard enough to deserve what I’m asking for? Am I performing at my best recently? If not, why not? Finally, being transparent with your manager can also open the door for them to be more transparent about your performance. I try to open this conversation by regularly asking “what can I do better”. In the past I’ve felt that some managers are too nice to deliver negative feedback. But if you’ve opened up to your manager about everything, they might be more willing to give feedback. For example, I’m now more aware that I have less SWE experience than most people my level, and I should work extra hard on that to catch up. Of course, all this going well is conditional on working in a healthy company and having a decent manager. I’ve been super fortunate with the managers I’ve had at OpenAI. But if that’s not the case, some honesty may be even more revealing—do you want to keep working for someone who doesn’t ask for feedback, or who doesn’t take your problems seriously? A quote I heard from someone else is “every meeting between you and your manager should be slightly awkward.” I think it captures this idea pretty well—you should talk about personal and important things, and transparency is the first step.