In a bigger company, you should be having a "career 1x1" conversation at least once every six months, and no more frequently than once every six weeks with each of your reports. Beyond feedback (which you should be giving weekly as well), it's also important to understand where is the report's head at. A good framework for it is Dream-Plan-Ask, which as far as I know I made it up. **What’s the dream**: Where are you hoping to be in 4-5 years? This should be pretty vague, and not necessarily tie to the exact company even. This is usually not updated super frequently, so it might not come up every time, but it's good to check in at least once a year that what you thought is the dream is still the dream. **What’s the plan**: What are you expecting to achieve in the next 12-18 months? This should be more concrete, e.g. management responsibilities, better WLB b/c baby is coming up, promo timeline etc. The plan should ladder up to the dream, hence it's helpful to have the idea of what the dream is. This is the most important part, as I've seen manager-report relationships derail because they were not aligned. **What’s the ask**: What's the one thing I can concretely do to help with the “plan”? This can range from “more speaking opportunities” to coaching on a specific issue. Anything really. Tips for executing it well: * The report should come with the dream-plan-ask ready. * Spend most of the time listening for subtle cues. * At the same time, be very transparent and don't lead on, especially if the plan is not realistic. * Take notes and keep the DPAs of all your reports. Boss move is to recap it from last time. #published 2025-01-30