Run Five Critical Conversations to Win Your Boss Over

Your relationship with your new boss can make or break your transition. The secret is not magic but method: five intentional conversations woven into your first 90 days. First comes diagnosis—align on how you both see the situation and its STARS portfolio. Next, expectations: define success metrics, deliverables, and timing. Then style—figure out how she prefers to communicate and decide. The resource talk follows, where you build a case for budget, headcount, or time. Finally, about three months in, you discuss your development and next steps.

Each dialogue builds shared reality and trust. When you align on the situation, your boss feels seen. When you negotiate expectations, you guard against nasty surprises. Style talks prevent miscommunication. Resource negotiations ensure you have fuel. The personal development check-in signals you’re in it for the long haul. Research on upward management shows that leaders who proactively structure these conversations double their credibility and cut feedback cycles by half.

You’ll create a simple blueprint with five columns—situational diagnosis, expectations, style, resources, development—and fill in bullet points for each. Then you’ll schedule those conversations at regular intervals, weaving them into your 90-day plan. Each meeting will be a chance to clarify, align, and co-create your path. Try slotting your first two talks this week.