How do you approach career development conversations with your direct reports?

Situation: I managed a team of 10 engineers at a growth-stage startup. We had a mix of levels—a few seniors, mostly mid-level, and two juniors. Career conversations were happening ad hoc, and people weren't sure how to grow or what opportunities existed. One engineer had been at the same level for three years and was considering leaving.

Task: I needed to establish a structured approach to career development. My goal was to make career conversations a regular, meaningful part of our 1:1s and connect people to real growth opportunities.

Action: I separated career from performance in our 1:1 rhythm. We had weekly 1:1s for work, and every six weeks I dedicated a full 1:1 to career—no project updates, just aspirations, strengths, and development. I came with open-ended questions: "Where do you want to be in two years?" "What would make you feel like you're growing?" "What's holding you back?" I listened first and helped people articulate vague goals into concrete milestones. For the engineer who'd been stuck, we identified that he wanted to move toward tech lead work. I connected him to a project where he could shadow our senior lead, then own a smaller initiative. I also created a simple "growth opportunities" doc—stretch assignments, mentorship pairings, visibility chances—and reviewed it with each person so they knew what was available. I followed up: if someone wanted to present to leadership, I made it happen within the quarter.

Result: The engineer who'd been stuck was promoted to senior within 18 months and stayed. Our voluntary attrition dropped from 15% to 6% annually. People told me the dedicated career 1:1s were the most valuable part of our relationship. I learned that career development requires dedicated time and follow-through—it can't be squeezed into status updates.