Successful career conversations

There isn’t a one size fits all approach to a good career conversation. Still, there are useful practices that everyone can lean into to talk about growth, whether you’re the manager or designer. A meaningful foundation can start with creating a trusting environment, reflecting on short-term goals with long-term aspirations, and building a support structure.

Label it. Treat career conversations differently than ongoing project conversations. Consider creating a monthly career calendar invite separate from ongoing 1:1s. When in person, go for a long lunch or walk to signify the difference in how you’ll spend the time together.

Build trust. As a manager you are here to facilitate, coach development, and support success, not be a judge or strict-authority. Be open and supportive.

Host the conversation. Leverage the template options as a starting point for the discussion. Share ahead of time to stimulate your direct report in thinking about their overall career aspirations.

Lead by example. Incorporate past experiences as a motivator to practice similar self-reflection. Cross-share what your goals are to create more visibility on what you are working on.

Look backward, not just forward. Understand what went well and what could have gone better in their last role. This includes their managerial relationships.

Energy mapping. Learn what energizes them and what depletes it (on the team, product, the org, company)

Emulating. Ask people who they admire, or hope to model themselves after.

Beyond Instagram. What are some possible future worlds they can imagine for their career? Not everyone has a singular aspiration so it can be helpful to consider different paths and how we can prototype aspects of each in their role today.

Time to reflect. Not everyone may know their career aspirations in 5 to 10 years, so make space to contemplate this on their own time first. Then talk about what skills/opportunities are most important to do those things.

Immediate barriers. What’s getting in their way of better utilizing strengths? What do they wish they were spending more time on that they’re not? why?

Role expectations. On the spectrum of what is expected for your role, where do they feel they peak/ need to work on? In some situations, you might want to use an Expectation worksheet to discuss what operating at the next level can look like.

What progression looks like. What do they want to be true at the end of half/quarter? What would they want to be able to say in their next self review? What will they be most proud of?

Support network. Introduce reports to others with similar career interests.

Align opportunities. Keep ear to the ground for opportunities outside of day-to-day work that align with how people want to grow and snag those opportunities for them.

Recognize Strengths. Call out when you see a strength displayed, even when they might not recognize it as a “call out” moment. Show how different moments ladder up into a larger theme.

Help them track. Discuss any components of their career aspirations that can be actioned on in the next 6-12 months. Create an action plan, potentially incorporating it into your directs goals for the half.