Choose Your Own Adventure

How to Have a Career Conversation

I used to hate having career conversations with my manager. I felt they were fraught, confusing, and best avoided. I used to do what most people do — wait for my manager to approach me. I figured they would have a magical plan on how to grow, but as I waited I was inevitably disappointed.

Your career should not be left to chance or your manager happening to make time. Armed with a few tools, you can have a great discussion about where you want to go and what you want to learn with your manager's support.

Career Conversations in Summary

Career conversations are not about a promotion. One of the reasons that managers avoid these meetings is because they aren’t ready to signal you should be promoted. But that's a misunderstanding about the goal of these discussions. While there is an aspect of direct advancement, career talks are about your career, not the next step.

When you have a career conversation, focus on the long arc of what you want to achieve and then how the next 6 to 12 months fit into that goal. You may be in this specific role with this specific manager for a year or two, but the skills and growth are things you take with you for the rest of your career.

The goal of a career conversation is threefold:

  1. Aspirations: Build a mutual understanding of what you and your manager value and what your long-term aspirations are

  2. Skill-building: Understand what skills you need to do your current job and what skills you need to obtain to get to where you want to be

  3. Alignment: Clearly communicate and align on mutual expectations and next steps

One caveat: These conversations are often challenging even in ideal circumstances, so they are most effective between two people who respect and trust one another. While it is possible to have a fruitful career conversation with someone you don't know well or you might have a tense relationship, trust is an important element of the exercise. If you have not yet built that trust, it may be worthwhile to set the foundation first before embarking on this together.

How to Maximize Effectiveness

  • Ask — Speak to your manager about wanting to discuss your future. Note to them that this is not a pitch for promotion but about skill-building and growth.

  • Prepare — Think about what you want ahead of time (see exercise at the end) and know what you value. I have had many career conversations with people on my team who didn't know what they wanted. I explained, “If you don't know where you want to go, I can't help get you there.” If you are not sure of your long-term plans, at least know what you value. That is a good starting point.

  • Make time — Career conversations should be separate from a typical 1:1. It should be scheduled at least a couple of weeks in advance so both of you are prepared. If possible, schedule an hour once every half.

  • Get feedback — Soliciting feedback and support is important in every relationship. A career conversation can help point out your blind spots and also clarify what your strengths and gaps are.

  • Document — A lot of times people think they are in agreement after a conversation, but in day-to-day work, you often forget what was discussed. After the conversation, write down what you agreed to work on, and send a written copy to your manager and ask if they agree.

  • Check-in — Each month or so, check in on what was written and see if you are making progress.

Promotion vs. Career Growth

Promotion and career growth are like weather and climate. They are linked but not the same thing. One is about what is happening immediately, and the other is about the long term. Many companies, like Facebook, promote when someone demonstrates the skills to do the role and the opportunity is open, but doing great work and having an impact is always valued. The best opportunity I ever took was three levels below where I was at the time, but it was also on a rocket ship to something new. I was getting restless in my role and not learning; the chance to build a new product at a new company set me up for a great adventure which brought me here today.

Focus on long-term growth. Just like you can't build a two-year roadmap six months at a time, you can't build a career one half at a time. Know what you want to learn and what impact you want to have. An engineer on my team was debating between two roles. One was a manager role supporting a broad product, strategy, and P&L responsibility while the other position was a deeply technical IC role in machine learning. I asked him what his long-term plans were, and he said he wanted to start his own company. After we talked about it, he realized the choice was clear.

Knowing what you are optimizing for. If your answer is short-term like a promotion or a strong rating, then you are not thinking long-term enough. I knew when I went to Facebook 11 years ago I wanted to build commerce at Facebook. I pitched it repeatedly for five years (and hacked on it many times) before we really got started. I knew what I wanted to work on and I built a lot of things I loved along the way, but I believed that someday we would build enough support to make commerce happen. Knowing where you want to go will help you take each opportunity to get you closer to that goal.

These conversations are hard, but if you go in with the mindset that they are tools for your long-term success, you will find that they will be more fruitful than you could have imagined.

What Matters Exercise

This is a two-part exercise best done together on a whiteboard. Rank these areas from 1 to 6 and then allocate 100 points to them. It helps you align to what you value. Note that this exercise is done with no judgment. What someone values is important to them. There are no right or wrong answers.

  • Impact

  • Promotion / Title

  • Compensation

  • Learning

  • Work-life Balance

  • Culture / Team