Effective career conversations

While I was learning to have effective 1:1s, the career conversation 1:1 was the one I dreaded most. Every skilled manager says it is a good idea to regularly sync on career growth, but who was I to talk about other people’s career? I had never done a round of performance review. My own understanding of the ladders and levels needed to be calibrated. Once again I turned to some structures to gain confidence. I leaned heavily on the advice from Jay Shirley and Julia Evans in doing so.

Recurring career conversations

While people may have different ideas on how often to have career conversations, the consensus is they should at least be more often than performance reviews. I am currently comfortable with a monthly cadence, which gives me ample opportunity to avoid surprises. As people say, the number one rule to performance management is no surprises.

Practically speaking, I schedule monthly career conversation 1:1s on top of the regular weekly 1:1s in the same time slots. It is a symbolic move, but I found it quite useful to help fight my internal procrastination. Without the reminder, I would dread, delay and eventually skip it. With the reminder, I would have no excuses to pretend that I “forgot” doing career conversations. The reminder also helps preparing the other person’s mind so that we could have effective conversations.

The monthly cadence turned out to be a lower bound, which is a big success to me. Sometimes we could not finish the conversation in one setting, and it would overflow to the 1:1 in the following week. My interpretation was that we did not do the career conversation just to check the box. Instead, we were having effective conversations, and, as a result, we needed more time.

Ladder reading

I started every series of career conversation with an open-ended question on the other person’s career aspirations. For the majority of them, the answer was to get to the next level on the Software Engineer track. Ladder reading, the first structured move, would then follow suit.

I was fortunate to have a suite of well-defined ladders and levels, but I also imagine it would be a fun exercise to create one if it did not exist. With the ladders and levels in place, I would follow Jay’s instruction to read them with the engineer, share comments, and write down notes. One trick we found was to always compare and contrast two adjacent levels to call out differences. Depending on the engineer’s confidence, we could start with L-1 vs L or L vs L+1, where L was their current level.

While doing the reading exercise, we tried to be generic and not to talk about the individual’s performance. I found that helpful to stay objective. That is not a hard and fast rule though, because at times we needed some concrete examples to pinpoint the differences across levels.

Performance Heatmap and Brag Docs

With a shared understanding of the ladders and levels, we would then move on to the performance heatmap exercise¹¹ I believe Amber Feng created the first version of Engineer Performance Heatmap at Stripe.. It is a spreadsheet mapping out every expectation from each level. For each expectation, there are columns for the engineer and the manager to fill in comments with specific examples and how well they are performing. Some people prefer to fill in the sheet asynchronously, while others like to do it together in the meetings. Regardless, the key point to me was to arrive at a shared view of their performance outside of a formal performance review. Building on top of that, we would find strengths where they could sustain the same behavioral patterns, and discover opportunities where they could take actions to improve.

The performance heatmap overlaps with the brag document. My view is that they are different projections over the same set of data. The brag document is better for creating a narrative in writing performance reviews, whereas the performance heatmap helps visualizing gaps to get ready for the next level. If the engineer keeps an up-to-date brag document, the heatmap exercise can be done much more effectively because relevant examples are ready to be fetched.

Career development plan

The final structured step would then be creating a career development plan. The plan would be comprised of four sections: current condition, target state, proposed projects and practical advice. The current condition and target state would be derived from the ladder reading and performance heatmap exercises. The proposed projects and practical advice would then be tailored to that condition and target. For example, suppose an engineer would like to move to the next level. They were technically competent, but needed to demonstrate project coordination and leadership skills. The proposed projects would be breadth-shaped and require cross-team or cross-functional collaboration. The practical advice would be to focus on communication and mitigating schedule risks.

I started the practice of writing career development plans recently in anticipation of my parental leave. I have not fully seen their effects yet, but the early feedbacks were positive. I intend to iterate on this practice and to keep doing it regardless of whether I would go on a leave. Jay has also made an insightful point to allow engineers to write their own career development plans, which would help with scaling this practice dramatically. I plan to experiment with that idea in the next round.

Rinse and repeat

The career conversations do no end there. They never end. Instead, they form a loop, especially when we are successful in those conversations. This never-ending quest presents as big a opportunity to their career growth as to that of myself. To make sure I stay organized, I keep links to all these documents in the master 1:1 doc²² See the Effective One-on-One post for my 1:1 toolkit.. For my structured mind, it appears the best thing to structure these structures is a meta structure.