Pay attention to time between wins

One metric that I’ve come to realize is important in management is what I like to call time between wins.

Time between wins is just the amount of time in between someone successfully wrapping up one piece of work and wrapping up the next piece of work.

This metric is important because, in my opinion, one of the strongest contributors to burnout is when the relationship becomes murky between the effort you put in and the results you get out.

The burnout cycle

The burnout cycle that I’ve experienced myself and seen happen to other engineers is as follows:

  1. An engineer takes ownership of a complex project and is excited about the challenge
  2. Because the project is complex, the number of tasks required to finish starts to grow quickly
  3. As the number of tasks grows, the total amount of work done remains high but the average pace per “branch” of the project decreases because the engineer is spread thin. At this point though, the engineer is still feeling good about the project, if a little overwhelmed.
  4. As the pace slows on each branch, they remain open for longer and longer. The engineer starts to lose the feeling that their effort brings them meaningfully closer to their ultimate goal. This is a dangerous place to be.
  5. Days start to slip away. What happened to today? This week? How does it take three days to reply to a relatively simple comment on a code review? “What’s wrong with me?” The engineer starts to feel bad about their work and they dread showing up to work, feeding into a negative feedback loop.

How can this be avoided?

As a manager, you’re the lifeguard on duty looking out for this anti-pattern.

This is where time between wins is important. Time between wins is a simple metric to tell you “has this person had any success we were able to celebrate recently?”.

What’s a healthy amount of time between wins?

In my opinion, somewhere between a couple of hours and a couple of days. Less than that and it’s unlikely that the task is large enough to feel meaningful. Greater than that and, in my experience, that relationship starts to feel fuzzy between effort and success.

How can a manager help decrease time between wins?

As a manager, you certainly can’t just hit the “easy win” button when someone’s time between wins starts to exceed your target threshold. You often lack the context to help the project along meaningfully and doing so would likely be construed as micromanaging, anyhow. So what can you do?

Ensure tasks are properly scoped

The most meaningful way that you can help is to make sure that tasks are well-scoped. Task scoping is mostly arbitrary, anyhow: you could have a task on your list of “Rewrite front-end in TypeScript” and it’s certainly a well-defined task, but if it takes three months it’s certainly too large to not be broken up further.

You should help your teammate break down any task that’s likely to take longer than a couple of days into smaller tasks. For my team, that generally means smaller GitHub issues. In each of those issues, you can say something like “Blocked by X” and then basically make the larger issue a list linking out to many smaller issues.

Ask that the owner delegate

Another empowering way to help decrease time between wins is to essentially make the issue owner a temporary team lead themselves. Are there any well-defined pieces that don’t require too much context ramp-up that can be handed off? If so, ask if you can take them yourself or delegate them to a teammate, accelerating the progress on the overall issue.

In my experience, it requires more prodding than you might expect to get someone to hand off subtasks. Doing so can feel like admitting weakness or failure. As a manager, you need to convince them that it’s neither and that delegation is a demonstration of leadership.

Pair program

Decreasing time between wins is, in my opinion, one of the great benefits of pair programming (in addition to knowledge sharing).

Paired tasks often take more than half the time they would have take if tackled alone, so from a “pure efficiency” perspective, pairing rarely seems worthwhile. However, you get to celebrate the win with someone else, making it sweeter. Furthermore, the win is shared by multiple people. In other words, you’re multiplying the emotional reward for the work, increasing morale.

A healthy, energized attitude towards work

Keeping time between wins low is a great way to help the people on your team enjoy a health, energized attitude towards their work. If they put in a full day worth of hard work on a worthwhile problem, it’s your job to make sure they know that work is valued and fits into a larger effort.

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