hyperbo.la :: Scaling Myself by Letting My Team Fail

Scaling Myself by Letting My Team Fail

Ryan Lopopolo | July 27, 2023

I am currently a Group Tech Lead for a developer productivity organization of 5 teams and 35 engineers. I am jointly accountable for the success of these folks with the Senior Manager I partner with.

With 5 teams, there is a lot happening concurrently. Each team is committed to 3 or 4 OKRs each quarter; combined with the writing heavy culture, it is rarely feasible for me to review every document and track every project directly. Each week, I find I can provide attention to 3 things at most (technical or not), so protecting my ability to focus has been essential to scaling myself.

Using Cost of Failure as a Proxy for Attention

One technique I've developed that has helped me be more ruthless with my focus is to distinguish between projects where it is ok for folks to fail on their own versus projects where failure is not permissible or is expensive. If it's ok for folks to fail, I spend way less energy on these projects.

Sketch of a dejected bear and a motorcycle.

One easy way I use to determine which projects can't fail is to listen to leadership and focus on what they think is important. This might look like:

  • Finding ways that my teams' committed roadmaps roll up a set of company "big rocks".
  • Reading the tea leaves around AI being the next big thing.
  • Tracking which OKRs are committed by the larger Foundations organization that my developer productivity organization rolls up to.
  • Aligning with my manager during OKR review on what projects we both believe are can't fail.

Leaning into this technique and being public about it with my broader team also aligns my actions with the making opportunities for others part of the Staff+ role. Leaving projects more loosely defined or less closely supervised provides space for Senior Engineers to gain project lead experience, gain direct exposure to the why parts of building scalable infrastructure, and build comfort with ambiguity.

Identifying Skill Gaps

As a precaution to the previously mentioned approach, if I notice a pattern of repeated failures among team members when they have the freedom to handle tasks independently, it is crucial to acknowledge that there may be skill gaps. This then becomes an area deserving of more dedicated attention. I mostly approach this area from a project perspective; but sometimes after digging in with the line engineering manager closer to the project, I might provide focused support to 1 or 2 ICs who worked on the project. Usually this manifests as a prolonged 1:1 engagement to build up systems thinking skills.

For example, a team I support owns a load-bearing (but legacy!) piece of infrastructure which has high operational burden and frequently fails to meet SLAs. Upon setting the direction for the team to improve things, I took a largely hands off approach to allow the Senior Engineers on the team to flex some design and project leadership muscles.

But when the changes the team were making increased the brittleness of the system (for example by directly porting bash scripts to golang instead of writing idiomatic go code) and caused more SLA violations, I pivoted my focus to upskill the team. Some techniques I used were:

  • Spend hands on time with the team writing code in the services they operate.
  • Introduce patterns in the codebase (like the command pattern) which are cargo-cultable.
  • Leading by example to build a culture of maintaining a quality bar in code review.


A failure mode I sometimes observe with Staff+ engineers is that they struggle to give away their LEGOs and try to have their hand in everything their group touches. This presents a very real risk of burnout, but it also limits the size of the group one can influence. The ability to let it go means other parts of the organization can carry the torch.