Transitioning to Managing Managers

Dmitry Alexeeko

Engineering Manager at Stripe



While at Airbnb, I was responsible for a payment risk team at the same time that I took on another team. That meant that I now had to support a bigger team. One of the engineers on the payment risk team was interested in managing and indeed capable of leading people. I needed to quickly learn how to take on the role of supporting a manager. 

Actions taken

A lot of what I did was trial and error from observing what other people were doing in the organization. I informally watched what other managers did and why they were doing it. 

  • I had to step away from teams and their weekly standups in order to give space to the new manager. They need to be able to figure out their team and grow into their new role. 
  • I switched gears to thinking about a more tactical and execution note for the team and helped managers bring more strategic questions with them. This included setting up conversations with the managers to discuss changes in the timeframe of what the team should be doing. Chatting on a weekly, monthly, or quarterly basis with concerns geared towards the next year or two ahead. 
  • I had to learn to be flexible and adaptive to the different sets of tools, support and help each manager needed. That meant working with more experienced people on strategy for the team’s future. It also included helping newer managers with execution and forming a feedback loop to hear what they should be getting from their teams. 
  • I became more vulnerable with people to the point that I shared my own performance review verbatim with my team. More specifically, the areas that I could improve on and if that resonated with them, I wanted to know. 
  • I gave managers the confidence to drop certain execution or implementation work and reiterated that constantly while giving them a framework of what isn’t working. I helped to better align expectations by establishing a set of personal OKR’s and goals to commit to and look back on in the future.

Lessons learned

  • It’s pretty easy to get stuck doing things within your comfort zone and that you excel in. I definitely made some mistakes along the way. This is, however, an ever-evolving process. Even now at Stripe people are inherently different in terms of strengths, weaknesses, and communication. For me, it’s a constant process of learning, adapting, and figuring out how I can be most helpful for my managers and how they can be most helpful for their teams. 
  • As a manager of managers, your voice becomes amplified and can have a negative effect if you speak up about something in the presence of the team and their manager. It can be misconstrued as a higher-up person holding more importance over the manger; even if just expressing a random thought. You must be very careful about what you say, and communicate it in a language which implies that it is more inquisitive than directive. 
  • Skip level one on ones helped me understand things that new managers may not digest, but that others are still frustrated about, and then relaying that back to those managers. It’s important to make sure they are on point with performance management. 
  • Having a feedback loop was the number one tool that helped me. The higher you go up in the organizational structure, the harder it is to get honest feedback. Setting up trust and feedback by being vulnerable allowed fear to dissipate, and people were able to show me where they thought something wasn’t working or if I had messed up.

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Dmitry Alexeeko

Engineering Manager at Stripe

Leadership DevelopmentCommunicationOrganizational StrategyFeedback TechniquesCareer GrowthCareer ProgressionSkill DevelopmentIndividual Contributor RolesLeadership RolesTraining & Mentorship

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