Managing a Manager for the First Time: Things I Learned the Hard Way

Cat Miller

CTO at Flatiron Health



A year after I promoted my best engineer to a manager of the team I had been running, the team started to perform poorly--engineers on the team were unhappy, they struggled to make progress on big picture improvements, and the team culture was far from good. It was hard to onboard a new person on the team or entice new engineers to the team.

It was only in hindsight that I realized how unclear I was about my expectations and the things that I cared about. After going through that experience, I came up with an explicit set of expectations and became very transparent to all of my reports what I care about and what I would hold them accountable for.

Actions taken

I stepped in too late trying to coach my manager. As I usually do, I had been letting him set the agenda for our 1:1s, which made our conversation focused on tactical and technical problems. One major switch was for me to start driving the agenda and try to address issues I was hearing about in my skip-level meetings. Unfortunately, by then it was too late to course-correct.

The end result was that he decided to transition away from management and moved to a new team in the company. That failure was a helpful catalyst to my own behavior change: now when I have a new person starting in a role, I am exceedingly explicit about things I care about, particularly those things that are not purely technical.

It is obvious that I want a healthy sprint velocity and external commitments to be met, but it is somewhat less intuitive that I care just as much about every engineer on the team being able to articulate the team vision, and feel that their career is moving forward.

I created an expectation template that evolves over time with every new person coming in. It is a clear list of what great team leadership looks like. It includes obvious items like meeting deliverables, but also other important things like team culture and happiness. This document ensures that my managers and I are aligned and have the same goals.

Lessons learned

Don’t assume that you and your direct reports are aligned on everything. Be explicit as a manager what you care about and what you don’t care about. This can change over time and should be discussed regularly but to ensure consistency and transparency, put it in writing if you possibly can.

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Cat Miller

CTO at Flatiron Health

Engineering LeadershipLeadership DevelopmentCommunicationOrganizational StrategyCulture DevelopmentEngineering ManagementPerformance MetricsLeadership TrainingPerformance ReviewsFeedback Techniques

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