First-Time Managers: An Answer for a Solid Organizational Structure

Andrew First

Co-founder & CTO at Plannery



A few years ago, I took over management responsibilities of our organization after our VP of Engineering had departed. I was acting as an interim VP of Engineering until we hired or promoted someone to that role. However, I inherited a difficult situation. The organization didn't have a solid structure, morale was low, and I had to manage over 20 direct reports.

Actions taken

To solve the organizational challenges, we had to understand what exactly we needed. Obviously, we needed more managers but before appointing people managers we had to learn how -- if at all -- the teams were structured and what their roles and responsibilities were.

These challenges were too large for me to solve, so we formed a small leadership team to design the next generation of our product development organization. At that time, none of us had much expertise in organizational design. To overcome this, we researched best practices, talked to a number of advisors, and explored different organizational models championed by other companies, such as Spotify and Amazon.

After gathering this information, the product development leadership team had a series of offsites and meetings to discuss the pros and cons of the different organizational models and common best practices, and how we could apply some of that to our own situation. We communicated regularly to the broader team on our progress, but it was taking more time than we initially thought. People were anxious and the sense of uncertainty was pervasive, but we tried to communicate our steady progress transparently. We also listened to their concerns and were open to feedback throughout the process.

Once we decided on the right structure, we garnered feedback from the team on who they would support or not support being their manager. We wanted to learn about their opinions, but it was hardly a democratic process aiming for a consensus. After all, as the leadership team, we were responsible for all consequences of that decision.

Then, I talked to the managerial candidates to learn if they were open to the new role. I carefully detailed our expectations, emphasizing that a managerial role significantly differs from an engineering role.

Once I got buy-in, I had them meet the rest of the team members in one-on-ones announcing the change and getting their support. We made several efforts and investments to help and support this new cohort of managers, including conducting management training, hiring management coaches, creating coaching circles and continuing regular one-on-ones to help them navigate through the transition.

Lessons learned

  • The majority of the new managers ended up deciding to return to ICs after some time, many of whom unfortunately did so by leaving the company.
  • People will usually say "yes" to new roles as they want to be team players. Also, many people are willing to take an opportunity without much thinking of what that would entail. To make better choices, the leader needs to better assess people’s motivation, capabilities, and commitment:
  1. Identify key challenges on the team and assess if the candidate is qualified to solve those challenges.
  2. Understand what drives the candidate to assess if they will be motivated in the new role.
  3. Explain that management is not engineering, and spend as much time as you need walking through the implications with them. Management is not a fit for the majority of ICs given the job is so different and may not be enjoyable by many. Also, the transition doesn’t happen easily. Given that we were promoting several people at once, we lacked a structure for the new managers to learn from and talk to other, more experienced managers about their experience, daily responsibilities, etc.
  4. Some other engineers were upset that they weren't chosen, especially when they saw how the managers were performing. Even though we established and announced a dual career ladder, we were busy with the manager promotions so we didn't do any IC promotions at the same time. As a result, many engineers didn’t consider growth through the technical career ladder as a realistic option, and that impacted their morale.
  5. Make it safe for new managers to fail and go back to being an IC without feeling that they had to leave the company. Our advisors urged us to create a safe environment for people who would take that risk and fail, but we didn't do enough to build a culture around it. Using "Interim" with the title, while it implies an amount of uncertainty, is a good designation to use and give a person some leeway to reconsider their options.

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Andrew First

Co-founder & CTO at Plannery

Engineering LeadershipLeadership DevelopmentCommunicationOrganizational StrategyDecision MakingCulture DevelopmentEngineering ManagementPerformance MetricsLeadership Training

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