Our Worst Mistakes as Engineering Managers

Engineering Leaders from Datto, Trello, and Uber shared their worst mistakes as Engineering Managers during the Plato event #1 hosted on May 15, 2017 in San Francisco.

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When transitioning from an engineer to an engineering manager, you will inevitably make many mistakes. The good news is you can learn a lot from those mistakes. We hosted a panel called “My Worst Mistake as a Manager” as part our of Engineering Management Talks with Plato event on May 15, 2017, in San Francisco.

What was your worst mistake as a manager?

Christian opened the panel with this question. Benjamin was the first to break the ice, and admitted that his worst mistake was not giving proper respect to people when he was addressing problems in a public setting. He was doing it in a non-constructive way in front of others. It was humiliating.

Brett felt his biggest mistake was trust — either trusting somebody too much or not enough. For example, he was trusting his own career to his manager too much and expecting guidance for things he should have learned on his own.

As an answer to Brett’s answer, Tasneem told a short story. Back in the day, someone asked her what she asked from her manager. Her reply was that she didn’t ask anything of her manager and just did things herself because she couldn’t trust her manager to do them for her. Her mistake was assuming that her interpretation of what people ask from her was aligned with their own expectations of what were they asking. Communication was a challenge, and misassumptions had led to misplaced trust, and all that spiraled into not achieving the common goal at the end of the day.

Christian asked Benjamin how he bounced back from losing someone’s trust, and Benjamin gave an interesting answer: “I learned how to breathe.” He explained that he learned to recognize his impulse to do something and learned to step back. For example, when he sees someone doing something he specifically asked them not to do, rather than immediately jump down the person’s throat (his initial reaction), now he calms down, writes down his thoughts, gains his composure, and then approaches the person.

Looking back at your career, what would you change?

“We’ve all made mistakes,” Christian concluded. “In your career, going back, is there anything you wished you did differently at some point?”

Benjamin used an example of humiliating someone, and said if that hadn’t happened, he wouldn’t have been aware of why this behavior was problematic. Although he wishes he hadn’t done it, at the same time, he is glad he did, because it was a wakeup call.

Brett agreed with Benjamin that most mistakes become experiences, but added that he wished that he could have learned it by seeing the behavior in someone else, rather than himself. He also wished he could learn some lessons more easily (the first time as opposed to the fifth time).

“I wish I could learn some lessons more easily. Like on the first time as opposed to the fifth time.”

Tasneem, on the other hand, thought that asking for the feedback on her mistakes made a difference. Her advice was to learn to read body language as soon as possible — that way, we can notice our mistakes sooner and correct them before they escalate. She said there are three things to look for in a person: authenticity, logic, and empathy. Everyone is weaker in one of these, and with engineers, it’s usually empathy.

How do you stop yourself from doing a task yourself rather than trusting your team to do it?

Christian McCarrick, VP Engineering and CTO at Telmate

Christian explained how in Google Project Oxygen, they did detailed analytics on what makes good managers. They also looked the analytics of terrible managers. It was interesting to find out that the worst managers were those who are too busy “doing” to be the manager — they continued to be technical versus being a people-oriented team expert.

All four participants admitted they had fallen into or were currently in this common trap.

Brett also pointed out that there is a different side of the coin. He gave an example of one of his worst managers, who knew the system, all the right cards to play, and all the right people to talk to, but nothing else, which blocked the team on a number of avenues and made things harder for them. “You need to know what to do; you don’t just run the system,” Brett said.

Tasneem explained that she coaches her managers about the “3Ps”: process, product, and people. They are all equally weighted. You should be sure you’re contributing to every level. You need to look at the big picture and see where the product is headed, and understand project-level and technical detail and decisions the team is making. You also need to know how to lead milestones and how to execute. A manager’s job is to make sure the team delivers. Finally, a good manager should know how to lead people so they achieve their goals and are successful.

Benjamin said that he usually skips Scrum meetings, so when he wants to jump in, he doesn’t really know what is going on. When it comes to self-organized teams, he emphasized that you need to trust the team will do it, but on the other hand, still occasionally check in and challenge some of their decisions.

How can new managers stop being afraid to make decisions?

Brett Huff, Engineering Manager at Trello

Christian mentioned Brett’s comment about managers who are afraid to make mistakes and avoid making decisions. The next logical question was how to help new managers stop being afraid to make decisions.
Brett said that if you are afraid to make a decision, you probably lack input, and to talk to other people. He tells the people he works with that he couldn’t do their job because he is not as good at coding as they are; he doesn’t spend too much time with the programming language they’re using. You should talk with enough people until you can reach enough clarity or consensus to make the best-informed decision.

What are your thoughts on the issues mentioned? Have you made similar mistakes? What would you do differently next time?

You can watch the full video below or check out all of the presentations from the event on our YouTube channel.

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