Identifying personality strengths in my reports
6 December, 2017
When I started as Engineering Manager at Trello, I immediately took on two teams, consisting of 11 direct reports. Trello was in the middle of doubling their headcount in one year, so I needed to get to know my direct reports rapidly, as there was no stable status quo to fall back on. With things changing so quickly, I needed to know who I could count on, and for what, so that we wouldn't crash and burn.
I knew that it would be difficult for people to open up to me, as I was new and they wouldn't be sure of what I would do with their secrets. During my first week, I spoke to each of my direct reports and told them what they could expect of me. This included assurances that I was there to help them. During my first two months, I continued having one-on-ones with each of my direct reports, and I made sure that I spent time talking about non-work related things, such as family, hobbies, and weekend plans. I also looked for areas in which they needed a little help, so I could contribute by helping them unexpectedly or meaningfully.
After two months, I sent an email to all of my reports, letting them know that I wanted to talk about career arcs in the following week, during their one-on-ones. The email included prompting questions, such as "What do you want to be doing in five years?", "What don't you want to become?" and "Who do you envy and why?". By giving them the questions a week before our meetings, I allowed them time to think over their answers. Through this process, I was able to identify outstanding people and technical leaders, as well as coasters and social butterflies. I got some very candid responses from my reports, such as "I know that I should want to be a leader, but I just want to code," and "My dream in five years is to leave this place and start my own company."
I think I took the right approach. Relationships grow over time, and I got more honesty from my reports by taking the time to demonstrate I was trustworthy before asking them to trust me. By starting with trust and then discussing motivators (such as envy and dislikes), instead of goals (which have a tendency to become trite), I was able to come to understand each of my reports on a much deeper level.
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