I started actively applying for management positions in late 2018. Granted, I personally held little hope for that particular position. I’d already clashed with the hiring manager on a number of occasions on the most fundamental of issues: feedback. In retrospect, I’m very glad I didn’t get the position.

I wanted to move into leadership for a number of reasons. I was doing a lot of mentorship, coaching, training, community outreach and support, and I wanted that work to count towards promotion. I had had a number of bad experiences with management which made me want to be part of the solution. And I wanted to figure out how to make the jump so that I could help other folks struggling with the same thing.

This first attempt was an opportunity to lead the team that I was on. At that point in time, I was the most tenured software engineer on the team. I had a history of the interns I mentored becoming valued full time employees. Most of the team consisted of folks I had onboarded. I had lead our team to organise various extra curricular events. I’d participated in customer onsites. I thought, barring the relationship with my manager, I was a shoe in. Except that I wasn’t. One of the more recent hires, who I’d also onboarded, had been hired with the intention to turn him into a team lead. He had an MBA, and a much better relationship with the hiring manager.

What I learned from the process was that I had a lot of ideas of what kind of manager I wanted to be, but I had no training, and no tools. I started reading books on the topic, asking for recommendations from the leaders at the company I admired. I read Radical Candor and How to Win Friends and Influence People. Aside from providing me with new tools, what both books had in common for me was that they highlighted the importance of sincerity and trust in all relationships, personal and professional. After a lot of reflection I didn’t see a future where I trusted that manager, or other important parts of that org. So I left that job.

I moved on to Cisco, under my, to-date, best manager ever, Dave Duchene. He was the opposite of my previous manager. I was listened to, trusted, given great feedback that I could action on. When I told him I was interested in leadership he and another manager got me into Cisco’s JUMP program for Women in Leadership in San Francisco. The day I was supposed to leave (I’d brought my carry on into the office) was the day the Cisco banned travel due to the Covid-19 outbreak.

A few months later, I was able to participate in the JUMP program virtually, and it was fantastic. A 4 day course covered leadership styles, feedback delivery, one one structure, presentation and self confidence. We had group sessions where I listened, and was listened to. My favorite part was getting to do a 1:1 session with a professional coach. I worked with mine on treating people who were my seniors like normal people. She used a card metaphor which I can’t remember but clearly worked as I haven’t struggled with it since.

I did leave Cisco. There weren’t any imminent opportunities to practice the skills I’d learned with JUMP. My accountability buddy and I met biweekly. She had great progress to share, mine was stagnant due to a lack of opportunity in my department. I moved to a new project I didn’t enjoy and my end date on that project kept getting pushed further out. The pandemic meant that I was also lonely, exacerbated by being on a team I didn’t technically belong to.

I was approached by A Thinking Ape. I was their first external Tech Lead hire. I made it clear in my interview process I was looking to move into engineering management. It still took a year and a bit and it was not easy.

My first boss had me run a project after 2 months. I created and presented project plans, estimations, technical design docs, evaluations of technologies that were being considered, all things I’d done before, no big deal. He’d reviewed everything and agreed it would be a good solution. There were two problems. Us. We were both unfamiliar with the codebase, and I didn’t know that. He was my other engineering resource on the project. I wrote the new microservice, and he said no problem to integrating it with the codebase. There were problems. We slipped all of our deadlines. I lost trust in him and some respect for him. I’m sure it went both ways.

I transferred teams. Thanks to the failure of the previous project, I had a lot of trust to build again. To do this, I doubled down on listening, I reported out more frequently, I flagged issues fast and otherwise prioritised communication. In our first 1:1, my new manager gave me feedback on my previous project I’d never received from my previous manager. It was a great way to establish the trust I didn’t even realised I’d lost in the company’s management. I found it much easier to succeed when I was getting critiqued on a regular basis, especially by someone I trusted.

After a few months, we disagreed on an approach I wanted to take to a problem. I said what is now my catch phrase for the first time “I’d like to run the experiment”, and he agreed. I got to run a lot of successful experiments over the coming months. I found a new passion in solving what looked like technical problems with training, communication, incentive structures and - ooh scary - just the right amount of process.

Eventually we began planning for him to hand over the team to me. I took ATA’s leadership training. I did roadmap planning. I started running regular meetings, I took on reports, I attended calibration meetings at the end of the quarter and then I took on the team. It went well. I’m so proud to say that year over year, I receive feedback that my team trust me.

TL;DR - Most impactful lessons I learned about becoming a manager…

Your relationship with your manager matters more than you think it does. They have to trust you to do your job, and to help them do theirs. You have to be able to trust them to tell you you’re right when you’re right and you’re wrong when you’re wrong. If you’re there, you have to do the work to maintain that trust. If you’re not there, you gotta get there, or you gotta get out.

You serve yourself best by learning leadership skills before you need them. Do people get jobs without doing this learning in advance? Yes. Can I tell you how to do that? No[1].

Giving and receiving feedback well is one of the most valuable skills you can have. And you can learn it [2].

Opportunities don’t always come up when you’re ready for them. Try to take them anyway. Run the experiment, worst case you learn something.

You have to trust yourself. What do you value. What’s your opinion about X. Where’s the line you won’t cross. Is Y a real problem or something you can work around. Don’t do things for your career, or for others, that will erode your self-trust. Sincerity isn’t just for other people.

  1. 1.Dave recommended The Manager's Path to me. This is a very dry book compared to the previous two I mentioned, but it contains practical information for anyone looking to understand expectations of the next rung of their careers. It did help me identify gaps I needed to fill in my understanding and training.↩
  2. 2.I might be telling on myself a bit here, I was recommended the book Thanks for the Feedback which is an excellent resource not just for those of us who default to a little defensiveness on receiving feedback, but also for giving better feedback. It has made my mandatory reading list for future leaders.↩