How I went from Tech Lead → Engineering Management
Part two of our series about everything I’ve learned going from a Senior Software Engineer to Tech Lead to Engineering Management.
Hey friends, Caleb here 👋 I hope these articles provide massive value as you look to level up in your software engineering skills and career. Because of your support and readership, we hit 28,000 readers this week. Let’s get to 30k soon! 🎉
In last week’s article I shared: How I grew from Senior Engineer to Tech Lead. It’s my story of breaking beyond senior engineer, and what life is like as a tech lead. Highly recommend reading if you missed it and are interested in going beyond senior!
I know a lot of us engineers hit senior engineer or tech lead and then wonder what’s next for our career. Should we go into management to get paid more and learn some leadership skills?
Maybe like me you’ve heard that you are good with people and projects, so you would be a good manager.
But what would it look like? What would it take to get there?
I’ve asked those questions so many times over the last 3 yrs or so.
Today I wanted to share my journey from Tech Lead → Manager and why I chose to go that route instead of towards Staff Engineer.
Again, if you missed last week’s article, check it out here: How I grew from Senior Engineer to Tech Lead
Let’s dive in 👇🏼
Why move to Engineering Management instead of Staff Engineer?
Great question. I’ve asked myself that very question many times.
A staff engineer once told me: “Caleb, you are such a great engineer, don’t waste all that skill on being a people leader.”
For me it’s engineering is more than just coding.
Early on in my career I had a really toxic boss who made things difficult for everyone on the team. It felt like I had to fight them to do my best work.
They forced poor technical decisions on the team, disappeared for weeks when we needed input, and constantly gossiped about other team members behind their back.
Later on I joined a startup, and had the opportunity to be managed by an incredible engineering leader. She was smart, empathetic, supportive, and pushed me to be better. She completely transformed my view of management.
I started to see that good managers don‘t just “schedule meetings”, do 1 on 1’s, and plan out projects. She showed me that good managers:
listen well
value honesty
empower all equally
are open to change and improvements
Good managers also:
encourage the team to bring their whole self to work
are force-multipliers that help their team level up and thrive
are concerned with their ICs success even outside of the company
care about people as humans, not as machines that make products
Having this kind of partner, cheerleader, and support was life-changing for me.
She challenged me to take on difficult challenges, to own my growth and go hard after new possibilities. It hasn’t been easy, but having that support and incredible management helped me break beyond senior and level up in new ways I didn’t know were possible.
It made me want to be that for others.
That’s why I’ve jumped head-first into this management track.
My goal is to be that authentic, supportive, transparent, force-multiplying leader for others.
I have a very long way to go still, but I’m excited to be on this learning journey.
How I went from Tech Lead → Engineering Manager
My last manager was awesome, but they were severely overworked and managing 20+ engineers across 4 teams at once. 😅
I started looking for things to take off their plate that would save them time, and give me the opportunity to help in a leadership role.
Some of the things I helped take on were:
Sprint planning
Mentoring new engineers
Quarterly OKRs and Planning
Meeting with external partners and clients
Running projects and managing up on status / outcomes
After 3-6 months of this, I had a conversation with my manager about looking to grow into a manager, and mentioned that I’d love to lead one of their current teams.
It was out of the promotion cycle, but because of the business need and my desire + proving myself in various responsibilities, it happened!
It was a win, win for all parties involved.
I got to move towards my goals. And the company gets a manager that’s already earned the trust of the business - and has all the context of the projects, tech, business and ICs on the team. ✅
A hell yes for all involved!
How can I replicate what you did?
If you are looking to grow into a leadership role, here’s several things that worked for me + others I’ve talked with:
Find something you can take off your managers / tech lead / staff’s plate
Ask if you can own it so they can focus on higher priorities and give you a chance to grow and stretch your leadership skills.
Do those things amazingly well. 💪
Keep them updated to build trust and confidence that you are owning it well. 🤝
Continue to grow your responsibilities and thinking as you take on more and more ownership and leadership in various areas
Bring up promotion with your manager and show all the areas you’ve been taking on ownership and impact above your current level
Work on any feedback they share and continue to repeat “The Magic Loop.”
You’ll need to be patient as a promotion into a leadership position – EM or Staff – will take a while and need business funding + justification.
What have you learned from your first 9 months as a manager?
As a new manager I feel like I started over… and I’m learning that’s completely normal!
People management is much different than even technical management as a Tech Lead. I knew that in theory from reading and coaching sessions, but I’m now experiencing the reality of that in my day to day work.
Here are 7 of my biggest learnings so far:
1/ Forming and Storming is Normal.
Anytime you introduce a team change – adding a new team member, a new manager, or doubling the team size + a new manager (as in my situation) – you are going to form, storm, and norm before you are a high-performing team.
During this season, you need to lean into growing together as a team. Figure out what works well for the new team. Learn what new processes are needed because of the new dynamics or tasks you are working on.
Change. Passionate disagreements. Joys. Going in Circles.
All normal when a team changes.
Don’t be like me and be surprised by this. Things might just get crazier before they get better.
2/ People are your new job. People are not tech.
As a recovering people-pleaser, passionate disagreements and difficult conversations are uncomfortable to me. My tendency is to want to pull away and hope they go away.
What I’ve learned through experience is that ignoring them will just make things worse.
The only way to improve is through.
You can’t avoid hard conversations. They are literally your job. Lean into them. Listen with the intent to understand. Build trust with your team.
I won’t be able to make everyone happy – that’s not my job.
But I can help us work towards a healthy culture of learning, growth, and failing or succeeding together. It’s all about healthy teaming now.
3/ Mentorship is huge.
One of the most helpful things to me these last 6+ months have been other EMs and engineering leaders I’ve been able to chat with and learn from.
There've been so many times where I felt crazy, or wasn’t sure if what I was doing was a good direction.
They’ve been able to remind me things like:
My job is not to get people to like me
Strong disagreements can actually be healthy
I’m building a team and a system, not a Caleb does everything checklist
Change takes longer with teaming, review progress every 3 months, not every 3 days
I know many of these in theory, but when someone can come alongside and remind me, or point to a situation I did well or could improve in, my eyes are opened and I level up again.
I’ve also started learning a lot from reading engineering newsletters by leaders. Here are a few of my current favorites:
- and – co-write the newsletter
- – writes the newsletter
- – writes
- – writes ’s newsletter
- – writes the newsletter
Level Up by Ethan Evans (not to be confused with Level Up Software Engineering 🚀– which I write 😅)
- – writes the newsletter
- – writes newsletter
- – writes the newsletter
Before they were all just theory. Now that I’m in the role, I devour them weekly and seek to apply what I’m learning.
Learning + doing + more learning + more doing = Leveling Up 🚀
4/ Public praise goes a long way for your team.
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If you are a paid subscriber, enjoy the rest of this deep-dive where we talk about planning work, mental health, how to stay technical with less / no coding time, and event more resources for learning! 👇🏼
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