Every Engineering Manager Needs a Sidekick
Why having a sidekick makes you a more effective leader.
A few years ago, my org went through a leadership shakeup. A new SVP arrived. A few days later, a new Principal Architect joined. They had worked together before. They seemed to make a good combo.
It wasn’t a coincidence.
I had seen this happen before. And chances are, you have seen it too. When leaders change, they bring in someone they trust. Sometimes, a whole entourage.
That’s when it clicked. As an EM, I needed to start building my entourage too. And it starts with a sidekick.
What Is a Sidekick?
Every hero has one. Batman has Robin. Frodo has Sam. Even the Avengers rely on each other to save the day.
As an Engineering Manager, you might not be fighting supervillains or trekking through Mordor, but your job is full of challenges. So, why do it alone? Ask for help.
For an EM, a sidekick is an engineer on the team. Ideally a senior or lead engineer, but really anyone with potential. Someone who challenges you, supports you, and keeps you grounded. Someone who:
Has complementary skills.
Is your trusted “go-to” person.
Challenges your ideas constructively.
Can be counted on when you’re on vacation.
They’re an active partner in making the team better. They make you a better leader.
What a Sidekick Is Not
A sidekick is not a personal assistant. They’re not there to do your job or clean up your mess or blindly follow orders.
And no, this isn’t about playing favorites or diminishing the role of everyone else. A strong sidekick strengthens the entire team by improving alignment, decision-making, and execution.
How a Sidekick Helps You Succeed
Now, don’t go to someone and ask, “Will you be my sidekick?” That’s weird. Just like in any good partnership, the bond forms over time. The trust is built through collaboration, tough situations, and shared victories.
But once you have a sidekick, they become a force multiplier. Here’s how they help you (and the team) succeed:
1. They Take On The Hardest Technical Problems
There comes a moment in every EM’s journey when they can’t stay in the weeds anymore. But that doesn’t mean the hard problems go away.
Your sidekick steps in where you can’t. They take on complex technical challenges that would otherwise require your attention.
That tricky migration project with lots of unknowns? They figure out the path forward.
That system design decision that requires deep technical knowledge? They lead the discussion.
That incident that needs hands-on debugging? They’re the first to jump in.
By handling these challenges, they keep you from getting sucked into details, while ensuring the team still has the technical leadership they need.
2. They Boost Your Confidence (When You Need It Most)
As an EM, it’s easy to get lost in self-doubt. A good sidekick sees what you can’t. They see your strengths in the blind spots.
When I first became an EM, I was suffering from a bit of imposter syndrome. I hadn’t fully accepted myself in the new role. I kept wondering: Am I even making an impact?
One day in my 1:1, I opened up a little with a reportee. Instead of judging me they reminded me of my strengths. They shared where I had helped the team and where I could focus on.
That conversation set me up to take decisions confidently.
3. They Give You the Feedback No One Else Will
Managers get very little honest feedback. Employees hesitate to share their true thoughts either out of politeness, fear, or company politics.
Most of the time, the real feedback only shows up in anonymous surveys. And by then? It’s too late.
But this reportee was able to call out where I could improve in real time. On one instance they said:
“Hey, the decision to invest in that project dragged on for months. Maybe next time don’t involve everyone until the details are clear? It created unnecessary anxiety.”
No fluff. No sugarcoating. Just honest, constructive feedback.
4. They Help Shape Team Culture
Culture isn’t what you write in a document. It’s what team members actually do. Especially when the manager is not looking.
A sidekick helps reinforce how things get done on your team. For example:
If you want a culture of psychological safety, your sidekick can lead by example—speaking up first in retrospectives and encouraging others to share.
If you want to raise the technical bar, they can set the standard through thoughtful code reviews and mentoring.
If you want to avoid burnout, they can model healthy boundaries and push back on unsustainable workloads.
In short, they amplify the culture you’re trying to build.
Wrapping It Up
As EMs, we often feel like we need to do it all alone. But great leaders know that success isn’t about going solo.
Find your sidekick. Think about the person on the team who makes you a better leader. Who would you take with you if you switched companies?
I know mine. Who’s your sidekick?
Further Reading: Remember your sidekick is not a lone genius. They’re the hero as well as the glue your team needs. More on that topic in this post by
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Thanks for sharing. It's so true that senior leaders usually form their own circle, and they bring the circle with them wherever they go. Only when the entire group present (i.e. value multiplied) can that senior leader demonstrate their true value.
"And no, this isn’t about playing favorites or diminishing the role of everyone else"- I absolutely agree with this sentence, but sometimes this is the hardest part for other people to understand. They tend to see it as favoritism and don't understand the advantage that such a strong connection brings to the team.
But, in general, I feel completely connected to the article and, in my case, I also add a Product Manager as another helper, a triangle therefore!