Taking just one step too far

A bit crazy approach to engineering management

My all-time favorite manager once told me in a feedback session:

“I really love your passion, but you always take just one step too far. Stopping just a bit before that last push can save you so much friction and headache”.

As I wrote in Safe vs ALL-IN Engineering Management, I’m an intense person at work. I don’t shy away from conflict, I say what’s on my mind, and I push hard for my agenda. I like that part about myself, and I’m usually ok with the drawbacks.

A few years have passed since then, but I still keep thinking about the ‘one step too far’ phrase.

Maybe I’m wrong? Maybe I should stop a bit earlier?

What does it mean to take one step too far?

First, here are some random examples from my career to explain what I’m talking about:

1. Critizing the CEO

I really like sharing my opinions, even if nobody asked for them. Especially with the senior leadership of the startups I’ve worked at.

A few years back, we had a change of CEOs. I used the opportunity to write a long email to the new one, covering all the parts I felt weren’t working well in the company.

As he was a great guy (unlike the previous one, who never replied to my emails), he replied after a couple of days, answering every single point with his take.

What do you think yours truly did?

I replied with an even longer email, criticizing his responses (instead of appreciating all the time he spent, saying ‘thank you’ and shutting up).

Yeah, I know. One step too far.

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Thanks Linear for supporting today’s article!

One place I (unfortunately) never pushed hard enough: good tools for my team. It was too easy to fall into the trap of using software everybody hated, and convincing myself that switching is just too hard.

That’s why I was so impressed with Oscar Health’s story. Atlassian once told them they had one of the three most complex Jira instances in the world (!). Years of customizations, countless fields, deeply embedded workflows.

Still, they moved 600+ people to Linear in under a month - and nobody had to be pushed. Engineers started using it, the rest of the org followed, and their VP of Engineering summed it up: "Everybody here seems happier with Linear."

If you're still telling yourself switching is too complex, read how they did it:

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2. Pushing the recruiter

6 months ago, I was interviewing for an engineering manager role. The process went great, and I reached the final stages.

I was surprised not to meet the engineers I’ll manage at any stage, so I requested to meet all of them for 30 minutes - both for me to get the vibe, and for them to ask any questions.

The recruiter agreed, and the meeting went great. (It was a good idea, should have probably stopped here).

Unfortunately it was late August, so half the team was on vacation.

A few days later, I came for the final HR interview. Right afterward, I told the recruiter that I’d like to talk with the rest of the team before I make my decision. She told me she prefers to respect their vacation (should have definitely stopped here).

I got the contract, but I still wasn’t satisfied. I asked the recruiter one more time if it would be possible to just message the engineers on vacation with my phone number, asking them if they would be willing to talk.

She politely told me to chill and move on…

See what I mean by ‘just one step too far’?

3. fighting for a 75$ budget (full story shared here)

Right after getting promoted to my first management role, I booked a $175 escape room for a team night out to bond, assuming reimbursement would be easy (5 people, including me).

Turned out the yearly budget had already been spent by the previous EM. My manager told me to just wait a couple of months for the new budget.

I felt it wasn’t fair, and I wanted the team to have a fun experience right now. So I went to talk with the director of HR to complain.

She was quite nice. She told me that the best she can do is $100, which will cover a small dinner or bowling.

I was furious. Come on, it’s $175, I’m a newly appointed team leader trying to bond with my team - who cares about yearly budgets? So instead of waiting or doing something cheaper, I covered the difference myself, convinced my righteous anger would eventually get it approved (it wasn’t).

Why I still believe in that approach

In all of those cases, I wasn’t completely blind to stepping out of normal social bounds. I felt a bit uncomfortable, but I decided to still take that extra step.

There are 2 main reasons:

1. That’s the best way to learn the limit (for me)

Every person, org, and situtation had a different ‘limit’. In some cultures, maybe none of those behaviors were ‘too far’. In others, it would have probably been 3 steps in the wrong direction.

I believe that if you always stop as soon as you feel ‘uncomfortable’, you’ll never learn where you can push and where you shouldn’t.

Each of the situations taught me some lessons (in hindsight…), improving the way I learn and communicate.

2. The good outweighs the bad

I believe that most people appreciate that tendency to push for your agenda - as long as you know to learn from your missteps and adjust. Being too timid is almost never good for a manager (and their team).

While I would have preferred to stop at the ‘perfect’ timing, I believe the outcome was better in all 3 situtations that if I hadn’t acted at all:

• I got at least some budget for the team night out, and we had fun at an important time for us.

• I’ve gotten that role, and the conversation with the future team members was a big part of it.

• Even after my reply, the CEO was respectful and even scheduled a 30-minute meeting to talk with me. He put me in place during the call, where I finally learned to shut up. We had a great relationship afterward.

Final words

For me, the biggest challenge is to take just ONE step too far, and not multiple steps.

I use that feedback from my previous manager as a ‘shield’ to test the waters. Before I send a controversial message or push for something that’s a bit out of my place, I often add something like: “I was told that I have a tendency to push just one step too far, so please forgive me if I overstep.”

Then I judge by the reaction whether I actually overstepped :)

(I was recently told: “yeah, I fully agree with your previous manager” 😂)

Discover weekly

1. Reversibility: The Joy of Starting From a Saved State by Michał Poczwardowski. A great mental model from an area I love - gaming :)

2. Product Management is all about people, not technology by Benedikt Kantus. As engineers take more and more product ownership, understanding the PM role became more important.

3. How to coach your team (without making them defensive) by Wes Kao. Another gem by Wes, a must read for any manager of people.