The NO Was Guaranteed

I have a friend who used to say, “The NO is guaranteed. So you might as well ask for what you want, and maybe you’ll get a yes.”

I don’t even know if that phrase makes sense for most people, but it makes sense to me. There is nothing to lose since I already know I’m about to get a no. Every now and then, I get a yes instead, which is a nice surprise.

And that’s how I got my first management position.

Many years ago, I joined a Point of Sale company that was still fairly small. Besides the manager, there were exactly two people in the IT department, and I was hired to replace one of them, who was leaving.

The manager was very hands-on. He had built much of the infrastructure himself and was by far the most technical person on the team. It took me a few months to catch up and understand how everything worked, but eventually I did.

About a year later, he announced he was leaving.

I remembered my friend’s advice. I assumed I wasn’t going to get promoted anyway, so I might as well ask. Being such a small company, I went straight to the COO and told him I wanted the position.

Well, it was one of those times when I didn’t get the no.

That was my first official leadership role.

Things worked out well, and I stayed in that position for many years. But looking back, I can see that I wasn’t doing leadership very well.

As the company grew, so did the IT department. We added more engineers, but I was still doing most of the heavy lifting. I was on call 24x7x365. I was the first point of contact for developers. I was usually the first person in the office and the last one to leave.

It was a relief when I hired some very strong technical people and started offloading work to them. But looking back, I can see that I never fully used their potential.

I still believe leaders should be technical. They should understand the work their teams do.

The problem is that the more technical you are, the more tempting it becomes to jump in and do the work yourself.

At first, that feels like leadership. Problems get solved quickly. Customers are happy. Systems stay online.

But over time, it creates several problems.

The first is burnout. There are only so many hours in a day, and eventually, you become the bottleneck. Every difficult problem, important decision, and emergency ends up on your plate.

The second is frustration. Nobody will do things exactly the way you would. If your standard is that every solution must look like your solution, you’ll spend your career disappointed.

The third is that you unintentionally train people to depend on you. Why take ownership when the manager will eventually step in and fix it? Why make a decision when the manager will make it for you?

And that leads to the biggest problem of all: people lose agency.

I’d like to say I eventually realized that every time I jumped in to solve a problem, I was creating a cascading effect that hurt both my team and me.

But that wouldn’t be true.

What actually happened is that I went back to the individual contributor track for a while. Years later, I found myself in a leadership role again. This time, instead of winging it, I decided to educate myself.

There are so many good books on leadership. I don’t know how many I read in a relatively short period, but eventually things started to click.

Not just the delegation problem. I began to see that I had made plenty of mistakes in the past. Not mistakes that caused major harm, but enough to keep both my team and me from thriving.

As technical people, we spend years honing our craft. We take courses on cloud computing. We attend computer science lectures. We read Clean Code and Code Complete (probably more than once). We invest thousands of hours becoming good at our jobs.

Then one day, we get promoted to management.

Suddenly, we’re expected to hire, coach, delegate, motivate, resolve conflicts, run meetings, communicate strategy, and develop people skills we may never have formally studied.

Looking back, what surprises me most is not how many mistakes I made.

It’s that I expected not to make them.

I treated leadership as the next step on the technical ladder, when in reality it was a completely different profession.

If you’re pursuing a leadership role, or you’ve recently landed one, invest in learning it with the same intensity you invested in becoming a technical expert. Read the books. Find mentors. Study the craft.

Because the most dangerous thing about leadership isn’t what you know you don’t know.

It’s what you don’t even realize you’re missing until it hits you in the mouth.