I’ll Never Be a Chief Technology Officer Again… Unless It’s for My Own Company

Here’s why.

James Williams
Jan 9 · 8 min read
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Photo by Andrea Piacquadio from Pexels

Chief technology officer is like being Jon Snow in Game of Thrones: you are the bastard executive.

I dreamt of this titled position from a young age. I wanted to change the world with technology. With ingenuity and a computer, I could do anything.
When I got my hands on my first coding magazine, I thought I had won the lottery. Letter by letter, I’d type in code to make things work. My fascination would lead me to college and later a career in technology.

I had no idea what life as an executive had in store for me. They say ignorance is bliss, but my moments of joy were far and few between. I thought it would be everything that I dreamt of, but it was a nightmare

The First Betrayal — Tricked by a Savvy Salesman

The first time you take the post as CTO, you fail without knowing it — at least I did. Everything you need to know about the job is cloak and dagger. Executives speak a secret language. There are signals you don’t know until you get your butt kicked over and over.

One day, the Executive Vice President asked me to lunch. He walked into my office.

“James, lunch is on me. Let’s go.”

I hopped in his pristine Mercedes. The leather was new; it smelled like a cow. He told me that we were a brotherhood connected at the hip. Together we’d turn the company around. He showed me pictures of the property he would buy as we traded stories about how we’d spend our cash once we sold our stock.

We pulled up to a trendy cafe with unique names for simple things like sandwiches. The waiter handed us cloth napkins, and food came to us at a wave of the VP’s hand. He didn’t bother to ask what I wanted.

He leaned in and told me the three features that would take us to the mountain top. “This is our last job, James.”

I explained that there were tons of things to fix. Before we could build those features, we needed time to shore up the foundation. The platform wasn’t scalable. The board trusted me to “do the right thing.”

He sat back in his chair. “James, I respect that. Now I see why we hired you.”

The rest of lunch was small talk. We both vowed to do lunch again more often.

Two days later, I walked into the executive meeting. The CEO had his arms crossed. He had the same look on his face that Mike Tyson had before he bit Holyfield’s ear.

Before I could sit down, the CEO went on a rant.

“James, how do you think we’re going to sell anything if we don’t build software? Steve tells me you plan to spend a year screwing around. Our customers will wait for critical features.”

He explained that my plan would lose critical customers. There was no way “the rest of the executives were willing to wait while you get your head out of your a$$.”

The EVP never lifted his head. Next, the projector turned on. The EVP stood up and proposed his technology plan.

The slides looked great.

Everyone’s a Technologist

Here are a few things I have never seen:

  • A financial plan completed, changed, or vetted by a CTO
  • A presentation about the company finances by a CTO
  • A CTO’s sales plan
  • An ambush meeting where the CTO takes over sales

But everyone thinks they can do technology. The Google search-bar created more Monday morning quarterbacks than in any other field.

Everyone thinks they can do better than the CTO. You know, the one with the esteemed career and credentials to back it up.

It’s easy to feel trapped. The moment you focus on technology, you forget to look over your shoulder for a coming dagger. If you focus on politics, your team and the technology suffer.

At many companies, walking the executive hallways is like navigating a minefield. One step to the left, and you lose the engineering budget. A step to the right and every engineer works an eighty-hour week.

Each time you start a new CTO job, you start all over. You set up your office, beaming with pride. Change is coming.

As soon as you set up that family picture, you get invited to lunch.

Office Politics Create Bad Technology

Politics rule executives.

At some point, you have to become a political animal. You must master finesse, but know when to use your hammer. If you’ve read anything I wrote before, then you’re aware of the poker chips analogy. You can’t keep this job if you aren’t willing to risk it.

Most of your colleagues mean well, except for the occasional bad apple (let’s call him Steve). Although free lunches are never free, it’s possible to avoid unnecessary power struggles. By losing political battles over the years, I learned to build solid relationships and commit without committing.

Your goal is to do the right thing, despite your colleagues. Playing the game will allow you to package up architectural fixes into features even Steve would like. Now and then, you have to toss the sales team a bone.

It’s a give and take. I’ve watched many purists lose their jobs. They took their pulpits with them, leaving room for the next guy.

The best approach is to make friends, rather than being right. Acting on your righteousness is a slow burn — like a candle. The trick is to motivate, convince, and sell. You’ll quickly learn to concede some battles to win the war.

The Second Betrayal — Ambushed by Colleagues

I got an email at midnight notifying me of a technology meeting at 7 AM. I arrived at the office. Clenching my coffee, I climbed the steps to the conference room.

Five engineers were sitting and waiting. None of them worked for the company. I had worked with two of them at other companies in the past.
Three weeks prior, I had outlined a new architecture. The approach would allow us to scale to a wicked number of requests. My technology choice wasn’t the shiny new toy that a Google search tells you to use, but I knew my plan was solid because I’d vetted it with industry experts. Besides, I had done it before.

Well, it turned out no one believed me. So the five goons in the office were there to ask probing questions. Let’s say they used to work for a well-known, respected technology company.

The CEO launched into leading questions to see if this surprise panel could stump me. I prepared myself, but I was more than annoyed.
I burned through whiteboard markers. I drew arrows, boxes, and sequence diagrams.

Two hours later, the witch hunt was complete.

When we left the conference room, one of the guys I knew said, “what was that?” I spent a day or so thinking. Should I be offended? I know my craft; why did this happen to me?

I played the victim for a few hours. Then I thought “this is a great idea.” For every major technology change, I’ll bring in my panel ahead of time.

The Burden of Proof in On You

Guilty until proven innocent is an understatement.

Executives should justify any effective plan, but it should be in the spirit of collaboration.

However, life is never fair, and this is no exception. Being prepared is a must because you won’t always work with good people. At times, executives do not align themselves with the business.

You don’t need thick skin; you need armor upon armor.

If you’ve done your job, you’ll have convinced everyone of your plans. No one is perfect, so sometimes you will have to prove it. By understanding what motivates people and working their desires into your strategy, you can make them feel supported and heard. Make people feel included in your vision, and you’ll win half of every battle.

Even with good intentions, you’ll have to prove your innocence many times over. It would be best if you reiterated your narrative countless times. “Stay ready, so you don’t have to get ready,” should be your mantra.

Deceptive Corporate Structures

I’ve never seen a stock package work as promised.

I didn’t have wild success, but I’ve had a few exits. Lawyers read all my documents, and I had smart friends to help me through financial terms. I consumed large volumes of financial books. Still, stock payouts managed to surprise me.

Before I learned to negotiate, I walked away with only memories. I had enough wins to start my own business, but none of the famous Internet stories.

I helped sell a company to a Fortune 200 company and take two companies public. I’ve learned that cashing out stock is a moving target. Unless you’re founder level, expect surprises.

Don’t get me wrong — it was worth it. Stories about overnight success may have clogged my brain. I can’t complain, but I will say there aren’t enough books about how all this stuff works.

It pays to surround yourself with people who study this for a living. I didn’t learn how to read a cap table until I was thirty-five. I was still befuddled when it was time to collect.

Getting what’s due to you is an ongoing negotiation. You don’t wait until a stock event. A money manager once gave me some great advice; he told me to meet once a quarter about my stock package to make sure that I aligned with the company, or it was time to leave.

What To Do If You Want To Start Your Own Business

If you can afford it, do it.

Running a business is challenging. Payroll, profitability, and people are a few of the things that will keep you up at night.

The freedom pays you back in spades. I’ve developed a passion for engineers getting what they deserve. I have a few horror stories, but I love this industry.

The entrepreneurial spirit lives in engineers. Many of us learned the hard way, but we can do it.

After years of pontificating out of fear, I took a little cash from an exit. I wrote a terrible first draft of a business plan, but kicked it around until it sucked less. I shared it with friends. One night, I was talking to a friend about ideas and uttered a mission statement by accident.

It occurred to me that technology should be in the hands of technologists. I formed a business, then called some friends to sell services.

If you want the headache and the freedom many business owners share, get started. You can do it.

Here’s an incomplete list of things I did to get started:

  • A business plan: Don’t be fancy; get something on paper.
  • Figure out what type of company structure you want (i.e., S-Corp, LLC).
  • A business account. I used Incorporation.com because they send a package with everything in it.
  • A list of 10 contacts you can use to sell your product or services to. A list of 10 targets you don’t know.
  • If you don’t have the cash to bootstrap, you’ll want to start a side hustle to seed your bank account. I was honest with people I knew, and they helped me get a few deals going before I quit my day job.

Final Thoughts

I’ll never be CTO again, not for anyone else. My passion is to see my people — the engineers — win. I am motivated by a mission to build an honest, profitable business. From our successes, we plan to develop our products.

I know engineers can build their own companies. I know that viable business plans aren’t beyond our capabilities. We can figure out financial models. We can raise our own money or deny funds altogether. I have confidence in engineers’ ability on and off the keyboard.

Running a company is not easy, and it may get more challenging. But no one will trick me at lunch.

Sorry, Steve.

Nerd For Tech

From Confusion to Clarification

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