Software Developer to CTO

Data is the difference.

At the beginning of my career I worked at a company that had this as its motto, and the truth then was as strong as it is now. If you are building software to solve user problems, you may be in an excellent position to do something amazing with the data you are managing. Even if it’s…

Infrastructure is important. And it’s not black magic.

I spent far too many years in my earlier career treating infrastructure, and its management, at arm’s length. Modern DevOps practices have really changed this philosophy and approach, much for the better, so embrace this, and take it a…

Get promoted. Here is how.

If your goal is to move into executive management from the starting point of an individual contributor, you have to get promoted. Often. Otherwise, it simply won’t happen. By now, I have been promoted multiple times. I have also had the fortunate opportunity to nurture and then…

Design for idempotency and commutativity, and for idempotency.

…And not just to impress others with fancy math vocabulary.

Have you ever scratched your head and said, or heard, the following?

Estimating is important. Be good at it.

Estimation is a cornerstone skill for technology leaders. Development teams often bristle at the activity of estimation, and for good reason: It’s hard. However, businesses run on predictions.

Fall in love with your product vision.

As a CTO, you will be in a product-influencing position. Your working relationships with your company’s product leader will be one of your most important ones. It will influence the commercial success of your product, your platform, and your company.

Never ask two questions in an email…

Maybe this lesson seems a bit “cheeky,” but it makes the list. Never ask two questions in an email. I still make this mistake, and if I had vacation accrual for every minute spent deciphering confused, half-answer responses to any of my “Please see below and…

Become a generalist.

“But wait, you’re the CTO, isn’t that a specialization?”

At some level, yes, and teams need position players. Your management team peers will appropriately see you as “The Technologist.” Like me, you will grow accustomed to questions phrased, “Yes, but from a…

Become a good interviewer. Here is what works for me.

If you are like 99% of managers, you will stumble through this for years, possibly with no training, and nothing but high expectations that you can review and vet someone in as short as one to two 1-hour interactions. I count myself in…

Your team is your greatest asset. Support them!

Once you find yourself no longer being an individual contributor, try to make this your mantra: Teams of smart, motivated people will do amazing things — support them!

Embrace technical debt. Manage it. Refinance.

Actively leverage and manage technical debt. It is a powerful accelerator. I firmly embrace the opinion that technical debt is a critical tool in solving users’ problems, and getting to market quickly. The key is to manage it.

Management problems are always two layers deep (at least)

Unity is plural and at minimum two — R. Buckminster Fuller

This can be a tough one to swallow, especially if you’re struggling with a bad manager who reports to you. I know. I have been there more than…

Lesson 8: Learn how to give a killer presentation (here’s a tip).

There is so much cynicism aimed at slide presentations, however, let’s not blame slides. It’s not slides that are bad, it’s bad slides…

Lesson 7: Trust is earned by delivering, not by adherence.

Process matters, and nobody cares about your process.

Trust is earned by delivering, not by adherence.

Lesson 6: Learn to think commercially (here’s how).

Often I hear, “I want to learn budgets and finance so that I can become more commercial.” Quick tip: thinking commercially has nothing to…

Lesson 5: Stop writing code, but never stop writing code.

You have to make a clean break at some point if you want to become an effective leader and manager — get out of the code. Your team needs…

Work in differently sized companies, with different funding models.

One of my early senior managers once said to me that if you know how a company is funded and structured you can predict how it will make decisions, and much about its culture. At the time I was too early in my…

Lesson 3: Contracts are for when things go wrong.

This was originally called, “Learn how to read a contract” but the real lesson is that vendor contracts are for when things go wrong…

Do not argue over curly braces (a.k.a Don’t be a zealot…)

Look to stack exchange, whose editors in response to the question, “Should curly braces appear on their own line?” said this:

As it currently stands, this question is not a good fit for our Q&A format. We…

Lesson 1: Write code for a decade.

The CTO is not a general management position, it is a functional leadership role, and as such needs line-level credibility. Heads of Sales…