Seven Stoic Lessons for the Interim CTO.

Seven Stoic Lessons for the Interim CTO

Table Of Contents

TL;DR

  • Interim work is short, high-stakes, and full of things you don’t control - which is basically the problem Stoicism was invented to solve
  • Find a mentor - even as the most senior person in the room. Someone outside the company who has seen your mess before is worth a lot
  • You don’t control the mess you inherit. You control how you respond to it. Start there
  • Be the outsider. Don’t quietly conform to the broken norms you were hired to fix
  • Anchor decisions to courage, justice, temperance, and wisdom. They age well in a way frameworks don’t
  • If you can’t do good right now, at least don’t do harm. Inherited systems deserve humility before action
  • Cato’s lesson: Find a compromise. Negotiate. Build alliances
  • Your engagement has a built-in end date. Use it. That clock is a feature, not a bug

Intro

Lately I’ve been reading Ryan Holiday’s book on the Stoicism again.

The more I do interim CTO work, the more the Stoics feel like colleagues. You walk into a company in distress. You have limited time. You don’t control the team, the history, or the politics. You have to be useful anyway, and then leave.

Reflecting on my work I found seven Stoic lessons I keep coming back to, mapped to the interim work.

1. Find a Mentor

“Choose a master whose life, conversation, and soul-expressing face have satisfied you… you can never straighten that which is crooked unless you use a ruler.” - Seneca

Stoicism literally begins with a mentor. Zeno was shipwrecked, lost everything, wandered into an Athenian bookstore, and asked “where can I find a man like Socrates?” A philosopher named Crates walked past at that exact moment. The rest is two thousand years of philosophy.

As an interim CTO you are often the most senior technical person in the room. That is precisely when you most need someone outside the room. A fellow interim, an old boss, a peer CTO who has seen the same mess five times. You need someone you can call at 21:00 on a Tuesday and say “this board meeting went sideways, here is what I think I should do.”

Seniority is not the same as omniscience. Only beasts do it alone.

2. You Don’t Control the Mess. You Control the Response

“The chief task in life is simply this: to identify and separate matters so that I can say clearly to myself which are externals not under my control, and which have to do with the choices I actually control.” - Epictetus

Epictetus was a slave. His most powerful teaching came from the daily experience of having no control. His rule: separate what is up to you from what is not, and then put all your energy into the first bucket.

The interim CTO inherits everything. The legacy system. The dysfunctional reporting lines. The tech debt nobody wrote down. The VP who doesn’t want you there. None of that is up to you. Raging at it is wasted energy.

What is up to you: your composure, your priorities, your first thirty-day plan, how you treat people in one-on-ones, whether you say no cleanly, whether you tell the CEO an uncomfortable truth this week or next week.

Stop fighting the shipwreck. Start swimming.

3. Stand Out and be the Red Thread

“It never ceases to amaze me: we all love ourselves more than other people, but care more about their opinion than our own.” - Marcus Aurelius

Epictetus tells the story of Agrippinus, who refused to keep a low profile under Nero when everyone else was blending in. Asked why, he said “I want to be the red thread - that small and brilliant portion which causes the rest to appear comely and beautiful.”

The whole reason a company brought you in as an interim is that the inside perspective got stuck. If you quietly absorb the existing culture, adopt the existing euphemisms, and stop calling out the obvious - you’ve failed before you started. You were hired to be the red thread.

This is the opposite of being rude or performatively contrarian. It is being willing to say “this meeting has no agenda” or “this reorg won’t fix the actual problem” or “this roadmap is five bespoke deals in a trenchcoat” when everyone else has decided not to notice. See also customer-driven vs. product-driven roadmap.

4. Anchor to Four Virtues

“If, at some point in your life, you should come across anything better than justice, truth, self-control, courage - it must be an extraordinary thing indeed.” - Marcus Aurelius

Stoicism’s four cardinal virtues are courage, justice, temperance, wisdom. That was twenty centuries ago. We have invented a lot of things since - OKRs, SAFe, microservices, LLM agents - but we have not invented anything better to steer a department by.

In interim work, frameworks are tools. Virtues are the anchor.

  • Courage - telling the founder a senior hire isn’t working
  • Justice - a fair salary range, a fair PIP, a fair exit
  • Temperance - not changing everything in week one because you could
  • Wisdom - knowing which fire to fight first

When a decision is hard, drop the framework for a minute and ask which of those four is at stake. The answer usually snaps into focus.

5. If You Can’t Do Good, at Least Do No Harm

“To do harm is to do yourself harm. To do an injustice is to do yourself an injustice - it degrades you.” - Marcus Aurelius

The Stoic Diotimus forged letters to slander the rival philosopher Epicurus. It was his only contribution to history, and it was a disgrace. Seneca, who wrote about the Epicureans eighty times, never once mentions him. That’s the cost of harm.

An interim CTO will sometimes arrive into a system they don’t yet understand. It is tempting to start swinging - reorgs, rewrites, firings - to signal action. Resist it. If you don’t yet understand the architecture, the people, or the customers, the bar is not “do good.” The bar is “do no harm.” Observe. Due diligence first. Intervene when you actually know what is in front of you.

The damage a confident-but-wrong interim can do in six weeks can take the permanent team a year to clean up.

6. Compromise Is Not Weakness

“We were born to work together like feet, hands, and eyes… To obstruct each other is unnatural.” - Marcus Aurelius

Cato was the most rigid Stoic in Rome. He refused every compromise, to the point that the expression “we can’t all be Catos” became a Roman shrug. When Pompey offered a marriage alliance - an unmissable opportunity to stabilize the Republic - Cato dismissed it rudely. So Pompey allied with Caesar instead. The Republic fell.

Cato did more than almost anyone to defend the Republic, and also more than almost anyone to bring it down.

Interim CTOs are usually pulled in precisely because something is broken. That tempts you into Cato mode - no compromise on quality, no compromise on process, no compromise on the people who have to go. But you are a guest in someone else’s company. You need the CFO, the CEO, the founding engineer, and the VP of Sales to actually execute with you. Pure inflexibility doesn’t produce change; it produces theater, followed by your replacement.

Pick the two or three things that must not be compromised. Compromise on everything else.

7. The Engagement Has an End Date - Memento Mori

“This is our big mistake, to think we look forward to death. Most of death is already gone. Whatever time has passed is owned by death.” - Seneca

The Stoics meditated on mortality not to be morbid, but to concentrate. If today might be your last, you stop wasting it.

The beauty of interim work is that memento mori is structural, not philosophical. Your engagement has an end date in the contract. Three months. Six months. Maybe nine. The clock is already running.

That clock should shape everything:

  • What is the one outcome that, if I deliver it, the engagement was worth it?
  • Who is my successor, and am I actively making myself redundant?
  • What am I doing this week that a permanent CTO would do better next year?

“Concentrate every minute like a Roman,” Marcus wrote, “on doing what’s in front of you with precise and genuine seriousness.” That is the job. Not to build a monument. To leave the team better than you found it, on a deadline, and then walk out.

Closing Thought

The Stoics were not theorists. They were doers - slaves, generals, lawyers, emperors - who needed philosophy to survive the actual conditions of their lives. That is why it still works.

The interim CTO role rewards the same disposition. Short time horizons. Things you don’t control. People watching you to see if you’ll panic. The Stoics already answered this one.

Pick your mentor. Control your response. Be the red thread. Anchor to virtue. Do no harm. Compromise where you can. Remember the engagement ends.

The rest is execution.

More

Related posts

Imprint | Privacy Policy