The Anti-Playbook: How to Be an Ineffective CTO

Being a CTO is tough. The expectations are high, the responsibilities broad, and the impact immense. But what if you're not aiming for excellence? What if your goal is to be the worst CTO possible? Based on true stories and hard-earned lessons, here's a (somewhat ironic) guide to CTO anti-patterns that no company should tolerate.

🚫 Avoid Leadership at All Costs

The first rule of terrible CTO-ing is to avoid providing any actual leadership. Let your engineers guess what the technical vision is (spoiler: there isn't one). Let improvement proposals linger and rot without support. When someone tries to challenge the status quo or bring new ideas, act vaguely supportive - but do absolutely nothing to help.

🧽 Be the Invisible Sponge

Soak up all the glory for past wins, but don't actually take responsibility for anything forward-looking. Far-reaching technical decisions? Better leave those to “the team” (but without actually empowering them). Ownership means accountability, and that sounds stressful.

🛠️ Focus on Your Weekend Side Projects

Make sure everyone knows about your personal weekend coding experiments - bonus points if they're in some obscure language or totally unrelated to the business. Ignore the fact that the engineering org is drifting, the roadmap is murky, and the tech stack is stagnating.

🪑 Let the Complacency Fester

Surround yourself with folks who got comfortable years ago. Make sure the loudest voices are the most resistant to change. Whenever someone proposes adopting a better framework or improving tooling, lean on the classics: "Why change what's working?", "That sounds risky." or "We've tried that before."

🤡 Hire a Proxy Manager with Zero Credibility

If things start getting dicey, deflect by hiring a middle manager as a human shield. Don't worry if they lack interpersonal skills, technical depth, or the ability to lead - just make sure they follow orders and don't question the status quo. Bonus points if they try to lead by decree and spark instant resistance from the team.

🤷 Never Commit to a Direction

Stay vague. Be noncommittal. Strategy? Vision? Roadmaps? Those are traps. Keep everything fuzzy, and avoid written documentation at all costs. That way, no one can hold you accountable when the company misses the mark.

🙈 Ignore the Naysayers (Unless They're Blocking Progress)

Ironically, your worst enemies will be the naysayers - unless they're your naysayers. In that case, promote them. Make them gatekeepers of progress. Reward skepticism, punish initiative. That way, everything stays nice and still.

Final Thoughts

The CTO sets the tone for the entire engineering organization. A disengaged or misaligned CTO doesn't just slow down progress - they can actively block it. Leadership isn't about side projects, titles, or org charts. It's about ownership, direction, communication, and creating an environment where engineers can thrive and grow.

If you're aspiring to be a great CTO - just do the opposite of everything above.