Most “CTOs” are still senior engineers with a fancy title — stuck in the code, fumbling in the boardroom, and bleeding money through bad tech decisions. This conversation shows you how to flip into a true business-first CTO who leads with strategy, ROI and systems, not commit history.

Perfect listen for aspiring CTO in a startup or scale-up who keeps getting pulled into delivery hell while your CEO wants commercial answers, not technical detail.

To unpack this, I sat down with Khalil Dimachkie, co-creator of Imperial College’s Emerging CTO Programme. He’s the CTO at Blue Light Card, leading technology for 5.7m+ frontline members, has grown teams from 1 to 100+, and has advised private equity firms through tech-heavy M&A deals.

https://www.linkedin.com/in/khalild/

In this episode:

• The “engineering trap”: how hands-on CTOs slow the business down, lose investor confidence, and what it looks like to escape into a true executive role.

• A simple way to “zoom out” and spot your own gaps as a CTO, plus how to use coaches, communities and structured programmes to build real business skills fast.

• The core operating system of a modern CTO: ROI as your north star, how to think about metrics beyond DORA, and why security posture belongs in every board pack.

• How to spend your first 90 days as a new CTO: the discovery pattern Khalil uses, who to speak to, what to map, and how to resist being dragged into firefighting.

• The meetings, habits and reports that signal you’re a business-focused CTO: daily trading checks, monthly operational reviews, one-to-ones that actually work, and non-negotiable release decision rights.

• Where most tech teams leak money in the cloud, why logging and microservices are often the culprits, and how to embed FinOps thinking into everyday engineering.

Get the links, notes and CTO resources from this episode at masteringtechgrowth.com.

Stop hoarding expertise. Start unlocking growth with real curiosity.

Most tech teams trust expertise. Leaders build, iterate, and launch what they “know”—but 8 out of 10 startups fail because experts don’t check if buyers want the solution. As expertise grows, so does risk: teams build in isolation, decisions loop inside closed rooms, and market changes pass by unseen.

Now, you flip the script. Winning founders lead with curiosity and humility. They ask great questions, engage real customers, and spend one day a month outside the office. Instead of perfecting the answer, they chase discovery—with rapid feedback, a culture of open debate, and constant relevance. Start with purpose, build in public, test ideas fast, and adapt before the data goes stale.

Bring your team together, not just engineers. Rotate pods, mix perspectives—then go out and find three ways anyone else would solve your problem. Seek the proof of discovery, not proof of expertise. Keep future-focused, stay a bit paranoid, and let curiosity be your growth engine.

Book one curiosity day next month. Walk your market, listen hard, then share what you find.

Alan Gregerman rewrites the playbook every day, so you learn from real-world results.

About Alan Gregerman: Innovation consultant, keynote speaker, author — trusted by 350+ global firms including Google and Mercedes-Benz.

What we discussed: → Why customers—not expertise—call the shots in tech growth

→ How the speed of AI changes experience and timelines

→ Real failure rates from assuming you “know” the market

→ Six skills that leaders must master (not just “soft skills”)

→ Concrete hacks: Lego tests, market walks, cross-silo pods

→ The role of humility and paranoia in fast-changing industries

→ How to stay relevant by getting out of the office

Where to find Alan Gregerman:

→ Website: https://alangregerman.com

→ LinkedIn: https://www.linkedin.com/in/alangregerman/

Where to find Mike Sirius:

→ Website: https://www.mikesirius.com

→ LinkedIn: https://www.linkedin.com/in/msirius/

👉 Grab the community playbooks and join us @ masteringtechgrowth.com

Question for you:

🗣️ What single customer need will you ask about before you build?

In this conversation, Mike Sirius and Matt Watson discuss the evolving landscape of tech growth, emphasising the shift from merely closing tickets to owning outcomes. They explore the importance of lead generation, building relationships, and the role of AI in software development. Matt shares insights on empowering engineers to think beyond tasks, fostering a culture of outcome ownership, and the significance of customer feedback. The discussion highlights the need for clarity in communication and the impact of leadership on team dynamics, ultimately advocating for a more holistic approach to software development that priorities customer value and collaboration.

Takeaways

• Tech growth is more about sales and marketing than technology.
• Being best known for what you do is crucial for success.
• Lead generation is more important than closing deals.
• Building relationships is key to successful lead generation.
• Engineers should focus on outcomes, not just tasks.
• AI is changing the landscape of software development.
• Clarity is essential for software engineers to be productive.
• Empowering team members leads to better outcomes.
• Celebrating wins fosters a positive team culture.
• Customer feedback is vital for continuous improvement.