The Question Every CEO Is Asking About You

Hey there,

As a fractional CTO, your success hinges on your ability to build deep trust with the CEO. But what many tech leaders get wrong is assuming that trust is built on technical expertise alone.

The truth? While your skills matter, what the CEO really cares about is whether you can think like them. Can you see beyond the code to the bigger picture of the business? Can you connect the dots between technology choices and bottom-line impact?

In other words, can you be a strategic thought partner, not just a tactical implementer?

This mindset shift is critical. Because when you show up as a peer to the CEO - someone who deeply understands their goals, challenges, and blindspots - you transform the relationship. Suddenly, you're not just a hired gun, but a trusted advisor and co-pilot.

So how do you demonstrate this strategic orientation? 

It starts with the questions you ask:

• "Why is this [initiative] important to you right now?"

• "What’s the underlying vision driving this project?"

• "How does this align with your long-term business strategy?"

• "What would success look like beyond just the technical implementation?"

Notice what's not on that list? Anything about tech stack, development methodology, or sprint schedules. 

Those details matter, but they come later. First, you need to show that you get the big picture.

This approach requires a bit of courage. It can feel safer to stay in your technical lane.

But remember: you're not selling time or projects. You're selling leadership, results, and positive impact. 

The fractional CTOs who truly thrive are the ones willing to step up and take co-ownership of the strategic narrative alongside the CEO.

At CTOx, we role-play these crucial conversations so you can build your strategic muscles in a safe space. I invite you to join us and experience the power of peer feedback and coaching.

Because when you learn to lead with vision, the tactics fall into place. And that's when the real magic happens.

To your continued growth,
Lior

Lior Weinstein
Founder & Head Coach, CTOx