“The CTO you want, or the CTO you need?”.
It’s a question I have asked many CEO over the years. Sometimes I was referring to myself, sometimes a co-founder, sometimes their existing CTO, or a candidate hire.

Like most executive roles, the CTO role changes with the business. But for clarity, when I think of a CTO, I think of the person who is accountable for everything that goes on in the technology organization. The part of your business that decides what you’re going to build, how you’re going to build it, and how you’ll deal with it when it’s live.

So let’s dive in to what that progression looks like, and how as a CEO you can get the most out of your CTO.

The Lean Startup CTO Link to heading

Team size: Small team (alone or just a few developers)
Focus: Hands-on coding and building the MVP
Responsibilities: Rolling up sleeves alongside the team, making quick technical tradeoffs based on execution speed
Value: Turning whiteboard visions into reality through direct technical contribution, focus usually on speed of change over anything else

This is perhaps the most stereotypical CTO stage. It’s the hands-on stage where the CTO is deep in the technical weeds. If they’re not the best programmer in the team, they’re certainly involved in every major decision. (sidenote: if your CTO isn’t involved in every major decision, your real CTO at this stage is the person who is)

More often than not this is exactly what you need at the early stages of a project or startup. Your only real strategic advantage is speed. So you need the shortest possible feedback loop, and optimize for speed of moving forward. The sooner something workable is in the hands of your audience, the sooner you get feedback. The sooner you get feedback, the sooner you can throw away what didn’t work.
It’s ok to build things that won’t necessarily scale well, optionality is more important. The goal of a CTO here is to build with an eye on changing things, rather than with an eye on being the 1 true way. That is perhaps the biggest challenge at this stage for most CTO.

A CEO’s perspective Link to heading

Your role as CEO here is to empower, drive focus and maintain optionality. The latter part is often where it gets tricky. A CTO will push for as complete a requirements as possible, as CEO you want the option to evolve in many directions.
The middle ground is frequent discussion on how the company, and therefore product, might evolve. But making clear when it is time to actively build and when you’re talking about what could happen.
The measure of good progress here is consistently putting changes in the hands of customers, and enabling quick iterations.
Focus your conversations on optionality,and the tradeoffs made during building.

Conversation starters: How will this scale when we onboard 10x new users? How hard would it be to undo our latest upgrade and take a different direction? How quickly can you gather and parse insight from our usage data?

The Managerial CTO Link to heading

Team size: 15+ engineering team members with specialized roles Focus: Establishing processes and coordination rather than direct coding Responsibilities: Owning architecture, security, and compliance while empowering teams to execute autonomously Value: Creating systems for how technology components work together and decisions are made. Basis of measuring in place, but close enough to know the details

The shift for a CTO here is subtle, and in larger companies they would likely carry a title such as engineering lead or head of engineering.
In this stage CTOs are still very close to the codebase, and probably at times hands on as they transition into this stage. But make no mistake, they need to pick up a new set of skills. It’s the first baby steps towards thinking in systems rather than focusing on what they can bring directly.

For many engineers this steps comes as a natural progression. As the technical decisions they make impact more of the product, so does the number of people they need to coordinate to achieve a result. And most good engineers are systems thinkers at heart. Once they’ve made the mental switch, they’ve won half the battle here. The other half is learning to delegate, even if that means the work might go a bit slower.

A CEO’s perspective Link to heading

The key here is to shift the conversation towards planning and acountability. In other words, ensure that your CTO understands the outcomes you’re after for the company, but also that they start thinking about actions they can take to get there.
And since they are accountable for the results of the entire team, make sure they drive actions through the team. The knee-jerk is often to “just do it themselves”, but that’s the enemy of scaling.

The Scaled CTO Link to heading

Team size: 50-100 people across multiple engineering teams Focus: Cross-team alignment and managing managers (not individual contributors) Responsibilities: Serving as the glue between departments, bridging priorities and making tradeoffs Value: Ensuring all teams are rowing in the same direction through unified progress and relying on measures/objective datapoint rather than gut feel

This is the hardest transition for a CTO. Partially because it means letting go of most of the technical details, and partially because it shifts the focus to dealing with people in a new way.
Your CTO is now likely managing managers, rather than individual contributors. It’s one more step removed from being able to directly impact the product.
And in this, the challenge becomes one of inspiring, motivating and aligning teams to ensure outcomes stay aligned to company goals. While building out adequate reporting to spot issues before they become a problem.

And while technical knowledge is still vital, it’s now no longer applied in creating the solution. Rather than knowing the answer, the challenge becomes knowing the question.

A CEO’s perspective Link to heading

While the first 2 stages were more akin to project management at times. The change here really is to elevate your CTO to think strategically.
Help your CTO stay focused on the big picture, and walk through the trade-offs you’re willing to make. It’s the CTOs job to lay out the tradeoffs in a way that makes sense to you and the wider business. Push back on overly technical and detailed explanations. The devil is in the details, but the big picture is what matters. Laslty, recognize that success metrics evolve - emphasize team alignment around clear vision over just roadmaps and delivery. Are you building the right things, rather than just building the things right.

The Strategic CTO Link to heading

Team size: 100+ Focus: Financial performance, competitive positioning, and business partnerships Responsibilities: Representing technology in the boardroom, delegating hands-on leadership to VPs Value: Guiding overall company direction through technology strategy while maintaining technical principles

The CTO is now well and truly out of the weeds, and more likely to spend time in excel than in the codebase.
Technical skills are now relegated to technology strategy, top level architecture and ensuring that VPs reporting to the CTO are aligned. The thinking should shift towards a 2 year window of change.
Short of emergency firefighting, the CTO shouldn’t be dealing with individual features or requests. Rather they should be thinking about the evolution of technology and how it can be used to improve the entire business.

A CEO’s perspective Link to heading

This is where your CTO really shines as a strategic partner. The conversation is as much business strategy* as it is technology.
The key is pushing the CTO to make sure the right information is flowing to the right people. And support them in the boardroom as you would any other executive. While it’s tempting to think someone without a technical background could do this; the reality is that the technical background is vital to understand the strategic trade offs that make the business strategy possible.

Conclusion Link to heading

The CTO you want and the CTO you need might not be the same after all. And reality is rarely as nicely delineated as the stages above.
In fact, the messy reality is that a crisis might drive the most strategic CTO to fall into a lean CTO phase. And a lean CTO might occasionally be your truly strategic thinking partner.

What is however important is that a CTO grows, and your company will need them predominantly in one of these 4 stages. And adds that business thinking to their skillset.