Challenges of a Modern CTO

In the early days of your startup, the Founding CTO is shipping code at record speed! The product is hitting every milestone, the team is on-boarding customers and building towards a prosperous future. The CTO is the hero of this early-days story.

Then you need to grow your team. As it turns out—to nobody’s surprise—hiring people is hard. Hiring developers and ensuring they are successful in their roles is even harder!

Hiring doesn’t end with signing of contract; it extends into on-boarding, training, integrating into the team, working together to establish cultural norms, and building trust and reliance on your developers to collaborate and move the business forward! These are all operational and growth concerns that somebody has to lead and focus on.

As the business, the team, and the technology platform grows, suddenly the CTO is no longer shipping code as fast as before, the velocity of your delivery is slowing down, more and more bugs are surfacing, and it takes even longer to fix them!

What happened?

Those early days of growth and team building are crucial to culture building. And sadly, for a small startup, there is not enough time to do that AND continue delivering product features at the same velocity. Hero mode doesn’t work for a team bigger than one.

Some CTOs sacrifice the culture and team building parts, to keep the velocity going by focusing on shipping code. Others will focus on culture over product, and sacrifice customers and potentially negatively impact the business’s survival.

There are no easy answers here, and it’s impossible to do everything at once and still give each side an appropriate amount of focus. There will be pain and debt to accumulate here, either cultural or technical debt, and so long as you measure and consciously choose a path while putting aside time in the future to pay back that debt, you should be able to persevere through it.

Many startups, though, do not survive this stage.

Founding CTOs have no choice but to learn on the job. Regardless of the product you’re building, there is always something new to learn or something different to apply your prior experience to.

Most founding CTOs come from a background of software development experience, that is: being a hands-on developer with a breadth of experience that you can build an end-to-end solution and go-to-market with a functional minimum viable product.

That experience is typically very tactical in nature, given the background.

A CTO needs to be able to operate and be experienced in many areas beyond just the tactical:

Tactical Experience

Write the code, track issues, manage a backlog, manage infrastructure, do code reviews, monitor deployments, and improve performance, among other things.

The CTO is effectively the Principal Engineer from Day 1. As the team grows and the tactical roles & responsibilities are distributed, the balance tilts from being a hands-on CTO to a Consulting CTO. You may not be looking at the code every day, but the team can still come to you for practical advice to solve tactical, technical problems.

Strategic Experience

• How does the technology investment of today align with the long term vision of the business?
• Is there a long term plan for the technology stack?
• How are your infrastructure costs growing in comparison to your user-base?
• Did you pick the right stack? Are you hiring the right people for the stack?
• How much technical debt are you paying back quarterly?

Development teams, when presented with these questions can’t help but dwell on them and overlook immediate tactical delivery needs. A strategic focus is needed outside the weekly & monthly focus of the team, one that extends into annual planning.

Thus the CTO is uniquely positioned to research and address those growing challenges without disrupting product delivery. As the captain of the ship, you can set your sight on the destination and plot the path for the journey, then let your team manage the individual work areas right in front of them.

Leadership Experience

To cite my favourite quote and programmer: Admiral Grace Hopper:

You cannot manage men into battle. You manage things; you lead people. We went overboard on management and forgot about leadership.

And while the context of that quote might not have been associated with programming/technology (rather a commentary on MBAs running military decisions), I find it most applicable in modern technology teams!

Enterprise CTOs often come in with zero hands-on technical experience, but are experienced in “people leadership”, having run large departments and operations in different contexts (marketing, sales, business, and so on).

While people leadership by itself is a valuable and required skill to have, leading development teams is ineffective if the CTO is lacking the core skill that team operates within: Software Development.

On the other hand, Founding CTOs are often missing the experience of People Leadership, or if they have been in a leadership role before, it wouldn’t have been at an executive level, where The CTO has to lead leaders.

Often I’ve heard directors and executives state “I used to be a developer once” believing this is a positive message to share with their reports, but now they are more concerned with: “leading the team instead”.

Being in the role of technical leadership (whether a manager or a CTO) you are directly responsible and accountable for the technology itself as well as the teams building it.

For CTOs to be successful, they require both a Technical & People Leadership experience.

Are You Ready For a Co-Pilot?

You might be reading all this and nodding along, perhaps considering the option to start looking for somebody to help you navigate the challenges your team is facing, or you need someone to take hands-on ownership of the team as you recruit and expand your strategy.

For the past few months, I’ve taken on the role of Fractional CTO for several startups at varying stages of their journeys. I’m focused on helping them avoid falling into the trap of reinventing the wheel, minimizing their technical debt footprint, all while pointing out the solved problems they can externalize and avoid wasting precious time on.

Get in touch to discuss any challenges you’re dealing with today.