Are you an Accidental CTO?

Andrew Weaver
March 17, 2023

if this were a term included in the Oxford Dictionary of Terms, it might read something like …

  1. someone accelerated ahead of schedule into the CTO role
  2. rapid promotion of senior software engineer to newly created CTO role ahead of Series A round


We coined this phrase in the early days of CTO Academy as we worked with many individuals who fell into one or both of these categories.

So this article looks at what we define as an ‘Accidental CTO’ and some of the managerial challenges they face when grappling with a fast growth environment

CTO Academy launched in 2019 with a mission, to help ambitious and talented technologists build the leadership skills required to be effective in senior roles and from that, to achieve their optimal career experience.

This came from our own experience of seeing brilliant technical talent stumble and struggle at senior level, where they have to transition into managerial and leadership positions.

Our work is based around helping individuals understand their leadership strengths and weaknesses, doubling down on the former whilst negotiating the latter.

As with every new business, we headed out into the market with high hopes and energy but unsure exactly how the market would react, how they’d use/value the product … normal stuff.

But one customer persona emerged quite quickly amongst our early adopters and we soon gave them a title of  “The Accidental CTO”.

In addition to the cheeky definitions listed above we might further define an Accidental CTO as …

(1) The tech founder of a fast growth start-up who quickly finds that growth is out sprinting his/her skill set;

(2) The senior developer (often in a similar environment) who has been rapidly promoted ahead of schedule but without the necessary rounded skills to cope.

What they both have in common is they’re spending much of their day having to fire fight with process, team, product, the CEO

We were contacted by a recently appointed CTO (falling into category 1) who was involved in a company that was moving much quicker than his skill set could handle, leading him to feel vulnerable of being exposed, the imposter syndrome writ large.

He didn’t feel comfortable telling anyone for fear of the impact on him personally and the business more generally, so was bottling it up with no outlet to let of steam or seek reassurance, with potentially serious consequences for his mental health and behaviour away from work.

This was not a unique call as we see a growing number of our clients we define as‘Accidental CTOs’, talented and motivated individuals beginning to feel isolated and vulnerable as the business and expectations accelerate around them.

What should be an exciting and thrilling ride, can very soon become a stressful and potentially damaging one.

In these scenarios, our role is often as much about providing support and reassurance, as walking our ‘Accidental CTOs’ through the management skills required to better negotiate these changes and demands.

So what managerial pressures can emerge for the Accidental CTO, that they might not have been fully prepared for. Every individual is different but some of the issues that have emerged recently include …

How to handle board meetings, particularly how to handle investor directors. What are the expectations and how do you handle the new pressure and reporting expectations that comes with the arrival of investors?

Working relationship with the CEO can change dramatically as you grow and both have to absorb new and sometimes contrasting pressures. The colleague you sat around the kitchen table with during pre-revenue phase, might require different handling as the company takes off.

They’re probably going through the same investor syndrome as you, but neither of you acknowledge or even recognise it.  Need to move away from the keyboard that emerges as managerial tasks soak up your time and intellectual capacity. There is a new discipline required in delegation and not taking over all technical tasks.

You need to start hiring for a good team fit and much less about whether it’s someone you personally like. Clearly hiring should remain personal but as the team expands and gaps emerge, you have to recruit on the basis of team fit.

Roadmap and deadlines have to be increasingly aligned within the strategy of the company. Structure and discipline and targets and reporting become onerous, to that free spirit who just wanted to create shiny new things. Extension of this is that quality issues are on your head but might have been outside your control.

Talking to the customer is not something the traditional techie has to worry about but at the senior level it’s increasingly crucial to be at the customer coalface in understanding how they interact with the product. You will need to have operational communication with sales and support and be developing products on the basis of direct customer feedback. These are not conversations you’re used too. Those marketing people speak a completely different language.

Budgets and financial language become part of the landscape and we know from the people who undertake our skills test, that this is clearly an area of concern.

Accidental CTOs go through the firestorm and often come out the other side with some impressive skills (and war stories).

But you they also need to check-in with colleagues, networks, families because it’s almost always a role with considerable demands and stresses, particularly for someone having to “learn on the job”.

The good news?

You’re not alone.

We defined this term because we saw so many people in exactly this position and it was one of the primary drivers for launching our courses and community – to give The Accidental CTO the support they most definitely need.

So if you’re in that space now, remember you’re not alone and many others are grappling with similar challenges so lean into a support network because you can’t do it all yourself.

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