Diary of an Accidental CTO: A Definition

Andrew Weaver
April 19, 2022

Mostafa Khattab is CTO at Wakecap Technologies in Dubai.

He has kindly agreed to blog for CTO Academy about his experience of being what we call an “An Accidental CTO” i.e. someone who arrived in the CTO role ahead of schedule and is grappling with new challenges and very steep learning curve.

Mostafa will be posting regularly with a birds eye view of what it feels like to be at the sharp end of a fast growing start up.In this series, I am going to write my experience of becoming ahead of schedule CTO.

“I wanted to start writing a blog about the challenges faced by young tech leaders who join early stage startups and as mentioned, suddenly become an accidental CTO.

From my perspective I struggled jumping directly from senior developer to CTO, especially during a time of growth where absolutely everything was running a full speed. The business, the tech challenges and the fundamental change in my role to become a technology leader.

These are my thoughts on what it looks like at the coal face. The types of challenge you might not anticipate in advance, well at least I didn’t see them all. Hope you enjoy.

Building Your Team

I have been working with teams for many years but the challenge now was very different. Rather than being part of the team, now I had to start building one. Figuring out the skills we need but working that out not on the basis of “like to have” but working within a tight budget actually, a very tight budget, this was about laser focus on what is the priority now. Everything else has to wait.

My dream of rapidly building an in-house high performing team and working on employee branding and cohesion, was very hard giving the budget constraints into account.

Best option for a tight budget is recruiting a remote team but that comes with its own challenges and often hidden management costs. Hiring a remote team brings with it different management challenges when trying to build an effective team. You need in particular in finding the right alignment and communication, when we don’t have the regular and direct human contact from my previous working experiences.

It’s always challenging to compare hiring a remote team or start building on-site team, the remote team fits more in the budget but the management is challenging, the on-site team is easier to manage but I had to sacrifice some skills and experience to get good enough junior engineers on-site.

From Team Player to Tech Leader

Of course I was (am) excited about being in a CTO role. Feels great and I love being able to impact directly on the company and the team we’re building. But I didn’t realise maybe as much as I should have that it’s good to have great technical skills and perform well on those terms with your startup, but watch out because the skill set is about to shift dramatically when stepping into that leadership role.

Instead of producing something, you have to inspire people and create an environment that enables them to produce that thing with better quality than yours. 

The main challenge I encountered was how to delegate, trust and get people accountable for what they are working on. You can’t sit behind your screen anymore (even though you are some days tempted to do that) but instead you need to start thinking differently, taking the initiative and leading the team. You need to expand awareness about yourself and also develop an understanding about your team members. Understand your own strengths and weaknesses but also build an ability that allows you to dive deeper into the skills and challenges for your employees.


Communication is one of the key issues faced by tech gurus landing into technology leadership positions, a challenge magnified if working within a multi-culture team for the first time.

You need to clearly and effectively communicate with your team members, you need to cross the language and culture borders and become a good listener. Listening is not always an easy skill but it’s crucial to encourage your team to speak up and make them feel comfortable about being heard.

If the company formal language is not your (or their) mother tongue then you need to create even more safe space to invest time in listening to team members and making sure everyone is communicating effectively.


If you can’t handle the stress, don’t continue please!

The burdens of being a leader can be overwhelming. You need to understand how and where those stresses might be impacting you and your performance. Check for the root of stress and lead your team to handle stress, to not be afraid to ask for help and don’t over work which so often leads to burnout.


You need to setup the processes so that you can effectively handle the technology management. As an Accidental CTO you will almost certainly need to learn these new skills quickly so they help managing the often complex processes and systems of your company.

You need to start managing work through ticketing, have a full understanding of code repositories and branch strategy and don’t forget the Quality testing and control. Plan for the CI/CD, prepare well for on-boarding sessions to save time in the future, and understand how to report to the upper-level management.

So these were the main challenges I faced in my new role. Next blog post will look at some of the mistakes made”

Mostafa Khattab, July 2020

Download Our Free eBook!

90 Things You Need To Know To Become an Effective CTO

CTO Academy Ebook - CTO Academy

Latest posts

Tech Strategy Discussion Panel Summary - blog post featured image

Aligning Tech Strategy with Business Goals – Discussion Panel Summary

An important part of each module in our Digital MBA for Technology Leaders is a discussion panel where a group of experienced tech leaders dive […]
Tech Leadership in So Many Words - #25 - Collaborative

Tech Leadership In So Many Words…#25: Collaborative

The essence of collaboration in tech leadership revolves around creating a culture where a common mission, openness, complementary strengths, and collective problem-solving are the pillars. […]
Responsibilities Strategy and Skills of Technical Leader

Responsibilities, Strategies and Necessary Skills of an Effective Technical Leader

A technical leader bridges the gap between technical teams and business objectives. Unlike general managers, they possess strong technical expertise and can therefore guide engineers and developers. […]

Transform Your Career & Income

Our mission is simple.
To arm you with the leadership skills required to achieve the career and lifestyle you want.
Save Your Cart
Share Your Cart