Diary of an Accidental CTO: Leadership Mistakes

Andrew Weaver
April 19, 2022

Mostafa Khattab is CTO at Wakecap Technologies in Dubai.

He is sharing with us some of his journey of what we describe as “An Accidental CTO” … aka someone who arrived in the CTO role ahead of schedule and has been grappling with various new challenges and a very steep learning curve.

You can catch up with Part 1 and Part 2 in advance of this latest instalment … but for now, over to Mostafa;

“With Part 3 of my series of blog posts I want to dig further into some of the leadership mistakes I made on this journey and thoughts about what I would do to avoid doing them again in the future.

One thing I know now for sure is that leadership seems easy to understand, but much harder to implement.

Being suddenly promoted to CTO of a fast growing technology startup I was faced by what I personally found to be a very hard challenge, how to balance at the same time between my past life of being a techie with the additional leadership tasks.

Thought it might be useful break my experience down into 4 phases with each having its own challenge, from which the real lessons and learning came from.

Hint: these phases are clearly going to be different for everyone but this is how I have experienced it …

Phase 1: I got excited!

Got the role and honestly thought I was about to fly,

Now I had a team and I was actually leading them. This was ahead of schedule for sure but I wanted to really take this opportunity and run with it. I was super excited, slightly nervous, but knew i could do it.

Initially I set out to talk to everyone, see how I could make their life easier and also help them understand the big picture of the solution we were creating and lead them towards the company vision.

Everything seemed smooth at this stage and to be honest, life felt easy even if I was spending too much time in the office.

The team was still small, the company young, we had some time to try different things.

Don’t let the nervousness overtake you. Really enjoy and invest in this high energy, excitable phase because you just soak it all up and anything you learn or achieve will be beneficial during the more challenging phases, just around the corner!

Phase 2: I got tired!

Suddenly I felt tired. More tired than normal.

The business was starting to face some challenges and as things started to move very quickly, I started to struggle with the pace of the changes, having to start things again from scratch, helping developers achieve business values faster. I was used to more structure but now I was having to cope with the changes and bring my new team with me.

I had to help people overcome the work load, absorb some of the negative energy building and trying to keep morale high. It was no longer just me, I was having to manage other people’s stress and uncertainty.

At times I became overwhelmed with so many new challenges of the work, alongside the new leadership challenges as well. I worked all the day and night, a big mistake, I was leading by day and coding by night which was the cause of mistakes and a real strain on my mental and physical health.

It also started to affect my morale and I sometimes tried to escape from the problems, feeling that I couldn’t handle everything and was losing control.

I definitely felt I needed help, someone who had come across this before. Budget constraints made that difficult so I definitely had to address lifestyle and make sure my morale was maintained until I could get more experience support. I guess the key learning point here is you might feel overwhelmed at times but you need to look after yourself or it can become a vicious circle.

Phase 3: Woah! Too much technical work

Having steadied everything I then found myself getting pulled into more of the technical work than I wanted. I was working in too many stacks and helping everyone to build faster and fixing technical issues. 

Too much time with the technical led to me losing some control on leadership.

The result was that people started leaving, hiring was bad, and morale was definitely down. This turned into the most difficult phase because this was not about me, this was about the impact that my leadership was having on others and the company.

Unfortunately it was not a short term phase, it lasted six months as the problems built up and I started to lose the trust of my team. I could sense and hear the frustration as I allowed myself to be dragged deep into the technical and away from being or having any capacity to be a leader.

Thankfully I was able to recognise the problem and in conversation with management, we all recognised that help was need to lead us away from this difficult phase.

Don’t be scared to talk about challenges. Do not take it all on your own shoulders.

That is not healthy and eventually will be very counter productive.

Phase 4: Back again!

Then we got investment and that definitely helps!

It not only helped us get more experienced people but was also a recognition that the hard work was worth it. We were growing a great business and people started seeing the value of WakeCap. You can only do so much yourself and as a small team. You need to understand your limitations but also give yourself some praise when it works.

I got more experienced people and tech leaders around me and we really took off. I was finally able to focus more on the real CTO role, leading, planning, learning and reporting.

I felt more confident, started understanding where mistakes were being made and getting feedback from other people – you have to take it all on board to grow.

Working with CTO Academy has been just the fresh start I needed.

I was shocked that someone out there can feel my pain and also realising it wasn’t just me, these growing pains were very familiar and shared by other tech leaders around the world.

It was like a dream to find someone with extensive experience to help me out and I have been working with them now for nearly a year and I cannot recommend it more highly. You cannot take this all on your own shoulders, particularly if like me you are a CTO ahead of schedule.

Remaining behind the keyboard, being too technical, not resting enough, thinking I could do it all, postponing asking for help.

None of this was good for me or my impact as a tech leader but I had to learn the hard way. Everyday brings new challenges but create the right environment for yourself to do your best and make an impact.

In this phase also, I made a lot of mistakes, which is postponing some work, I was feeling tired, and I thought it’s time for taking a rest. The bad thing that came in the future is, everything I postponed, never got done.

I hope you got the lessons that I learnt the hard way. I hope this article is beneficial to you as well.

In the next phase, I will talk about my experience after the mentoring sessions and how it helped me understanding my new role dimensions. 

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