Donovan Frew

Name: Donovan Frew

Current position: CTO, Goodlord


I’ve been a technologist for the past 20 years. I studied Computer Science at university in Jamaica and spent the formative years of my career there working on a number of projects in collaboration with companies such as IBM, Peoplesoft and Nortel Networks.

I moved to the UK to do an MSc and have remained here ever since. I got my first taste of the startup scene with and have been playing an active role in startups ever since. These range from developer and CTO  to mentor, advisor and board member.

My favourite pastime is writing code which means I’m always working on a side project usually as a means to learn a new language. I’m also into strategy gaming so I spend a fair amount of time doing that as well. I do move away from the computer from time to time in which case you’ll find me playing/watching football or dancing salsa.

Tell us about your life before leadership – what kind of roles and projects did you work on?

Before taking on a leadership role I had the opportunity to work in multiple roles across a number of sectors and range of projects. 

Straight out of uni I worked as a software engineer for a telecommunications company in Jamaica and was fortunate enough to participate in a number of projects including the first telephone bill payment service in the Caribbean. That project was so successful that my team was asked to roll out the solution across all the Caribbean territories.

Eventually I moved to the UK where I worked as a web developer for which was part of the Priceline group. When they acquired I was given the responsibility to sync the hotels database of the two companies which was one of my favorite projects. 

I left Active Hotels a few years later and transitioned into a Product Manager role as I wanted more exposure to the earlier stages of the SDLC. That decision would turn out to be a huge contributing factor to me taking on a CTO role.

How did your first leadership position come about, and was it intentional on your part?

I feel like I’ve always had some kind of leadership role throughout my career. This came down to having amazing bosses who put a lot of confidence in my ability and gave me room to make mistakes.

My first official leadership position was at Secret Escapes where I joined as employee a Senior Engineer with the intention to learn more about entrepreneurship and work alongside a CTO who I greatly admired. Within a few months however the CTO decided to move on and I was promoted on the basis of my technical background and crucially my product management experience. It turns out the mix of the two was ideal for a small consumer focused startup.  

It wasn’t intentional on my part at all and in fact I doubt that if I had seen an ad for a CTO at that point if I would have even applied. As it turns out I had 7 successful years where the company grew into a European heavyweight, which just goes to show that we sometimes underestimate ourselves.

How did you manage the transition? What came easily / what was difficult?

In a lot of ways the transition was simple. I was already working quite closely with the CTO and was heavily involved in a lot of the activities he was doing. The big difference was one of ownership. Before I was merely contributing to the delivery of software, I was merely contributing to hiring, I was merely contributing to the roadmap. Then I became CTO and I was no longer merely contributing, it was my responsibility. I had to build the team, I had to build the roadmap, I had to lead.

In the early days it felt more like business as usual however as the company grew and I was required to be less hands on, then the  real challenges arrived. My software engineering skills that I had been honing over the past decade or more wasn’t sufficient. Now I had to think more strategically and tackle problems that were much more complex than writing code, such as building and maintaining morale, plotting the trajectory for the next 5 years (in a company that wasn’t 5 years old), assisting with fundraising, etc. I would often retreat to my comfort zone and start working on individual features as this was much simpler and pretty much guaranteed to end in success. 

What was your biggest failure in that first leadership role?

I was lucky at Secret Escapes to have amazing support from the founders, the wider management team and my team. I probably took longer than I should to break away from day-to-day coding but I wouldn’t consider that to be a failure. It wasn’t until I was leaving that I really realised what my biggest failure was, I did not have a succession plan.

When I decided to move on it was obvious that the next person would have to come from the outside as there was no one in my team ready to step up. We definitely had the domain knowledge and technical acumen in-house and if I had planned effectively the company would have saved time and money while giving someone the same opportunity that I had. 

This is a lesson that I intend to keep in mind for all future roles.

What made you keep doing it?

It’s not important how many times you fall but how many times you rise.

Tell us a fun fact that nobody knows about you

In my first job fresh out of university I got a company phone and for my voicemail I recorded a message of myself answering and pretending not to hear the person on the other side. After about 10 seconds I revealed that actually I’m not available please leave a message after the beep. Within an hour of setting up the voicemail my boss walked over and gave me the looked and simply said “your voicemail”. This man would eventually put me in charge of a multi-million dollar project so  guess I managed to rescue my reputation.

What are the three key skills you think every lead needs?

Leadership is all about people and so the key skills in my opinion are all people related.

To be a good leader you need to be able to listen. For a lot of people the opposite of speaking is waiting and that just doesn’t work as a leader. You have to patiently listen to what people are saying. As a matter of fact you often have to listen for what they are not saying. Either way you have to listen keenly because you will never understand someone if you don’t listen to them and you can never expect someone to follow your lead if they think you don’t understand them.

Flexibility is also crucially important. When you’re dealing with people, every individual comes to the table with a different set of strengths and weaknesses and their own motivating factors. You need to be able to adapt to their unique requirements in order to maximise their chances of success. This is not to say that there isn’t value in standardisation but conformity is probably not what you want either.

Finally people look to their leaders to make decisions even when there isn’t perfect information. Lots of time avoiding a decision seems like the safest thing as anything else feels like a gamble. In my experience though, nothing drains morale like lack of clarity and so a good leader needs to be prepared to make a decision even if it might turn out to be the wrong one. Which would bring us on to communication but that’s a fourth skill.

What have you learned about acquiring and retaining talent?

The key lesson that I have learned is that there is no silver bullet. Attracting/hiring talent is hard work. It’s a full time job, it takes a lot of time and you will get it wrong. So doing what Google does or jumping on the latest trend while useful as a baseline won’t guarantee results. You have to identify the unique needs of your organisation and of your team and find a way to assess for that while recognizing that interviews are an imperfect process. 

As for retention, it has to be top of mind from day 1. In fact, you have to start thinking about it before writing the job description. I find that your plans for retention end up influencing your entire process, from job description and interview all the way through to onboarding. When treated as a process that happens after the person passes probation, it tends to be self defeating. 

How do you motivate your team and manage their stress levels?

I’ve had a lot of success with Daniel Pink’s advice from Drive where he proposes focusing on Mastery, Autonomy and Purpose as the pillars of motivation, or more accurately, avoiding demotivation.

In practice this means giving each member of the team a personal development objective where we work with them to identify areas of their skillset to improve then providing them with the time and material to work on these skills.

With regards to autonomy, I try to leave the How to the individuals and instead focus on Whats. This is one of those places where flexibility is really important. In my experience too much autonomy can actually be stressful for some people, especially the more junior members of the team. It’s therefore necessary to understand where it’s safe to leave the decision making to the individual and where it makes more sense to be directed.

Purpose actually comes easy when you work in a company like Goodlord. The whole mission of the company is around making the renting experience better for everyone and as most of the team are part of generation rent they readily empathise with what we’re trying to achieve.

How do you manage your own stress levels and productivity?

I make sure that I limit the number of goals that I’m pursuing simultaneously. I’d rather do a few things well and some none at all than try to do everything and then not do any well. Specifically I have a maximum of 3 priorities. I communicate these to the wider business and I make it clear that the only way for me to focus on anything else is by removing one of the current priorities. Of course this can lead to some frustrations however in the long run everyone usually recognizes this as a net positive.

Additionally I ensure that I have interests outside of tech/startups. I find that these extra-curricular activities help me to detach which in turn helps to keep my productivity up for a much more sustained period of time.

How do you stay in sync with other parts of the business?

In my current organization we have a weekly senior management meeting where we discuss the key priorities of the day as well as the topics of interest within each department. This provides an excellent forum for transparency, accountability and the sharing of ideas. 

Alongside that I have a fortnightly 1:1 with each head of department head in order to check in on their current challenges, understand how they’re progressing towards their objectives and identify ways my team can help (or may be hindering) them. This ensures that there’s a regular, more personal communication channel where we can discuss topics that may not be best done in a group setting. 

Finally I try to set myself an objective each quarter to help improve another department within the company, either using my technical background, lending my experience or even just acting as a sounding board. 

Where do you see yourself in 5 years’ time?

5 years from now I hope to still be at Goodlord. We’re onto something good and I want to see it through which I don’t think will happen in 5 years although by then we would have made significant progress. At some point I would like to take up a CEO role. I’ve spent all my career in Tech but the more time I spend in leadership the more I recognize that the key skills are transferable and so a more commercial/visionary role would represent a new and interesting challenge. For now though, CTO at Goodlord is the plan.

What product do you wish you’d invented?

Stack Overflow. When I started my career the only options for help were man pages and MSDN. There were so many problems that I lost days of my life trying to solve. I can think of very few products that have had a bigger impact on developer quality of life than SO.

Thanks very much, Donovan!