Some lessons I learnt from a top level CTO

So on Wednesday night, after a long day at work, I gave myself a pep talk and dragged my ass along to an event at Skyscanner HQ In Edinburgh. The event was part of a 6-session series of workshops led by the key influencers within their business and it was facilitated by my good friend Michael Cockburn of Shoal. The key note speaker of the evening was Skyscanner’s Chief Technical Officer, Bryan Dove.

I am a big believer that every day presents us with an opportunity to learn, although often this belief can become clouded by symptoms of mental health and just life; exhaustion, tiredness, stress & so on. Wednesday night however was a big, overwhelming touchdown when it comes to learning!

Lesson #1 — Turning up.

Let me sprinkle a little perspective on the evening.

I had a relatively busy day on Wednesday, 4 coaching sessions, some admin, a bunch of calls all left me feeling a little tired, in fact I almost talked myself out of getting in my car and driving to the event.

Bryan on the other hand, the leader of a fundamental part of a global business that employs circa 1000 employees, who probably attends more meetings in a day than most of us do in a month and flies all over the world to fulfil these meetings, turned up in Edinburgh with a huge smile on his face to have a conversation with 20 people he has never met before.

And as the rest of the lessons should convey, boy am I glad that I turned up!

Lesson #2 — Fortunate.

From what I understand Bryan has held top level executive positions in companies such as Amazon, Skype, Microsoft & Skyscanner and he displays a wealth of skill, leadership qualities & wisdom. But that isn’t what stood out for me last night, what really stood out, in a sort of screaming in your face kind of way, was how grateful he was for everything in his life, even to be in the room speaking to us. He repeated words such as “luck” and “fortunate” over and over in the conversation. I believed that he was truly grateful for everything he had in life.

It got me thinking about most of the successful people I come across, often they are grateful & happy. Not in a superficial way, but in a way that stinks of authenticity. They are appreciative and consistently grateful for all the little small components, opportunities & decisions that make up their lives.

So perhaps there is a valuable lesson to be learnt here in that we know these high achievers were not always by default born into these executive roles, but instead their reality in the not too distant past may have been similar to our own, by “own” I mean striving entrepreneurs in the earlier stages of understanding the value we offer the world and tackling the steep trajectory of the business world. Maybe they have simply been grateful for their reality in every moment, and that in turn has manifested into more fortune and success?

Lesson #3 — Self-aware.

In a world where everyone and everything demands your time without any apology; emails phone calls, notifications, meetings, kids, family, clients, accountants & friends as only a few examples it is so easy to hit burnout very, very quickly!

Bryan spoke about saying no to 9 out of 10 “requests” for your time. This struck a chord with me, as entrepreneurs we want and feel the need to do absolutely everything, maybe this comes from a desire to succeed or maybe just from a controlling character trait. It is age old entrepreneurial guru advice; focus your attention on a select few things and say no to everything else. Easier said than done though, right?

I think the reason that this resonated with me so much is due to my current relationship with self-awareness. As entrepreneurs we go all in, 100% of the time and often give our soul to the challenges at hand. But the reality is that we only have a limited amount of energy and time to give. Entrepreneurship is physically & mentally demanding, and I think part of becoming more self-aware is beginning to treat your energy as the valuable resource it is. I believe that your energy is your most valuable resource and by learning how much of it you are willing to give to others, what tasks deserve the use of your energy and what your limits are when your energy reserves are running low is a crucial part becoming the most efficient and happy version of you.

Lesson #4 — Aggressive learner.

Like I have wrote about it previous pieces, most successful entrepreneurs will openly admit that they have no idea what they are doing, most experience imposter syndrome and you could even say have “faked it till they made it”. Bryan was no different and was impressively humble and open when it came to him describing his career path and how as a leader he has experienced impostor syndrome throughout his career.

This could be perceived as weakness, but it reveals a beautiful strength in leaders, and Bryan hit the nail on the head when he described himself as an “Aggressive learner”

The great leaders and achievers that I have met so far all share this unique approach to learning and problem solving.

Naturally, it would be fair to say that most entrepreneurs are problem solvers. The very nature of identifying a problem and creating a business that presents a solution clearly portrays the required character traits.

However, the great leaders, entrepreneurs, and ultimately the most successful businesses all share the additional trait of being willing to go “all in”. They take absolute responsibility for aggressively learning, seeking out opportunity to gain knowledge or wisdom from everything they do in life, down to the most menial of tasks. They become a sponge to not only learning, but also to positivity, opportunity and eventually to fortune, wealth and wisdom.

“How do they find the time to learn?” How about flipping that question to “Can they afford not to learn?” Looking back to lesson #3, it is all about committing energy to the tasks that will elicit the highest value return and learning, when we openly admit we have no idea what we are doing, will surely provide the best ROI?

Look at my Laptop at any one moment and I have 10–15 tabs open with articles from various educational sources on varying business, self-help, political, fitness, leadership topics.

Open my laptop bag and you will find 4 or 5 books crammed in

Then I set aside a daily 30-minute walk in between my appointments and use it to listen to an audible book or podcast.

It’s not easy finding the time, but I make it work because I view by ability to “aggressively learn” as my most valuable asset in life.

Lesson #5 — Declare calendar bankruptcy.

I loved this one, like our email accounts our calendars become an absolute riot, filled with demands on our time, appointment after appointment and before we know it we have spread ourselves so thin that we can’t sustain it (Remember that energy reserve)

Bryan, spoke about declaring calendar bankruptcy and I fell in love with it instantly.

An audience member posed the question “how far to you block your calendar out in advance” and his response was “for as long as it works”

Every now and then he declares calendar bankruptcy and deletes every commitment from his calendar (Excluding what he referred to as sacred meetings, these being necessary staff meetings and commitments that would have a disproportionate ripple effect of negative impact if he were to remove them) and he started a fresh. From there he explained how he blocked out his calendar in the following order:

1.) Me first (Important time for learning, relaxing and balancing that all important energy reserve)

2.) Sacred meetings (As above, the meeting he values as important and non-negotiable)

3.) Cascade out from there (Anything else)

I think this is a great strategy to help with assessing how your energy and time is being utilised and a nice reminder that ultimately you are in control of your time and you don’t need to be a slave to your calendar.

Lesson #6 — Authentic.

“Bring your authentic self, every day” was the answer to a closing question posed by the host Michael, in which he wanted to understand one thing that Bryan would post on a billboard to be read by entrepreneurs.

I think we can summarise this very briefly. If leaders of multi-billion-pound companies choose (and are encouraged) to be their authentic selves when the stakes are extremely high then surely, we should all consider removing the multiple false masks we wear in our working lives and begin to be our true selves.

And maybe by being this authentic we will unlock a potential that we have not yet experienced?

Thanks to Shoal for organising an awesome event and thanks to Bryan for being so honest and present.

As always I would appreciate comments & feedback and I hope that you enjoyed reading this piece.