CTOs share advice to their 25-year-old selves

We asked a wealth of CTOs to share the advice that they would give to their 25-year-old selves.

Mike Adler, CTO and CPO, N-Able

What advice would you give to your 25-year-old self?

Don’t be afraid to take a few risks. Don’t do anything too crazy, of course, but at 25, I know I had far fewer responsibilities than today, and no one relying on me if things went wrong. Taking a risk with a new role in, say, a new startup, or in a different part of the world, is something that a young person can do—if it turns out to be a complete disaster, there’s no great loss. In fact, it’s the sort of experience that’s incredibly useful when someone reaches a senior level. Someone who has experienced choppy waters is far more likely to be able to navigate them.

The other piece of advice I would give is to protect and nurture your personal brand, though we wouldn’t have used those words 25 years ago. This is much more than looking after your social media profile—it’s about ensuring that the people you meet and work alongside today have a good impression of you. We work in a smaller world than many people realise, and networking is crucial to new opportunities. You want to be well-known and respected, rather than infamous, and you can’t start that process too early.

Danny Allan, CTO and SVP, Product Strategy, Veeam

What advice would you give to your 25-year-old self?

For someone getting started in their career, I would definitely recommend learning as much as you can about all the different business functions. The more you know about the different areas of a business that you yourself might not necessarily work within, the more well-rounded a perspective you can bring into your future roles. This is particularly true if you want to be a future leader. Take the time to listen to others, understand their roles and responsibilities, ask as many questions as you can, and stay curious. Try not to get too complacent, and always try new things. Because of the roles I’ve held and the certifications I have earned, I’ve always loved the underlying technology, the code, and how technology is used to solve problems and get things done. Looking back, I was slow to understand how the rest works – everything from how sales negotiation works, to legal contracts, to customer support escalations, to financial and regulatory compliance – and it’s this that you need to have an appreciation of to become a well-rounded leader.  The broader perspective also leads to better communication and cross-team support.

Rob Knight, CTO at SUSE

What advice would you give to your 25-year-old self?

Embracing change and keeping an open mind is a cherished piece of advice I would give to my 25-year-old self. A career in technology is definitely THE place to be today, at the pulse of innovation. Take a look at the open-source community: through these millions of individuals, we experience a level of rapid innovation that is unique in history, with the goal to make the world a better place. An open mind, and an appetite for collaborating with others, plus a laptop to start coding, is all you need. The world’s largest open-source community project Linux started 30 years ago with a single line of code – and today, with open source, there are literally no borders – Ingenuity, the tiny Mars-helicopter, flies with open source.

So do not settle for mediocracy. If you are unhappy and do not get pleasure from what you are doing, you have the power to change it, especially with a career in open source technology, where many tech companies realised that employees with diverse backgrounds can empower teams with new ways of thinking.

And mentorship! Look for a mentor and become part of a mentorship program. A mentor is somebody who supports you in making the right decisions for your career. Grow your own network, not only on social media but by attending live events such as job fairs or technology events. And become a mentor and share your knowledge with others; that is the true power of open source.

Frances Sneddon, CTO at Simul8:

What advice would you give to your 25-year-old self?

Don’t expect to follow a determined path. Instead, feed off the things that you’re naturally drawn to and that bring you passion, and things should work out ok. I joined Simul8 as an intern when it was a startup with three or four employees. I would be doing a bit of everything from shrink wrapping orders to taking on the company website. Over time, there became a need for me to code and build applications which I really enjoyed. I got the bug. The CEO at the time then helped me upskill and build my knowledge so I could fully understand not just coding but principles too. Now I’m CTO for Simul8, and I am responsible for the strategic direction of our products.

Adam Dossa, CTO, Polymath

What advice would you give to your 25-year-old self?

In order to remain motivated and engaged over a long career, it’s important to focus on how you can best add value in any given role, rather than being constrained by a particular organisational structure. This can be hard, especially at a more junior level, but over the long term serves both individuals and their employers very well. 

Being willing and able to change direction, take breaks, and throw caution to the wind in terms of career progression and direction is important. There were times in my earlier career where I could have made changes faster with more confidence!

Formal qualifications aren’t necessary for a career in blockchain. However, some of the theoretical knowledge offered through higher education underpins the ability to work and reason with technology across a wide range of domains. It’s also about continuous education during your crypto career, both formal and informal. Choosing a company that has a learning and development budget is important for keeping your skillset fresh, relevant, and updated – whether that’s used to learn a new coding language, new technology or dipping your toes into an entirely new area. The blockchain world moves at a remarkable pace, which means your skillset must too.

Ron Kol, CTO, Bright Data

What advice would you give to your 25-year-old self?

I would explain two pieces of advice which, if followed, would have avoided years of very costly mistakes in my career:

– When developing a new product, you need a good long-term roadmap and the flexibility to change it a week later. Agility really is the key to success in fast-moving sectors such as technology.

– An underperforming team member’s impact is not self-contained; they can take you and the rest of the team down with them. This shouldn’t be swept under the carpet, and the quicker you act to resolve situations, the better the outcome.

In business, and especially technology, learning from and acting on your mistakes is crucial to success. In your mid-twenties, you are still learning and will no doubt make mistakes. However, you have many years ahead of you to embrace past experiences and support others who might find themselves in a similar position to what you were towards the start of your career. 

 James Shannon, CTO and CPO, essensys

What advice would you give to your 25-year-old self?

I would tell myself to focus on finding my passion and what really excites me. Also, finding people you like working with is important. Chase your passion, and the rewards will follow naturally anyway.

Another important message is knowledge is power. I’d encourage myself to keep learning, keep reading and experience as many things as possible – and not to rely solely on others to teach you.

Inevitably things may go wrong at times, but that’s fine. Don’t be afraid of failure – it’s ok to make mistakes, as long as they’re different mistakes every time. Persistence is very often a common feature in successful people, whatever success looks like for them.

While on the subject of not being fearful, an important message is to not be afraid of change. Ultimately, change is inevitable – especially in technology. Often, if the change is embraced, then positive things happen.

And don’t be afraid to be different. Try not to conform to others’ trends or expectations. Embrace your own differences, and be confident about selling your own unique strengths and attributes.

Looking back, I’ve also learnt it’s important to lead as varied a life as possible outside of work. It’s amazing how different experiences and hearing different thoughts and ways of thinking can give you a better perspective on life, more energy and vitality, and a far better ability to really connect with people. This also makes you a far more effective and empathic leader.

Gareth Cummings, CTO at eDesk

What advice would you give to your 25-year-old self?

The first thing I would advise my 25-year-old self is to continue focusing on job opportunities that offer a steep learning growth and some risk attached. This will mean turning down offers from more established companies with higher salaries to work in tech startups. However, in the medium term, the experience and knowledge you gain allow you to progress further in your career and build a skill set that you wouldn’t have gained from a more traditional path.

Secondly, continue focusing on your education; returning to university in the evenings and weekends to gain your Computer Science degree is hard work. Your studies, alongside a full-time job at the same time as your first child being born, ensures you won’t have much time for yourself! However, it will give you the confidence to push towards more senior roles and remove doubt around your ability to work alongside deeply talented technical people.

Thirdly, continue listening to your gut instinct. At times you’ll be advised by different (well-meaning) people on what to do in your career. Continue to follow your gut, even if it means going against this advice. You (mostly!) make the right decisions.

Lastly, like everybody, you’ll face setbacks; there are highs and lows like anything in life. Keep a level head, and don’t get too discouraged by the lows or too carried away with the highs. Always remember what your Dad said to you: ‘Keep her going’. Whether it’s for work or personal life, keep going, moving forward and pushing on.

Gary Ogasawara, CTO, Cloudian

What advice would you give to your 25-year-old self?

Work and play with a diverse set of people that will provide opportunities to learn and focus on new and good ideas. As a future Marc Andreessen will later say, software is eating the world. Think about how software can run together in different shapes and sizes and work in distributed environments where things (hardware and software) will fail, and networks will be unreliable.

Build software that expects and thrives in that type of uncertain and unreliable environment. Bayesian probability and decision theory is an effective framework to build complex systems for AI/ML, so continue to study that. Then, it’s all about the data, being able to collect, clean, and process data in order to effectively bring it to bear on the problem being solved.

Finally, always start with first principles, drilling down on thoughts until you get to the fundamental assertions. Then reason up from there. That solid foundation makes it possible to branch out and work on the details.  In contrast to first principles thinking, comparing similar situations and acting because they seem the same is an incomplete way of reasoning.

David Walker Field CTO, EMEA, Yugabyte 

What advice would you give to your 25-year-old self?

GO TO BERLIN! In November 1989, we could sense something was happening, and the Berlin Wall was about to come down. I suggested to my then-girlfriend, now my wife of 30 years, that we go for the weekend. She thought it was rash; where would we stay; would we be safe? It’s a lasting regret that we didn’t go. It reinforces my belief that everyone should take full advantage of opportunities when they arise and occasionally do something rash. It’s the things we don’t do that we end up regretting and furthermore that we should do the things that make us happy – provided, of course, that these things don’t hurt others.

It’s also about taking managed risks. A couple of times in my career, I have really stepped beyond what was comfortable. The first was in agreeing to scale a Sequent system beyond what anyone had done before; at the time it seemed massive, 1000 concurrent users. The second more recently was to build a Hadoop system straight into a bank’s production environment and get it DSS PCI certified. rather than building in dev, test before being able to get the business benefit.

In both cases, it was a calculated risk. It paid off. Most importantly, the team of people who came together to achieve this is what I value most.  

And finally, buy and hold some Apple stock!

Martin Biggs, VP and General Manager, EMEA, Spinnaker Support

What advice would you give to your 25-year-old self?

As an industry, ours is fraught with potential misunderstandings. Apparently unambiguous words like ‘support’ and ‘service’ can mean entirely different things to different people (as I know all too well as Vice President of a third-party support provider!). At the other end of the technical spectrum, it’s all too easy for IT experts to become so immersed in their specialism that they assume what they’re saying is clear. This is compounded while working internationally when sense can be lost in translation.

If we want to grow professionally and personally, we have to keep questioning, challenging and learning, however old we are. I remember not understanding something in my 20s, but being too afraid to ask for clarification because I didn’t want to appear stupid. Today, I wouldn’t hesitate.

No question is stupid if you don’t know the answer. I just wish someone had told me this when I was 25!

Ian McShane, Field CTO, Arctic Wolf

What advice would you give to your 25-year-old self?

They say hindsight is 20/20 and believe me, I have had plenty of “learning moments”. Skipping the obvious answers like “buy bitcoin in 2009” or “invest in FAANG”, my advice from product requirements and delivery perspective is simple: spend more time thinking about how users can and will adopt what you are building. 

Cybersecurity has long appeared to be a cutting-edge industry with vendors racing to announce the next futuristic-sounding capability or brand name and talking about nation-state threats. Meanwhile, relatively few organisations have the means – both from a people and fiscal standpoint – to implement the constant stream of new and advanced security capabilities. In my opinion, the “skills crisis” is caused just as much by this repeated explosion of new tools, buzzwords and frameworks, as well as controls, as it is with the lack of human talent.

If technology vendors can continue to improve their focus on the user experience and on the path to adoption, end-user organisations can move beyond the ‘skills crisis’ by hiring people rather than just certifications and by moving towards tools and processes which elevate their existing IT staff to be more productive and most importantly, avoiding burn-out. After all, we know that there are plenty of people looking for work and plenty who would love to get into the info-sec field. What’s more, the recent embrace of remote work opens up many more hiring and job opportunities.

 Andy Harris, CTO, Osirium

What advice would you give to your 25-year-old self?

My top tips for my 25-year-old self are to remember that all successful software-based products require ground-up re-writes, and these can be very expensive, so the art to master is picking the right time. Consider that version 2, or around 50 customers, is a super rough but helpful guide to follow – also remember that this advice doesn’t include Apps. Be warned; if you ever find yourself, or your team, creating a new language for operation or configuration, then you are almost certainly committing a crime against software development. Just don’t do it; use the most appropriate existing language.

Avoid creating a ‘God Box’ product.  If you do create a product that everyone has to use, please recognise that this has special responsibilities and take far more effort to ensure that these products fail gracefully; which certainly requires more effort than getting the product to work in the first place.  Testing is insufficient for this class of product, only the evilest beatings will do.

Usability will trump functionality far more times than you think!

Your customers and users will often tell you WHAT they want, so keep communicating until they have told you both what they NEED, and WHY they need it.  Only at this point will you have a true definition of a feature. Keep asking the questions.

In nearly all circumstances, what your sales team tells you about the competition is far less important than they think. On the other hand, what customers say about the competition is golden information. Choose carefully which conversations you take the most notes from.

Whilst testing, there are issues that may happen just once, and odd messages may appear in your peripheral vision.  These are the ‘canaries of doom’ – track them down until you are satisfied they are vanquished.

Try a different language or operating system at least once a year, you need to be exposed to different paradigms.

Ultimately, the pursuit of art is the balance of technical achievement; do more art achieve more tech.

Bob Petrocelli, CTO at Datto

What advice would you give to your 25-year-old self?

The year was 1991, I was a twenty-five-year-old graduate student, working full time in an imaging research laboratory. “(Everything I Do) I Do It for You” was top of the pop charts and Apple was trading at a split-adjusted US$1.20/share. Obviously, the best advice I could give would be to borrow from friends and family and buy and hold AAPL!

Seriously, much of the pattern for my future was already beginning to solidify. Computer science and digital imaging would consume my attention for the next 15 years. During this time I founded a medical imaging startup and eventually sold that business in 2005.

This stage of my life – and the pivot to data storage optimisation as a focus (and my next startup) – would be the focus of my advice: “take a breath – live in the moment – take inventory”. Every decade or so I had set big goals and I focused on that imagined future – but eventually, we will all run out of decades. So my advice to that younger self is simple: “Keep those big goals – but enjoy the journey – the future will unfold in ways you will never predict or completely control – and of course buy AAPL.”

Martin Rudd, co-founder and CTO at SECQAI

What advice would you give to your 25-year-old self?

It’s interesting, as I tend to always look forward rather than back, but I’d certainly be telling myself to listen, never underestimate the value of being creative, keep exercising (you only get one body!), and don’t be afraid of risk or opportunity. I truly believe that wisdom isn’t exclusive to the old, and innovation isn’t exclusive to youth – 25 is a great age to really reach out and test the world. Expand your mind and read voraciously – explore philosophy, foreign languages, strange food, and art. Understand cultures worldwide; we all breathe the same air; if we can be sensitive to culture and history but encompass differences, we can achieve so much. All of these things will get brought together into your own experience of life and, as you grow professionally, give you an added dimension and significant extra value.

I don’t do now professionally what I did then (derivatives trading vs quantum computing), but by seeing opportunities and keeping a healthy, balanced mind and attitude things evolved, and working in areas that are interesting, not just paid well. 

If I had to choose a couple of things then listening and putting myself in other people’s shoes is invaluable for a whole range of reasons, also moderation in all things (including moderation).

 Chris Royles, Field CTO of EMEA at Cloudera

What advice would you give to your 25-year-old self?

My first tip to my younger self: what you learn at university is less about content and more about the skills that help you undertake research and inspire you to be forever curious. 25 years ago I was fully invested in completing my PhD at Liverpool University.  In the intervening years, I have recognised that the value of my research has diminished as approaches to AI such as Deep Learning have moved the lens. However, what I took with me was a set of principles, linked to scientific rigour, research and writing that have stayed with me. 

Secondly, apply your skills across a breadth of roles. My first job out of university was as a Java software developer, and I will always be grateful to Brendan Treacy from Vicorp for his trust in me. It gave me the foundations of software engineering and enough experience to have insightful conversations with product management and engineering. Being a small business, everyone had many roles, which helped me understand customer service, software development, requirements capture, and implementation.

The final piece of advice is a personal one. It relates to those closest to you and having their support, patience, and help when necessary. My wife and family have been a key foundation throughout the last 10 years, and without their support, my career would be very different. We talk about building successful teams and businesses, but as leaders, let’s not forget that having a strong support system is key.

Zeki Turedi, the CTO, EMEA at CrowdStrike

What advice would you give to your 25-year-old self?

People drawn to technology tend to think logically: you simply have to in order to operate successfully in the field. It doesn’t matter about age, everyone still has a huge amount to learn about their technology area, its history, and how practitioners have been succeeding with critical thinking and problem-solving tools like mental models. And every day, there are even more challenges, opportunities, and ideas.

Particularly in a very practical field like cybersecurity, there are ways to learn what works, but then there are the mental tools to deconstruct and consider if an approach works well enough. For example, the world’s best cybersecurity tools have been beaten in the past with social engineering tricks hacking the brains of users. That way, adversaries don’t need to program a line of code: they just need to sound convincing enough on the phone to trick someone with access.

So I would tell my 25-year-old self to keep on learning. However smart you are, the field is continually moving forward. There’s never a limit to what you can learn from experts, practitioners, the people around you and from getting stuck in with some hands-on activity. The more you know, and the broader your skill-set from a young age, the better you can make connections, solve problems, and manage every aspect of a complex field like cybersecurity. Where humans, businesses, and technologies interact there are always ways to make processes better and more secure.

It’s never too early to become more expert and better in all areas of your field.

Chris Wood, CTO, Spicy Mango

What advice would you give to your 25-year-old self?

Listening to the wisdom of elders can often be one of the greatest gifts we are bestowed. That said, it’s often very hard to relate what we’re told to personal circumstances – and in the heat of the moment, even harder to act upon.

Here are four statements I’d probably throw my way in hindsight:

1. Everything takes longer than you think it will. Despite your ambition, dedication, pace (and lack of sleep), others around you don’t always have the same desire to move at the same speed. Be patient; it will come.

2. Experience brings familiarity. The more you deal with similar clients, projects and situations, the more familiar doing the job will become, and familiarity seems to correlate to less stress too.

3. Trust your judgement and that of others around you. Hire people smarter than you and listen to what they say. Make informed decisions based on the things they tell you – you hired them for a reason. Have faith in your decisions. You won’t always be ‘right’ – but you’ll be comfortable you made the right decision based on the right reasons at the time.

4. Take downtime. I’ve been terrible at this – and now I’ve aged a little, it’s taking longer to recover from a mentally tough few months. So you’ll think a little more clearly with some regular downtime.

READ MORE:

• The challenges of being a CTO in a post-COVID era
• How CIOs can become CEOs: tips from a tech leadership headhunter
• SolarWinds IT Trends Report 2021: Building a Secure Future
• Snow Software on cybersecurity trends and challenges in 2021

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