The Secrets to Becoming a Technology Leader

Many technologists have big dreams, big ambitions, they want to be the CTO of Google, they want to have a million technologists listening to them in awe, they want to be immortalised in tech. Sure buddy, it’s all about you; and guess what, it doesn’t work like that. Technologists can see through self-serving leaders, because they’re usually pretty smart.


I’ve been lucky enough to find myself in a very privileged position; one I always wanted, and one I spent time really fighting for… Except for much of my career I was fighting the wrong way, I was fighting for my own progression and wondering why I wasn’t really getting anywhere.

I’ve done a little research and introspection and tried to organise my thoughts on how I’ve changed and which philosophies I’ve taken on board to enact that change, because none of it is taught to you in school or university and some of it almost feels counter-intuitive. There are a bushel of self-help books on leadership out there, but I’ve tried to tailor this content to my field, technology, which you may or may not find helpful.

With that in mind, this post takes a blended approach between and quotes from Thich Nhat Hanh, Leo Babuta, Alfred Adler, Alejandro Jodorowsky, Georges Gurdjieff and Simon Sinek. I’ve tried to cite quotes where possible, but it was all inspired by a mishmash of their ideas in conjunction with my experiences.

Many of the problems you will find in progressing your career are due to smoke and mirrors created by the ego. The harder you push to “win at technology” the harder your life will become (and the harder my life became when I bought into it all). However, you can change, it just takes an antidote to the poison of ambition, and this article is my antidote, what works for me. Your mileage may vary and you may disagree with me, that’s cool, leave me a comment and I’ll consider making additions and changes.

But, to get to the heart of the matter, what makes a good technical leader? It’s subjective, but here’s my humble opinion… Generally great technical leaders don’t:

  • Make all the technological decisions
  • Own an area or technology, creating a fiefdom
  • Keep the good work for themselves
  • Create a hierarchy under them
  • Hoard and hide information
  • Take all the glory
  • Be nice upwards but nasty downwards
  • Make the entire show about themselves

But they do:

  • Understand the power of positive delegation
  • Empower technologists to be creative with their choices and designs
  • Have oversight, accountability or responsibility but that’s to protect the project and the team
  • Try to create horizontal relationships, treating people equally
  • Give all of their information away, fully, openly, honestly
  • Try to create information flows, that are more of a snowflake pattern than a tree
  • They understand how great information flow can be used for education, sharing and growth
  • Enjoy but not steal the successes of others, including the ones they’ve helped succeed and possibly surpass them
  • Make the entire show about technologists as a community, including acting as advocate for them to clients and the business

People in leadership positions often misunderstand the terms power and wealth, this is where they lose their way. In short, leadership should be a serving role, it should be there to lead people and projects to improvement and delivery of value.

In this article, I’m going to cover:

  • Some core psychological concepts that we should consider as leaders
  • Working with the technical community
  • Working with your organisation
  • Working with individuals
  • Working with teams
  • Working with yourself (this is the scary one)

So, brace yourself, this might be a bumpy ride for some of you as you have to dispel your own myths.

Some core concepts

The infinite game

The great writer, optimist and thinker Simon Sinek hypothesised that there are two types of game out there: finite and infinite.

The finite game is one like chess, which is a complex game, but it has set rules, set players and a fixed set of endings, when you resign, are checkmated, stalemated or a draw occurs. But real life isn’t much like the finite game.

The infinite game has an endless play-field, it has players that dip in and out, the rules can change and there are no winning conditions (although you can lose). This means that means the game will never end, you are a player who dips in and out, and while you’re in a game that is continuously moving you have to keep improving and changing.

The ego and how you should work with it

The ego, along with the superego and the id, is part of the human mind. It operates on a reward system and often out of fear. It may ask you to tread on toes to reach your goals, or to hate people as an enemy (more on this later). You must learn to recognise when it is trying to be in control. One mistake people make is thinking they can destroy it. Alan Watts once likened the ego to a burglar in a house… When the police come in the first floor, it moves to the second one (a higher state ego) so you think you’re free of it, but really it’s just doing its job on a slightly different level (now it might try to tell you to do acts of charity or spirituality to gain fame and reward). You can keep chasing your ego up the floors of the house, but it will probably always be there. The trick is to accept that and live with it, recognising when it’s trying to asserts its dominance.

Horizontal and vertical relationships

Alfred Adler wrote a lot about relationship building in his books on psychology and he discussed two main types: vertical and horizontal.

A vertical relationship is by its nature hierarchical, and is established through direct use of power but also more subtly through praise and rebuke. The seemingly innocuous phrase “good job, that was very good work” is actually you creating a vertical relationship as you’re actually saying “I have judged this work as your superior and I decree that it is good.

A horizontal relationship is one of peers who do different jobs, they have “separation of tasks” (another Adler concept). A horizontal interaction might be “thank you for that work, I have taken great value from it”. Notice how that doesn’t judge its quality, just that the recipient has benefitted.

Implementing this in the workplace is really quite difficult, as I keep catching myself using vertical words when I should be thinking and speaking horizontally.

Working with the community

Launch something, be a part of something. Start something new. But start small and make it so easy that the unhelpful bits of your brain can’t say no. – Leo Babauta

The technical community is not small; there are around 26 million developers in the world, that’s quite a large community indeed (more than five times the population of Scotland), and it’s growing, furthermore it isn’t going to stop growing anytime soon. The larger we grow, the more concentrated (in each area) we get and thus the more opportunity and requirement for community.

Everything is a community

The only worthwhile achievements of man are those which are socially useful. – Alfred Adler

As soon as you have more than one person in the equation, you’re in a community and there are layers of community: your home, your work, your city, your industry, your county etc. 

You will need to consider which communities you’re going to engage in, the technical community in your organisation, in your city and maybe in your specialist field. You should be positively inputting into each of these as best you can, but your positive input doesn’t necessarily mean your own words or presence, it can be your influence on encouraging others to engage.

Open-source your thoughts, and encourage community input

“I do not want anything for myself that I do not want for others”

“Do not regard anyone or anything as your possession.” – Alejandro Jodorowsky

Write about your learning, what drives you, your mistakes, your successes, your “secrets”. Leave nothing back for yourself, open-source everything in your head. There will always be more, trust me! Your potential for new learning, experience and insight should be almost limitless, if you truly want to be a leader in a field as fast-moving as technology.

Actively plan to talk at events, run workshops and round-tables, but here’s the important part (in my opinion), when you do these things, take others on the journey with you, try not to be the only voice in the room, don’t make it the “you show”, make it the “us show”. 

Support others’ ideas, help a friend pitch an idea to the board. Be dogged in helping them structure their ideas, visualise it through visual storytelling, be there in the room for the pitch.

Helping the community doesn’t mean doing it yourself

You are one person, you cannot be in multiple places at once, you are single threaded. With that in mind, often the best path is to encourage others to be community minded, to attend meet-ups, to speak, to write, to innovate. It can be hard, but community engagement by people within your sphere of influence is crucially important.

Help grow talent in the community

How can you help more talent entering the industry and growing the people already in it? For every engaged member, I’d wager there is one who is disenchanted. Things like the Leeds, Halifax and Manchester Digital Festivals have really helped create engagement from some who might otherwise not have bothered. I feel that initiatives like this are invaluable. But we can’t just keep growing the industry with the same kind of person, we need diversity, we need to help the neurodiverse into the industry, we need to help others who are otherwise finding it difficult to find a way in. We can do this through signposting, careers advice workshops, making the industry attractive to other demographics. But that’s a huge topic in itself.

If you consider growing talent important, you could consider something like teaching in your spare time. Many colleges and universities are crying out for guest speakers to teach technology fundamentals and practical engineering principles.

Saving the community from itself

The technology industry is growing in power and influence, technologists now make business work, as almost all businesses need IT to function. An example being that all supermarket chain are 100% reliant on technology for their stock and order management. This means that conduct and ethics are more important than ever. As a member of the community, especially in a privileged position of a leader, you should be thinking about how you can inject ethics into your conversations. The community is full of hot-headed, highly intelligent, but in many cases, slightly naive technologists. Hubris can lead to disaster, so it’s your role as a responsible adult to help ground people just enough to remain ethical.

Working with your organisation

Show your colleagues why they need you (and your peers)

Thanks to my colleague/friend Jo Crossick (sadly @mentions don’t work in articles) for mentioning this key attribute of being a technology leader in a growing organisation…

Part of being a technology leader is being a good storyteller (don’t misunderstand me, I’m not using that as a euphemism for lying), as you need to create that shared vision of a cohesive group of technologists who are working to form a community with the same values, quality and ethics. Even great technologists start to struggle without a shared vision, and worse still can end up lone guns, going native or moving to your competitors. You should include as much of what we’ve discussed in this article possible, including your technical direction, values and even your weak points, be honest and open but give them hope that somebody is at the wheel who cares about them.

Be an advocate for technologists

Some organisations “tolerate” engineers, which is a slightly absurd view as many of them are nowadays almost 100% reliant on technology to operate. Helping your organisation’s board level members understand the value of their engineers as well as how precarious the situation could be without them is crucial. At the time of writing, the job market in IT is very much a “candidate’s market”, meaning that if nobody is advocating you as a technologist, you will be unhappy and eventually leave. Become the buffer between management and technologists, explaining the importance of both aspects of the organisation, which leads me on to the next point…

Champion your organisation’s values, framed in the context of technology

The IT jobs market is very “hot” and there are roles everywhere, which means you can afford to be picky. With that in mind, you should seek to work at an organisation that:

  • Has core values, 
  • that are clearly defined,
  • which are people oriented,
  • preferably designed up-front as part of the fabric of the organisation,
  • and crucially roughly align with your own values

If you cannot say the above of your company, you can either try to create and instil these values (hard) or move somewhere that has them already (easier). Once you’ve found an organisation with real values, you need to start living them and most of all become an amplifier for them to others.

However as the aforementioned colleague of mine pointed out, while they can form an excellent “starter culture”, you have to vigilant that these values don’t just become a hollow marketing technique, they have to be exhibited on an ongoing basis (and remember, you’re part of making that happen), as if you let core values slip, the organisation’s culture will suffer, which will lead to attrition, poor delivery and a poor reputation within the industry. As a technology leader, these values should be embodied in how you both deliver technology and deal with people (be they clients or colleagues).

If you work in a place you don’t believe in, you will quickly find yourself jaded and you will stop trying, which is the worst thing you can do in this industry, given its pace of change. Worse still, you might even start letting your own core values and ethics slip in your apathy, which is the path to the dark side.

Be the engineer of information flow

Organisations often suffer from information flow problems, as a technology leader, you should be interested in how information flows through your organisation. It is the conduit for your messages and more importantly others’ you’re helping grow.

Hierarchical power is not really what we should be aiming for, you will never get your message across clearly or in a timely fashion. You should be looking at information flow rather than power hierarchies.

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You could flatten that hierarchy out so you communicate with everybody directly, but that only scales to a few people in a small number of locations. You will either start cutting corners or exhaust yourself as your organisation scales up, so this approach is an interim measure, at best.

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Information should flow horizontally like an irrigation system across the different fields that are the departments of your organisation. But this flow should be bi-directional.

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Technical innovation flows to “interest” (personal or corporate), which flows to blogs, talks, open-source contributions, then often to more formal learning pathways. In the near future, I’ll share my full vision for information flow with you. It’s a complex topic in its own right.

This bidirectional, “many-to-many” flow is more complex and requires the right tools and practices to make it work, so you’ll need to put in some leg-work to get the fundamentals right, but you’ll be rewarded with a working community, where people feel like they can contribute.

Be an inclusivity champion

Recognise that all engineers are of equal worth even though some of them think quite differently. Our industry has long been plagued with a diversity and inclusivity problem. We need a better mixture to help with creative problem solving as well as giving a step-up into the industry for those who may find traditional recruitment processes and working practices problematic. This is something I’m particularly passionate about, coming from a class of 120 people, only three of whom were women, it’s clear that for some time, we have had a big problem. The situation is improving, but it could always use your help to accelerate that improvement. If you are a white, male, straight technology leader, you have a beautiful thing called “privilege”, which can be used for terrible things but conversely can make you a powerful champion. You will be heard because of your privilege, so don’t beat yourself up about privilege, you didn’t choose it, but you can choose what to do with it, which is a crucial difference.

Help build and retain the talent pool in your organisation

Don’t just talk with, work with, and hire copies of you, that’s not inclusive or helpful to the expansion of our industry. It’s effectively a form of nepotism/inbreeding, which is rarely a good idea, and living in an echo chamber invariably holds your own thinking back. Once that kind of inbreeding becomes the norm, a company can become utterly toxic.

But you should interview people to see what makes technologists tick and what drives them. When you do, try to find the best in them, make your questions a dialogue, not just barking factual single answer based questions. But be clear about what you’re asking for, don’t beat around the bush.

Work closely with your learning, marketing and recruitment departments to help them understand the mysterious ways of technology, as not everybody is from a technology background. This can be done in an adult, tactful way and they will often than you for what they’ve learned along the way.

You should also look at retention, is it falling? If so, can you find out why? Technologists are not all about the money, many of us enjoy the intellectual stimulation, our colleagues and the variety a technology career can bring. When technology is stale, clients or colleagues are toxic or a programme is so restrictive no real creativity and problem solving can be exhibited, you will end up with a retention problem.

Pull the strings in the background

As a technology leader, often we are the best placed to be in the background making a difference. Remember, we’re leading, not trying to turn ourselves into a reality TV star, this includes:

  1. Helping guide, mentor and grow our colleagues
  2. Helping promote our colleagues’ events, talks, writing
  3. Making a client look good by guiding them wisely
  4. Making the organisation look good by embodying their values
  5. Furthering diversity, inclusivity and reducing exclusion and bullying through “right action”

And crucially, don’t ask for (nor expect) reward or thanks, much of the satisfaction of this should come from your “feeling having contributed to your community” (which is an Adlerian concept). Also, it’s really hard to criticise somebody who is doing the above and making a positive difference. Do not, however, use this as an excuse to engage in double-dealing or sabotage.

Working with teams

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Working with Agile teams in full-flow can be difficult, you will have to show your leadership skills more often, and you will be pinned to deadlines. This means that things will get a bit shouty at times, which can threaten egos and thus drive fear-based behaviour.

However, you don’t wan’t to appear to be an autocratic leader, and this kind of “leader” can often be identified by:

  • Strong chain of command, downwards
  • Often an inability to reflect things upwards (i.e. escalate)
  • Clear separation of leader from the body of the team
  • Rigid definition of “how” things should be done

Your main role should be “to protect and to serve”, which means that you should be the buffer-zone between nasty nonsense like:

  • The blame game from above
  • Tedious talk about contracts
  • Constant demands for team flux

Blame from above

Criticism from outside of your team is a poison as an attack on one is an attack on all of you. The reason this is so poisonous is because it creates division within the team, which is crippling.

So any talk of “oh Roger on your team is rubbish, we should have them shot” should be carefully managed and is one of the really tough situations in life. You can be smart and say “well, maybe Roger has something going on in his life right now, I agree he doesn’t seem himself, let me go and have a one-to-one with him to figure out where his head is at”. Don’t just blindly agree to get yourself off the hook; that isn’t leadership.

Programme noise low-pass filter

Your team should get a digest from you about the state of the programme that is honest and of use to them. They don’t need to know about the individual tiresome clauses your organisation might be in contravention of. By all means end your updates with “there’s a bunch of other tedious stuff I’m not going to bore you with and I’ll tell you if you want, but that’ll have to be over a coffee”. By doing this you’re not “hiding” information, just giving them the important parts, and if they want to know about cross-team IPR wording then fine, you can buy them a coffee and bore their socks off.

Protect and serve

You should protect your team from the mad-hatter’s tea-party style of management that changes team and working structure every two weeks because somebody has gotten spooked. Sometimes, that might mean nodding and smiling at unreasonable demands before figuring out how you can make it look like you’re complying without disrupting your team’s cadence.

Become the blame sponge

Part of protect and serve is becoming the blame sponge. Your team, if under expert leadership (i.e. you) should actually be doing the right kinds of things, it’s quite often that the rest of the programme might be on fire and not see your team as working optimally. Sometimes you’ll have to suck it up to protect your team. This is one of the hardest parts as you’re definitely getting career recognition, just maybe not for the reasons you’d hoped. However, what will result from this is ultimate team respect as trust will flourish.

Democratise your autocracy

Often, you will have a standard or way of working that you will want to put in stone somewhere in the 10 commandments of your project. Just telling them “thou shalt” doesn’t work well with a group of strong thinkers, they will be aggrieved and not want to follow your rules. But it is also crucially important that you have invariant quality bars you don’t lower as nobody wants rubbish code! But you can’t just dictate these, you agree them as a community of peers. 

How do you do this? Here’s one idea…. Instead of just dropping a set of standards into Confluence , set up a workshop, with a solid agenda, some suggestions (obviously asking them to bring their own), then you can manage it. By giving everybody a voice, they will usually sign-up to the outcome, even if that outcome looks suspiciously like your original idea.

Encourage your team to make small experiments

Be prepared to sign off tickets into a sprint that are PoCs where there is a reasonable chance that it could provide benefits to the programme. You’ll need to take one for the team when it comes to the blame around it, but that’s your job and you need to put your big-person pants on.

Be there for them

This doesn’t mean you have to be at your desk 24/7, but always try to respond to calls, Slack messages, emails, make each member of the team feel equally important, because for the most part, they are! If you have “golden time” then tell them you need to concentrate, but get back to them when you’re out of the time you need your “flow”. Being there for them can include their personal problems too, which

Always grow a backfill

As a technology leader, you won’t want to be on the same project forever, in fact that’s really quite a poor use of your time. Find your second(s) in command and pair with them, invite them to the right meetings, delegate some of your review work for them, go for coffee with them. Then, when the time is right, ask them “would you like to be doing what I’m doing”.

You will be surprised how many say no, from experience it’s about 50%, which can be through fear, lack of ambition, personal circumstances, differing career goals or a whole raft of other things. But grow enough of them and you’ll find your backfill, and then it’s time to slowly start dialling back. Once you’re completely removed (safely) from the picture, congratulations, you just grew a new technology leader. Which leads me nicely on to…

Working with individuals

Working with individuals means working with people, not “resources”. This might mean you will get tied up in their personal problems, but that is not always a bad thing. With the right kind of compassion and “deep listening” (see the further reading for a link on this), you can build up meaningful working and personal relationships with your colleagues.

Help one person, help another, then another. Write about what you learned helping them. Create something for someone and give that creation to others. – Leo Babauta

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Grow others, and never hesitate or hold back

Don’t think “how can I get the most out of my people” like you’re wringing out a towel, instead think “how can I help people be their natural best?” – Simon Sinek

Line management and mentorship are huge opportunities to help people to grow and you should seek them out or accept any reasonable requests for mentorship. When you do so, be consistent and give them 100% of your tips, tricks and techniques. There should be no secrets or things you keep just for yourself. As mentioned in the previous section, grow as many backfills as possible,

By mentoring somebody, not only will you make a friend but you’ll learn a lot yourself, honestly, it is transformative for both parties involved.

My final word on this is, do not expect them to actually be you, they will have their own style and this is healthy, just try to give them as many tools as possible.

Switch technology off

Online can be exhausting and very isolating, but remember, there’s a life beyond technology, in the real world, one with real relationships.

With that in mind, put your tech away when mentoring or talking to somebody. Don’t just put your phone down, or even upside down. Put your phones and laptops away, use a notepad if you need to, but technology creates a gap between you and the person you’re supposed to be making important.

Remember, the bottom line with your interactions is that you’re trying to bring people closer together, not push them further away, so get close, so close you can see their excitement, suffering and anything else they might not even realise about themselves just yet.

Form horizontal relationships

 “A true partner or friend is one who encourages you to look deep inside yourself for the beauty and love you’ve been seeking.” – Thich Nhat Hanh

Don’t technically micromanage people as this creates a vertical relationship (which leads to hierarchy, instead allow for creative and personal freedom. Talk about how much value you get from something rather than judging it as “good” or “bad”, which is inherently vertical.

Be generous with your time, accepting that you might have to travel a bit to make real connections with colleagues in offices. People appreciate you coming to visit them, it shows that you value them enough to sacrifice time for them, to come to them, to treat them as if they matter. Time is a non-redeemable commodity, you can’t have more of it, so people appreciate it when you spend that finite resource on them.

Be approachable and open to opinions

Hopefully, you’re working in a non-hierarchical organisation, you’re not the “boss” or “special”, you’re a human being and people should feel like they can talk to you as peers. You should broadcast that far and wide, ensure people know that “your door is open”. Never ignore a Slack message or email, it can be tiring but it’s worthwhile.

Also, listen to your team more, to be a technology leader, you don’t have to be the only voice in the room. Good listeners are hard to come by; zen master Thich Nhat Hanh notes that deep listening can help a person suffer less, even if you don’t agree with their perceptions and opinions, just listen, you can discuss your differences at a later time.

Never be dishonest

Do not lie or steal, for you lie to yourself and steal from yourself. – Alejandro Jodorowsky

Never lie to people or violate their expectations, trust is built up and hard to rebuild once it has been broken. Represent things fairly and for the love of your own integrity, do not take credit for their work.

If you get to a position of power through lies and double-dealing, you’ll enjoy it up until times get tough. Then you’ll see how many people are willing to help bail you out, then you will reap the rewards of your behaviour, you will have stolen from yourself.

Finally, never undermine people. Unless it’s a matter of quality, honesty or ethics. Even then, approach them first before escalating.

Working with technology

Build up Credibility

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Building up a portfolio of projects/programmes you’ve really invested yourself in delivering, ones that even if they weren’t easy, can be looked at as success or growth. Having a rich history of actual delivery of complex systems brings a huge amount of credibility to a leader. It’s crucially important that you engage in a retrospective and some introspection to figure out what worked and what could be changed to have made things better or easier. I don’t believe there’s a shortcut to this, as people see straight through a leader who doesn’t know the material of the people they’re leading. Your formative projects are your training to be a leader. Remember the old adage “train hard, fight easy”.

Keeping your technology fresh

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Example technology radar from Making Waves

I find it helpful to keep myself a technology radar, and I’d encourage you to do the same. Keep a track of what interests you, what’s emerging and useful in the industry, what work your company are engaging in, what work you’re bidding for and what technologies your colleagues are taking an interest in.

Many technology leaders, do not have the time to spend eight hours a day coding, maybe not even one or two, we can end up being very busy and detached. So if you haven’t time to code, pair program with a colleague or do some clean code refactoring with a more junior member of your organisation. Immerse yourself every so often in technology in a way that won’t be too impactful to a project.

In addition to the above, you should ask to show up to standups, walkthroughs and demos of other projects to see how technology is being leveraged in differing ways.

When it comes to choices of technologies, I find it useful to be broad yet deep. T-shaped is so last year as it implies as single depth, In reality, great technologists are M-shaped, with multiple depths and also wide shallower qualities. Taking a holistic view of technology gives you a lot of insight and leverage.

Encourage Innovation

Find accelerators to show your ideas. The record companies didn’t come up with Spotify, the media didn’t come up with facebook. You can do something different and with tech the entry bar is pretty low. 

Learn how to pitch things and what matters to stakeholders of different brain types.

Learn to be an excellent storyteller-diagrammer. Forget pure UML, learn to tell a visual story to people, knowing which levels to pitch it at

Be a Disruptor

Do not eliminate, but transmute. – Alejandro Jodorowsky

As a leader, being a bland, silent party can be damaging, so be a rebel and a punk, be you, make yourself the agent of change!

Take a positive outlook on disruption, find things that need changing and make them an opportunity. As long as you’re not violating security or licensing constraints, you can spend an evening knocking something up.

Often this can mean just disrupting a project that has gotten stuck in a bit of a rut, with outdated practices. Don’t just let the status quo rule the roost, most technologists crave change.

Working with yourself

Define your values

Your own values and ethics may vary from mine, and that’s ok, but you should have some. If you don’t start from a clean sheet of paper and write them down as bullet points. You only need a handful and these will be your guiding values, which will form the principles and even ethical framework upon which you stand. I’d then make those your desktop, your phone background, a daily reminder in your calendar or similar. Something to remind yourself about who you are, or who you’re aspiring to be.

It doesn’t matter if those values evolve over time, in fact, it’s a healthy thing. You’re not the best you right now, there’s always room for improvement in your thinking.

Find your passion

Don’t do things that you aren’t passionate about, at least not as your main occupation. Everybody has to do things that bore them every so often, but your long-game, your main role should be something you have a passion for. It is my opinion that it is pretty important that part of that passion is for people

Work using the Golden Circle (a Simon Sinek concept)

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Diagram stolen from

Find the “why”, your purpose, which will probably link in with your values. Why do you come to work in this industry?

Find out about your “what”, what you’d like to actually achieve and before you start talking about the “how”, have a bit of a think if the “why” and the “what” are actually compatible

Then, finally, figure out the “how”, i.e. how the “what” can be achieved because of the driving “why”, and importantly how the “what” can be maintained, some of which I discuss below.

Be the role you want

Just start doing it, seriously. Go and read a job description for a Technical Lead, Chief Engineer, CTO or whatever you’re interested in and start doing the bits on the “Essentials” list, and preferably on the “Optionals” list also. This might mean you have to shadow, work extra, read on a topic, go to conferences… But one of the key things is to ask somebody to delegate work to you. If you ask a technical architect if you could help in their architectural duties and see a bit more of what they do, they’ll either say yes or no and that’s a good yardstick for which one you really should be learning from.

It’s the exact opposite of “fake it until you make it”, as you’re really doing the things for the role without the title. Some people will feel aggrieved that they’re not being paid for this extra effort, and to them I’d say “stop thinking so transactionally”. Often, good work that is outside of your current job role involves learning new skills while providing value/benefits. I’d argue that it is its own reward and that payment in some cases would even cheapen that experience. Remember, “wealth” isn’t just about money.

Accept you won’t be right all the time or know everything

“I realised that, as a leader I did not know have to know all the answers, and if I didn’t know the answers I didn’t have to pretend that I did” – Simon Sinek

Technology is the largest and broadest set of ideas in human history, it is a thousand years’ of learning, you will not live that long. Trying to define technology is also impossible as it’s a moving target, even trying to define what is not technology is shaky ground (e.g. smart-nappies are now on the tech radar).

Don’t compare yourself to others, compare yourself to how you were and where you’d like to be. Your own direction and velocity is the metric, don’t be blinded by anything else.

Accept that you won’t be loved by all

“To be beautiful means to be yourself. You don’t need to be accepted by others. You need to accept yourself.” – Thich Nhat Hanh

Some people aren’t going to like or accept you and that’s ok, don’t let it destroy your confidence as a leader. Adler called this separation of tasks i.e. it’s not your task to make somebody like you, as the task of liking or disliking is left to the other person, but it is your task to act in good faith and be likeable person. You can lead a horse to water, but some will never be willing to drink. You can win some people around by being consistent and showing you’re not there to steal their lunch, it might just take some time.

Make yourself an idealist and an optimist

As a leader, it’s your job to remain realistically optimistic. Granted, sometimes it’s hard to keep the faith, intrusive thoughts can ruin your optimism and idealism.

I learned to let these thoughts go. They are just thoughts — they don’t control me. They are just things that happen, like a leaf falling from a tree as I run by. Interesting phenomena, but not a determination of my life. – Leo Babauta

Life is largely experienced through your perception and attitude, the good news being that you can change those things.

I think it’s also crucial as a leader to have strong ethics, don’t just watch unethical things happen, escalate them in polite but firm language, in writing if necessary. In short, you should commit to using your “power” for good.

This becomes much easier when you only work for places that meet your values, or have values you aspire to, then you can take them on and work hard to embody them and both parties help each other evolve.

Be a paragon of integrity to those around you; you shouldn’t be swayed by the wrong perceptions of “wealth” or “power” into dropping your standards, values or ethics. Once people get a feeling that you’re “for sale”, it can be hard to shake, even if you’re penitent after the fact.

Operate on a kaizen basis

Stop defining yourself – Alejandro Jodorowsky

Kaizen is the Japanese term for continuous improvement. Make improvement a journey, not a goal. Try to play “the infinite game” as Simon Sinek would put it, in order to keep thinking of new and helpful, useful and innovative ways to lead.

The key is staying motivated to learn and change, but that can be draining if all you’re doing is learning new frameworks, software providers, architectures. With that in mind, don’t just learn about technology. Learn to draw, make music, meditate, write poetry, make it harder to define you by making yourself broader than a coder or an architect. It will change how you think about things and how people think about you.

Learn to say yes! Go outside of your comfort zone and sphere of knowledge

Apply for a role, position or responsibility where you don’t meet all of the criteria written down on paper. Most adverts are worded to sound like you need everything on the list, but you really don’t. This isn’t faking it, it’s just that you need to know that you’re more than a bullet list of technologies and experiences. People will buy and value you, the person, not Java or the Cloud as tech skills can be learned quite quickly, leadership cannot.

Get out there in the community, go to events, even stuff that’s “not in your wheelhouse”, even if it makes you feel uncomfortable. Network a bit, even if it’s like nails down a chalk-board to you.

Embrace the power of your “yes” muscle, it will unlock so much of the industry to you!

Learn to say no! Know when it’s time to push back

There will be a huge amount of pulls on your time, many of which will not be opportunities to learn, grow or do something positive. By being the “yes” person I mentioned above, some people will take it upon themselves to outsource all of their work to you. Not just delegation of tasks as they’re overworked, but their entire job barring them claiming the credit.

Also, there will be times you have expended your energy, you’ve done too much, you need a break, time to unwind. In these cases, you should be honest and tell them no, but give them a really honest reason why. It’s hard to argue with somebody telling you that they’ve done so much that they’re at the brink of exhaustion.

Also, say no to things that need precision, speed and expert knowledge, unless you can help lead an expert in delivering it together. Know your limits… Saying yes is your opportunity to grow, but don’t do it at the expense of pushing out a poor quality product to paying clients.

Introspect and Retrospect

Just like a Scrum sprint has a retrospective, a couple of my colleagues recently mentioned their weekly personal, internal retrospective. I think it’s a fascinating tool and one that could bring you many benefits.

List your positive points and journal your achievements, it’s a lot easier to write about the past if you have the details there for you.

Refine your ideas, writing and talks over time. There’s always room for improvement, more research and obviously the landscape changes constantly, so advice you wrote three years ago may need a bit of a dusting off and rewrite.

Here’s a hard one for you though… allow yourself to be wrong and vocally admit it when you were wrong, especially if your incorrect words or behaviour led to embarrassment or suffering of others.

Take feedback on board, you can always change and you will always change. You cannot remain the same, nature won’t allow it, so you may as well make the most of it.

Understand your long game

Many people want to be a CTO three years into their technology career, some even make it, but at the cost of credibility, they end up as salespeople or worse, an inconvenience to the real technologists.

My advice on this would be “don’t rush” as being a great technologist is a mixture of knowledge and experience and people will respect a technology leader much more if they’re actually a great technologist.

Learn as much about computer science as possible… it largely hasn’t changed in 35 years, that is a jewel that you can keep for your whole career.

Have goals, don’t just let the years fly by. Interview every year or so, see what is out there. It’s often not what you want, but staying sharp helps you when you need to work.

Understand how you can use the above, including the infinite game to figure out what your journey might be

Expect that you’ll make route changes when you decided that something isn’t for you, or a road is closed

Also understand that you can’t always make an impact within a month… Long-term value is less a two-minute long pop song, it’s more like a Godspeed You! Black Emperor piece, slowly building to a crescendo of potential, hope and call to action.

Build and market your brand, but indirectly

Obtain things in order to share them – Alejandro Jodorowsky

Your technology brand should be one that shows your wisdom, inclusivity and curiosity, not how skilled you are at React or Blockchain.

Share others’ success on LinkedIn, embrace people doing something community driven or inclusive, you’re not just a technology leader, you’re a member of the community with the responsibility to help be a voice of improvement for it. This means commenting on and sharing posts, helping others write blogs, letting people use your words (remember, you’re open-source!).

Also, don’t just make friends in high places, give equal time to those starting out in the industry, they will value your friendship and insight and you will certainly learn from them in turn.

Start being the first technologist the client sees, for bids, for proposal presentations, for the onsite pioneers, but try to include others in that, bring along a more junior person to shadow in bids, interviews, talks.

Tame your mind

 Smash your ego and rid yourself of the great fears:

  • What if that person I mentor surpasses me
  • What if that person I hire will get promoted ahead of me
  • What if the stuff I’m doing doesn’t get me recognised
  • Why is it taking me so long to make an impact
  • That mistake I made will never be forgotten, I wish I could just disappear
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You need to stop your ego from ruling you. Everybody has an ego (the term egoless culture is noble, but poorly worded, we all have egos) but you can work on taming it. If somebody you have mentored has a stratospheric rise, great, and they won’t forget it. If you hire great people, wonderful, that means your projects are more likely to deliver quality on time. 

Watch the thoughts that pass through your mind and learn to let them go. Get good at discomfort. Triumph over the childish, selfish scared mind. 

Also, don’t be too afraid of making mistakes; “spotlight syndrome” is the cognitive phenomenon is that people often think that their own, often minor faux pas will never be forgotten, will define their career, will make them a laughing stock… But the truth is, most people probably didn’t notice and those who did have probably forgotten ten minutes later. So rid yourself of that fear.

Being right is an art and is often contextual, and one should always try to qualify your words with in my opinion or to the best of my knowledge as there are often other viewpoints or contexts. It’s better that your input is “useful” rather than “right”.

Stop trying to “win”

You need to recognise when your ego is trying to “win”. Let me be clear, there is no exterior enemy or adversary; the only adversary is you. As long as you try to “win” at the infinite game of technology, as long as you keep acting against the principles of trying to help build this industry, the people, the world and just keep trying to serve your own needs, you’ll get further and further away from where you want to be. Not only that, but people will stop listening to you and then bitterness and anger can arise, which could ultimately destroy you.

But sadly, some people just aren’t open to that and they end up embittered and confused with the lack of their progression or the fact that everywhere they go, they seem to have people turn their backs on them. Don’t be that person.


“I ask you to believe nothing that you cannot verify for yourself.” – George Gurdjieff

This piece has been highly opinionated and it is what has worked for me so far, I found a lot of this out through making mistakes, trying to “win”, letting my ego speak for me. So maybe try some of the above out, see if it works for you, treat it empirically.

In a few bullets as a summary, I encourage you to:

  • Understand that there is no winner in technology, it is an infinite game
  • Understand that you’re the servant leader, not the boss
  • Stop striving for something as a selfish goal as you’ll move further from it
  • Understand what “power” and “wealth” really mean
  • Hold yourself to a higher standard than you do others
  • Believe that your ethics, behaviour and inclusivity should be the ground you stand on
  • Trust in and grow other technologists, passing on the above qualities to them, so they in turn can become great leaders
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I realise this is all quite preachy, and it’s really more of a note to self, as I’m nowhere near done, I can’t be defined, I can’t be constrained, I can’t be bought. I choose to be somewhere because of the values, culture and people, but I have a long way to go. Not because I have an infinite lust for “power” or “wealth” (in their negative meanings), but that the industry deserves people who care and try. I actually do have an infinite lust for true power and wealth and I’m going to tell you, finally what I mean by that.


  • Finite game definition – Authority that is given or delegated to a person or body
  • Infinite game definition – The ability or capacity to do something or act in a particular way


  • Finite game definition – an abundance of valuable possessions or money
  • Infinite game definition – abundant supply

I have an infinite passion for the ability to do and act in a right-thinking way, with an abundant supply of community and progress. Hierarchy and portraits of the queen don’t enter into it, because I know that as part of an infinite game, I’ll be gone eventually and I don’t want to leave the industry a worse place than I entered it (and if that isn’t egotistic, I don’t know what is!).

Finally, you should remember that technology (like life) is a journey, so you might as well make it a pleasant one; ride in the sun, enjoying the fields. You could take the highway with all the traffic and pollution, but that’s no fun. The destination is death anyway, so you might as well take the scenic route. Once you’re dead, you can be defined, as that’s the final product, but not one day sooner.

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