90 Things You Need To Know To Become An Effective CTO

90 THINGS YOU

NEED TO KNOW

TO BECOME AN
EFFECTIVE CTO
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CTO Academy delivers online leadership courses, private coaching and
community support to technology leaders around the world.

The original version of this eBook ("How To Become CTO Fabulous")

was released in 2019 since when it has been downloaded by tech
leaders in >100 countries many of whom have helped us evolve the
content you're reading today.
It's an eBook like few others.
60+ pages packed with insight collected from our global community of
technology and business leaders but focused primarily around the soft
skills (aka the hard skills) essential to you both achieving and having an
impact in senior technology roles including the CTO.
Please get touch with any of your own comments or feedback.
It's how we've been iterating since 2019.
Good Luck.
Andrew Weaver
CEO
[email protected]
June 2023
I was recently promoted to CTO and the CTO Academy course has helped prepare
and equip me for the next stage of my career.
I have been changed for the better as a result of working with CTO Academy and the
incredible lecturers they have on their course.
-Evan Tanner, CTO, Florida, USA

CONTENTS
SECTION 1
04 PERSONAL GROWTH
SECTION 6
SECTION 2 37 IT'S NOT ALL CODING
09 MANAGEMENT & TIME
SECTION 7
43 COMMERCIAL &
SECTION 3 OPERATIONAL
17 BUILD YOUR SOFT SKILLS
SECTION 8
SECTION 4
49 START UPS & FAST GROWTH
21 MAINTAIN YOUR TECHNICAL

SKILLS
SECTION 9
52 MINDSET & WELLNESS
SECTION 5
24 LEADERSHIP
SECTION 1
PERSONAL
GROWTH
90 THINGS YOU NEED TO KNOW, ...
KNOW THYSELF, DO WHAT YOU LOVE 1

There is a reason why this topic heads our eBook and comes early in our executive
leadership course, The Digital MBA for Technology Leaders.
If you don't know yourself, you're going to struggle to deliver the authentic
leadership required to be effective in senior roles. In addition, to which leadership
comes more naturally when individuals find alignment and flow between their
career and their values.
What does your definition of success look like?

What drives your intrinsic motivation ... money, status, purpose?
We like this quote from Paul Graham (one of the founders of Y Combinator) about
the false friend that is prestige:
“What you should not do is worry about the opinion of anyone beyond your friends.
You shouldn't worry about prestige. Prestige is the opinion of the rest of the world.
When you can ask the opinions of people whose judgement you respect, what does
it add to consider the opinions of people you don't even know?
This is easy advice to give, hard to follow, especially when young. Prestige is like a
powerful magnet that warps even your beliefs about what you enjoy. It causes you
to work not on what you like, but what you'd like to like.
It's what leads people to try to write novels. They like reading novels. They notice
people who write them win Nobel prizes. What could be more wonderful than be a
novelist? But liking the idea is not enough; you have to like the actual work of novel -
writing if you're going to be good at it.
Prestige is especially dangerous to the ambitious. If you want to make ambitious

people waste time on errands, the way to do it is bait the hook with prestige. That's
the recipe for getting people to give talks, write forewords, serve on committees, be
department heads, and so on. It might be a good rule simply to avoid any prestigious
task. If it didn't suck, they wouldn't have had to make it prestigious”
96 TIPS TO BECOME AN EFFECTIVE CTO | 6
DISCOVER YOUR CORE VALUE 2

So, the next necessary step is to ask if you understand your core values? How do
you identify your intrinsic motivation?
How do you discover your intrinsic motivation?
You might think you already know your core values but ask yourself,
have you ever put your feet to the fire and really focused on what five values
matter most to you and are you living your life based on them?
Many people don't get to that core ... they think they know but have never drilled
down deep enough to find out.
Once you understand those core values, they need to be central to every decision
you make in your career and life.
And don’t compromise. Don’t build anything around values which are not core
because, ultimately, you’re not giving yourself the best chance of an optimal career
experience.
Do you really know your core values?
There are lots of online tests you can use to explore your core values. We include
some within our course material. The results may surprise you and lead to some
reflections on both career and life choices.
CELEBRATE SMALL WINS 3

Jeff Bezos talks about taking 10 years to become an overnight success.
We’re all building things and it can be a slow, daunting challenge to achieve the
success we crave.
Which is why it’s so important to keep a note of the small wins that can aggregate
over time into a sense of real achievement, both for yourself and your team.
FIND NEUTRAL VOICES 4

The CTO role is different from other c-suite roles.
Other executives tend to learn on the job throughout their careers. Technology
leaders, by contrast, must execute a handbrake turn, shifting from a technical skill-
set to commercial and soft skills that might not come so naturally. We know, we've
been there.
You might also find yourself becoming increasingly isolated as you move into
senior roles, particularly if surrounded by non-technologists.
Having access to peers and neutral voices can be vital.
If you’re an experienced CTO, they can provide a sounding board that can help
reduce your sense of isolation.
If you’re an inexperienced CTO it’s about leaning on the expertise of others when
you need it.
STAY CURIOUS 5
As a technologist you’re always learning — new language, a new version of a
language, new frameworks etc.
When you move into a leadership role this process of acquiring new technological
expertise tends to drop away. In its place, you must force yourself to develop a
much broader perspective when it comes to new knowledge.
So, keep updating your skills, particularly when it comes to leadership and
commercial aspects of heading a business.
Many of the tech leaders we work with at CTO Academy are lifelong learners,
constantly challenging themselves to grow by acquiring new insights
As start-up guru Eric Ries, says: "The only way to win is to learn faster than anyone
else."
And those who lead, read.
Warren Buffett and Bill Gates famously consume huge amounts of reading
material to maintain their edge and it’s a consistent theme that leading
entrepreneurs spend a significant amount of their working time, reading.
This is where the art of delegation becomes so important — not just to offload
tasks and upskill your direct reports, but also to buy you the time needed to read,
study and strategise.
You need to understand what's coming over the horizon and how that might
impact the business, and you can’t do that by sitting behind a keyboard.
.
WHAT ROLE FOR AMBITION? 6

“Ambition is desire frozen, the current of a vocational life immobilised and over-
concretised to set unforgiving goals” — David Whyte, Consolations
Everyone we deal with at CTO Academy is ambitious - they want to achieve the
optimal career impact.
But we recommend that ambition is balanced alongside a holistic approach to
quality of life.
Ambition helps fuel progress but can cast a shadow upon that wider journey of
personal growth.
Don’t become overwhelmed by it. Understand what matters to you and prioritise
it. Don’t sweat the small stuff.
No matter how ambitious you are or how great the demands placed upon you,
never lose focus on the importance of carving out time with those you love.
We are social creatures. To live a full life, we need to maintain tender
connections with people who are important to us.
So, take care of your relationships, as well as your career.
“A life’s work is not a series of stepping stones onto which we calmly place our
feet, but more like an ocean crossing where there is no path, only a heading, a
direction, in conversation with the elements. Looking back, we see the wake we
have left as only a brief glimmering trace on the waters" - David Whyte
SECTION 2
MANAGEMENT
& TIME
MOVING FROM TECHNICAL TO LEADERSHIP TIP

7 7
Moving into a senior tech role is unlike the equivalent move into senior marketing,
sales or finance positions.
With other c-suite roles there is a more natural learning path with the skills
acquired through your career carried into the senior level.
The leap from technical into managerial is more challenging.
Having spent most of working lives in front of a screen we now have to accelerate
our understanding of softer skills that don't always come naturally.
And it’s that fundamental shift of priorities, coming out from behind the keyboard
and leaving the coding behind, which can make the transition daunting.
One stark example is learning the art of delegation.
From personal experience it's not something that's easy to do — the engineer in
you will want to continue overseeing every detail.
You're used to getting under the bonnet of the technology so it’s quite a mindset
shift to step away from those day-to-day issues and start to delegate.
But if you’re going to meet the demands and expectations of a senior

management role, you will have to learn how to do it.
Time management as a tech leader is about focusing on higher value tasks

appropriate for your role.
Spending hours conducting a code review is not a good use of that time,
Perfecting the architecture of a new product most certainly is.
STRATEGIC THINKING TIP

8 7
Part of that shift into leadership includes taking a more strategic role and giving
yourself the time and capacity to understand what is ahead and how it might
impact your organisation.
Effective CTOs develop a strategic vision that can anticipate future trends and
opportunities, and prepare the ground for the significant changes required.
Equally important is your ability to communicate the technology vision across the
company and in a language that resonates with all stakeholders.
MANAGE WITH COMPASSION 9

Recognise that colleagues' behaviour and performance might sometimes be
affected by external pressures.
Managing team dynamics requires an emotional intelligence allowing you to

understand the individuals around you — how and when they perform at their best
and what might be the issue behind any sub -standard performance.
Learn how to spot signs of burnout and maintain an open-door policy that
encourages staff to feel comfortable discussing issues affecting their work.
Managing through the recent pandemic brought new challenges, where the
pastoral care of your team was never more important.
No one is perfect — all of us have times of stress and distraction away from work,
so it’s important that compassion is at the core of your leadership approach.
MASTER THE ART OF SAYING NO TIP

10 7
No is a simple word, with complex applications.
As a developer you might view the word as anathema to progress.
As a leader, you need to understand when it's the right thing to say.
You might have to use the word “no” to protect yourself and your team.
You might need to deploy it to manage the expectations of customers and the
CEO, pressuring you to achieve the impossible.
You must learn how and when to apply it to a product — to say: “no, that version is
just not good enough” rather than allow something sub-standard through.
Much rests with the amount of autonomy and trust there is within an organisation.
If you’ve built a team and work within a culture based on trust and honesty, then
the word becomes far less loaded - it’s a mechanism for review rather than
confrontation.
If you haven't and you don't, then it might be time to reflect.
LEARN TO MANAGE THE CEO 11

These days it's true to say that every company is (or should be) a tech company.
Which means the CEO:CTO dynamic is ever more crucial to success but it's also
the relationship that CTOs find difficult to manage.
Your ability to work with and manage the CEO, often a very different character to
you, will impact on the enjoyment and success of any senior role.
The CEO is generally a born optimist, the best ones being a driving force and
inspiration, the worst ones being deluded and destructive.
To soften their whims of fancy, the CTO and other senior executives might have to
play a calming influence and provide the voice of (tech) reason.
TIP 7
PRODUCTIVITY TRICKS 12
How to get the most out of your working day and not feel overwhelmed? You may
have a favourite productivity trick, but if you don’t, you should.
One of ours is “Eating the frog”, which stems from an Amazonian tribe who
claimed: "If you eat a frog at the start of the day, anything else that day is plain
sailing".
Whether that tale is true or not, the productivity frog is the item on your to-do list
that you are least motivated to complete and are most likely to procrastinate on.
When organising your day, get the nasty task(s) out of the way early - don’t leave
them to gnaw away at the back of your mind.
The rest of your day will be an easier ride from there.
PUT THOSE DISTRACTIONS AWAY 13

Obvious, this one. But still, it something always worth emphasising when you're
If it’s your job to eat a frog, it’s best to do it first thing in the morning.
looking at time management because those tech giants have a lot to answer for,
And if it’s your job to eat two frogs, it’s best to eat the biggest one first
not least their ability to distract.
Give yourself a break now and then — force yourself to switch off.
Turn off notifications, go on a social media detox, have software that blocks it out
for a period of time and aim to have one day of the weekend tech-free.
Initially you might feel as if you’ve lost a limb, but you'll soon get a sense of
liberation — that's if our experiences are anything to go by
DO YOU REALLY NEED THAT MEETING? TIP

14 7
Oh, the curse of long meetings and with #WFH bringing a Zoom culture into our
lives, what used to be five-minute chats in the corridor have turned into 30-minute
calls that no one feels comfortable terminating.
When is a two-hour meeting ever necessary?

When are most meetings really necessary?
All meetings need keeping under tight control. The following steps will help:
Have a clear agenda
Install an efficient chair
Fix a clear timeline and schedule for the finish
Never allow a meeting to run close to 2 hours
TRUSTING YOUR TEAM 15

There is a lot of talk about trust but what does it mean?
Clearly, hiring strategy and getting good people in is vital. But is encouraging trust
as much about your ability to let go, than you team's ability to work autonomously?
Trust and autonomy are key pillars in determining employee engagement,
performance and cohesiveness. That’s the bit we all get.
But it's also crucial for you to create the time and space you need to lead because
it's only when you trust your team that you learn the art of delegation.
You therefore need to break down what trust means to you and how you can try to
measure and act upon it.
Ask yourself, which team members have the capability to deliver to the standard
you need? Which colleagues have the curiosity and judgment to handle key tasks?
Who “gets” the bigger strategic picture and how their work fits in?
TIP 7
APPLY THE 80/20 RULE 16
We understand this rule is anathema to most of our readers (and some of our
team), schooled as you are in science and the pursuit of perfection.
But in fast-paced companies it's a principle often necessary for managing the
demands on your time.
For those unfamiliar with the Pareto Principle, it was introduced by Italian
economist Vilfredo Pareto who stated that for many events, roughly 80 per cent of
the effects come from 20 per cent of the causes. He developed the concept in the
context of the distribution of wealth among the population.
From our experience, the principle is particularly applicable when managing heavy
workloads and tight deadlines.
Focus on what is absolutely necessary — what will give you your 80 per cent - and
delegate, defer or lose the rest.
With B2C products, think about speed, not perfection.
With B2B, get products out, build credibility pdq and then fine-tune towards the
perfect version of that product - you may never reach it, but it's a nice aspiration.
ADOPT THE LEAN START-UP METHODOLOGY TIP

17 7
We're fans of the Lean Start-Up methodology and in our view, you should carry the
philosophy with you whether in start-up, scale-up or innovating within an
enterprise.
Too many companies build products that customers don’t want or get. Their lines
are developed in a silo away from the market, burning cash, time and morale.
Being lean and building on the basis of validated learning should be at the core of
anything you create.
Very few people get away with “build it and they will come”. Steve Jobs and Henry
Ford are notable exceptions.
For us mortals, success will be elusive if we adopt the same philosophy. So, we
need to build on the basis of what the market is telling us.
Take the concept of incremental improvement and marginal gains which means
reducing perfectionism and increasing market interaction and validation.
When launching a new SaaS product, don’t start with a fully formed product and
expect subscribers to fawn all over it.
Build lean.
Start with manual product, lots of non-scaleable activity and market testing.
Measure the results and start to respond/iterate accordingly.
Validate (or not) each step of your build process.
Iterate into providing it as a service.
Then start the process towards productising it. Then, SaaS the hell out of it!
SECTION 3
BUILDING YOUR
SOFT SKILLS
IT'S RARELY ABOUT THE TECH TIP

18 7
Transitioning from the technical to the managerial is about learning how to move
from being a player to being a leader.
And one of the key lessons is that success in senior leadership roles is rarely
about the tech. It's almost always about the people.
You must understand the nuances of stakeholder management as you interact

with everyone from CEO to engineer, investor to customer.
Here are four steps to achieving that goal:
Become different things for different people.
Find the right balance between technology and people.
Learn to communicate clearly with all stakeholders.
Protect the team while preserving the interests of the organisation.
WHAT SKILLS DOES AN EFFECTIVE CTO NEED? 19

How long have you got?
Let's start with these ...
Good Technical Core

Self Awareness
Empathy
Vision
Resilience
Humility
Ability to Listen
Growth Mindset
Ownership
Eye For Talent
Creativity
... added bonus, is having an effective CEO, supportive executive team and
money in the bank ... (Ed: now you're just getting greedy)
TAKE YOUR HANDS OFF THE KEYBOARD 20

Most tech leaders want to stay in the weeds.
It’s what you've grown up with and where you feel safe.
But you can’t stay behind the keyboard and simultaneously be an effective leader.
You have to learn to trust your team.
You have to learn to delegate.
MANAGE THE ECOSYSTEMS AROUND YOU TIP

21 7
One vital skill is understanding the ecosystems operating around you and how
they interact (or don’t) with each other.
When organisations get to 50-plus employees, you can be sure they're already
suffering the effects of staff politics. Your task is to become adept at foreseeing
and recognising the nuances of these dynamics.
Ask yourself:
What department feeds off what?
Which individuals bounce off which others?
Where are the major players?
How does everything fit together?
Who are the hawks and doves within your organisation?
What are the value drivers of your business?
HYBRID ROLE OF A CTO 22

The CTO can’t exist in a silo anymore. The job has become a hybrid, integrated
with other senior roles.
You might be cross-pollinating ideas and tech with the CMO or staying close to the
sales and customer services team to get a grip on market reaction.
Understanding (and negotiating around) how other teams operate in the business
has become an important element of the CTO role.
THE ART OF NEGOTIATION 23

If you’re uncomfortable with negotiation then brace yourself for some discomfort,
because the more senior you get, the more negotiation you'll have to deal with.
Remuneration, recruitment, budget, investors, employees, suppliers, department

heads, partners at home as well as at work (personal experience speaking there)
are just some of the areas requiring constant negotiation.
It can be a fun part of the job, but it is a skill that CTOs need to build through their
career.
THE ART OF COMMUNICATION 24 7

TIP
We often hear from customers about operational challenges and blockers, but
more often than not what they're really talking about is poor communication.
A failure to communicate effectively is at the heart of many leadership issues.
You need to develop the ability to get your message across to all stakeholders and
pay grades, using language that each audience will understand, particularly if
they're non-technical.
That can include the customer. It often includes the CEO.

SECTION 4
MAINTAIN
YOUR
TECH SKILLS
NAIL YOUR CORE TECHNICAL SKILLS TIP

25 7
Effective tech leadership is driven by a mastery of the soft skills.
Your technical skills should be a given so this section doesn't aim to teach you
anything new, it just provides a few hints about where you might want to keep a
focus.
CUSTOMER BEFORE COMFORT ZONE 26

When is it best to build Web vs Native PC application vs Native mobile
application?
Don't always use the same method and don't always use the one you know best.
The CTO needs to be flexible enough to understand and use the correct method
for the situation, the client and the business.
KEEP YOUR UNDERSTANDING DEV 27

What are the programming languages and what are those languages similar to? If
you need to cross-train your team, what are the skill sets you will need?
If this is not central to your business, should you be looking at using a framework
that builds both iOS and Android apps, but at the cost of losing some of the power
of being deep in that platform?
DON'T FORGET HOW TO CODE 28

We've emphasised the challenge presented by the move from technical to
managerial, getting out from behind the keyboard and away from programming.
But it's a source of debate because some experienced CTOs think you should keep
your hand in coding.
Here's what one of them says:
I am likely in the minority, but one skill I think any CTO should have is the ability
to write code. Gives them an appreciation for what the developers who report
to them do and insight into how complex various projects can become. Most
CTOs don’t actually take part in development, although many I know do.
Programming, like any other perishable skill, will atrophy if it's not practiced
and maintained.
- Chris Kirby, CTO at Voices.com

UNDERSTAND ... TIP

29 7
Front end development
What is popular and where certain libraries should be used (when to use React vs
Angular vs another library?)
Databases
Relational vs NoSQL vs time series vs something else?
When should you put in clustered DB or geo-replicated systems?
Understand these concepts so that you can migrate or upgrade your system
as your business requires.
Backend technologies
NET, Java, Node.js etc.
Typically, your business will have already picked a framework but understanding
the pros and cons will allow you to challenge the status quo when appropriate.
Application architecture styles

When to use what?
DON'T FORGET ABOUT TESTING

Simply start with manual testing and tests cases.
30
Eventually move to test automation, unit testing and testing all executed on the
CI/CD pipeline.
Appreciate this can’t all be done on day one and that your job is to prioritise when
it’s important to move to the next stage.
SECTION 5
LEADERSHIP
WHY BECOME A LEADER? TIP

31 7
The only answer that will get you where you want to go, is because you simply
cannot not be a leader.
Your instinct to lead is so strong that it’s part of who you are.
Leading for you is a process of personal development, a journey of fulfilment.
Leadership:
Grows you as a person

Gives you purpose
Helps you make a difference in others
If this vision doesn't resonate with you, then maybe you're pursuing the wrong
path and need to redefine your values.
TIP 7
HIRE SLOW, LOSE FAST 32
Hiring is one of the most challenging tasks for any manager or leader, particularly
when there is a fight for the best talent and compromises need to be made.
Keep fundamental rules in mind when building a high-performance team: hire the
best people, even if they cost more.
If there’s any doubt about hiring someone, then’s there no doubt - don't hire them.
If a hire isn’t working, end it quickly. Poor performing employees drain your
resources and team morale.
You need to be clear about what you’re looking for in terms of job specification,
character and fit.
If your team culture is already established, recognising fit is relatively easy. But if
you’re recruiting for an early-stage business, you are helping to create that cultural
DNA and you need to certain about what you want it to be.
The "guard rails" of company culture form quickly and are difficult to shift.
Encourage diversity by not employing the same type of people and proactively
advertising in different types of channel.
Reach out as widely as you can. Narrow recruitment strategies lead to narrow
teams and empirical evidence shows that's bad for market perception, innovation
and profitability.
If you have an HR team, you probably don't need to follow relevant employment
legislation when hiring and firing. But be aware that how your organisation handles
both ends of the process will reflect on you and your brand.
And you certainly should know what is required if you are ever involved in a
downsizing or redundancy process.
Companies rarely lose employment legal cases based on their original decision,
but more often than not on a failure to follow correct procedure.
THE FAILURE-TOLERANT LEADER TIP

33 7
"Success is stumbling from failure to failure with no loss of enthusiasm" — Winston
Churchill
Failure is the prerequisite for invention.
A business can’t develop the breakthrough product or process if it’s not willing to
encourage risk-taking and to learn from mistakes.
Failure-tolerant leaders strive to help employees overcome their fear of getting it

wrong and, in the process, create a culture of intelligent risk-taking that leads to
sustained innovation.
This type of executive doesn’t just accept failure; they will encourage it. They
engage at a personal level with the people they lead.
They avoid giving either praise or criticism, preferring to take a non-judgmental,

analytical approach as they interact with staff.
They openly admit their own mistakes rather than covering them up or shifting the
blame.
And they try to root out the destructive competitiveness built into most
organisations.
Failure-tolerant leaders push people to see beyond simplistic, traditional

definitions of failure.
They understand that as long as failure is viewed as the opposite of success

rather than its complement, their team will never be able to take the risks
necessary for innovation.
BUILD AN EFFECTIVE TEAM CULTURE TIP

34 7
Culture is set by the founders and grown by those leading the business. They
establish the template, language, norms and the "guard rails".
Your role is to shape and adapt those elements into an effective team culture.
It needs to be inclusive, supportive and diverse.
Great teams emerge as a result of thoughtful and patient recruitment, bringing

together talented people who are working towards a clearly communicated vision.
Your focus is on getting in the right people and giving them the confidence and
autonomy that inspires them — and you — to exceed expectations.
THE BENEFITS OF AUTONOMY

35
Researchers at Cornell University studied 320 small businesses, half of which
granted autonomy to their staff and half relied on top-down direction.
There should be no surprise about the results.
The businesses that offered autonomy grew at four times the rate of the control-
oriented firms and had one third of the staff turnover rate.
Hiring is a significant burden on your time and cost to the company, therefore
retention is crucial in running a high-performance team.
For all the camaraderie of Friday drinks and endless games of ping pong, giving
individuals the autonomy and training to thrive is about the best perk you can
offer.
Having the confidence to manage in that way goes back to some of the earlier
points about developing a growth mindset, allowing your decisions to be
challenged, and giving others space to flourish.
Teams which play together do get to know each other better and this often is a key
element for success and for battling through the tougher times.
TIP 7
Water-cooler conversations are important, even if small talk is not your natural
habitat. With remote teams it’s even more important to understand the personal
as well as the operational. It's been interesting to hear how many tech leaders
missed those daily interactions during lockdown.
Try to keep daily stand-ups as a mixture of social and professional, as much about
what a team member did last night, as what KPIs they’re hoping to achieve this
month.
People contribute more effectively when they feel valued and part of a wider story.
Recognition enables them to dig in when times are challenging and will help
reduce staff-churn. Show gratitude, often
"BUT IT'S ALWAYS BEEN DONE THIS WAY" 36

Just because it has, doesn't mean it should.
This is a very common problem with established teams, lacklustre leadership and
institutionalised practices.
There is a reticence about challenging the status quo. But not doing so can result
in a staff stuck in a rut, lacking motivation, vision and incentive.
MANAGING THE DISRUPTIVE SUPERSTAR 37

Watch out for loud team members who try to dominate.
From our collective experience there are two types of "loudness'.
Firstly, there's the “superstar developer” — the individual who you over-rely on and
who can be a disruptive force because they know you can't easily do without them.
This situation often arises when inheriting a team with poor legacy hires and/or
weak management controls.
You need to employ a strategy that counters this risk, and one option is to double
up.
Try to make sure that the knowledge is shared and that nobody becomes too
important and therefore has too much power.
Secondly, you have the team member who has “all the gear, but no idea”.
They pick up the latest wheeze from Wired or Tech Crunch, love to talk over others
and dominate the discussion. But those who speak loudest often have the least
value to add and need to be managed.
Be aware. Be inclusive. The way you manage disruptive team members can define
your success as a tech leader.
VISION ALIGNMENT AND STAKEHOLDER SUPPORT TIP

38 7
KPIs and OKRs can play an important part in driving the business forward. But they
can also take over, which is why vision alignment and stakeholder support are
crucial.
You need to measure progress and success. But data and stats don’t build the
belief-system that make teams successful. That comes from a vision that
everyone can focus on, a culture of respect and diversity that people want to be
part of, and the support of key stakeholders.
These take time to build but they are the driving force behind achievement —
which can be measured in due course.
MISSED DEADLINES / CLEAR COMMUNICATION 39

This is a common issue that tends to get blamed on the technology team.
Deadlines are missed for a variety of reasons — for instance, because

specifications were incomplete or key development personnel weren't available.
Growing companies can struggle to deliver on promises (particularly if the sales

team have failed to manage expectations), so you need to communicate clearly
and quickly the deadlines you believe are achievable. This will allow the rest of the
business to make decisions on the basis of your clarity.
It's especially the case if you use third-party suppliers where you need to
understand their road-map, development processes and reliability.
As a recent example, we had to deal with a data supplier whose quality of data
was subjective at best, and whose delivery soon became intermittent.
Be aware of these issues and box them off before they become a problem.
CROSS POLLINATE DEPARTMENTS TIP

40 7
The tech team shouldn't be working in a silo - those days are long gone.
Building an organisation based on the cross-pollination of people, ideas and

cultures is fantastic for motivation, wellness and performance.
It’s not always easy or natural to break out from the tech bubble so it's important
to encourage even small steps such as sharing food breaks and events with other
departments and teams.
Don’t just lean on technology to try and knit people together. Sometimes we spend
too much time congregating on Slack rather than actually talking to people and
getting to know them.
DIVERSITY IS ABOUT PRO-ACTIVE LEADERSHIP... 41

Diversity breeds creativity and outside-the-box thinking. Evidence suggests the
more diverse a company is, the more profitable it becomes.
And yet diversity is often treated as a tick-box exercise.
Some leaders hide behind the excuse that they tried to encourage diverse talent
but struggled to find it. Make sure your recruitment process is not unconsciously
(or consciously) maintaining the status quo.
Build a procedure that encourages diversity in a proactive way. If you’ve not found
what you're looking for during the initial hiring phase, extend the timeline or look in
different places.
TAKE RESPONSIBILITY 42
TIP 7
This is not the same as being accountable.
Accountability is related to outcomes but taking responsibility as a leader goes

much deeper.
It's about standing up to be counted.
It's about not offloading blame.
It's about providing support and encouragement when needed.
It's also about a mindset that removes you from being “one of the team” and lets
you take charge and make key decisions.
Five steps to being a responsible leader:

1. You need to lead by example and be willing to commit as you'd expect your
team to commit.
2. Leave room for your team to grow, take initiatives and responsibilities,
observing them humbly from the outside.
3. Create opportunities for recognition of individual wins.
4. And give public recognition when deserved.
5. Do not be afraid to encourage individual growth, even if it means staff ultimately
moving on.
THE ART OF LISTENING 43

Enlightened leaders strive to be collaborative rather than controlling.
Only through engaged conversations over time can managers create failure-
tolerant work environments that invite innovation.
This is not to say that a major achievement shouldn’t be applauded, or that

avoidable or repeated mistakes should be tolerated.
But astute managers mark the daily small successes and failures with an even-
handed, open curiosity about the lessons learned and the next steps to take.
Listening is more central to this process than talking. Research on workplace

creativity shows that it’s not the individual employee’s freedom as much as
managerial involvement that produces creative acts.
No incentive can match the obvious appreciation shown by a manager’s interest

and enthusiasm. Mould-breaking leaders such as Thomas Edison, General Motors’
Charles Kettering, the Watsons at IBM, and 3M’s William McKnight were famous
for schmoozing with employees — not second-guessing or criticising, but
engaging in animated discussions about projects.
Nothing does more for productivity, morale, and employee retention.
“Edison made work interesting,” said a machinist and draftsman who spent a half a
century working for the inventor. “He made me feel that I was making something
with him. I wasn’t just a workman.”
CREATE REALISTIC EXPECTATIONS TIP

45 7
So much of what we do and how we communicate is about setting the right
expectations, and then going all-in to over-deliver.
Managing expectations happens across different aspects of business:
New Hires: No matter how young your company is, you should have a well-defined
on-boarding process that articulates key points, such as job specification,
reporting lines, performance and behaviour expectations.
Probation Periods: These are particularly important when putting a potential new
hire through a trial period. If you think they’re a good fit and it’s just about
measuring their capability, set the bar at a level where you can encourage them to
significantly over-deliver. This encourages to show what they’re capable of, rather
than putting too much pressure on performance.
Sales Team: How many times have you worked with a sales and marketing team
who fail to understand the product properly and pave the way for customer
disappointment by failing to manage expectations?
Board Meetings: Managing expectations at board level can be as simple as

making sure colleagues have understood the state of play. If you fail to
communicate clearly, you risk them leaving the meeting with false expectations of
what’s going to happen next. This is a particular problem when dealing with non-
technologists. Make sure your colleagues are not just nodding in agreement, and
that they understand what has been agreed.
The CEO: If there is one point of friction that regularly comes up with clients, it's
the CEO-CTO dynamic. Characters can often very different so communication
becomes challenging and expectations need to be managed carefully, particularly
if you're working with one of those overly optimistic CEOs.
CRUCIAL CONVERSATIONS
46
Confrontations are never easy.
We cover this area within our course material but also recommend an excellent
book called Crucial Conversations in which the authors outline a method for
approaching conflicts when the stakes are particularly high.
They recommend focusing on facts, remaining calm, listening to the other person
with respect and working to motivate them and bring about a change in behaviour.
TIP 7
PRAISE GENEROUSLY AND SINCERELY 47
People love gratitude and it goes a very long way, particularly when building and
managing a team.
It doesn’t matter how far up the corporate food chain you go, a simple “thank you”
or “well done” can work wonders.
Empathy is not just something you should reserve for your team. Be
understanding of the stress that comes with roles across the company. No matter
how senior or experienced or self-sufficient a colleague may appear; the benefits
of showing them gratitude shouldn't be underestimated.
AVOID TENSION BETWEEN PRODUCT AND TECH 48

Positive collaboration yields smarter solutions that are faster to develop and test.
We often see tension between product and tech. You have to manage any divide
and maintain a healthy and communicative bridge between two crucial
departments.
OPTIMUM SIZE FOR A TECH TEAM? TIP

49 7
TECH TEAM?
“Price’s law pertains to the relationship between the literature on a subject and the
number of authors in the subject area, stating that half of the publications come
from the square root of all contributors. If 100 papers are written by 25 authors,
five authors will have contributed 50 papers.”
Applying Price's Law to team-building, it’s our conclusion that you get diminishing
returns with team sizes of more than 10 members.
Of course, it’s rarely possible to grow a team to 10 and then stop!
Look at splitting a team once it gets to 12. How you split it will depend on the
product, company and skills of the developers.
You might split by functional areas — with an e-commerce-type web application

that could mean dividing the team into admin functionality and user functionality,
with each taking back-end and front-end developers.
Alternatively, you could split by type of work, creating a front-end and a back-end
team, for example.
To prevent silos, you must ensure that each team talks freely with each other, as
well as move members around occasionally to develop their skills.
TRAITS OF HIGHLY EFFECTIVE AGILE SOFTWARE 50

AND PRODUCT TEAMS
Many executives, managers and professionals want to join the agile movement,
considering the favoured approach to software development as well as overall
product development. At the same time, agile can't just be thrust on the
organisation with the expectation of overnight, collaborative results. The people
participating in agile teams need to be ready and motivated to achieve a
successful workflow.
-
The report found there were some ideal personality traits and work values that
separate the winners from the stragglers:
They think as disruptors, fighting the status quo

They are agreeable and straightforward
They are able to handle ambiguity
They are close -- very close -- to the customer
They are self-directed
They take pride in the final product.
For agile teams, "pride in the product (the outcome) sits higher than pride in the
work (the process). Being proud means more than being happy with the work; it TIP 7
also means wanting to be associated with the product and taking ownership of its
values and contributions."
It also boosts innovation.
WHY SOME LEADERS FAIL ... 51

Adapted from Napoleon Hill's motivational best-seller, Think and Grow Rich, here
are 10 key reasons for manager failure
1. Inability To Organise Details: Efficient leadership calls for ability to organise

and to master details. No genuine leader is ever “too busy” to do anything which
may be required in their capacity as leader. The successful leader must be the
master of all details connected with that position.
2. Unwillingness to Render Humble Service: Truly great leaders are willing, when
occasion demands, to perform any sort of labour which they would ask another to
perform. “The greatest among ye shall be the servant of all” is a truth which all
able leaders observe and respect.
3. Expectation of pay for what they KNOW: Instead of what they DO with that
which they know
4. Fear of competition from followers: The leader who fears that one of their
followers may take their position is practically sure to realise that fear sooner or
later.
5. Lack of imagination: Without imagination, the leader is incapable of meeting

emergencies, and of creating plans by which to guide his followers efficiently.
6. Selfishness: The leader who claims all the honour for the work of their team, is
sure to be met by resentment. The really great leader claims none of the honours
because they know that most will be more committed by commendation and
recognition than money alone.
7. Intemperance: Teams do not respect an intemperate leader. Moreover,

intemperance in any of its various forms, destroys the endurance and the vitality
of all who indulge in it.
8. Disloyalty: Perhaps this should have come at the head of the list. The leader
who is not loyal to those around him/her cannot long maintain any trust and
therefore effective leadership. Disloyalty marks one as being less than the dust of
the earth, and brings down on one’s head the contempt they deserve. Lack of
loyalty is one of the major causes of failure in every walk of life.
9. Emphasis of the authority of leadership: The efficient leader leads by

encouraging, and not by trying to instil fear in the hearts of the team. The leader
who tries to impress with “authority” comes within the category of leadership
through force.
10. Emphasis of title: The competent leader requires no “title” to gain respect from
the team. Those who make too much over title generally have little else to
emphasise. The doors to the office of a real leader are open to all who wish to
enter, and without formality or ostentation.
SECTION 6
IT'S NOT ALL

CODING
DEFINE YOUR QA PROCESS TIP

52 7
Make sure the QA process is put in place from day one and select an automated
system that best fits your needs.
Automating testing will enable your product to grow safely and steadily and will be
especially valuable when doing major changes or significant refactoring.
UNDERSTAND YOUR IP 53
Always be familiar with the company’s intellectual property (IP) and which parts it
owns outright.
IP is often where the core shareholder value is being increased so retaining

ownership of what gets built is crucial.
Weaknesses in IP ownership sometimes emerge only at the due diligence stage

when a company is fundraising or selling and that can be disastrous.
You need to make sure any agreement with an outsourced developer is explicit
about who owns the IP. Further, if you set up a joint venture, it’s vital to define
ownership — all of which can easily be overlooked in the heat of the moment.
You need to be clear how to protect your rights and whether you need to consider
applying for any patents.
AVOID REINVENTING THE TECH WHEEL 54

Identify where the value for the company is and concentrate on that.
Use what is out there and innovate on top.
Make sure what you work on is aligned to the strategic goals of the company
BUILD A DEFENSIBLE MOAT TIP

55 7
Always look to build a defensible moat around your products to lock in value.
You need to make products sticky and difficult to remove or switch.
By doing so, you’re cementing key value-drivers into the heart of your business.
This can be done by providing integrations with your products and/or embedding
them into everyday processes.
EXPERIMENT WITH CLOUD SERVICES 56

Play with different cloud services to understand the strengths and weaknesses i.e.
understand differences between marketing and reality.
ADOPT THE KISS PRINCIPLE 57

Aka Keep It Simple, Stupid
Become adept at explaining technical stuff to non-techies and watch out for the
body language or expression changes that suggest someone doesn’t understand.
You need to be able to identify when someone is nodding in agreement, but
doesn’t really get it.
If they walk away having agreed to something they don’t understand, the fallout
might be on you and your tech team, not on them!
Remember, most people fail to retain more than three ideas per session. Don't
overload them.
TIP 7
SECURITY & DATA 58
Security should always be at the forefront of your mind. There are several areas to
deal with:
1. Security within your products (protecting user data)
2. Infrastructure security (who has DevOps access)
3. General company security (employee access)
4. Code security (who has access to code)
Users should only have access to what they need.
During the past 10 years cyber security has probably become the most business-
critical topic for any tech leader, so ensure that you and your team have annual
security training, even basic GDPR and cyber security instruction.
Think about how sensitive data is stored and encrypted, and about access control.
Who SHOULD have access to data?
Just because you are the CTO, should you really have access to the production
environment? Do you really support it?
Think about the data in your test environment - is this real data copied from the
live environment? If so, is this environment secure? If not secure, does it need to
be real data?
Get a third party to test the security of your platform. Carry out pen-testing, social
engineering security testing, etc. Get a certified agency to do this at least once a
year.
Do not panic over the results. Gaps are always found and this is good news as you
can now do something about them. The key is to have a clear plan to fix any issue,
with dates and owners. Put in temporary fixes for any problems at the top-end of
the scale.
BUY vs. BUILD TIP

59 7
Make sure your team is spending their time most effectively.
There is a natural assumption that you can build it, but always ask whether you
can buy it instead?
As a CTO, the key is building what is core to your business, not your whole
platform — i.e. if you’re building a FinTech platform, then do you really need to
provide your own CS app, BI portal, etc. Or can these be bought and plugged in?
Spend your development dollars very carefully so you can drive the biggest gains
and outputs.
UNDERSTAND YOUR PLATFORM USP

Put your coding time, energy and resources into this part of your platform. Worry
60
about the rest later.
PLATFORM LATENCY
Think about your users and latency. In an age when your phone’s internet speed is
comparable to your home broadband speed, platform latency should be a priority.
Consider where your code is hosted?
61
Ask yourself:
Do you need to co-locate your software in different regions with your cloud
provider?
Do you need to use Edge services?
Do you need to consider using CDN’s?
LOW CODE 62
Low-code frameworks are becoming more pervasive (even though similar systems
have been around for years).
Low code allows development of systems quickly, assuming you can accept the
restrictions.
LEAN APPROACH TIP

63 7
Pick a development methodology — Scrum or Kanban, etc — but always choose
what is appropriate for your business at its current stage of development.
CTOs should ideally review and potentially change a methodology every 18

months to ensure it's still relevant.
Put in a change-and-incident process for your live environments.
Put in monitoring. Basic uptime monitoring using a third party is a minimum

requirement. As you grow build in a third-party metric/monitoring system.
10 PAYING CUSTOMERS 64
Don’t build anything other than a basic product, until you’ve got at least 10 paying
customers.
When you’ve got 10 in the bag, survey them relentlessly. Find out what they
do/don't like then start to accelerate development. But always have that lean start-
up methodology in mind, building on the basis of validated learning.
SECTION 7
COMMERCIAL &
OPERATIONAL
GET STRATEGIC TIP

65 7
You need to become overtly strategic in a senior leadership role.
You also need the ability to communicate a strategic direction to the team and
inspire colleagues to deliver what they didn’t think was possible.
You're likely to be the poster boy/girl for the technology and the futurologist for
what's emerging on the tech horizon.
Your ability to judge genuine opportunity vs threat vs flash in the pan will be crucial
to the growth and good health of the company.
LEARN THE ART OF COLLABORATION 66

Hone those collaborative capabilities, even with your competition.
Managers, particularly in early-stage companies, are often over-protective of

"ideas", but that can be a misguided approach.
Get out there, disclose as much as you feel comfortable with, build relationships,
don’t over-protect what you have because you need to give, to get.
Don’t be nervous about the competition. Watch them closely but reach out. Most
markets are big enough for more than one of you and if you’ve hit on anything like
a good idea then you’re going to be surrounded by competition.
If you’re in an early-stage company and/or fast-growing sector you’re going to

bump into each other quite often and most sectors go through phases of
consolidation, where historic relationships can be useful when significant money
starts to enter the space.
BUILD STRONG PARTNERS & TRUSTED NETWORKS 67

Partnerships can be an opportunity and a distraction. They can give you enormous
leverage. But they can take time to set up, be difficult to integrate and promise
more than they can deliver.
Start-ups tend to overestimate the potential, scale-ups tend to underestimate.

Any new partnership will need to provide mutual benefits and not just favour one
party, or it will fizzle out quickly and have been little more than a distraction.
Be cautious about chasing partnerships that are not the right fit.
And be realistic about who you're trying to work with. Everyone wants to partner
with Google but is it sensible to be chasing them at this stage of your evolution?
CHECK STABILITY & VIABILITY 68 7

TIP
Always investigate the stability and viability of any company that’s providing your
tech.
One area of particular risk, with such rapid technological change, is being dazzled
by new kit and extravagant claims. It's easy to get locked into a nasty contract for
a piece of kit that over-promises and under-delivers.
Ask yourself, how financially solvent are your partners and suppliers? You don't
want to be investing a huge chunk of time and cash in a company about to go
under.
It's not always easy to predict but it happens — that’s business.

When dealing with new suppliers you need to conduct appropriate due diligence to
be as confident as possible that you’re dealing with companies who are not about
to go bust.
SHARPEN UP YOUR SALES SKILLS 69

Sales is not a natural discipline for most tech leaders. It’s not for us either.
But the modern-day CTO needs to be able to sell or at least have the competency
to operate on the customer frontline, liaising with client technical teams and
understanding market reaction, demands and requirements.
Customer retention can be the key difference between success and failure and
part of the Customer Relationship Management (“CRM”) process will be based on
how you and your team deal with technical challenges and communication with
clients.
KEEP CLOSE TO CUSTOMER SERVICES 70

The truly effective tech leader wants to understand everything about the customer
and what they're thinking about the product.
Customer services are closest to the client, closest to market feedback and
closest to what is bad about your product, because that’s generally all they ever TIP 7
hear about. So, it's important to maintain good relations.
You and the customer services team have to deliver on the expectations created
by the sales and marketing team. Look after them and think about when you last
called a customer services department and showered them with praise.
THE ROLE OF MARKETING 71

Understand the part played by your marketing department and be able to critique
their tactics.
Marketing is about garnering interest in a product or service to generate leads, but

it almost always comes down to a numbers game.
A good marketing team aims to discover the most effective channel for your
products by understanding the Cost of Customer Acquisition (CCA) and Lifetime
Value (LTV) for each.
This should enable them to assess the Return on Investment (ROI) for each
channel and conduct a successful campaign on that basis. Well, that’s the theory.
In truth, not many marketing departments reach this level of insight and
sophistication, rather spending much of their time throwing mud at the wall and
hoping some of it sticks.
In some companies the CMO will have a larger tech budget than the CTO. They
love their new data-analytic products in the marketing department.
For many of you close collaboration with marketing is necessary to ensure they
understand the product and its impact on target customers.
TIP 7
NICE TRAFFIC, SHAME ABOUT THE SALES 72
Similarly, get close to the sales team and make sure no blockages on sales are
caused by their lack of knowledge about the product.
How many of you have been frustrated by a sales team’s ignorance of what they’re
selling?
Buyers need to feel that the sales people have credibility. And product knowledge
is key to building that trust.
The sales team needs to deliver compelling solutions to prospects and a clear ROI
case. If they try to BS the buyer about the product, the buyer will walk.
If product knowledge is lacking, you need to ensure there is a detailed training

tutorial available and that those unable to deliver detailed impact models for
clients are retrained or released.
BEWARE OF GROUPTHINK 73
This can become a real problem at the executive level where less technical
members might be uncomfortable or embarrassed to question important issues.
Executives need to challenge where others are afraid to speak out.
Try to ensure that people around you are not making business-critical decisions
based on false assumptions.
WHO WANTS TO JOIN THE BOARD? 74

If someone is trying to join the board, question what value they bring to your
organisation. What does it say about the direction you're taking?
Boards can become very unwieldy and some appointments are made on the basis
of an old-boys network rather than real added-value.
“I definitely think 'Glenn' (replace name accordingly} will be a great chairman.”

Really. Why?
This is particularly an issue with early-stage companies where boards should be

lean and effective. TIP 7
You must be sure about what aspiring board members can provide. Introductions,
network, market gravitas, fundraising capability? If it's cash, does that require a
seat on the board?
Everyone needs to make a meaningful contribution - it's should never be about

someone adding another ‘Non-Exec’ bauble to their CV.
UNDERSTAND BASIC FINANCE & ACCOUNTING 75

You might feel that balance sheets, CAPEX, OPEX and accounts are outside your
comfort zone and they probably will be, but to operate at board level you need a
basic understanding of business finance and management accounts.
Not least because as a director you have corporate responsibilities to uphold and
need to have a grasp of the financial decisions being made on behalf of the
company.
NEVER BADMOUTH YOUR SALES TEAM 76

Despite the above-mentioned misgivings about some sales teams, never speak
badly about them because ultimately they're helping pay your wages!
SECTION 8
START UPS &

FAST GROWTH
COMPANIES
START A COMPANY AND INSTALL YOURSELF 77

TIP 7
The quickest path to becoming a CTO is to start you own company. Failure rates
are high, though, so build up market experience and expertise before taking the
leap.
Evidence suggests the optimal age for starting a successful start-up is 45.
Beware also the start-up founder who decides not to go for a technical co-founder.
He/she is immediately making survival more difficult and it's highly likely they will
hire a talented technologist but plan to keep them in subordinate role.
Don't be seduced by a fancy start-up title. If you're a key member of the team, if
you're driving value, you should be sharing fully in the rewards.
If you’re being asked to join an early-stage start-up, temper your excitement with
some caution. It could be a life-changing opportunity where you learn more in six
months than in six years working elsewhere. Then again... it could go pop
overnight.
FIND AN AMAZING CO-FOUNDER 78

This is not always straightforward.
Being involved in an early-stage business is like being in a marriage, just more

intense. It’s easy going into the relationship, not so easy getting out.
What are the ideal qualifications for an amazing co-founder?

Personal chemistry: Do you like this person? It's an important question as you’ll be
spending a lot of time together.
Aligned commitment: Is he/she going to be distracted with other projects?
GSOH: Can you laugh together?
Complementary expertise: Are they the yin to your yang?
No ego: They need to leave theirs at the door
Resilience: Can they hack it? Will they stick with the project when the going gets
tough?
Direct experience: What do they bring that will help the project?
UNDERSTAND HOW MUCH EQUITY TO GIVE/TAKE 79

You’ve joined a hot start up, you bring significant talent to the table, they want to
pay you below market rate on the basis of an ambitious exit strategy and the
potential of much jam tomorrow.
Is their ambition realistic? Do their numbers make sense? What is your opportunity
cost and is the equity package sufficient reward for the risk?
It might look shiny and exciting on the surface but conduct a sense check on the
people, opportunity, forecasts and deal being offered. TIP 7
Working at below market value is no fun if the chances of a return are super slim,
as is often the case in startups. You need to find the right balance.
DON'T STRESS ABOUT DILUTION ... 80

Dilution is often a concern for early-stage companies that have to purchase
growth by giving away equity. You should be cautious because equity is very
expensive, but as with most negotiations, it's often about timing and valuation.
Problems can emerge when start-ups raise money too early and at too small a
valuation, so founders quickly get diluted out of existence and motivation is lost.
Growing fast and raising lots of cash does lead to a reduced equity position but
hopefully you will be receiving a smaller slice of a much bigger pie.
Key to protecting your equity stake is to raise as late as possible at each stage.
Be realistic and sensible in negotiations with investors. Consider carefully

valuations, founders' earnings and items such as anti-dilution clauses, an issue
likely to lose investors unimpressed by any offer that creates shareholder
hierarchies.
... BUT GIVE AWAY EQUITY AS LAST RESORT 81

If you are part of a founding team, give away equity as a last resort, particularly
during the early days.
When you’re starting out, equity is super, super, super expensive and valuations
painfully low. Bootstrap as long as you can or find a co-founder with rich parents
(see above).
SECTION 9
MINDSET &
WELLNESS
NEVER STOP LEARNING TIP

82 7
As we've said, those who lead, read.
Carve out quality time most days to read and absorb and learn.
Don’t let work, pressure, team and other excuses distract you from this ongoing
process of self-improvement.
Constant reading is not only good for your learning, it’s great for your soul.
IT'S OK TO ASK FOR HELP 83

Strong leaders are not the ones who never require help, but the ones who know
when and where to ask for it.
Successful senior executives acknowledge blind spots in their skill set and build a
highly effective safety net around them, based on the following pillars:
Encouraging expertise and recruitment of the best talent in support of your

own aims.
Understanding you can't do everything and even if you could, quality suffers.
Creating a culture where vulnerabilities can be discussed.
Not bottling up pressures.
Leading by example.
HEALTHY BODY = HEALTHY MIND TIP

84 7
The stress and strains of work, management, and leadership can impact your
lifestyle and before you know it, bad habits become ingrained.
Don’t ignore physical limitations.
It’s very easy in a demanding role to put off your wellbeing to tomorrow but you
are more than your new release!
Maintain a healthy lifestyle and control your consumption of the bad stuff.
You don’t need health tips from us but here are some of the things our team does
to relieve the stress:
Use a fitness and step tracker (targeting 8,000 steps per day)
Lunchtime cycle every other day
Work standing for part of the day
Use the stairs instead of the lift
Not skip meals
Book in a regular check–up (eyes, blood, etc)
Run up mountains at 5am (according to our Richard ... this is not universally
accepted BTW)
SOAK UP REAL LIFE CASE STUDIES 85

Study how others did it, how they messed up, where they could have done better,
what worked and what failed.
Avoid the obvious mistakes, but don’t overlook that most situations are unique.
Most of the success stories you read about, in many appallingly written business
books, suffer from "survivor bias".
The people, the market, the finance, the luck, the timing. Those combinations
might never happen again and even leaders who achieve success with one project,
sometimes struggle to replicate that winning formula again.
So never forget the one consistent theme about how success is achieved. Graft.
PIONEERS GET SHOT FIRST 86

It's good to be visionary and innovative but use common sense when deciding
whether your ideas will work. Get sound advice from your network, colleagues,
mentor.
Anyone remember 3D TVs being the next big thing? The obvious flaw was that no
one wants to sit with goggles on but, hey, that didn’t stop the hype brigade getting
into full OTT mode.
It’s very easy to be tempted by the latest hot product. It’s very easy for members of
your team to suffer the same.
Tread cautiously when planning to be a true pioneer. Assess new opportunities TIP 7
rationally, not emotionally.
Assess new opportunities rationally, not emotionally.
POSITIVE PSYCHOLOGY vs. TOXIC POSITIVITY 87

Which side of this fence are you on?
The general concept of positive psychology could be narrowed down to the motto
"always look on the bright side", describing an outlook that searches for the
opportunity hiding in any crisis.
If something has been bad for you, think of how you can turn it into a positive
experience instead.
Being optimistic is, of course, not only healthy, but also a necessary skill in any
leader's emotional intelligence toolkit.
But looking on the bright side should never entail ignoring negative emotions and
acting positive no matter the circumstances.
True optimism means you are able to recognise your emotions, embrace them and
manage them towards a more positive angle, as a result of your values-driven
approach in life and your general self-awareness.
However, there are many who exploit this approach and have pulled the basic
principles so much to their edge, that we have a troubling “toxic positivity”
movement instead.
This trend is upcoming, powerful, and extremely dangerous for our mental and
emotional health.
For example: do any of the following mottos ring a bell?
Don’t get depression. You can do anything. You can do everything. Never quit.
One can say they’re inspirational, but the truth is they ignore all the contextual
factors and leave you alone with your personal responsibility.
But luck isn’t zero sum. The society we live in isn’t zero sum.
When you are made to believe that you hold all the power, that you have total
control, how are you going to feel once something turns out wrong, even if you
have done everything right?
ELIMINATE UNNECESSARY STRESS TIP

88 7
Have you ever thought that you might suffer from stress that is completely
avoidable? We are human and by nature imperfect.
If something is constantly causing you stress, then maybe this aspect of your life
should be removed.
Life is too short and the CTO role too demanding for you to be burning energy on
any unnecessary pressures in your life. So, every now and then, conduct an
introspective stress audit.
Look at your commute, relationships, colleagues, time management, technology,

social media use.
And talking of which...
WEEKENDS Sans ecran 89

Sans ecran is French for "without screen".
They introduced the concept as a way to “encourage” their teenagers to spend

time away from their phones.
So how would a day sans ecran sound?
Turn off the notifications, go on a social media detox, download software which
enables a temporary block out as you aim for a tech-free day during the weekend.
LIVE IN THE PRESENT ... ALWAYS 90

If the pandemic taught us anything, it is to appreciate what we have and to live in
the present.
Be ambitious, be hungry, be everything you want to be, but remember to

appreciate each and every moment.
“Realise deeply that the present moment is all you have. Make NOW the primary
focus of your life”
A little more about CTO Academy ...
We work with technology leaders around the world (91 countries

at last count) from Global CTO to Team Lead.
Our focus is on accelerating the Professional Growth of tech

leaders so they can achieve the career impact they want and help
their organisations gain the competitive advantage they need.
We provide courses, coaching and community support including

the following;
The Digital MBA for Technology Leaders is an executive

leadership course that has been accredited as "conforming to
professional development guidelines" and delivers a blended
learning experience via online lectures, live sessions and
community.
CTO Leadership Foundation Course is for those at the start of

their leadership career and takes a look at the shift in mindset and
responsibilities as you move into senior roles
CTO Academy Membership (available from July 2023) will

provide a range of tools, advice, coaching and community for you
to learn and lean into the support you need as a busy tech leader
"CTO Academy is a brilliant platform and urgently needed as the CTO role
becomes ever more central to the success of organisations and the need
to bridge the technology with the commercial becomes more business
critical" - Jim Mortensen, CTO/COO, USA
Website: https://cto.academy/
Email: [email protected]
Twitter: @ctoacademy
It's Rarely About The Tech
We recently conducted a series of candid interviews with senior technology
leaders which included the following Q ...
What are the key attributes of a successful tech leader?
“Authenticity, humanity and empathy”

– Marcin Floryan, Director of Engineering, Spotify
"Empathy, an eye for talent, interest & an aptitude for technology and how, when it’s applied with flair
and creativity it almost always acts as a force for good. Anyone can read books but you need genuine
empathy for the people around you. The ability to build teams is also critical. The cult of personality that
builds up around some people is ultimately in the medium or long term quite destructive.”
– Colin McQuade, Head of Technology, Barclays International
“Part of our job is to speak the language of the business and be an advocate for the technology on the
board where maybe not everyone else is from a technology background. But technology has become as
important as an understanding of finance or marketing or sales and not every CFO or CEO comes from
that digital background. So it’s important that we speak the language of everyone else and champion
technology at that level and make sure we do put technology at the heart of the business”
– Ben Jones Group CTO, Growth from Knowledge
“I’m careful to make sure that I’m working with all the different team members at the different levels of
engagement that they require and that I’m demonstrating through my actions that I have their best
interests at heart while I do my best to marry their interests with the interests of the business. And if I do
those 3 things, as well as I can, in relation to how I work with my team, that makes me a successful
leader from the point of view of my team. Then from the point of view of my leaders it’s really just about
transparency and visibility as well as accuracy and detail”
– Jerome Pimmel, Software Development Manager, AWS
"I think these have changed. If it used to be; having a strong vision, hiring the right team, picking the
right toolset. Nowadays it’s more about; building the right ecosystem of partners, having the right
platform to enable innovation. Those are the two things that senior tech leaders really need to focus on
these days”
– Tim Hooley, Chief Technologist, EMEA FSI at Red Hat
"I’d say the key are human characteristics of creativity, risk taking, innovation and putting people first”
– Shilpa Shah, Programme Director, Deloitte Delivery

SOMETHING ABOUT THE AUTHORS
ANDREW WEAVER
CTO Academy Co-Founder
With 20+ years of C-level commercial and strategic
experience, Andrew has launched, managed, fund-raised,
bought and sold a range of businesses across sectors as
varied as e-commerce, legal tech, property, travel &
tourism, energy and professional services.
Alongside CTO Academy he also leads a Start Up

accelerator in London and regularly mentors individual
entrepreneurs at different stages of their journey.
With a Cranfield MBA, he focuses around non-tech topics

like sales, marketing, strategy, fundraising, M&A,
communications and business psychology.
JASON NOBLE
CTO Academy Co-Founder
The driving force behind us, an entrepreneur with extensive

board level IT innovation and computer science experience,
he has been technical director of several software
businesses and managed large and complex enterprise
projects with a number of successful exits.
Jason's wider interests and experience include geo-fencing,

big data predictive analytics, machine learning, grid & high
performance computing, complex algorithms, e-commerce,
mobile, and high volume web applications.
ZOE FRAGOU
Organisational Psychologist
& Leadership Coach
Organizational Development Leader, Culture Change Agent,

Psychologist.and Leadership Coach. Zoe is based in Athens
and is a trusted advisor with a strong executive-influencing
presence, She works with corporates and individuals
thriving in particular with driving transformative change as a
key link between higher business strategy and talent
management
SANJAY MISTRY
CTO/COO, Leadership Coach
Experienced in applying intelligent solutions engineering

expertise in directing the design, development and launch
of scalable and robust software able to manage over 20
million transactions per month, such as direct carrier billing
applications and services for Infomedia. Sanjay is skilled in
providing expert technical advice to both customers and
colleagues on software design and development, from pre-
sales consultation through to implementation and launch
the in UK, European and Middle Eastern markets.
Richard Weaver
Head of Careers
Highly experienced recruitment professional with 20+ years

industry expertise having delivered large technology and
business transformation programme teams into Online,
Broadcast and Telecommunication sectors.
Driven by a vision to transform the career development

process by linking the user experience to our holistic
approach of integrating recruitment with professional
growth programs of learning and coaching.

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90 THINGS YOU

The original version of this eBook ("How To Become CTO Fabulous")

It's an eBook like few others.

Please get touch with any of your own comments or feedback.

It's how we've been iterating since 2019.

-Evan Tanner, CTO, Florida, USA

SECTION 2 37 IT'S NOT ALL CODING

09 MANAGEMENT & TIME

21 MAINTAIN YOUR TECHNICAL

KNOW THYSELF, DO WHAT YOU LOVE 1

What does your definition of success look like?

Prestige is especially dangerous to the ambitious. If you want to make ambitious

DISCOVER YOUR CORE VALUE 2

How do you discover your intrinsic motivation?

Do you really know your core values?

CELEBRATE SMALL WINS 3

FIND NEUTRAL VOICES 4

Having access to peers and neutral voices can be vital.

WHAT ROLE FOR AMBITION? 6

So, take care of your relationships, as well as your career.

MOVING FROM TECHNICAL TO LEADERSHIP TIP

The leap from technical into managerial is more challenging.

One stark example is learning the art of delegation.

But if you’re going to meet the demands and expectations of a senior

Time management as a tech leader is about focusing on higher value tasks

STRATEGIC THINKING TIP

MANAGE WITH COMPASSION 9

Managing team dynamics requires an emotional intelligence allowing you to

MASTER THE ART OF SAYING NO TIP

As a developer you might view the word as anathema to progress.

If you haven't and you don't, then it might be time to reflect.

LEARN TO MANAGE THE CEO 11

The rest of your day will be an easier ride from there.

PUT THOSE DISTRACTIONS AWAY 13

DO YOU REALLY NEED THAT MEETING? TIP

When is a two-hour meeting ever necessary?

Have a clear agenda

Install an efficient chair

Fix a clear timeline and schedule for the finish

Never allow a meeting to run close to 2 hours

TRUSTING YOUR TEAM 15

With B2C products, think about speed, not perfection.

ADOPT THE LEAN START-UP METHODOLOGY TIP

Measure the results and start to respond/iterate accordingly.

Validate (or not) each step of your build process.

Iterate into providing it as a service.

IT'S RARELY ABOUT THE TECH TIP

You must understand the nuances of stakeholder management as you interact

Here are four steps to achieving that goal:

Become different things for different people.

Find the right balance between technology and people.

Learn to communicate clearly with all stakeholders.

Protect the team while preserving the interests of the organisation.

WHAT SKILLS DOES AN EFFECTIVE CTO NEED? 19

Good Technical Core

TAKE YOUR HANDS OFF THE KEYBOARD 20

MANAGE THE ECOSYSTEMS AROUND YOU TIP

HYBRID ROLE OF A CTO 22

THE ART OF NEGOTIATION 23

Remuneration, recruitment, budget, investors, employees, suppliers, department

THE ART OF COMMUNICATION 24 7

A failure to communicate effectively is at the heart of many leadership issues.