Professional Documents
Culture Documents
90 Things You Need To Know To Become An Effective CTO
90 Things You Need To Know To Become An Effective CTO
NEED TO KNOW
TO BECOME AN
EFFECTIVE CTO
eBook powered by
CTO Academy delivers online leadership courses, private coaching and
community support to technology leaders around the world.
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.
Good Luck.
Andrew Weaver
CEO
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.
SECTION 1
04 PERSONAL GROWTH
SECTION 6
SECTION 7
43 COMMERCIAL &
SECTION 3 OPERATIONAL
17 BUILD YOUR SOFT SKILLS
SECTION 8
SECTION 4
49 START UPS & FAST GROWTH
PERSONAL
GROWTH
90 THINGS YOU NEED TO KNOW, ...
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.
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.
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.
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.
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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 7
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.
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.
.
96 TIPS TO BECOME AN EFFECTIVE CTO | 8
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.
“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
96 TIPS TO BECOME AN EFFECTIVE CTO | 13
With other c-suite roles there is a more natural learning path with the skills
acquired through your career carried into the senior level.
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.
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.
Spending hours conducting a code review is not a good use of that time,
Perfecting the architecture of a new product most certainly is.
96 TIPS TO BECOME AN EFFECTIVE CTO | 14
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.
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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 15
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.
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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 16
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.
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
96 TIPS TO BECOME AN EFFECTIVE CTO | 17
All meetings need keeping under tight control. The following steps will help:
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?
96 TIPS TO BECOME AN EFFECTIVE CTO | 18
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 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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 19
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.
Then start the process towards productising it. Then, SaaS the hell out of it!
SECTION 3
BUILDING YOUR
SOFT SKILLS
96 TIPS TO BECOME AN EFFECTIVE CTO | 21
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.
... added bonus, is having an effective CEO, supportive executive team and
money in the bank ... (Ed: now you're just getting greedy)
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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 22
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?
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.
It can be a fun part of the job, but it is a skill that CTOs need to build through their
career.
96 TIPS TO BECOME AN EFFECTIVE CTO | 23
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.
MAINTAIN
YOUR
TECH SKILLS
96 TIPS TO BECOME AN EFFECTIVE CTO | 25
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.
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.
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?
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.
Databases
Relational vs NoSQL vs time series vs something else?
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.
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
96 TIPS TO BECOME AN EFFECTIVE CTO | 27
Your instinct to lead is so strong that it’s part of who you are.
Leadership:
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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 27
A business can’t develop the breakthrough product or process if it’s not willing to
encourage risk-taking and to learn from mistakes.
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 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.
Your role is to shape and adapt those elements into an effective team culture.
It needs to be inclusive, supportive and diverse.
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 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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 29
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
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.
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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 30
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.
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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 31
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.
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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 31
TAKE RESPONSIBILITY 42
TIP 7
This is not the same as being accountable.
It's also about a mindset that removes you from being “one of the team” and lets
you take charge and make key decisions.
Only through engaged conversations over time can managers create failure-
tolerant work environments that invite innovation.
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.
“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.”
96 TIPS TO BECOME AN EFFECTIVE CTO | 32
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?
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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 33
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.
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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 34
“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.
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.
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.
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:
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.
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.
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.
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.
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
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.
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.
Make sure what you work on is aligned to the strategic goals of the company
96 TIPS TO BECOME AN EFFECTIVE CTO | 38
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.
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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 38
TIP 7
SECURITY & DATA 58
Security should always be at the forefront of your mind. There are several areas to
deal with:
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.
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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 39
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.
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?
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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 39
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
96 TIPS TO BECOME AN EFFECTIVE CTO | 41
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.
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.
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?
96 TIPS TO BECOME AN EFFECTIVE CTO | 41
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.
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.
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.
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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 43
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.
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.
Boards can become very unwieldy and some appointments are made on the basis
of an old-boys network rather than real added-value.
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.
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.
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?
Is their ambition realistic? Do their numbers make sense? What is your opportunity
cost and is the equity package sufficient reward for the risk?
96 TIPS TO BECOME AN EFFECTIVE CTO | 50
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.
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.
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
96 TIPS TO BECOME AN EFFECTIVE CTO | 52
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.
Successful senior executives acknowledge blind spots in their skill set and build a
highly effective safety net around them, based on the following pillars:
Understanding you can't do everything and even if you could, quality suffers.
Leading by example.
96 TIPS TO BECOME AN EFFECTIVE CTO | 53
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)
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.
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.
96 TIPS TO BECOME AN EFFECTIVE CTO | 54
Tread cautiously when planning to be a true pioneer. Assess new opportunities TIP 7
rationally, not emotionally.
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.
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?
96 TIPS TO BECOME AN EFFECTIVE CTO | 55
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.
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.
“Realise deeply that the present moment is all you have. Make NOW the primary
focus of your life”
A little more about CTO Academy ...
"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 ...
"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.”
“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”
“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”
"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”
"I’d say the key are human characteristics of creativity, risk taking, innovation and putting people first”
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.
JASON NOBLE
CTO Academy Co-Founder
SANJAY MISTRY
CTO/COO, Leadership Coach
Richard Weaver
Head of Careers