From code to C-Suite: How I got into strategy

I realise I have answered this question in so many conversations, but never written it down.

I started my career in software development in the 90s. It was a heady time, with the advent of client server computing, object-orientation, and, of course, the internet.

By the time of the dot.com boom, I as already rising through middle management into more senior roles, eventually running the software development capability for a very well funded startup online bank based in Cape Town, South Africa.

At the same time I was doing my MBA.

Well before the dot.com crash, I realised that, while the question I was being asked was "can you build it?", the more important question was "should you build it?"

It turns out I was exactly right. A lot of dot.com business that could be built shouldn't have been.

What followed, of course, was the crash.

But I had already made the transition for technology into strategy. I started by pointing out that the startup bank I was working for was trying to replicate a model from the UK into South Africa. I pointed out that the markets were very different, and therefore, so was what would and wouldn't work. I was tasked with remediating the problem. (Which I did.)

My journey into strategy initially led me away from technology and deep into financial services.

However, it quickly became apparent that lots of the problems and opportunities in financial services were very technologically oriented. So things tied together quite neatly.

It is also how I came to found StratNavApp.com. It was born out of a personal realisation that digital transformation was impacting almost every aspect of life, but the practice of developing and executing business strategy remained stubbornly unchanged. Most organisations I encountered relied on little other than Microsoft PowerPoint, Word and Excel.

There had to be a better way!

And, of course, as AI slowly emerged (even when it was still machine learning rather than Generative AI) it became evident that the digitisation of strategy was fundamental to its continued evolution. And StratNavApp.com was ideally placed to capitalise on it.

So my story is essential one of technologist turned strategist turned technologist!

If you found that at all interesting, please feel free to follow my continuing journey on:

What is human intelligence exceptionalism?

Human intelligence exceptionalism is the (almost certainly mistaken) belief intelligence which resides in a carbon-based life form is inherently different from and superior to intelligence that resides in any other medium.

Human intelligence exceptionalism is the belief that human intelligence is fundamentally unique, inherently superior, and cannot be meaningfully replicated in non-biological forms. This perspective is deeply ingrained in philosophy, religion, and culture, often rooted in the idea that consciousness, self-awareness, and higher reasoning are exclusive to humans—or, at most, to carbon-based life forms like ourselves.

However, this view is increasingly challenged by advancements in artificial intelligence (AI) and our growing understanding of cognition in non-human species. There is little scientific evidence to suggest that intelligence must emerge from biological processes alone. Instead, intelligence may be an emergent property of complex information processing, independent of the medium in which it occurs. If this is true, then a sufficiently advanced AI, or even an intelligence emerging in an entirely different non-carbon substrate, could exhibit capabilities equal to or exceeding human cognition.

Rejecting human intelligence exceptionalism does not necessarily mean denying human uniqueness. Rather, it invites us to consider that intelligence may be a spectrum that transcends biology. Just as silicon-based computers have surpassed humans in raw computation speed, non-biological intelligences may one day surpass us in creativity, reasoning, and problem-solving—challenging long-held assumptions about what it means to be intelligent.

Historically, human intelligence exceptionalism has been deeply tied to philosophical, religious, and scientific thought. Ancient civilizations often placed humans at the centre of the cosmos. In Western thought, this idea was reinforced by religious doctrines, such as those in Christianity, which asserted that humans were created in the image of God and granted dominion over nature (Genesis 1:26). This perspective positioned human intelligence as divinely ordained and distinct from all other forms of cognition.

During the Scientific Revolution, thinkers like René Descartes (1596–1650) reinforced human intelligence exceptionalism by arguing that only humans possessed rational souls. Descartes viewed animals as "automatons"—mechanical beings that lacked true thought or consciousness. This mechanistic view of non-human entities contributed to the notion that intelligence was an exclusively human trait, tied to a spiritual essence rather than a material process.

The 19th and 20th centuries saw significant challenges to human intelligence exceptionalism. Charles Darwin’s On the Origin of Species (1859) demonstrated that humans evolved from other life forms, suggesting that intelligence is not a divine gift but a product of natural selection. Later, cognitive science and artificial intelligence research further questioned whether human intelligence was unique. Alan Turing, in his seminal 1950 paper Computing Machinery and Intelligence, proposed that intelligence should be measured by functional performance rather than by the nature of the entity in which it resides. The Turing Test challenged the assumption that only biological beings could "think."

More recently, advances in AI, neuroscience, and synthetic biology have reinforced the idea that intelligence is a substrate-independent phenomenon. Machines now outperform humans in many cognitive tasks, from playing chess and Go to diagnosing diseases. This raises profound philosophical and ethical questions about the future of intelligence—suggesting that human intelligence exceptionalism may be less of a scientific reality and more of a psychological bias rooted in historical tradition.

The Role of Data in Strategy: Learning from the Past to Shape the Future

I am often told that data looks to the past while strategy looks to the future. And while this is true, some take it a step further and suggest this as a reason for not overly relying on data when developing strategy.

But if we don't rely on data, what should we rely on? 🤔 Not relying on data because it reflects the past doesn’t make much sense. After all, the past is all we have to inform us about what works, what doesn’t, and why.

The Past is Our Only Reference Point

When strategising, the future is inherently uncertain. No one can predict it with any certainty. But by looking back at past trends, patterns, and experiences, we can make educated guesses about where things are heading. Data helps us do exactly that—whether it’s quantitative metrics or qualitative insights. It serves as a reflection of what's happened before and, more importantly, why.

For instance, when market researchers examine customer behaviour, they aren’t just looking at yesterday's purchases. They’re analysing patterns — patterns that reveal how customer preferences have evolved and how they might continue to change. This kind of analysis allows companies to stay ahead of trends and innovate in ways that resonate with their target audience.

Steve Jobs and the Calligraphy Example

A common counter-argument to the use of data in strategy is the case of Steve Jobs, who famously designed the fonts for Apple based on his study of calligraphy during his college years. At first glance, it might seem that this story is about inspiration, creativity, and thinking outside the box, which aren't typically associated with data.

But let’s look at this a little more closely. What is the study of calligraphy, if not a form of qualitative data? Jobs was drawing from historical knowledge and techniques. He wasn't reinventing the wheel — he was building on the artistry, precision, and discipline of centuries-old traditions. By studying calligraphy, he was collecting data about the past in order to innovate in the present and future.

His decision wasn’t purely whimsical or gut-driven. It was an informed choice based on patterns of visual appeal, readability, and user experience that calligraphers had discovered and refined over time. In essence, it’s another example of how understanding the past can inspire future breakthroughs. 📜✍️

Data Provides Context and Insight

When we say strategy is about the future, what we really mean is that it’s about making decisions that will have future outcomes. The only way to make informed decisions is to understand the context, the landscape, and the forces shaping it.

Data — whether qualitative, like Steve Jobs' study of calligraphy, or quantitative, like sales reports and customer analytics—provides critical insights that help businesses assess risks, identify opportunities, and anticipate future trends.

Here’s why relying on data is crucial for strategic planning:

Trends and Patterns: Data reveals long-term trends that would be impossible to spot otherwise. It shows how things are changing and helps us anticipate future changes.
Risk Mitigation: By analysing past mistakes and successes, businesses can reduce the likelihood of repeating errors and increase their chances of success.
Informed Innovation: Data doesn’t just tell us what happened—it can also reveal why it happened. Armed with this knowledge, businesses can innovate more intelligently.
Competitive Advantage: Competitors who ignore data run the risk of making poorly informed decisions, leaving the field wide open for those who leverage data-driven insights to make smarter moves.

Balancing Intuition and Data

Of course, strategy isn't purely data-driven. There’s still room for creativity, intuition, and vision. Some of the best ideas come from out-of-the-box thinking, and not every decision can be backed up by numbers. But these creative decisions should still be informed by data. They should be rooted in an understanding of what’s been tried before, what succeeded, and what failed. Just like Jobs' development of Apple's fonts was.

The real magic happens when you balance intuition with data. Visionary leaders can see beyond the data, but they use it as their foundation. Without that solid base, even the most inspired ideas run the risk of being disconnected from reality.

So, Should We Rely on Data in Strategy?

Absolutely! While data reflects the past, it is our most valuable tool for shaping the future. Whether it's a market analysis, customer feedback, or even the study of ancient calligraphy, data provides a foundation for making informed decisions. Without it, we're left guessing or gazing into a crystal ball — and neither of those approaches is a sound business strategy.

The next time someone suggests we shouldn’t rely on data because it looks backwards, remind them that the past is the only lens through which we can view the future. What we choose to learn from it will determine how successful we are in charting the course ahead. 🌍🔮

Odysseus: The original strategist

I like to think of Odysseus as the original archetypal strategist.

(In our western tradition, at least.)

Odysseus was known was the wiliest of the Greek kings that laid siege to Troy. A bit of a trickster, really.

The siege lasted for 10 years. It was a war of attrition. Sometimes the Greeks won a bit. Other times the Trojans won a little bit. Mostly, people died and little progress was made.

It was Odysseus who came up with the idea of the Trojan Horse (see below).

(Actually, the myths tell us it was the goddess Athena who whispered it in his ear.)

The Trojan horse allowed a handful of Greeks to defeat the Trojans where the whole army had failed for a decade.

And that is the heart of strategy. Winning by being cleverer and by doing something different. Not trying the same thing harder (longer, faster, better, etc.) despite disappointing results.

These are lessons from history which we would do well to apply when developing modern business strategies:

Don't try and match your competitors' strategies.
Look for a different, novel and surprising approach.
Focus on small things that can make a disproportionately big difference.
Don't show your hand too early.
If what you're doing hasn't been working, its time to try something else.

What do you think?

By the way: Stephen Fry's retelling of Troy (see right) is a fantastic read. If you want to know more about Odysseus and his tricks, I highly recommend it.

A quick summary of the Trojan Horse

If you're not familiar with the story of the Trojan Horse, here is a quick summary of what is one of the most intriguing and well-known tales from Greek mythology, particularly from the epic conclusion of the Trojan War.

After a gruelling and unsuccessful siege of Troy that lasted ten years, the Greeks devised a cunning plan to break into the city's impregnable walls. The brainchild of Odysseus, the scheme involved constructing a gigantic wooden horse, ostensibly as a peace offering to the Trojans but secretly harbouring elite Greek soldiers inside.

The Greeks built the horse and left it at the gates of Troy, while the main Greek army pretended to retreat, hiding out of sight. The Trojans, believing they had finally seen the Greeks off and won the war, debated what to do with the horse. Despite warnings from Laocoön and Cassandra to distrust the Greek gift, the Trojans, overwhelmed by curiosity and the thought of a Greek surrender, pulled the horse into their city as a trophy of their apparent victory.

The celebration was short-lived. Under the cover of night, the Greek soldiers hidden inside the horse emerged and opened the city gates to the rest of the Greek army, which had returned under the cover of darkness. The Greeks launched a surprise attack, leading to the fall of Troy. This pivotal event effectively ended the war, with the Greeks using deception and tactical ingenuity to overcome their enemies. The term "Trojan Horse" has since become synonymous with trickery and the subversive infiltration of an enemy, making it a lasting symbol of strategic deception.

Integrate generative AI into your business strategy

Has Generative AI lived up to its transformative promise?

2023 was undoubtedly the year we all played with Generative AI. 2024 should be the year it could transform your business.

Now, a little over a mere 13 months since ChatGPT launched, we can reflect on how it's changed things.

There is already a sense of the hype-cycle shifting with increasing frustration over what it can't do.

In my experience, a lot of this is based on a combination of misuse and unrealistic expectations.

Where to from here?

I remain optimistic about the possibilities of Generative (and other forms of) AI.

Like any tool, I am sure it can - and almost certainly will - be used badly and for bad purposes. But that doesn't detract from the opportunities to use it well and for good purposes.

So, how can we ensure that we remain on the right side of that equation?

Here are my tips:

Always start with a business need. As with most new technologies there will almost certainly be more things that you *could* do than that you *should* do with it. Trying to everything at once, or prioritising at random will leave you chasing your tail. A clear business strategy will help you to prioritise where to put your efforts.
Think different, not just better. AI will enable us to do many things that we already do, but better - faster, more consistently, more cheaply and at higher volume or with fewer people. While that's invariably a good thing, let's not lose sight of the opportunities to do things differently or to do different things. We need to be thinking about new products, services, processes, business models and strategies as much as we are thinking about improving the efficiency of existing ones.
Think beyond chatbots: We've got think beyond typing questions into the ChatGPT/Bard etc. prompt box and then copy/pasting the answers into whatever else we're doing. We need to seamlessly integrate AI into our existing tools and processes, making it as ubiquitous and unintrusive in our daily operations as electricity or Wi-Fi.

(We're already building it into StratNavApp.com where it helps users develop and execute better business strategies without them being aware of the details of the prompts and responses being written and consumed in the background!)

Reach out if you need help integrating AI into your business strategy.

The Critical Gap in Business Strategy Execution: Insights from Jan 2025

Reflecting on 2023, I made a startling discovery about business strategy! I have now updated this to reflect data from 2024.

I analysed* thousands of projects on StratNavApp.com during 2024. I found that of those that got as far as setting strategic goals and/or strategic initiatives:

A few more than 25% got as far as setting KPIs.**
Fewer than 18% actually tracked those KPIs.

That means that more than 82% of those strategies never progress beyond being a theoretical assumption about what should work. Even if they're executed, there is no way of knowing if they're producing the intended outcomes or not. They're flying blind!🚫👀

I challenge these organisations to:

Break your strategic goals down into SMART objectives.🎯

SMART stands for Specific, Measurable, Achievable, Relevant and Time-bound.
Establish clear Key Performance Indicators (KPIs) for tracking each of them.🔍

Together, these objectives and KPIs are often called Objectives and Key Results (OKRs).
Regularly track actual performance against them.⏰
Analyse your performance against expectations.📊

It's important to set expectations in advance, otherwise you risk simply settling for whatever results you get.
Make appropriate adjustments to your strategy if the results aren't what you'd anticipated.🔄

There is no point in just carrying on with your strategy if it is not producing the intended results.
Keep repeating as you watch your business flourish.🌱

Fortunately, StratNavApp.com provides you with all the tools you need to do this in one convenient place. It even uses AI to help break through any barriers you might encounter. You can learn more about how it does this at Goals, Objectives, KPIs, Targets, Initiatives and Actions and Creating a Strategy Scorecard.

If you need more help than that, please contact me.

But don't hesitate. The sooner you start the sooner you can start enjoying a more successful 2024!

Share your thoughts and questions in the comments below.👇

Notes:

* NB: StratNavApp.com provides the ability to do this kind of analysis without ever looking at what your strategy actually is. Your strategy is always confidential to only you and those you choose to share it with.

** The actual figures are 25.59% (up from 23.9% in 2023) set KPIs and 17.42% (down from 19.1% in 2023) tracked them. The decrease in strategies tracking KPIs may reflect an increase in the total number of strategies analysed, rather than an absolute decrease.

*** Some strategies built in StratNavApp.com may have built and tracked their KPIs on another platform. We estimate this number to be small as a virtue of StratNavApp.com is that it provides an integrated platform for strategy development and execution.

How KPIs Bring Your Strategy to Life

Strategy: More Than Just an Annual Ritual - It's a Continuous Discipline

It's very important that your business complies with the law.

You need to enter into contracts with employees, suppliers, distributors, and customers. You need to make sure that those contracts are fit for purposes, and that both you and your counterparties comply with their terms.

One way to ensure your business remains legally compliant is to take your top leadership team on an Annual Legal Retreat. Over the course of 1-3 days, you can discuss all of the legal issues that might apply to your business, update yourselves on recent legal developments, and make all the decisions you need to make until next year's Legal Retreat.

And since your organisation's leaders are your top employees in disciplines like operations, marketing, human resources, and finance, they should have no problem covering the full gamut of the law in just a few days once a year.

I am, of course, joking! That would be absurd!

We don't expect to handle everything to do with the law - or with financial management, human resources, marketing, operations - in a short off-site once a year.

So why do so many organisations think that they can get away with doing that with strategy?

Is having - and successfully executing - a sound strategy less important than any of those other things?

You don't go on an annual marketing retreat, you hire a CMO or a marketing consultant. You don't go on an annual HR retreat, your hire a head of HR or an HR consultant. You don't go on an annual legal retreat, you hire a lawyer or engage a law firm. You don't... you get the picture.

Like all those other disciplines:

strategy is a unique discipline requiring specialised skills and experience.
effective strategy demands year-round attention, not just an annual review.
modern strategy needs tools - which in today's world means software like StratNavApp.com - which are fit for purpose.

Your strategy is executed in everything you do - in every decision you make - every day. And it is impacted by and may need to be adjusted in the face of external market events which can arise at any time. This can't be handled on a 2-day offsite once a year.

Your options are:

Hire someone: You can hire a Chief Strategy Officer (CSO) with the right skills and experience in doing business strategy and give them a seat at the top table, just as you're hire a Chief Financial Officer (CFO), Chief Marketing Officer (CMO), HR Officer (HRO), etc.
or
Use external consultants: If you're a smaller organisation and can't afford permanent dedicated resource, or even if you just need some extra lifting power from time to time, you can hire experienced and expert strategy consultants (like Chris C Fox Consulting!) to help,
and
Use purpose-built software: Both of the above approaches are significantly enhanced by using dedicated software, like StratNavApp.com, for strategy development and execution, just like you probably use dedicated accounting software, marketing tools and an HR Management System (HRMS). This will ensure that your strategy is both soundly formulated and executed with discipline.

Share your thoughts in the comments below: Does your organisation take strategy seriously enough? Or does it pay lip-service to strategy once a year and then hope for the best? Let's discuss how we can shift the narrative from strategy as an annual event to a continuous discipline.

If you need help with you business strategy or any related issues, contact me for a no-obligation consultation.

P.S. Remember, strategy is not just an annual checkbox. It's the guiding force that drives your business forward every single day. 🚀