What five decades in business taught me about judgement, resilience, and momentum

 

From Buttons to Boardrooms: Setting the Scene

Picture this: 1972, a dimly lit computer room in, then, Salisbury, Rhodesia. I’m a 17-year-old trainee operator, feeding punch cards into a hulking mainframe and pushing buttons to relay binary commands because someone had to make the beast hum. The air smelled of hot electrical circuits and ozone. “What the boss says, goes” – no debate, no questions, no second-guessing. Punch the clock at shift start, follow orders, climb the ladder rung by rung. That was business life.

Fast forward five decades, and my day now often starts before sunrise, coaching SME CEOs and business owners across multiple time zones. The conversations are very different. Today’s leaders are expected to listen more than they speak, make decisions with incomplete information, and adapt constantly as conditions shift around them.

While my earliest years were spent in technical and specialist roles, the shift into business leadership brought a very different set of lessons – lessons that have endured remarkably well, even as technology, markets, and expectations have changed almost beyond recognition.

As the final article in my series, “The Business Year – Lessons, Patterns and the Road Ahead,” in which we first unpacked 2025’s BANI shocks and then mapped SME strategies for 2026, this article explores leadership and how it has changed during my five-plus decades in the business world.

It is not a memoir, and it is not a recap of recent years. It is a reflection on how business leadership itself has evolved, what no longer works, and what still matters when uncertainty is no longer a phase but the permanent backdrop.

 

What business leadership used to be, and why that way no longer works

For much of my early career, leadership was defined by hierarchy and authority was equated with certainty. Organisations were built around clear chains of command. Obedience was valued more highly than challenge, and certainty was expected from those at the top.

That model worked reasonably well at the time. Information moved slowly – think telex, fax, 9600 bps modems (even these were rare then), typed memos and no internet. Markets were largely local or regional. Competitive variables were fewer, and change happened at a pace that allowed leaders to think, decide, and then act.

Today, that environment no longer exists.

Modern business leadership operates in a world where complexity outpaces individual expertise. Information flows continuously, often contradicting itself within hours. Consider just US tariffs through 2025 alone, flipping from broad country-wide edicts one month to product-specific tweaks on coffee beans or steel pipe fittings the next, all announced via X posts reaching suppliers instantly.

Speed is no longer a competitive advantage; it is a requirement. No leader, regardless of experience, can be omniscient.

In this context, leadership has shifted away from authority and towards coordination and judgement. The most effective leaders are not those with all the answers, but those who know how to bring the right expertise together, ask better questions, and listen carefully before deciding.

Listening, in particular, is not a soft skill. It is a core leadership discipline. Leaders who fail to listen to their teams, customers, suppliers, and markets inevitably make decisions based on outdated or incomplete assumptions.

I see this weekly coaching CEOs who still route every decision through themselves – every purchase order, every hire, every pricing adjustment needs their personal sign-off. The result? Bottlenecks everywhere, growth starved.

Reader reflection:

If every decision in your business still requires your approval, what does that say about how your business is really being led?

 

Career pivots and the discipline of unlearning

One of the hardest lessons in leadership is that growth often requires letting go of what made you successful in the first place.

Fairly early in my career, I moved from a deeply technical role into product management and then into marketing. It was an uncomfortable shift to move from binary code to boardroom presentations, from reactive problem-solving to proactive value creation, from fixing issues to shaping markets. That transition changed not only what I did, but how I thought about business.

Later, stepping into a CEO role reinforced this lesson even more strongly. Hands-on control may drive early progress, but it does not scale. Micromanagement exhausts everyone, including the leader. Sustainable growth demands delegation, trust, and systems that allow the organisation to function without constant intervention. These lessons were learned as we scaled through 100x top-line and 200x bottom-line growth over my 15 years there, ten of them as CEO.

Looking back, a clear pattern emerges. Every meaningful step forward required unlearning something that once worked well. Technical excellence became a constraint. Personal involvement became a bottleneck. Familiar strengths had to be re-examined.

This pattern is one I now see repeatedly in SME leaders. What built the business to its current size is often the very thing preventing it from moving to the next level.

Reader  reflection:

Which of your current strengths may already be turning into a constraint?

 

Decision-making when uncertainty becomes permanent

One of the most profound shifts in business leadership over the past two decades has been the nature of uncertainty itself.

In the past, uncertainty tended to be episodic. A recession, a regulatory change, a new competitor. Leaders could reasonably expect periods of relative stability between disruptions.

Information now arrives in greater volume, at greater speed, and is constantly revised. The result can easily lead to analysis paralysis, as leaders wait for clarity that never arrives, convinced that acting too soon is riskier than waiting.

This challenge is not unique to SMEs – research and practitioner work have long shown that information overload often leads leaders to delay decisions rather than improve them.

In practice, the opposite is often true.

I learned an important lesson about decision-making through sailing Hobie-16s in the Indian Ocean. When conditions are changeable, you rarely head directly towards your destination. You tack, adjusting your course to the wind and sea state. Movement creates options. Standing still removes them. Not being alert to changes and maintaining course regardless will spell disaster.

The same applies in business. Judgement is not about having perfect information. It is about making timely decisions with incomplete data, while remaining ready to adjust course as conditions evolve.

Doing nothing is rarely a neutral choice. More often, it is the riskiest option available.

Reader reflection :

Where are you standing still because conditions are “not clear enough”?

 

Planning, risk, and agility in a fluid environment

Planning still matters. Its purpose, however, has changed.

In a fluid environment, plans should be treated as assumptions, not promises. Medium-term planning remains essential, but leaders must accept that underlying conditions are unlikely to persist unchanged.

This is where tools such as risk registers and scenario thinking move from boardroom financial director theory into practical leadership necessity. Identifying key risks, assessing their potential impact, and considering how the business might respond is no longer a governance exercise reserved for large organisations. It is a survival skill for SMEs.

Resilience, in this context, is not simply about money in the bank. Financial buffers matter, but over-caution can also restrict growth. True resilience comes from preparation and spread. That includes limiting customer concentration, reducing dependency on single suppliers, and ensuring the business has multiple options when conditions shift.

The businesses navigating current conditions most confidently aren’t those who predicted what happened – they’re those who prepared for multiple possibilities and can pivot quickly when assumptions prove wrong.

I have written elsewhere about practical approaches to risk and resilience in SMEs, including the importance of scenario thinking and living risk registers (see, for example, my earlier articles on risk management and operating resilience).

 Reader reflection:

If one assumption in your current plan proved false tomorrow, how exposed would your business be?

 

People, delegation, and the self-inflicted ceiling

In my experience, most SME growth limits are internal rather than external.

Leaders often underestimate the capability of their people. Fear of mistakes leads to over-control, which in turn creates dependency. It also creates serious bottlenecks in the system which adds considerably to leadership stress. Delegation is not abdication. It means providing clear parameters, appropriate support, and room for learning. It also means accepting that some mistakes will happen, while addressing repeated ones.

Delegation, when done properly, is not a loss of control; it is a growth multiplier.

Hiring plays a crucial role here, too. Too many businesses recruit for the organisation they have today, rather than the one they are trying to build – generally because it is cheaper in the short-term. Delegation becomes impossible if the team lacks the capability to take on greater responsibility.

The ongoing development of your team is not a luxury – it is a resilience factor. When people grow, they can handle more complexity, take on greater responsibility, and make better decisions independently. This doesn’t diminish your role; it elevates it from operational firefighting to strategic leadership.

I’ve written elsewhere about delegation and founder dependency as constraints on growth and value, but the pattern is always the same: until the business can function without the founder at its centre, scale and sustainability remain elusive. This pattern is so common that it has been repeatedly identified in leadership and growth research as a primary constraint on scaling founder-led businesses.

Having led and worked across different regions of the world, I have also learned that leadership norms vary widely. Some cultures expect strong direction, others value challenge and debate. There is no universal template. Effective business leadership requires informed judgement and an ability to adapt style without compromising principles.

 Reader  reflection:

What would genuinely break if you stepped back from day-to-day decisions for a week?

 

Energy, endurance, and leadership over the long haul

Leadership is not a sprint. Sustained effectiveness requires managing the leader as a system.

Nobody talks about this enough: your energy is a leadership responsibility. When you’re depleted, your judgement suffers. When your judgement suffers, your business suffers. Managing yourself well is not selfish – it is strategic. That includes routines around health, movement, rest, and creating space for thinking. Time blocks in the diary for reflection are not indulgent; they are essential. Taking a multi-week break at least once a year should be a KPI – the strategic thinking you can do while relaxing away from your office can be game changing.

Over the years, I have learned that momentum matters, personally as well as professionally. Health challenges in recent years, now fortunately behind me it seems, reinforced this lesson rather than changing it. Maintaining routine, staying engaged, and continuing to move forward proved far more valuable than withdrawing or waiting for perfect conditions.

Judgement degrades quickly when energy is neglected. Leaders who are constantly exhausted tend to become reactive, risk-averse, or both.

 Reader reflection :

How sustainable is the way you are currently leading?

 

What has changed, and what stubbornly hasn’t

Much has changed over five decades in business.

Information exploded from punch-card batches processed overnight to AI models analysing global markets real-time; even solopreneurs now seize global reach through being able to reach thousands overnight; careers move fluidly across functions, industries, even countries for as long as health and purpose align; technology evolved from tactical support to strategic core, reshaping every decision.

Pre-internet eras offered one edge today’s leaders lost: opaque global pricing yielded fatter margins routinely (high shipping costs aside – sourcing competitive steel pipe or electronic components took weeks of phone calls and faxes across time zones). Global price transparency now cuts those edges razor-thin but demands and necessitates correspondingly sharper execution.

Yet some fundamentals remain stubbornly consistent.

People still need clarity and trust. Making a decision still beats doing nothing. Execution still matters more than strategy alone. Cash flow continues to be a leading cause of business failure. Delegation remains the dividing line between scalable businesses and those that stall. Leadership will still feel lonely at times.

The pace has changed. The complexity has multiplied. The fundamentals have not disappeared.

 Reader reflection: 

Are you over-investing in novelty and under-investing in fundamentals?

 

Perspective from coaching: patterns that repeat

Working with SME CEOs and business owners, the same patterns appear again and again.

Time pressure is usually a symptom, not the underlying problem. Leaders are trapped in daily operations because they have not delegated effectively. Forward planning suffers. Succession thinking is postponed. Founder dependency quietly erodes business value.

The difference between having a valuable business and just an expensive job comes down to systems, people, and independence from founder involvement. Can it run without you? Can it grow without you? Would someone pay for it without you? If the answer to any question is “no,” you’ve identified where to focus your development effort.

I see this pattern so often that it has become one of the core themes of my coaching work. Addressing it changes not just growth prospects, but the quality of life for the leader as well.

 Reader reflection:  

Could your business function and grow without you at its centre?

 

The long view

We opened with two contrasting moments: a teenage computer operator in the early 1970s, and a business coach in the 2020s. The gulf between them isn’t just technological or generational – it’s philosophical.

Success has been redefined over these decades. It’s no longer about climbing a corporate ladder to retirement at 65 with a gold watch. It’s about continued contribution for as long as health and purpose align. It’s about ongoing learning, because the moment you stop learning is the moment you begin irrelevance. It’s about building value beyond your personal effort – creating businesses, developing people, sharing insight that persists after you’ve moved on.

The enduring lesson from five decades is this: business leadership has never been about certainty. It’s about judgement, preparation, and movement. The best leaders I’ve worked with, observed, or aspired to be like weren’t those who always had the right answer – they were those who asked better questions, made timely decisions with imperfect information, learned from outcomes, and adjusted course intelligently.

The business landscape will continue evolving. Information will accelerate further. Technology will disrupt more industries. New challenges will emerge that we cannot currently imagine. But the fundamentals – clarity, execution, delegation, cash management, sound judgement under pressure – these will remain as relevant in 2030 as they were in 1970.

Your task is not to predict what’s coming. It is to build the leadership capabilities that allow you to navigate whatever arrives.

 

Your turn:

As you move into the next year, what belief about leadership or business are you now ready to question?

 

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This month, we’ve been exploring “The Business Year – Lessons, Patterns and the Road Ahead.”

We started with a retrospective on 2025 in a BANI world, then looked ahead to the priorities for SME leaders in 2026. This final piece has stepped back further, to reflect on what has changed in business leadership over the years, and what stubbornly hasn’t.

If you’d like to catch up, here are the earlier articles in the series:

• 2025 Business Retrospective: How a BANI World Sorted the Strong from the Fragile
• Business Strategy 2026: The 11 Priorities SME Leaders Must Focus On

I’ll be taking a short publishing break over Christmas and New Year, and I’ll be back in January with the next series of business leadership articles.

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Let’s talk

If you’re an SME CEO or business owner and you want to free up time, improve margin, and build a business that does not depend entirely on you, I can help.

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