There is a great deal written about building enterprises. We speak about ideas, capital, strategy, markets, leadership and execution, and naturally all of these matter. But having spent years building businesses, I have increasingly come to believe that the real complexity lies elsewhere. It lies with people.
People come into an enterprise carrying their own ambitions, insecurities, loyalties and expectations. Some will stay with you through extraordinarily difficult periods. Some will surprise you with what they are capable of. Others will disappoint you, and a few may eventually betray the trust you placed in them. Over time, however, I have learnt not to look at these experiences simply in terms of loyalty and betrayal. There is another force at work, and that is opportunity.
Betrayal and opportunity may seem like strange things to put together, but I think they are far more closely connected than we generally acknowledge. Somewhere between them sits ambition, and understanding ambition is perhaps one of the most important lessons a founder eventually learns.
The People Who Push You
While building an enterprise, your strongest asset is not always the person who agrees with you. Quite often, it is the person capable of pushing you to the brink.
These are not necessarily easy people to work with. They question decisions, argue when they believe you are wrong and occasionally test the limits of your patience. For a founder, particularly one accustomed to carrying the ultimate responsibility for an organisation, it is very easy to interpret this behaviour as resistance. Persistent disagreement can begin to feel like defiance, and defiance can easily be mistaken for disloyalty.
Experience has made me much more careful about that distinction.
The person who challenges your authority and the person who seeks to undermine it are not necessarily the same person. In fact, someone who is prepared to argue with you may be demonstrating something more valuable than the person who agrees with everything you say. He has a position of his own. He has enough confidence in his judgement to defend it, and quite often that confidence comes from ambition.
Of course, an organisation cannot function if everyone behaves this way. If every decision becomes a contest and every employee considers himself a general, very little will actually get done. An enterprise needs people who trust its direction and are prepared to execute without questioning every instruction. There is nothing inferior about that role. A kingdom may have its king and its generals, but without its people there is no kingdom at all.
The difficulty for the founder is therefore not deciding whether he wants followers or challengers. He needs both, and he needs to know the difference.
Ambition and the Opportunist
We tend to use the word opportunist almost entirely as an insult. I am not sure that is always useful.
An opportunist, at the most basic level, is someone who recognises opportunity and is prepared to act upon it. Naturally, this can become destructive. The same person who quickly recognises an opportunity for the enterprise may also recognise an opportunity for himself. But it would be a mistake to assume that this quality has no value simply because it carries risk.
In my experience, some of the people most capable of betrayal are also people with considerable ambition. That does not excuse betrayal, nor does it mean that every dishonest person should suddenly be viewed as an undiscovered leader. It simply means that when something goes wrong, I have learnt to look beyond the act itself and ask a more useful question: what was driving it?
Was it money? Authority? Recognition? Ownership? Independence? Was the person seeking a larger responsibility than the organisation was prepared to give? Or was it simply greed and poor character? These distinctions matter because the response should not be the same in every case.
This is where I often think of enterprises as kingdoms. A kingdom can perhaps survive with a king and a population willing to follow him, but expansion requires generals, and good generals are rarely people without ambition. They want responsibility. They want victories of their own. They want territory, figuratively or sometimes literally, upon which they can demonstrate what they are capable of.
That makes them useful, but it also makes them dangerous.
The answer, however, cannot be to eliminate everyone capable of becoming dangerous. You may secure the throne that way, but you will eventually find yourself ruling something that cannot grow. The more difficult task is to understand ambition well enough to give it a productive direction.
A capable person who joins an organisation today will not necessarily want the same things five years from now. If the enterprise grows, that person grows with it. Their experience changes, their confidence changes and quite naturally their expectations change. Yet founders sometimes continue to see people as they were when they first joined.
We are happy to benefit from their growing capability while being considerably less comfortable with their growing ambition.
That is an unstable arrangement.
If you employ ambition but refuse it opportunity, you should not be surprised when ambition eventually creates an opportunity of its own.
Opportunity Is Part of Loyalty
Loyalty is often discussed as though it is entirely the responsibility of the employee. Someone joins an organisation and, if they are a good person, they are expected to remain loyal to it. If they leave for something better, negotiate aggressively or begin seeking greater authority, their loyalty is questioned.
I think founders need to examine their own part in this relationship.
You cannot ask ambitious people to help you build something larger while expecting their own world to remain exactly the same. If someone has contributed meaningfully to the growth of an enterprise, taken risks with you and developed the ability to carry greater responsibility, then the organisation must eventually create somewhere for that ability to go.
That does not necessarily mean a larger salary. Money matters, but motivation is rarely that simple. Opportunity may mean authority, recognition, ownership, independence within the larger organisation or the chance to build something new. Different people want different things, and part of leadership is understanding the difference.
I have increasingly come to see this as one of the founder’s responsibilities. We spend enormous amounts of time thinking about opportunities for our enterprises. Perhaps we should spend more time thinking about opportunities for the people building them with us.
Because ambition does not disappear when it is ignored. It merely begins looking elsewhere.
There is an important qualification here. No amount of opportunity can purchase character. Some people will betray trust regardless of how fairly they are treated, and a founder who refuses to recognise this will eventually pay for his naïveté. Giving people room to grow does not mean surrendering judgement, and understanding someone’s motivation does not require excusing their conduct.
But the opposite mistake is equally expensive. A founder who responds to every disappointment by trusting fewer people, concentrating more authority and surrounding himself only with those who never disagree may protect himself from some betrayals. He may also slowly remove from the organisation precisely the people capable of helping it become larger than him.
What Betrayal Can Teach
Betrayal is difficult precisely because it requires trust to have existed in the first place. A stranger cannot really betray you. The act has weight because it comes from someone to whom you had given access, confidence or responsibility.
The natural response is anger, and perhaps for a time that is unavoidable. But anger is not particularly useful for building an enterprise. Eventually the more important task is to understand what the experience exposed.
Perhaps your judgement of a person was wrong. Perhaps your systems depended too heavily on trust where checks and balances should have existed. Perhaps one individual had accumulated more influence than the structure could safely accommodate. Or perhaps someone had simply outgrown the role you had created for them and you failed to recognise it until their ambition found another route.
Understanding this does not make betrayal acceptable. It makes the experience useful.
There is little value in spending years resenting the person who exposed a weakness in your organisation when you could spend that time correcting the weakness. If an experience forces you to build better systems, distribute authority more intelligently or understand people more carefully, then something intended to weaken you may ultimately contribute to making the enterprise stronger.
There may even be occasions when someone who once stood against you can later stand beside you. I do not believe this requires forgetting what happened, and trust once broken should never be restored casually. But neither do I believe that permanent hostility is necessarily a sign of strength.
A founder has to ask a colder question: what serves the enterprise?
If a person possesses exceptional ability, understands the organisation, has learnt from what happened and can be aligned with where the enterprise is going, there may be more value in giving that ambition a direction than in spending years fighting it. The sharpest sword is not always the easiest one to hold. It is valuable because it is sharp.
What the Journey Actually Teaches
When I began building enterprises, I thought considerably more about businesses. Today, I find myself thinking considerably more about people.
A strategy can be changed. A product can be withdrawn. Capital can be raised again. An organisation can be restructured. People are more complicated because they cannot be reduced to what appears on an organisational chart. They carry histories, ambitions, fears, loyalties and their own ideas about where their lives should go.
Building an enterprise therefore requires more than learning how to manage people. It requires learning how to read them.
You need the people who believe in what you are building and are prepared to carry it forward without turning every decision into a contest. They are the continuity of the enterprise, and without them there is no institution to build upon. But you also need the difficult ones: the people with enough ambition and conviction to tell you that you may be wrong, who push against the boundaries you have created and who sometimes force you to rethink decisions you were certain about.
The founder’s responsibility is to know which is which, and more importantly, to recognise when one of those people is capable of becoming a general.
Over the years, betrayal has taught me to observe more carefully, while opportunity has taught me to look beyond the immediate behaviour and understand what motivates it. The two lessons eventually meet at ambition.
Ambition can build for you. It can compete with you. Left without direction, it can eventually turn against you. But if you understand it, challenge it and give it genuine opportunity, it can become one of the most powerful forces within an enterprise.
Perhaps that is one of the less comfortable lessons of building anything substantial. Loyalty is not always found in the person who agrees with you most. Sometimes it is found in the person who argues with you, pushes you to the brink and still chooses to build beside you when the argument is over.
Those people are difficult to find. They are even more difficult to lead.
But every kingdom needs its people, and every empire eventually needs its generals.