Most founders don’t struggle with leadership because they’re unwilling to lead. They struggle because they’ve never actually had to.
Before they start a company, they’ve mostly worked in environments where alignment was a given. Small teams, shared context, people who already wanted roughly the same thing. In those conditions, work moves quickly, decisions don’t require much explanation, and direction doesn’t need to be reinforced. Things just seem to line up.
It feels like leadership.
It isn’t.
It’s alignment by default, and the difference between the two doesn’t really become obvious until that alignment disappears.
Leadership, at its core, is the art of influencing human behavior so as to achieve the mission in the manner desired by the leader. In other words, leadership is about getting everyone else aligned with your vision of where you need to go and how you want to get there. Early on, that alignment is really not difficult to achieve. You hire people you know, they trust you, they believe in what you’re trying to build. When you explain what you need and how you want to get there, they go along with it—not because you’ve done anything particularly sophisticated as a leader, but because the conditions are doing most of the work for you. Everyone is already motivated in the same direction, so there’s very little to reconcile.
The first real change happens when you hire outside that circle.
When you hire someone with experience you don’t have. Someone who has done this before. Someone who believes, with good reason, that they know what they’re doing. Usually nothing breaks immediately. The new person listens, they engage, they contribute. But instead of things snapping into place, you start to feel friction. Not failure. Not poor performance. Just more discussion than you expected. More time spent debating what the priorities are, what the objective actually is, and how to get there.
From your perspective, this is confusing, because you think those things have been settled. You explained what you need and why. But suddenly those things are being questioned.
What you’re running into isn’t resistance. It’s interpretation.
Experienced people don’t see their role as executing someone else’s thinking. They see it as improving it. They take what you say, process it through their own experience, and then act on what they believe makes the most sense. From their perspective, they’re contributing constructively. From yours, they’re drifting. Both views are reasonable. They’re just not aligned.
The mistake founders make at this point isn’t arrogance. It’s assumption. They assume that because the goal is clear, alignment will follow. Not because they’ve thought it through, but because they’ve never seen a situation where it didn’t. Up to this point, they haven’t had to deal with people who are motivated by something different. They haven’t had to ask why someone would choose one approach over another. They haven’t had to actively shape how their direction gets interpreted.
So, when alignment fails, they don’t recognize it. They just feel like something isn’t working.
A common version of this shows up when a founder hires an operational counterpart. The founder is comfortable working from broad intent—set the direction, sketch the objective, let people figure out how to get there—so they assume that’s what good leadership looks like. Then they hire someone who is structured, detail-oriented, and experienced in execution, and almost immediately friction appears.
From the founder’s perspective, they’ve been clear. They’ve explained what they want and why it matters. From the operator’s perspective, they haven’t. They’re looking for specific priorities, clear expectations, and a shared understanding of what “done” actually looks like. Without that, they don’t feel empowered. They feel exposed.
This is where it starts to drift into something personal, even though it isn’t. The operator thinks they’re not being given enough direction. The founder thinks they’ve already given it. The founder believes they are delegating. The operator experiences it as ambiguity. So, the operator asks for more clarity, and the founder, trying to be respectful, gives them space instead.
Which only makes the problem worse.
What’s happening here is simple, but not obvious. The founder is leading the way they themselves would want to be led. If they were in that role, they wouldn’t want detailed direction. They would see it as constraint. So, they withhold it, assuming they’re being deferential.
But the person they’ve hired isn’t wired the same way. They experience that lack of clarity as a lack of trust. Since the leader won’t share the details, they assume that it is because they cannot be trusted to know them. This introduces doubt into the whole dynamic. Doubt which starts to inject itself in ways that are completely unrelated and which may be very troubling to the leader.
This is the part most founders don’t see coming, and it’s the part that makes leadership hard. The fundamental issue that is being missed is that you don’t lead people by changing how they think. You lead them by understanding how they already think—and working from there.
People are wired the way they’re wired. Some are motivated by autonomy. Give them a problem and space, and they’ll figure it out. What drives them is the act of solving it. Others are motivated by clarity. Give them a well-defined objective and clear expectations, and they’ll execute consistently. What drives them is knowing exactly what good looks like and being able to finish the job cleanly.
You will have both types on your team. And they will respond very differently to the same direction. You don’t get to change that. You don’t get to convince people to be motivated by what motivates you.
You have to meet them where they are, understand what drives them, and connect that to what you need them to do. Not by persuading them to adopt your motivation, but by helping them see that what you need done fits with how they already want to work.
Don’t get me wrong. That’s a much harder problem.
Especially when you don’t realize that’s actually the problem you are supposed to be solving. It’s not that they don’t get it. It’s that you don’t get them.
The problem isn’t that people don’t understand what you want. It’s that they don’t have a reason to want it the way you do. They don’t ignore your direction. They reinterpret it. They contribute, they engage, they try to help—just not always in the direction you intended.
And when that happens, a leader’s reaction is predictable. The leader spends more time re-iterating the same arguments, assuming that the issue isn’t a misunderstanding, it’s lack of attention to the direction being provided. When that doesn’t work, the leader starts to take the work back. To supervise it more closely or to redo it themselves. They think that will show what “good” looks like, so people will finally understand.
That may solve the immediate problem. But it also guarantees that the problem will persist.
Because now the team is no longer responsible for getting it right.
The founder is.
Which is when founders start to feel like hiring more people is making their life more difficult, which was not the point of the exercise.
What new leaders often fail to see is that this is exactly this is why leadership is hard and why it requires constant attention. It is an art, a skill, it only improves with practice. It takes a real shift in thinking to realize that issues do not arise because people are difficult, and not because teams resist direction. The issues arise because none of this happens automatically. You don’t get alignment just because the goal is clear. You don’t get consistency just because people are capable of it. And you don’t get execution just because everyone agrees in principle.
You get alignment by doing the work. You get it by understanding what drives each person, figuring out where that overlaps with what the company needs, being explicit about what matters, and adjusting how you lead depending on who you’re leading. You get it by knowing how to influence human behaviour and using that knowledge to create alignment with what you need to do.
And you need to do this over and over again.
There isn’t a point where this is solved. As the team changes, the problem resets. New people, new motivations, new interpretations.
And the work starts again.
If you do this well, you spend less time doing the work yourself—and more time making sure other people want to do it the way it needs to be done.
It turns out that THAT is really your job.
For most founders, it’s not the one they thought they were signing up for.
- Read more columns from Iain Christie