There’s a particular kind of founder that I have encountered in my coaching work that stands out. This is the founder who came to the decision to found a business later in life. Often, quite a bit later in life.
They are people who did not set out to become entrepreneurs because they dreamed of being “the boss.” In many cases, quite the opposite is true. They spent years inside organizations where they experienced poor leadership firsthand—leaders who created confusion instead of clarity, politics instead of progress, pressure instead of purpose. Over time, they became frustrated not simply with the work itself, but with the feeling that things did not need to be as dysfunctional as they had become. Eventually, a quiet conclusion formed. This doesn’t have to (not) work this way.
And so they left.
Not necessarily because they wanted to build a company, but because they no longer wanted to spend their professional lives trapped inside systems that felt disconnected from reality.
What makes these founders interesting is that they often become leaders almost accidentally. They are usually highly self-directed people. That self-direction was often forged precisely because they learned, over many years, that waiting for permission, waiting for clarity, or waiting for organizational alignment was usually a good way to remain stuck forever. So, they developed an internal compass. They learned to solve problems independently. They became comfortable operating without much reassurance or direction from others.
When they found a company, it works remarkably well–or at least it does in the early stages of a company.
At first, they are often the only employee. If they do have anyone helping them, they are probably people they know well who help out when needed with very specific jobs. So everyone involved in the business is close to the founder. Communication is direct. Priorities are obvious because tasks are handed out when there is a clear and immediate need.
And because the founder is deeply self-directed, and because they are giving work to people they know and trust, they often assume other people want to work the same way they do.
That assumption is where the trouble begins.
A lot of these founders do not realize how naturally authoritative they actually are. Inside their own heads, they still feel like the same person they have always been—figuring things out as they go, improvising constantly, uncertain more often than they would like to admit. But that is not how they appear to newer (and younger) employees.
When the founder finally does bring in someone at an entry level or not much past it, the new employee looks at the founder and sees experience. They see someone who seems to know the answer before the question is asked, who navigates uncertainty cleanly and without a lot of fuss or second guessing. They are seeing someone who has become comfortable dealing with contingency.
They also assume, often correctly, that the founder knows things they themselves do not. In fact, that is usually one of the main reasons they agree to join the company in the first place. Startups are uncertain by nature. And, people generally do not accept that uncertainty unless they believe strongly in the person leading it.
And so, a subtle misunderstanding begins to develop.
The founder thinks they are being respectful by giving people space and autonomy. If they themselves were in that role, they would not want somebody constantly directing them. They would experience (and have experienced) that approach as constraint or micromanagement. So, they deliberately avoid imposing too much structure because they do not want to become the kind of leader they once disliked working for themselves.
Meanwhile, the employee often experiences the exact same behaviour very differently.
What the founder new experiences as respectful distance, the employee experiences as ambiguity and maybe even a lack of trust.
What the founder is trying to project as trust, the employee experiences as lack of direction and even lack of trust.
The point is that the employee is not necessarily resisting leadership. Very often, they are actually just waiting for it.
This becomes even more complicated because the founder and employee are often different personalities. The founder has usually built their professional identity through independence. They value it in themselves. They value it in others. Many younger employees, on the other hand, are still in the process of building theirs through recognition.
Over time, the founder often stopped caring long ago about external validation in the normal organizational sense. Promotions, titles, approval from management–these things lost emotional importance after years of watching organizations reward the wrong behaviours. Their motivation became internal. Solving the problem mattered more than being praised for solving it. They come to see this as the natural way of things, but they forget that is actually learned behaviour borne of long experience.
Younger employees who join someone else’s company probably operate differently, especially early in their careers. They care deeply about making a good impression. They want to demonstrate competence. They want evidence that they are progressing professionally and building a reputation for being capable and reliable. Although they may appear confident, they only really gain confidence through reinforcement.
More to the point, they usually do not say this out loud.
Instead, what it looks like in practice is that they are waiting for clear direction that they can execute successfully.
That is the part founders often misunderstand. The employee is not sitting there waiting because they lack initiative. They are waiting because they want to succeed. They want to avoid making avoidable mistakes. They want to contribute effectively in a way that will be recognized positively by someone they respect and, often, are slightly intimidated by.
The founder, meanwhile, interprets the hesitation very differently.
They think:
“If this person really cared, they would just take ownership.”
The employee thinks:
“If this really mattered, and they trusted me, they would tell me what they wanted and I would show them I could get it done”
Neither side realizes they are waiting on the other.
And because the founder is trying so hard not to become controlling, they often fail to provide the clarity that would actually unlock initiative safely for less experienced people.
I guess what I am saying is that often these kinds of founders just underestimate their own ability to lead. They think leadership is something faintly obnoxious. Something that can easily become manipulative, overbearing, or authoritarian because that is how they experienced it in the past. They associate leadership with the negative professional experiences they had inside poorly run organizations, so they become reluctant to exercise authority clearly even when the people around them are actively looking for it.
And, of course, the people they hire are not usually recoiling from their leadership. They are actually drawn to it. These employees probably had other options, but they joined the company because, after even a short exposure, they trusted the founder already. They saw competence, decisiveness, and momentum. In many cases, they are looking not merely for employment, but for mentorship, direction, and the opportunity to grow around someone they believe knows more than they do.
The founder, though, is not used to seeing themselves as a paragon of any of those things, and so they often fail fully appreciate the extent to which this trust already exists.
So they hesitate to be assertive or directive, thinking that it would show a lack of trust. But in fact, the opposite is true. But, that hesitation often becomes a hidden barrier to growth. Not because the founder lacks leadership ability, but because they are uncomfortable accepting the responsibility that comes with possessing it naturally so they agonize over hiring new full-time staff. And they become the bottleneck that is throttling growth.
In the end, this is why leadership is hard for these kinds of founders. Not because they are poor leaders.
Quite often, because they are naturally gifted as leaders. The difficulty is that they must learn to trust something they spent years learning not to trust.
They must trust themselves enough to exercise leadership clearly without feeling guilty for doing so. They must trust that structure and direction are not automatically oppressive simply because they were poorly applied by someone else in the past. And perhaps most importantly, they must trust that other people do not operate mentally the way they do. Not everyone is a self-reliant individualist (thank heavens). There are people in the world who want and need to be led.
It just takes someone who wants to use that desire to influence those people’s behaviour and let those people help them go where they need to go.