I read a lot of leadership books in my early years running AppMakers USA. Good ones, too – the kind that get recommended in every founder circle. I absorbed the frameworks, took notes on the concepts, and went back to work feeling prepared. Then real situations happened, and I realized pretty fast that being prepared to talk about leadership and being prepared to actually do it are two very different things.
Nobody tells you that.
The books give you models and principles, which are genuinely useful. But the skills that determine whether a business grows or stalls out – those tend to show up as problems you have to solve before you figure out you needed to know how.
The Gap Between Knowing and Doing
There is a statistic that stuck with me when I came across it: only 14% of CEOs have the leadership talent they need to actually grow their businesses, according to DDI’s research. I used to read that and think it was about other people. Now I think it was probably describing me for a good chunk of my early years running this company.
The thing I underestimated most was how differently leadership feels when the stakes are real. Reading about giving difficult feedback and then sitting across from someone who has been with your company since the beginning, knowing this conversation might be the one that ends that, are not the same experience. The emotional weight of it does not show up in a chapter.
What I found was that the skills I needed most were not strategic or conceptual. They were relational and situational – the ability to stay clear-headed in uncomfortable moments, to say the thing that needed to be said without either softening it into meaninglessness or making it harsher than it needed to be.
That kind of skill only gets built by doing it badly a few times first.
Making Calls With Half the Information You Want
One of the things that catches founders off guard early is how often you have to make significant decisions with incomplete information. You want more data. You want more time. You want someone to confirm that the choice you are leaning toward is the right one. Most of the time, none of that arrives.
I spent a lot of energy in the early years of building AppMakers USA either delaying decisions because I did not feel ready or making them too quickly because sitting with uncertainty was uncomfortable. Neither worked well. What I eventually had to build was a tolerance for deciding when I had enough to go on, not when I had everything I could possibly gather.
A good example of where this shows up constantly is managing client expectations mid-build.
Halfway through a development project, a client might ask whether we can add a feature that was not in the original scope. The honest answer is almost never a clean yes or no. It depends on where the build is, what the feature would touch, and what the timeline looks like – none of which I always have a complete picture of at the moment the client is asking.
Early on, I would hedge. I would say I needed to check with the team and get back to them, then delay that follow-up longer than I should have. What I learned is that clients do not need certainty from you. They need directness.
Saying “based on where we are right now, adding that feature will push your timeline by two to three weeks – here is why” is more useful to them than a careful non-answer, even if the two-to-three-week estimate turns out to need adjusting later. The willingness to give a clear, reasoned answer with the information you have – and update it when you get more – is what actually builds trust in a client relationship.
Waiting for perfect information before saying anything just makes people nervous.
That is a skill. And it is not one that gets discussed enough in leadership content, which tends to focus on the quality of thinking rather than the quality of deciding under pressure. The deciding-under-pressure part is where a lot of leaders, including me early on, run into real trouble.
The Conversations I Kept Putting Off
This one cost me more than anything else. I am talking about the pattern of knowing a conversation needed to happen and finding reasons to delay it – usually some version of “I’ll give it one more month” or “things might improve on their own.”
They rarely did. And by the time I had the conversation I should have had weeks earlier, the problem was usually larger and the other person was usually less surprised than I expected them to be. People almost always know when something is not working. The delay does not protect them. It just extends the uncertainty for everyone.
Trust in managers dropped from 46% in 2022 to 29% in 2024, according to research from Exec Learn. I think delayed hard conversations are a significant reason for that number. When people sense that leadership is avoiding something they already know is there, it erodes confidence – not just in the individual manager, but in the organization’s ability to deal with real problems honestly.
Learning to have the conversation earlier, more directly, and without the buildup of weeks of avoidance was one of the most practically useful things I worked on as a leader. It still is.
What Actually Helped
Formal leadership programs were not the thing that moved the needle for me, at least not significantly. Only 18% of organizations report that their leaders are “very effective” at achieving business goals, according to High5Test’s 2025 research – which suggests most conventional development approaches are not delivering what they promise either.
What actually helped was a few specific habits. Getting feedback from people who would give me an honest answer, not just a comfortable one. Reviewing decisions I had made – not to second-guess them, but to understand what I was working from when I made them, and whether my instincts were getting sharper or just more confident. And paying attention to where I was consistently avoiding something, because avoidance is usually a signal that a skill needs work, not that the situation should be ignored.
None of that is complicated. But it requires a level of honesty with yourself that is actually harder than most leadership frameworks suggest.
What I Would Tell Someone Starting Out
If you are building a company and trying to develop as a leader at the same time, the most useful thing I can offer is this: the skills that will matter most probably are not the ones you are currently focused on.
The strategic thinking, the vision-setting, the culture-building – those matter. But the ability to have a hard conversation clearly and early, to make a call when you do not have everything you want, and to learn quickly from the moments when you got it wrong – those are what actually determine how far the business goes and how functional it stays while getting there.
The books are a starting point. The work is everything after.
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