You’ve probably heard the idea: “Ask who can do this instead of how can I do this.”
This concept was life-changing for me as it has been for others. As an entrepreneur, founder, or leader, it’s the right frame when you find yourself micromanaging, feeling stuck, or striving to scale. It’s a powerful shift when you stop trying to figure everything out yourself and instead, find the right people so you can move faster.
But I’ve also seen this idea misapplied in a way that quietly undermines execution.
Because in certain cases … “How > Who.”
The Problem with Always Skipping “How”
Entrepreneurs especially love leverage. So, they jump quickly to “who,” because it frees them to do what they do best. They hire someone to run the system, organize the work, or build the process.
But if they haven’t taken the time to understand the basics themselves, they don’t understand what good looks like, what questions to ask, or what’s not working. When results fall short, they assume they don’t have the right person, but that’s not always the problem. The problem is that they outsourced clarity.
I would venture to say that “Who not How” works best when you’ve already done the “How” over and over, and you’re wasting precious time on something someone else could do better and faster, or you understand the “How” but you aren’t necessarily quick or good at it.
Let me offer two possibilities, where skipping some of the “how” creates unnecessary damage and execution risk.
1. Building Leadership Identity
You don’t become a leader by delegating everything you don’t know how to do, and you certainly can’t delegate character building or learning how to become a better decision maker. In fact, you become an effective leader by developing the judgment to know what matters, what good looks like, and where execution breaks down.
That requires understanding and at least a little bit of “how to.”
If you skip “how” too early, you don’t build leadership identity—you build dependence.
2. Having Difficult Conversations
This is where the lack of knowing how causes multiple problems, most of them invisible before they become visible. (This is exactly why I developed The Performance Coaching Model: To teach leaders a framework for having these hard conversations.)
When leaders avoid learning how to have difficult conversations about behavior and performance, they go straight to the “who.” That who is generally Human Resources. I can’t tell you how many times I’ve seen an HR person write up the PIP or do the “dirty work” that the manager wouldn’t do or didn’t know how to do. This is an example of abdicating responsibility and outsourcing real accountability.
Why should the employee be disciplined when his own manager didn’t have the capacity to have a conversation? Execution broke down at the conversation that should have happened, but instead got delegated to HR. And over time, HR becomes responsible for work that belongs to the manager, the director, and the senior executive.
The Real Equation
What’s the real distinction between who versus how?
“How” creates discernment.
“Who” creates scale.
Without discernment, scale just multiplies problems.
The Leadership Shift
The real issue isn’t whether you choose “how” or “who.” It’s whether you have the discernment to know the difference.
Discernment comes from understanding:
- What good looks like
- What’s required
- Where things break down
And that doesn’t come from delegation. It comes from development. You can outsource and delegate almost anything. But you can’t outsource your own development.
The Bottom Line
“Who not How” creates leverage. You can outsource someone to pay your bills, clean your office, and manage your calendar. But you can’t outsource your inner game—your clarity, your judgment, your discernment.
There are some things you have to learn “how to” do. Not to master them. But to recognize what good looks like. Because if you don’t understand the basics, you won’t build something better. You’ll accept something that reflects your confusion—not your goals.
And if you avoid learning how to lead conversations, you don’t build accountability. You outsource it.
Execution doesn’t break at accountability. It breaks at clarity—and at conversation.
