What Exceptional Leaders Ask That Others Don't
Most executives are fluent in their problems. Fewer are fluent in their challenges. The difference matters more than you'd think.
There’s a question I open our Elite Executive calls with: ‘What is the biggest challenge you’re solving for right now?’
It sounds straightforward, but in practice, it almost never is.
What I’ve noticed, consistently, is that the first answer most people give is actually the answer to a different question: ‘What’s the biggest problem you’re solving for right now?’
They describe a situation: a difficult board dynamic, a hiring gap that won’t close, a revenue target that’s drifting. All legitimate, real, and all focused entirely on what’s happening outside of them, which is exactly the distinction that matters.
A problem lives outside of you; a challenge lives in the relationship between who you are and what the situation is asking of you, and that’s not the same thing.
What the problem framing costs you
When you focus on what “problem” you’re solving for, your mind starts to engage in tactical, responsive problem-solving. The goal is operational resolution, which, while valuable and often effective, leaves something important invisible.
A problem ends when it’s resolved, but a challenge reveals something about how you operate, and that something doesn’t disappear when the immediate situation does. It travels with you into the next role, the next company, the next relationship, the next version of the life you’re building. The women I work with are not just thinking about career trajectories or organizational outcomes; they’re thinking about the full architecture of their lives, because they’ve already learned, often at significant cost, that success without alignment tends to hollow itself out. They came to the top expecting a return on that investment across every dimension, and they’re right to expect it.
If you’re only solving for the problem, you’re solving for this instance. If you’re solving for the challenge, you’re building capacity that compounds across all of it. When you understand the difference between those two questions, you can start thinking not just one level deeper but three or four levels deeper about who you are and how you operate. You begin to see not just what’s standing in your way within a single situation, but the patterns that travel across the span of your career and your life.
When the question shifts everything
One of my Elite Executive clients came in with a life that looked, by any external measure, exceptional: a successful career, real freedom, a life most people would envy. And underneath all of it, she could name exactly what was wrong. She was bored, she was overworked, and she was aware that she struggled to say no, which meant her calendar and her energy were consistently organized around other people’s priorities rather than her own. She also knew there was more available to her, more excitement, more depth, more of the kind of challenge that actually lights something up rather than simply demanding more of her.
If you asked her what problem she was solving for, she’d give you a thoughtful, articulate answer about time, about her standards of execution, about the demands of her clients and her own perfectionism. All accurate, all worth examining, and none of it the actual thing.
Ask her what the biggest challenge she’s solving for is, and the conversation shifts entirely. Not toward dysfunction or crisis, but toward the deeper questions that govern everything else: what she believes makes her valuable, what she thinks other people actually see when they look at her, what she’s been equating with worth, what she would say if someone asked her plainly and without agenda what brings her joy. I’ve sat across from enough extraordinary women to know that last question is harder than it sounds. Many of them, after years of being extraordinarily goal-directed and focused, find themselves genuinely uncertain how to answer it. These are not soft questions; they are the structural ones, the ones that determine whether the next decade looks like the last one or like something genuinely different.
The quality of insight available at that level of inquiry is categorically different, and so is the quality of what becomes possible once the question is fully answered.
The decision beyond the challenge
I built Elite Executive exactly for this purpose. Not to develop competencies or address performance gaps, but to create a space where women operating at the highest levels could finally think at the depth their lives actually require, and do it in the company of peers who understand the terrain because they’re navigating it themselves.
We’re in our second year now, and what I observe is this: the leaders who can answer the challenge question, really answer it, are the ones with the most interesting, most durable, and most genuinely fulfilling lives and careers, in the way that actually counts when you’re truly ambitious and refuse to settle for meh.
If you’ve been orienting around the problems in front of you and something in this is making you wonder what the challenge underneath them might be, that’s worth paying attention to.
Elite Executive is enrolling now for Q2.
Elite Executive is designed for leaders who are already exceptional and are ready to operate at the level that reflects it fully, sustainably, and across their work and their lives
If that’s where you are, I’d like to hear from you: click here to find out if it’s the right fit.