One of the most ironic conversations I have from time to time is with senior executives who want me to coach one of their direct reports, usually a VP or SVP, as part of succession planning. We get on the phone or Zoom and it goes something like this:
Them: “I'd like you to work with (Bob) on his communication skills.”
Me: “Sure. Can you be a little more specific?”
Them: “Well, he just doesn't communicate very well.”
Me: “Okay. In what way doesn't he communicate very well?”
Them: “I mean, he's just not a very good communicator.”
Me: “I see…”
At that point, I’m tempted to offer a two-for-one deal.
Why Communication Skills Are So Hard to Define
That interaction is funny—not because it's rare, but because it's so common. And it illustrates a major blind spot in leadership communication: It’s hard to improve what you can’t clearly define.
One of the greatest challenges in executive communication coaching is that people often lack the vocabulary or framework to articulate what the actual issue is. They know something feels off—but not what, or why.
It’s the same frustration leaders feel when presenting to a Board of Directors, only to be hit with questions that feel off-topic or out of left field. Those questions can feel like a personal attack, but in reality they typically signal a misunderstanding or a knowledge gap for the person who asked it. But they don't know how to identify what it is they're missing that's creating the problem for them, much less the ability to articulate it.
Identifying the Secret Ingredient
By analogy, my 23-year-old son was helping me make dinner one evening over the summer, and at one point he gave it a taste test.
“It’s pretty good,” he said, “but I feel like it needs something.”
I tasted it for myself. “Acid,” I said. “It’s missing acid,” and I squeezed some lemon into it.
He tasted it again and nodded. “Yes! That did it. But how did you KNOW to add that?”
At his age, I probably wouldn’t have known either. But by now I’ve been cooking longer than he’s been alive, am constantly experimenting and learning, and have built up an entirely different level of skill, intuition, understanding and expertise.
He knows WHEN something tastes good and when it doesn’t; I know WHY it does or doesn’t, and how to fix it.
It’s the same with communication.
How Being a Master Communicator is like being a Master Chef
It isn’t that surprising when you think about it: The senior executive is an expert in finance, or healthcare, or technology, not language-as-science. They simply know that, in their ears, a message is clear, compelling, and effective… or it’s not.
My job is to dissect what’s happening and figure out what’s creating the disconnect between what the speaker wants to convey and what the listener is hearing, then determine how to close that gap.
Maybe the speaker is:
- Speaking way too fast in run-on sentences and not stopping to take a breath
- Getting stuck in the tactical details without telling the story behind the big picture
- Completely missing the mark on intercultural nuances in an international engagement
- Misjudging how much technical expertise the audience has
- Projecting their nervousness through vocal tonality patterns and physical fidgeting
- Burning bridges by being too harsh for fear that anything else might seem weak
- Using vague, metaphorical phrases that make sense to him/herself but are otherwise meaningless “word soup” to everyone else
The possible causes are limitless, and chances are there are many all at work at the same time.
This is particularly frustrating for the person receiving the feedback; there’s nothing worse than being told that you have a problem to solve, but not what the problem is in the first place.
How to Be Your Own Executive Communication Coach
Let’s go back to our original scenario.
When I’m told, “Bob isn’t a good communicator,” I don’t just nod and dive in. (After all: Dive into what?) I start with multiple-choice-style questions to help define the real issue:
- Is it about how they show up in presentations?
- Do they struggle in executive meetings, or when interacting with clients, peers, or direct reports?
- Are they missing executive presence—the confidence and gravitas needed to lead?
- Do they get long-winded or fail to tell stories that make data come alive?
- Are they lacking diplomacy in high-stakes situations?
Once I offer enough of those kinds of options, the decision-maker usually finds the words to say, “Yes, that’s it!”
So if you’ve been told to work on your communication, but nothing more specific, start with some of these questions to help narrow it down and prioritize your efforts.
That’s when change becomes possible—when we can concretely define the problem and create a roadmap to real improvement.
Success (and Succession) Hinges on Communication
Whether you’re evaluating leaders as part of succession planning, navigating executive transitions, or simply trying to build high-performing teams, communication is the differentiator. These are just a few of the reasons why leaders want to engage in executive coaching.
And not just your communication; you have to help your people develop theirs too.
Here’s the challenge: Communication skills are typically labeled as “soft” skills— which sounds like a “nice to have” until someone doesn’t get promoted or another opportunity is lost because of them.
But by then–at least for the moment–it’s too late.
So don’t wait until you get vague feedback to start looking into honing your skills; use those questions to start getting more specific feedback now.
Call to Action: Ready to Define the Problem?
Whether you’ve got a “Bob” on your team, or you’re the one looking to level up your leadership communication, many leaders just need help defining the problem before they can solve it. And once they can name it, anything becomes possible.
That’s when you can truly lead with clarity, confidence, and impact.
Want help identifying what’s really holding someone back—whether it’s you or someone on your team? Feel free to reach out to me here. Let’s set up a quick call to define the problem, so we can start solving it, together.
