Like many people, I have lately been using ChatGPT more and more. Don’t worry, I am aware of the downsides and am not letting my brain rot.
But one thing it keeps highlighting to me is the quality (or, in some cases, lack thereof!) of my communication and how much the answer I get changes drastically with different ways of querying.
It got me curious about how I communicate with actual humans. For example, yesterday I asked it a question and got back a completely useless answer. At first, I thought it was a technical error. But when I looked back at my prompt, I realized the problem was in the way I had asked the question.
I knew what I was thinking. But because I didn’t clearly and specifically communicate the situation, context, and what exactly I wanted, I got a non-answer in return. Could this be happening with live conversations??
I was distracted and in a hurry and hungry and stressed (sound familiar?). Surprise! It acts the same way a human might when you think you are being clear. Just like with humans, there is often a gap between what we think we are communicating and what is actually being said and heard.
The Illusion of Clarity
I was working with a candidate recently who, when she went to resign, was surprised by how angry her boss was. He said he had no idea she was unhappy and wanted to know why she hadn’t given him a chance to make changes. In her head, she had clearly signaled her unhappiness on more than one occasion; she thought he should not have been surprised. In the end, they were both frustrated and blaming each other.
This is not an uncommon occurrence. We believe we’ve said something clearly. We assume we’ve been understood. Even if we have been clear, how stressed, or hungry, or tired, or whatever was the receiver of our communication? It’s no surprise the core message they hear is often very different from the one we intended to deliver.
This week, a CEO told me they made it “abundantly clear” to their SVP that their current pace and approach are not cutting it. But when I later spoke with that SVP, they described the same conversation as a general nudge to work more efficiently. The CEO intended to draw a line in the sand; the SVP heard a suggestion to pick up the pace.
Most of us — especially when delivering difficult feedback — tend to soften the message and don’t take the time to ensure it was received as intended. This leaves room for gross misinterpretation.
Meanwhile, time passes, expectations go unmet, and trust begins to erode. Eventually, what could have been addressed and corrected early becomes a regrettable loss or a terminated employee.
Here’s what I’ve learned about delivering critical messages:
#1. Be crystal clear.
As a leader, it’s easy to forget that the way you see a situation is shaped by information, context, and experience that others don’t necessarily have. What feels obvious to you may be entirely unclear to someone else. That’s why vague directions or half-explained expectations often lead to confusion or misunderstanding.
Just like my experience with ChatGPT, the quality of the response is directly tied to the quality of the input. Vague or overly general statements lead to results that don’t line up with what you are looking for.
In my work with clients, I’ve had literally thousands of conversations with leaders across every function. I can tell you that many of the toughest performance issues are not the result of a lack of capability, misaligned values, or poor intentions. Rather, it’s often due to unclear communication.
The more precise you are in how you frame a request or deliver feedback, the more likely others will truly understand and respond in the way you intend. Be brief, be direct, be specific.
#2. Do it in person (please!).
Both conversations I mentioned above happened over Zoom.When you’re trying to help someone understand your priorities or adjust their behavior, it is far better to do it face-to-face. This way, you emphasize the importance of the message, read nonverbal cues, and check for understanding and clarification. No one is distracted by something going on in the background or is having a bad case of “Zoom fatigue.”
I know sometimes it is not feasible, but think about the “cost” of the message not landing. If it is high enough, it may make sense to get on the plane.
#3. Have the hard conversation early.
When you sense something isn’t right, address it immediately. Too many leaders hesitate, thinking the issue will resolve itself or that it’s “not urgent yet.” But silence creates ambiguity.
This is especially important when someone is new to the company or stepping into a bigger role. These circumstances are filled with so many unknowns; people naturally fill in the gaps with their own assumptions.
That’s why clear, ongoing conversations matter. Create space for real check-ins. Ask questions like, “How are you interpreting…?” or “What does success look like to you right now?” Misunderstandings are easier to fix when they’re caught early — before they turn into larger performance issues.
A Real-Time Feedback Tool
The beauty of tools like ChatGPT is that they offer instant feedback on how clearly we’re communicating. It’s a luxury we don’t often get in real-life interactions.
Whether you’re managing a team or prompting AI, the outcome depends on your ability to be clear, direct, and intentional. If you find yourself frustrated when someone on your team “just isn’t getting it,” take a step back and ask whether you were as clear as you thought.
It’s not always easy, especially when the conversation is uncomfortable. But it’s far easier than cleaning up the mess that follows when clarity is missing.
ChatGPT is a mirror. Use it to pay attention to the quality of the response versus the quality of the question. It might be eye-opening.
