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Hosted by Tom Henschel

How to Talk So People Understand You
April 2025

254

A leader is losing credibility with her senior leaders. Her boss thinks she can turn it around by learning the sorting tool that transformed him as a communicator, so he brings in the coach who taught him.

April 2025

254

How to Talk So People Understand You

Tom Henschel

Senior Leadership Loses Faith in Her

Carolina was one of three leaders helping spin off a division into its own company. Every week, she and her colleagues reported to the senior leadership … and Carolina was driving them crazy.

I had coached her boss, Matt, the COO, when he was a rising junior executive at another company. He reached out to me now, saying, “I’m worried the team is losing faith in her. I’m not. She and I meet all the time. When we’re one-on-one, she’s not confusing at all. But when she gets in front of the team, it’s a mess. You know what she needs? That sorting tool you taught me all those years ago. I still use that. Can you teach it to her?”

“Sure,” I said, “but I’m curious about something. You said she’s okay one-on-one but not in front of the team. Could the issue be nerves?”

“Maybe, but even so, she’s got to start organizing her thoughts so people know what she’s talking about. I want everyone to think she’s as amazing as I do.”

“Does she know you’re talking to me about coaching her?” I asked.

“I told her, yes. I told her she should call you years ago, but she never did. Now, it’s not a choice. And she’s fine with that. She knows she’s not getting the results she wants.”

And so Carolina and I dove into the tool I call Sorting & Labeling.

Sorting & Labeling

At our first session, Carolina said, “Matt talks about this sorting tool like it’s some magic wand.”

I laughed. “In a way, it is. It uses a trigger that just seems to work every time. And it’s not that hard.”

Now, she laughed. “Oh, gosh, now you’ve got me hooked. So, what is it?”

I said, “It’s what happens when our brains hear a number. I’ll give you an example. This sorting and labeling tool has four steps. Four things for you to do. Okay, time out. Now, here’s what I believe. I believe that the instant I said the number ‘four,’ your brain started clicking into gear, making buckets or folders or slots or windows, to receive four items. I believe my saying a number triggers something in your head that makes it easier for you to learn the tool, than if I’d said, ‘there are several steps’ or ‘certain steps’ or ‘important steps.’ When I say a number, you’re more likely to listen to me.”

Asking to be sure, she said, “The magic isn’t in which number you say, it’s in using a number at all, right?”

“Right. Well, with exception. You probably don’t want to say, ‘We have seventeen items on the agenda.’ Pick a number your listeners can manage mentally. I rarely say a number higher than four.”

“Really?” she said. “But I’ve always got more than four things to say. Am I going to have to dumb everything down?”

“No, no, no, this tool doesn’t want you to change your content. It wants to give order to your content. It sorts your content, and labels your content, so people can follow along. It creates a mental map you can use to guide your listeners through as much detail as you want. Nothing needs to get dumbed down. But start with the bird’s eye view.”

“Like a table of contents,” she said.

Hierarchy of Folders

“Yes, a table of contents is a great way to think of it. I picture a hierarchy of folders, like on a desktop. At the highest level of hierarchy, I have to create one folder for my content. I ask myself, what folder at that top level is going to lead logically to the lowest level? What’ll get me down to those complex details?”

She looked off, thinking, then looked back, a little grief-stricken. “Oh, my goodness, I’ve been talking about stuff that’s probably two or three levels down! I’ve never really given them the bird’s eye view. Do you suppose that’s why people think I’m confusing?”

“Maybe. You think that’s it?”

She said, “Well, if my content makes sense to me but nobody else, I must not be doing a very good job of explaining my map. Okay. So, I’m supposed to use a number to sort my ideas. By the way, were you serious about there being four steps, or were you just making a point?”

“No, the tool really has four steps,” I said.

“Can you teach them to me?” she asked.

Step One: Create a Headline

“Sure. Using a number is actually the second step. Here’s what comes first: ‘Create a headline.’ Tell us the name of the folder at the top level of hierarchy. Tell us what you’re talking about. Six words or less. Not a sentence. Short. Something people can remember. A stand-alone headline.”

She asked, “You mean like for my presentation to leadership next week? I’m going to give that a headline?”

“Yes,” I said. “Because if you do, you can start by saying, ‘Today I’m going to talk about…blah.’ You name an idea, and everyone’s mind turns in that direction. People are ready to listen.”

She laughed. “That’s wonderful. I love that. Golly, why haven’t I always done that? Okay. So, let me figure this out. Next week, I have two things to report on: separating the accounting functions and supplier facilities in Asia. Can I do that? Have two topics as my headline?”

I made a so-so gesture. “I’d challenge you to see if you could put them both into one higher level folder, but yes, those two could be a headline.”

“Listen,” she said, “I think the top level folder for me is always going to be the spin-off. That’s why I’m in the room. Maybe that’s a given.”

I nodded. “Good point. Maybe it is. So, back to the tool. To help you learn this tool, between those two topics, accounting functions and supplier facilities, which would be easier to play with?

Steps Two & Three: Sort & Label

“Oh, I don’t know. Supplier facilities, I guess.”

“Okay, so for now, let’s imagine ‘supplier facilities’ becomes its own headline. You could say, ‘Today, I’m updating you on Asian supplier facilities.’ That headline would be accurate, right?”

“Right,” she said.

“Okay, headline’s done. Now, when you think about the topic, how many things are there that you want to tell senior leadership about next week?”

“Probably two,” she said.

“Do you know what they are?”

“One is, yes, we’ll have to move, the other is about a provision in the contract.”

I made a ‘time out’ sign with my hands. “And that, Carolina, was step one, two and three in Sorting and Labeling.”

I looked at her. She was waiting for more.

I went on. “Step one. Supplier facilities. That created the headline. Step two: ‘use a number.’ You said, under that headline, there were two topics. That’s step two, use a number. Then, step three: ‘label the numbers.’ And you did: facilities and contracts. One, two and three: headline, numbers and labels.”

She nodded, replaying it. Then she said, “What’s number four?”

Step Four: Transition with Clarity

I laughed. “That’s part of the magic of using numbers. Our brains don’t want gaps. We want to fill the buckets that’re in our heads. I said there were four things, and you want to hear all four. I love that. So, okay, here’s number four. Transition with clarity. At every stop on the map, tell me where we are. Tell me which level of hierarchy we’re at, and which folder we’re in.”

“Oh, I don’t do that,” she said.

“Most people don’t,” I replied.

“I think part of why I confuse people is because I jump around. My husband tells me I do that.”

“Sorting and Labeling can help with that. You can jump around as much as you want, as long as you use transition statements.”

“What would that sound like?” she asked.

“Oh, okay, here you go: ‘So, I want to talk for a minute about the supplier’s facilities. We’re tracking three factors. Before I tell you those three, I want to explain a provision we found in one of the contracts.’ Okay, time out. I jumped from three factors to a provision, but I think you could follow me, couldn’t you?”

“Yes,” she said.

“That’s step four. Transition with clarity.”

She took in a breath and shook her head. “Boy, I think I would jump around a lot less if I started doing that. It sounds hard to do.”

I shrugged. “When the tool’s new, it takes mental energy, like anything new, right?”

The four steps appealed to Carolina’s engineering mind. The easiest one for her was number two: use a number. She found herself using numbers even in casual conversations. She told me it clarified her thinking. Using the four steps also changed the impression she made on the senior leadership team: Sorting and Labeling gave her The Look & Sound of Leadership.

Core Concepts:

Sort and Label when you want people to understand you.

  1. Use a headline. Short. Memorable.
  2. Number how many topics are under the headline.
  3. Label each number.
  4. Transition with clarity.

Related Library Categories:

Free Essential Tool:

Sorting & Labeling
Sorting & Labeling

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