Just tell me when you’ll be here.

The other day, I was waiting for a traveling nurse to come by my house to do a blood draw. We’d scheduled an appointment for 10:30 a.m., but she texted me the day before saying she might be a bit late. No big deal.

The next morning, I got up and went to the gym, keeping an eye on my phone. I was eager to know what time she’d arrive because I was planning my day around her.

Then suddenly, I got six messages from her.

"Stuck in traffic for the last 30 minutes." Then a screenshot of her GPS showing two cross streets I didn't recognize. Then a third text saying "traffic is really jammed up."

The meaningless messages kept rolling in. And I was left scrolling through the noise, hunting for the only piece of information I cared about: The time she’d arrive.

I finally texted back, "What's your ETA?"

Crickets.

I walked home from the gym to get ready for the appointment. We always put our little dogs away when strangers visit, and I planned to move my car so the nurse could park in our driveway. And we had several other things going on that morning, so we were planning our day around the nurse’s arrival.

I texted again. No response.

Then she arrived thirty minutes early without warning. Ding dong. The dogs went crazy, and Jenn wrangled them while I sprinted outside to make room for her in our driveway. The whole thing was a mess.

All those messages, and she never gave me the one piece of information that would have made everything easy: The time she’d arrive.

To be clear, this was a small thing in a low-stakes situation. I’d call it mildly irritating more than anything else. But it reminded me of other situations that I’ve seen play out at much higher stakes.

The worst board meeting

The last seven years of my startup career were spent reporting directly to the CEO and running sales departments. And every quarter, we had incredibly important board meetings with our investors and the whole executive team, where hundreds of millions of dollars were at stake.

I remember one of those meetings where a senior executive came in to pitch the board on restructuring a part of our data collection program. He had a polished, well-designed, story-driven, and (unfortunately) completely theoretical deck. Here’s what could happen. What might improve. What the potential upside looked like if things went well. How he thinks about it.

He didn't bring any numbers or a timeline. No cost or headcount impact. No estimate of hours spent. He didn’t include any information that the board actually cared about. And I saw the bloodbath coming from a mile away.

Our most senior board member cut him off mid-presentation.

"I didn't come here to get a PowerPoint presentation about how data collection works here! I don't give a shit! I care about how fast, how much, current impact, future impact, and what this means for the money I'm spending. Come back when you have the right information ready, or don't come back at all."

The room went dead silent, and I kept my eyes on the floor.

After what felt like a lifetime, my peer in Marketing, Jared, caught my glance from across the table. We'd seen this before, and it was exactly why we never walked into that room without making sure this would never happen to us. We spent weeks preparing for every possible question we could imagine the board members might ask.

How Jared and I showed up

Jared and I didn't prepare presentations for the board. We prepared a communication plan that delivered clear answers.

His department’s job was to drive the leads, and my department’s job was to close them. If the board spotted a gap between what Jared said about the marketing pipeline and what I said about the sales revenue, then we were both screwed. So that’s where we started.

We made sure our numbers and stories connected, and that when the board followed a thread from marketing into sales, it held together without contradiction. Then we wove a single, cohesive narrative through every department so that nothing we said in our portion of the meeting would conflict with anything that other execs included in theirs.

After that, we’d jot down questions we thought the board might ask and get on the same page about exactly how we'd answer them in lock-step. And lastly, we identified the biggest risks in our plan and built a risk adjustment plan for every one of them. If risk 1 came true, here's plan B. If all five risks hit at once, here's plan C. And so on.

By the time we sat down at the board meetings, we were a pair of synchronized swimmers. The board could ask us anything (and believe me, they did). And we always had clear, specific, data-backed answers. So they always left feeling comfortable. Not because the news was always good. There were quarters it wasn’t. But the board always knew exactly where things stood.

What stories like this have in common

The nurse and the data exec made the same mistake. They communicated from their perspective instead of considering their audience’s perspectives. But neither bothered with the only question that actually mattered:

What specific information does this person need from me right now?

I needed an ETA. That was it! And the board needed numbers and a plan. And in both cases, the answer existed. But the information wasn’t shared.

This is where most people lose their audience, whether it's a high-stakes boardroom or something as simple as a text message. People share their thinking, or behind-the-scenes context, instead of the conclusion that the audience actually cares about. And the person on the other end is left trying to extract that one thing they actually need from a pile of stuff they don't.

The nurse sent me six or seven messages that morning, so she probably thought she was keeping me informed, or over-communicating even. And in a way, she was. I knew she was in traffic and that she was near some intersection in the state of California.

That's what most poor communication looks like. Lots of effort and information, yet the recipient is still wondering:

“OK, but what about the thing I need to know?”

The executive with his theoretical deck felt the same way to the board. Thorough, polished, and completely useless to the people sitting across the table. Meanwhile, Jared and I walked in knowing that every sentence we said was built around what the board needed to hear, and not what we wanted to talk about.

Retraining the brain

I think about this stuff whenever I write a newsletter, send an email, or explain something to someone. Am I communicating what's in my head? Or what they need? Because those are rarely the same thing. And the gap between those things is where you lose people.

I don’t always get this right. It’s one of the toughest things to do when communicating. Because it’s natural to express yourself. But it’s challenging to consider what your audience needs first and to then express yourself accordingly.

So here’s a question I have for you this week:

Go look at your landing page, your last newsletter, the last pitch you sent someone, or even a text message to a friend or family member. And ask yourself: Is this built around what I want to say, or what they need to hear? Who is the focus of this message? And if I reconsider this message, with my audience's needs in mind, how could I say (or write) this differently?

Reply and tell me what opportunities you find. While I can't respond to everyone, Jennifer and I read every email, and we love to hear from you.

That's all for this week.

See you next Saturday.