Before I get to this week's theme, I want to pause.
This week we lost Om Malik — journalist, photographer, founder of GigaOm, and a person whose curiosity was as deep as anyone I've ever sat across from. When you were with Om, you had his undivided attention. He didn't listen for the headline. He listened for the paragraph no one reads out loud.
Om was a mensch. In every sense of the word.
He wanted us to slow down. Think deeper. Retain our humanity. Care for each other. That's not a bad compass for any conversation worth having.
I learned of Om's passing through our mutual friends Andy Abramson and Alec Saunders, who are carrying this loss personally. I'm thinking of them both this week, and the countless others who's lives he deeply touched to name only a few Jeff Pulver Thomas McCarthy-Howe Rich Tehrani Ken Camp Craig Walker Mathew Ingram
May his memory be a blessing.
I mention Om because this week's newsletter is about the first bearing on the compass — and it happens to be the one Om lived every day without ever needing a name for it.
Clarity.
Not the word. The practice.
Most people walk into important conversations knowing what they want to say. Very few walk in knowing what they actually want. Or understand what the others might need.
Those sound like the same thing. They're not.
What you want to say is a script. It's the opening you've rehearsed, the points you've organized, the argument you've sharpened.
What you actually want is the need underneath all of that. The thing that matters when the script stops working — which it always does.
I watched it happen in a negotiation that should have been straightforward.
Both sides wanted a deal. The terms were close. The relationship was solid. And yet the conversation kept circling — three meetings deep with no forward movement.
On the surface, it looked like a pricing disagreement. One side wanted a lower number. The other side couldn't go lower. Classic impasse.
But the pricing wasn't the problem.
The person pushing for a lower price didn't actually need a lower price. What he needed was to walk back to his board and show that he'd fought for something. He needed a win he could point to — not a discount. A story.
The moment that became clear — the moment someone asked "what does this need to look like when you take it back to your team?" — everything shifted. Not the number. The conversation. The energy. The pace.
Within an hour, they had a deal. The price barely moved. What moved was the understanding.
That's what clarity does. Not clarity about what to say. Clarity about what you actually need — and what the person across from you actually needs.
Here's what I've learned about clarity after decades of these conversations:
It doesn't come from preparation alone. You can prepare exhaustively and still walk in aimed at the wrong target — because you prepared for the conversation you expected, not the one you got.
Clarity comes from a question most people never think to ask themselves before they walk in:
What do I actually need from this?
Not what do I want to say. Not what's my opening position. Not what's my walk-away number.
What do I need?
And then the harder question: Am I sure?
Because most of the time, what we think we need is a position. A price. A concession. A specific outcome we've already decided on.
And most of the time, there's something underneath that — something more honest, more flexible, and more useful — that we never examined. Because we were too busy preparing what to say.
In the book, there's a line that I keep coming back to:
What if clarity doesn't come from control — but from curiosity?
I wrote that as a question because it still surprises me every time I see it proven true. The clearest people in a room aren't the ones who've memorized their talking points. They're the ones who walk in curious about what they'll find — because they've already done the harder work of knowing what they need.
A question to sit with
Think about the next conversation you're walking into that matters.
Do you know what you actually want from it? Not what you're going to say. What you need.
If those are different things — and they usually are — that's where the work is.
If this landed, forward it to someone heading into a conversation this week. Sometimes the most useful thing you can share isn't advice. It's a question.
And if you have a story about a conversation where clarity — or the lack of it — changed everything, I'd love to hear it. Reply to this email. I read every one.
— Howard