Every Monday at 11am, I get on a call with Doug.

I'm usually holding coffee. Sketchbook open. Pen in hand. Often Megan joins us, occasionally its just me.

We talk about the business, about clients, about whatever's been rattling around in my head that week. And while we talk, I draw.

The same thing I do for clients, Doug does for me. He listens. He asks questions. He catches the thing I said in passing that I didn't realize mattered.

I sketch what's coming out of these talks.

I’ve spent years helping other people see their thinking. Standing in conference rooms, drawing while teams talk, reflecting back so they can see the shape of it.

What seems strange is that doing that for myself is sometimes difficult, or at least challenging. I’m too inside it. Everything feels either obvious or like a tangled mess. I can have a hard time telling which threads are worth pulling and which ones don’t really amount to much.

So now I have someone to hold that space for me… Doug. It works because he ISN’T Megan, who as my partner is often too “in it” to mine that good content as well. So we all chat and I sketch while we figure it out together.

Most weeks, I don’t know what I want to talk about when the call starts.

That used to bother me. I felt like I should come prepared. Have an agenda. Know what I needed to work through.

But the not-knowing is actually the point.

I’ll start talking about something that happened with a client. Or something I noticed at a conference. Or a frustration I can’t quite name. And Doug just lets me go. He doesn’t try to fix it or rush me toward a conclusion. He just pays attention.

Sometimes he’ll ask a question, and I’ll realize I’ve been circling around something for twenty minutes without actually saying it. The question cracks it open.

Sometimes he’ll say, “Wait, go back to that XYZ thing you said before.” And we’ll circle back, or circle back again. Sometimes even looking down at my sketchbook and realizing I’ve already drawn it. Then we delve into whatever that topic is further as he helps me develop a narrative around it which turns into a newsletter. Doug’s a creative guy himself, and the combination is really enjoyable.

To pull back the curtain a bit: most of these newsletters started as Monday morning rambling.

The one about being annoying at parties?

That came from me venting about a dinner where I couldn’t stop noticing group dynamics. People talking past each other. Someone getting interrupted and nobody catching it. I wasn’t trying to write anything. I was just processing out loud.

Doug said, “There’s something there.”

The one about “perfect” clients?

That started as me talking about a project that didn’t feel right. We talked through what made working with places like PNNL and ASHA feel so different. What made those projects energizing instead of draining. By the end of the call, I had a sketch and a rough idea.

A few days later, it was a newsletter and intentionality about the groups I wanted to work with the most.

That’s how it happens. I talk. We explore. I draw. Something emerges.

I used to think I should be able to figure everything out alone.

(Or at least between Megan and me). I’m the one with the sketchbook. I’m all about listening and synthesizing. I make a living helping people see what might not have been so obvious before.

Why would I need someone else to do that for me?

But here’s why I do need that.

Being good at facilitation doesn’t mean you can facilitate yourself. The tool only works when someone else is holding it. Or when someone else is holding the space while you hold the pen. I’m not thinking out loud and sketchnoting or graphically recording myself.

The good news is the client work has gotten sharper because of these Monday morning calls. So have the decisions Megan and I make about where RedTale is headed.

Who we want to work with.

What we want to say yes (or no) to.

How we talk about what we actually do.

All of it gets clearer when I’m not trying to think through it alone.

Do you already have someone like this in your life?

A friend who asks good questions. A colleague who notices things. A coach. Someone who lets you think out loud and doesn’t rush you toward answers.

If you do, you probably know how valuable that is.

If you don’t, it might be worth finding.

Grateful you are here,

Wade

PS - If you want any other info on how Doug and I work together, shoot me a reply. Happy to connect!