Hey :)
There’s a pillar in the work we do at The Question First Group called Vanguarding. The short version: get ahead of problems before they become problems. Shine a light down the dark path. Anticipate where the friction is going to come from before it shows up and bites you.
I’ve been thinking about how much it applies to everyday communication inside organisations — and how rarely people actually do it.
Here’s what triggered this.
I was working with my team recently and I had to explain something that, honestly, I shouldn’t have to explain. Before you send something out — a message, a memo, an update, anything — stop and ask yourself: what questions is this going to generate? Where’s the resistance going to come from? What’s still unclear?
Because if you send something and all it produces is questions, that’s a signal - the thinking wasn’t done before the sending.
As an owner, few things frustrate me more than an off-the-cuff, half-baked message landing in my inbox or popping up in Google Chat. Not because I don’t want to hear from people. But because what’s actually happening is someone has outsourced their thinking to me. They had a half-formed thought, and instead of sitting with it, working it through, they just…sent it. And now I’m carrying the cognitive load that they should have carried.
The irony is that the tools we use every day — Slack, Google Chat, all the instant messaging platforms — make this worse. They’re designed for speed. They reward immediacy. But speed and quality of thought are often in opposition, and I don’t think we talk about that enough.
I’d rather hear from someone less often and have it mean more every time.
Ask yourself a question before you send anything significant: if I imagine the person on the other end reading this right now, what are they going to ask me?
And because we have AI tools, you can actually test this. You can ask Claude to read your message as if it were the recipient and tell you what questions it raises, where the resistance might be, what’s still unclear. It’s a remarkably useful pre-mortem check.
But the tool isn’t really the point. The point is the habit of mind behind it — the willingness to slow down, project yourself into the next person’s experience, and do that extra 1% of thinking before you hand something off.
I got this framing partly from Liz Wiseman’s Impact Players — this idea of thinking beyond your immediate task to whoever picks it up next. Have you made it easy for them to continue? Have you actually completed the thought, or just completed your part of it?
Those are very different things.
Here’s what I think the gold standard looks like: someone sends me a message that ends the conversation rather than starts one. Not because they’ve suppressed something or left things out, but because they thought it through well enough that there’s nothing left to ask.
Even better? Sometimes the message never gets sent at all. Because when you actually sit down and think something through — really think it through — you realise you already know the answer. You didn’t need to involve someone else. You just needed to have the conversation with yourself first.
That’s not a failure of communication. That’s communication working perfectly.
I know this might sound like I’m just saying think before you speak, and I suppose I am. But I think there’s something deeper going on.
We’re living in a culture that’s slowly convincing us we don’t need to think anymore. AI can do it. Just send the message. Just ask the question. Move fast.
And I’m pushing back against that.
Not because I’m against AI — I use it constantly and I think it’s genuinely powerful. But there’s a difference between using AI to extend your thinking and using it to replace your thinking. One makes you sharper. The other makes you dependent.
The skill I want to see more of — in myself, in the people I work with — is the ability to sit with a problem long enough to actually understand it before doing anything about it. To write something out fully even if nobody ever reads it. To do the thinking in private so the communication in public is clear, complete, and worth someone’s time.
Quality over quantity. Always.
🗣️👀
Chris.
There’s a pillar in the work we do at The Question First Group called Vanguarding. The short version: get ahead of problems before they become problems. Shine a light down the dark path. Anticipate where the friction is going to come from before it shows up and bites you.
I’ve been thinking about how much it applies to everyday communication inside organisations — and how rarely people actually do it.
Here’s what triggered this.
I was working with my team recently and I had to explain something that, honestly, I shouldn’t have to explain. Before you send something out — a message, a memo, an update, anything — stop and ask yourself: what questions is this going to generate? Where’s the resistance going to come from? What’s still unclear?
Because if you send something and all it produces is questions, that’s a signal - the thinking wasn’t done before the sending.
As an owner, few things frustrate me more than an off-the-cuff, half-baked message landing in my inbox or popping up in Google Chat. Not because I don’t want to hear from people. But because what’s actually happening is someone has outsourced their thinking to me. They had a half-formed thought, and instead of sitting with it, working it through, they just…sent it. And now I’m carrying the cognitive load that they should have carried.
The irony is that the tools we use every day — Slack, Google Chat, all the instant messaging platforms — make this worse. They’re designed for speed. They reward immediacy. But speed and quality of thought are often in opposition, and I don’t think we talk about that enough.
I’d rather hear from someone less often and have it mean more every time.
Ask yourself a question before you send anything significant: if I imagine the person on the other end reading this right now, what are they going to ask me?
And because we have AI tools, you can actually test this. You can ask Claude to read your message as if it were the recipient and tell you what questions it raises, where the resistance might be, what’s still unclear. It’s a remarkably useful pre-mortem check.
But the tool isn’t really the point. The point is the habit of mind behind it — the willingness to slow down, project yourself into the next person’s experience, and do that extra 1% of thinking before you hand something off.
I got this framing partly from Liz Wiseman’s Impact Players — this idea of thinking beyond your immediate task to whoever picks it up next. Have you made it easy for them to continue? Have you actually completed the thought, or just completed your part of it?
Those are very different things.
Here’s what I think the gold standard looks like: someone sends me a message that ends the conversation rather than starts one. Not because they’ve suppressed something or left things out, but because they thought it through well enough that there’s nothing left to ask.
Even better? Sometimes the message never gets sent at all. Because when you actually sit down and think something through — really think it through — you realise you already know the answer. You didn’t need to involve someone else. You just needed to have the conversation with yourself first.
That’s not a failure of communication. That’s communication working perfectly.
I know this might sound like I’m just saying think before you speak, and I suppose I am. But I think there’s something deeper going on.
We’re living in a culture that’s slowly convincing us we don’t need to think anymore. AI can do it. Just send the message. Just ask the question. Move fast.
And I’m pushing back against that.
Not because I’m against AI — I use it constantly and I think it’s genuinely powerful. But there’s a difference between using AI to extend your thinking and using it to replace your thinking. One makes you sharper. The other makes you dependent.
The skill I want to see more of — in myself, in the people I work with — is the ability to sit with a problem long enough to actually understand it before doing anything about it. To write something out fully even if nobody ever reads it. To do the thinking in private so the communication in public is clear, complete, and worth someone’s time.
Quality over quantity. Always.
🗣️👀
Chris.