Prepare to be disappointed
Nov 13, 2025
Prepare to be disappointed.
How’s that for a strange way to close a leadership team offsite?
But it’s what I say all the time.
I mean, come on, we just spent two whole days conjuring up an exciting picture of what we’re focused on over the next 6-12 months, and how we’re going to work together to make it happen. We had some laughs, we got to know each other better. A pinot noir or two. Everyone’s tired - but that good kind of tired, when you've done good work.
And now everyone’s turning their mind to the things they need to do back at the ranch.
So I step in and say: “Prepare to be disappointed.”
Why? Because all this optimism and aspiration we’ve created here together… it’s about to be subjected to the brutal realities of “business as usual”. When we all slip back into our usual habits and start chasing the urgent. (Or is the urgent chasing you?) Which means it won’t be long until someone says or does something that will make your shoulders drop, and you’ll protest, “But that’s not what we talked about at the offsite!”
And that’s the moment. The moment of choice. Because it’s what you do with that disappointment that makes or breaks a team. To grow or to flatline.
Notice the disappointment and, instead of thinking, “I knew it! They were all talk at the offsite!”
Instead of that, choose to ask. To coach. To hold a kind of tension between the current situation and the aspired-for state.
“When we were together at the offsite, we spoke about XYZ. How do we achieve that in this situation?”
Or maybe, “This feels like a moment of truth for the kind of thing we were talking about at the offsite. How do we want to approach it in light of that conversation?”
Or perhaps just, “This feels like the usual way of handling the situation, but in light of the conversation we had last week, why don’t we try…”
All of these are the moments in which the goals, the aspirations and the pure belief that was dreamed up in the oasis of an offsite get forged into reality, or washed away by the raging river of BAU.
But that’s not an inevitability. That’s a choice.
Until next time,
Simon
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