Your strategy offsite could have been an email

Diane
July 27, 2026

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Last week was about the people side of an offsite. This week is about the strategy, and why most so-called strategy off-sites contain very little of it.

You know the format. Each leader takes a turn presenting their department. "Here is what my team does, here are our goals for the year." Everyone asks a couple of polite questions. We move on to the next presenter. By mid-afternoon, people are checking their phones under the table or just openly typing away on their laptops. Afterward, quietly, leaders are commenting to those they trust:

That was a waste of my time. Who cares what others are presenting? i didn't. It had nothing to do with my work. 8 hours I could have used elsewhere.

They are not being rude. They are reading the room correctly. There was no shared stake in that day, so there was nothing to care about. It was a series of monologues. And all of it could have been sent around in a document.

Presenting is not strategy

Here is why this happens. Presenting is safe. It fills the day, it looks productive, and it asks nothing hard of anyone. You control your slides, you answer a few questions, you sit down.

Real strategy is uncomfortable, so teams avoid it and reach for show-and-tell instead.

Because strategy is not each department reporting what it is already doing. It is the whole group stepping back and asking a harder question together. Not "what are we doing," but

"Where are we trying to become and What has to be true for us to get there."

That is a group conversation. It cannot be pre-written on a slide, because nobody has the answer yet. That is the point. If your offsite could have been an email, it was not strategy.

Start with who you serve

Start with the questions most teams cannot honestly answer.

  • Who is our customer?
  • What is the hardest thing they are dealing with right now?
  • What do they actually value from us, not what we assume they value?
  • And what would we have to become to give them that?

Every team has a customer, even the ones who think they do not. And most have never defined theirs with any honesty. So they keep doing the work in front of them, and slowly become an order-taker, the team people call to execute something, not to help them think. The demotion is quiet. Nobody announces it. One day you just notice you are in the room to take notes, not to shape the decision.

Picture the failure, not just the win

The move that makes any of this real is a simple one, and it is the one teams skip.

Do not just picture success. Picture failure. Say out loud what happens if you do not become what your customer needs. Name who it affects. A vision is easy to nod at and quietly ignore. A failure you have looked at directly is much harder to walk away from.

That is when an offsite stops being a show-and-tell and starts being strategy. When the room stops presenting and starts reckoning with where it is actually headed.

One question

So before your next offsite, ask one thing. If we sent each other the material in advance, what would be left to actually discuss in the room?

If the honest answer is "not much", you are planning a show-and-tell. The strategy is the part that could never have been an email.

And here is the harder truth. These conversations are difficult for a team to have on its own, not because the people are not capable, but because they are all inside the same system. They share the same blind spots, and the same things no one wants to say out loud. Someone has to ask the question the room is avoiding, and hold up a mirror to where the team is actually heading.

That is the work I love most: helping a team have the conversation it cannot quite have alone. If this has sparked some curiosity, I would love to continue at diane@ptminsights.com.

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