“We have six months before we fold.”
That’s what a startup CEO told me. They needed a new strategy. Not just any strategy. One that set a course for survival. They wanted to bring the team together to figure it out — and there was no time to waste.
Your approach to strategic planning can make or break your year. Or your company.
And the reality is, strategy offsites usually fail to live up to expectations.
Too much debate.
Not enough decisions.
Then there’s the guy who launches into a 12-minute monologue about “the real issue” that has nothing to do with the topic at hand.
Momentum dies.
Time disappears.
Everyone silently wonders when happy hour is.
But you don't want that to happen at YOUR strategy offsite. You want yours to be different. People are flying in. Calendars are cleared. You’ve got a few precious days to set direction, align the team, and unlock new growth.
You want this time to be:
- Hyper-productive
- Aligned to real business results
- and maybe even… enjoyable
Designing a great strategy to change the trajectory of your organization takes smart leadership. Setting the stage for those leaders to define a great strategy over the course of 3 days? That's a design problem.
So — how do you design a strategy off-site that actually works?
Here's how I approached it with the startup team.
Ready to design your strategy for 2026? Download the free Strategy Canvas to guide your next strategy meeting.
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Start With Clarity: Define Success Before You Walk In
I've never met a leader bringing a group together without a goal in mind. What separates a good strategy offsite from a great one is the depth of the goal setting process. You need to make tough choices about what you can and should accomplish.
When I meet with a leader about their strategy retreat, I don’t start with the agenda. I start with these questions:
- If this was the most successful offsite you’ve ever attended, what outcomes would exist at the end?
- If you could only get ONE of those outcomes, which would it be?
- How do you want people to feel as a result of this time together?
- What does a “finished strategy” look like for you? What are the components?
- How will the outputs be used going forward?
Then we pressure-test those answers with the team. And we keep chipping away at the responses until the goals feel concrete and meaningful.
Tip: Aim for one or two primary goals — not eight.
The more you cram into the agenda, the less meaningful the work becomes. Build your ideal plan… then cut it back.
Make Something Tangible
Most offsites fail because they are:
- Heavy on debate
- Dominated by a few loud voices
- Light on actual decisions
The antidote:
Build something together.
You want a tangible artifact that captures decisions, priorities, and next steps — in a format people can use.
It could be:
- A strategy presentation
- A vision statement
- A manifesto
- Company priorities or pillars
- A product prototype or website mockup
- Or something else
The shape of the artifact doesn’t really matter.
The act of building together does.
Here’s a simple example:
By the end of the offsite, we will create a strategy slide deck that includes:
- Our vision and ‘why’ for 2026
- Areas of focus and clear owners
- 2–3 team goals or OKRs
- A shared progress tracker
- A date we intend to share the new strategy
I've seen incredible results when asking leaders to design a fictional website landing page for their strategy. A landing page needs a compelling headline, concise supporting points, and a clear call-to-action — all of the elements a good strategy should include.
When teams know what “done” looks like, energy focuses and progress accelerates.
Keep the Conversation Focused on these 3 Things
If you take anything away from this guide, it should be this point:
Most of your time should be structured around activity — not in open discussion.
Open conversation without constraints leads to:
- Derailment
- Repetition
- Power dynamics
- Frustration
- Exclusion of introverts
Instead, design 90% of your agenda around these three modes of activity.
Be explicit about which mode you’re in — and for how long.
1. Ideation
What it is:
Generating ideas — individually first, then as a group.
Why it matters:
You brought smart people together. Use their brains.
How to run it:
Individual → Share → Decide
Output example:
“2–3 compelling strategic options for growth in Product Line X.”
2. Sharing
What it is:
Participants share written or verbal insight, context, or updates.
Why it matters:
Context helps people make better decisions.
How to run it:
- One person speaks at a time
- Time-boxed
- Everyone gets a turn
Examples:
“Each leader shares one big win + one challenge in 5 minutes”
3. Building
What it is:
Turning decisions into tangible outputs.
Why it matters:
Building feels like progress, tests assumptions, and clarifies thinking in a way discussion never can.
How to run it: Divide & conquer — small groups own components of the whole.
Output examples:
- One group refines the vision statement
- Another drafts the OKRs
What's Next?
This approach will go a long way to improving the productivity of your offsite. People will have more fun simply by virtue of making progress. Of course, there are other big questions and challenges you might be facing:
- "How should we design the business strategy?"
- "How do we do team building — that isn't lame?"
- "How do we know we're making the right decisions for our organization?"
If you'd like some tools to help answer these questions, I’m writing a series on strategy. Everything from planning to defining the direction of your organization.
Subscribe and you'll get:👇
- The Strategy Canvas I use
- The Strategy Series to design your best year yet
- Practical tools to design a better future — in your work and your life.
Back in the day, a mixtape served as a creative way to share your moods and passions with others. It captured the things you were excited about for a moment in time. This newsletter is an effort to share a mix of my passions and the things I'm excited about in work and creativity — things like design, workplace culture, leadership, art, and yes — music too. Life is more fun when we blur the lines. Thanks for reading.
🎵 Here's what I'm listening to this week:
The soundtrack to the new Timothée Chalamet movie Marty Supreme is great. One key moment features a song that might have you wondering "whoa, this is cool and intense, who is this?" It's none other than Johnny Rotten himself, post Sex Pistols era.
The Order of Death by Public Image Ltd.
— Adam Allred
