A leadership offsite is two days of expensive time, so the agenda should be built backwards from the decisions you need at the end. The work that makes it productive happens in the three weeks before: interviews, a short survey and a pack of numbers everyone has read. This guide gives you that pre-work, a timed two-day agenda, a one-day alternative and the follow-up that keeps the decisions alive.
Decide what the offsite must decide
Write down, before you book a room, the three to five decisions the session must produce. If you cannot name them, you are planning a discussion, not an offsite.
Typical decisions for a strategic planning offsite are: the year-three destination in numbers, the three to five priorities, who owns each one, the stop list, and the first 90 days. Put these at the top of the agenda and read them aloud at the start of day one. Every block in the agenda should contribute to at least one of them.
Pre-work: survey, interviews and the numbers pack
Pre-work moves the information-sharing out of the room so the room can be used for deciding. Plan for three weeks.
- Short survey (week 1). Six to eight questions, sent to every attendee, answered privately. Useful questions include: what should we stop doing, what is our biggest risk over three years, where do we lose money, and what would you change if you owned the company.
- Interviews (weeks 1–2). Forty-five minutes with each attendee, one to one, by video or in person. Interviews surface what people will not say in a group.
- Numbers pack (week 2). Revenue and gross margin by line for three years, overhead trend, cash position and the current scorecard, in no more than eight pages.
- Themes memo (week 3). A two-page summary of survey and interview themes, anonymised, sent with the pack five working days before the session.
Ask everyone to read the pack before arriving and to come with one question about it. Then do not present it again in the room.
A two-day agenda with timings
The two-day format gives the team time to disagree on day one and decide on day two. The timings below assume a 9:00 start and include breaks.
| Time | Day 1 | Day 2 |
|---|---|---|
| 9:00 | Purpose, decisions needed, ground rules | Recap of day 1 and open questions |
| 9:30 | Themes memo: what we heard, what surprised us | Choose three to five priorities |
| 10:45 | Break | Break |
| 11:00 | Where we make and lose money | Owners and year-one milestones for each priority |
| 12:30 | Lunch | Lunch |
| 13:30 | Year-three destination: options and numbers | The stop list |
| 15:00 | Break | Break |
| 15:15 | Strategic choices: where we compete, how we win | Risks and two scenarios to test |
| 16:30 | Parking lot review, evening reflection question | First 90 days, decision log read-back |
| 17:00 | Close | Close |
The evening question on day one matters more than it looks. Something like "if we could fund only two of today's ideas, which two?" gives people a night to think, and day two starts sharper.
A one-day version
A one-day session works when the destination is broadly agreed and the team mainly needs priorities and owners. Cut the exploration, not the decisions.
- 8:30 Purpose, decisions needed, ground rules.
- 9:00 Themes and numbers: discussion only, no presentation.
- 10:30 Year-three destination confirmed.
- 11:30 Three to five priorities chosen.
- 12:30 Lunch.
- 13:15 Owners and year-one milestones.
- 14:45 Stop list.
- 15:45 First 90 days and decision log read-back.
- 16:30 Close.
If the destination itself is in dispute, do not try to settle it in a single day. Book two days or split the work across two sessions a week apart.
Facilitation rules that keep the room honest
Ground rules sound bureaucratic, but they protect the quieter people in the room and keep the owner from accidentally closing every debate. Agree them in the first fifteen minutes.
- Phones away except at breaks.
- The owner speaks last on contested choices.
- Disagreement is about the idea, never the person.
- Anything off topic goes to a visible parking lot, reviewed at day's end.
- A decision is recorded only when the owner of that priority repeats it aloud.
- What is said in the room stays in the room; what is decided goes in the log.
A good facilitator also watches the clock firmly. A block that runs twenty minutes over usually steals time from the stop list, which is the session people least want to have.
The decision log
The decision log is the single most valuable output of the offsite. It is a running list, kept on screen or a flip chart, of every decision with its owner and date.
Each entry has five fields: the decision in one sentence, why it was made, who owns it, the first milestone and its date, and anything that was explicitly rejected. Recording what was rejected matters; it stops the same idea from returning in three months as if it were new. Read the full log back at the end of day two and correct it while everyone is present.
Handling the hard conversations
Every useful offsite has at least one uncomfortable moment, usually around the stop list, a struggling division or the owner's own role. Plan for it rather than hoping it does not come up.
Three techniques help:
- Silent writing first. Before discussing a contested choice, give everyone three minutes to write their own view on a card. This prevents the first confident speaker from setting the answer.
- Separate options from decisions. Spend one block listing and testing options without choosing, then a later block choosing. Mixing the two makes people defend positions too early.
- Name the trade-off aloud. "If we keep the low-margin contract, we cannot staff the new service line until next spring" is easier to decide than an abstract debate about focus.
When the owner's role is the issue, which it often is in owner-led companies, the facilitator should raise it in the interviews first, privately. The owner then arrives knowing it is coming and can open the topic personally, which changes the tone completely.
Logistics checklist
Small practical details decide whether people are focused or distracted. Settle these at least two weeks ahead.
- Venue booked with a main room and one breakout space.
- Screen or projector for the live decision log, plus two flip charts.
- Printed packs for those who prefer paper.
- Lunch served in or beside the room, so the break does not stretch to ninety minutes.
- Office coverage arranged so attendees are not called out.
- Travel times agreed for anyone coming from another city or province.
In person or online by video
Both work, but they need different designs. In person suits a first planning session or a difficult conversation; online suits a shorter follow-up or a team spread across provinces.
For an online session, cap blocks at 75 minutes, add a ten-minute break every hour and a half, and split a two-day agenda into three or four half-days across a week. Use a shared document for the decision log so everyone sees it being written. For in-person sessions, choose a room away from the office with natural light and space for small-group work, and keep the leadership team off their inboxes.
What to send afterwards
Send a written summary within three working days, while memories agree. Delay is how offsite decisions get quietly reopened.
The summary should include the decision log, the draft priorities with owners and milestones, the stop list, the parking-lot items with a decision on each, and the dates of the next steps. Within two weeks, the decisions should be drafted into the three-year plan and the first quarterly review should be in everyone's calendar.
Getting help with your offsite
StrategyPlanning.ca is a Canadian business consulting service in the Sedighi.ca and SAZ.ca group, based in Vancouver and led by Ali Sedighi, MBA. We prepare and facilitate leadership offsites in person or online by video, including the interviews, the pack and the written summary. See pricing for how a facilitated session is scoped, or the FAQ for common questions. Call or text (604) 632-4959 (texting is welcome), or email us with your preferred dates.
Frequently asked questions
How many people should attend a strategy offsite?
Five to nine is the workable range for decision-making. Fewer than five usually means the owner is deciding alone; more than nine and the discussion splits into side conversations.
Should the owner facilitate?
Usually not. The owner has the strongest views and the final say, which makes neutral facilitation hard. An outside facilitator lets the owner take part fully and keeps the agenda on time.
Can an offsite work online?
Yes, with changes: shorter blocks, more breaks, and pre-work done in a shared document. For a first strategic planning session, many teams still prefer to meet in person.
What should we have at the end of the offsite?
A decision log, a draft list of three to five priorities with owners, a stop list, and a dated plan for what happens in the next 30 days.