Planning an Offsite or Away Day? Start With These 10 Questions

If you’re planning a leadership offsite, strategy workshop or team away day, pause before you start booking venues or building slides.

Offsites, Workshops and Team Away Days can build trust, clarity and momentum or leave your team asking, “What was the point of that?”

Before the calendar invitation goes out, ask these ten questions. They’ll help you design an offsite that delivers real results and avoid the “nice lunch, no outcomes” trap.

7 Questions to Answer before holding an Offiste, Workshop or Away Day

1. What are we trying to achieve?

Every offsite should have a clear why. Without it, the day risks feeling vague or performative. Being clear on the purpose shapes everything: format, facilitation, outcomes, energy. Without this clarity, the day risks feeling vague or performative.

Ask:

• What’s the problem or challenge we’re trying to solve?

• Is it to solve a problem (misalignment, disconnection, lack of clarity) Is it to respond to a shift (new CEO, strategy change, growth) or is it to unlock new ideas and momentum?

• Why now?

Try this: Write your purpose in a single sentence — and use it to brief your team, venue or facilitator.

2. What outcomes do we want?

Get specific. Whether your off-site, away day or workshop is about setting strategic priorities, exploring culture and values, building trust, communication or collaboration. Outcomes don’t need to be rigid but they should be meaningful, specific, and linked to business need

Ask:

• What decisions do we want made?

• What conversations need to happen?

• How will we know if the day has been successful?

3. Who needs to be in the room and are they prepared?

Who’s in the room matters. So does their mindset. It’s not just about who’s invited, but how ready they are to engage. Prepare people to engage, contribute, reflect and commit. Make sure people know:

• Why they’ve been invited

• What the day is (and isn’t) about

• What they’re expected to bring to it?

4. What do we want people to think, feel and do afterwards?

A successful offsite should shift something mindset, motivation, behaviour, or direction. Avoid vague goals like “alignment” or “team bonding.”

Ask:

• What impact do we want this to have?

• What new behaviours do we want to see?

• What conversations are overdue?

• What actions should people commit to?

5. What’s likely to get in the way and how will we handle it?

Tension, cynicism, unspoken issues, unresolved conflict, cynicism or fatigue. Every offsite has potential blockers. Ignoring them doesn’t make them disappear, but designing with them in mind makes the day more honest, useful and inclusive. This is where a skilled external facilitator can help to surface the tough stuff and move forward constructively.

Ask:

• What’s not being said?

• What might stop people being honest?

• How can we create a safe, inclusive space?

6. Is everyone clear on why they’re invited and what’s expected?

Offsites work when people show up ready to participate, not just spectate. When people feel prepared, they engage more fully and bring better energy to the room. So make sure people know:

• Why they’re there and the purpose of the session

• What kind of conversations will happen

• What kind of mindset or preparation is expected

7. How will we balance structure and flexibility?

Too much structure can kill creativity at an off-site or away day, while too little can lead to chaos. A well-designed day includes:

• Time to reflect on the big picture

• Space to connect as people

• Opportunities to make real decisions

• Flexibility to adapt in the moment

A structure around presentations and breakout can feel stale and rigid, so build in movement, variety, and breathing space, so include plenty of opportunity for individual reflection, small-group work, open conversations, and collaborative planning.

8. What will make this feel different to a regular meeting?

Your offsite should feel like a different kind of conversation, not just another agenda-heavy session. The best workshops spark insight because they feel different.

Ask:

• How can we use a different space or setting? That’s the value in getting away from the office, to somewhere new, away from distractions.

• Can we include storytelling, vulnerability or creativity?

  How will we make it human, not corporate?

9. How will we make sure this leads to action, not just good intentions?

Too many offsites end with a flurry of ideas and then no real follow-through. Creating accountability makes sure you see real shifts. Before the day ends, build in:

• Time for decisions, priorities and next steps

• Clear next steps and timeframes

• Clear ownership (who will do what by when)

• A plan to revisit and track progress in a month, a quarter and a year.

10. Should we bring in someone external to facilitate?

If you want honesty, momentum, and real progress, consider working with a facilitator. A good facilitator holds the space, creates safety, encourages participation, and ensures real outcomes, not just good vibes. Especially if:

• There’s low trust

• You need to shift dynamics or challenge the status quo

• You want leaders to participate fully, not run the room

• You want actionable outcomes

Final Thought

A brilliant offsite doesn’t just happen. It’s designed with intention, curiosity, and care. Start with these questions, and you’ll already be ahead of most teams that just hope for the best.

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Are you planning an Away Day, Off-site or Workshop and looking for support?

Whether you’re planning a leadership strategy day, team away-day, or culture workshop, I’ll help you design and facilitate a session that delivers real outcomes,

We’ll bring people together with purpose, create space for the right conversations, and leave with clarity, connection and action.

If you’ve got ideas, plans or challenges that would benefit from getting people in a room together, I’d love to hear about them.

• Give me a call on 07966 475195

• Book a time straight into my diary: Calendly >

• Email me: polly@pollyrobinson.co.uk

• Learn more about Growth Space Workshops & Facilitation >

Not sure if you need a facilitator?
Read my blog: Do I Need a Facilitator for My Away Day?