A Founder's Guide To Planning an Offsite or Company Retreat

A Founder's Guide To Planning an Offsite or Company Retreat

Your roadmap for creating meaningful team connections and powerful strategy sessions without getting a headache as a busy founder!
Introduction: Why Most Corporate Offsites Miss the Mark

As more founders and HR teams notice that traditional corporate team building in the boardroom isn’t rendering the desired effects, everyone is exploring new options. Researching takes time though and if you’re a busy small business it’s hard to find time, so we’ve put together this guide to help you plan the perfect off-site for your team!

Part 1: The Foundation - Setting Your Intention

Start With Purpose, Not Activities

Before choosing a venue or planning activities, ask yourself:

What specific challenge is your team facing?

  • Lack of cross-department collaboration?

  • Remote team members feeling disconnected?

  • Leadership alignment issues?

  • Low employee morale?

What would success look like?

Write down 2-3 specific outcomes you want to achieve. For example:

  • "Leadership team agrees on Q4 strategy direction"

  • "Team feels energised and connected to our company mission"

Part 2: The Logistics

Location: The 90-Minute Sweet Spot

Distance from your office:

Aim for 45-90 minutes travel time. Close enough that it doesn't feel like a major journey, but far enough for a substantial change in environment.

In Nature:

Research shows that exposure to nature reduces cortisol levels and improves creative thinking.

Timing: Day Time

Consider a day retreat or activity so that staff do not need to organise childcare and you don’t have extended time away from operations.

One Contact Rule:

Choose a venue with a single point of contact to make planning easier!

The Planning Rule:
The best team connections happen in the gaps between activities, during coffee breaks or walking between sessions, so don’t overfill the schedule.

Part 3: Creating the Right Environment

What Doesn’t Work:

Icebreakers that make people feel forced to connect Presentation-heavy sessions
Rigid schedules with no breathing room

What Does Work:

Shared experiences (cooking together, outdoor activities) Problem-solving sessions in nature
Open space for informal, authentic conversations

Part 4: Make it Sustainable

Attending or organising a corporate off-site is great so long as you can bring the results back to the office to implement.

Consider an office day the day after your off site to implement your new learnings and look at quarterly activities for employee wellbeing and strategy sessions in nature.

Conclusion

Planning a stress-free corporate offsite isn't about finding the perfect venue or the most innovative activities.

It's about creating space for your team to connect authentically while advancing your business goals.

Bring your team to The Shire

If your team could use a day to reconnect, relax and return to work feeling genuinely refreshed, we’d love to host you.

Get in at touch to plan your next company retreat, meeting or event.

Published on

Nov 18, 2025

George Taylor

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Co-Founder

Pury Hill Farm, Alderton Road,
Towcester, Northamptonshire, NN12 7LS

FIND US

Pury Hill Farm, Alderton Road,
Towcester, Northamptonshire, NN12 7LS

FIND US

FIND US

Pury Hill Farm, Alderton Road,
Towcester, Northamptonshire, NN12 7LS

FIND US

FIND US