How to organise a Company Off-Site that pays off – An Executive PA’s Guide.

We understand that too often, the role to organise a company off-site falls into the lap of the Executive’s PA. After all, Executive PA’s are often the ‘bridge’ between senior/C-level management and the rest of the company, hence, in principle, it is a logical decision to empower this task to this engaged and very connected person.

However, in our experience, taking on this responsibility to organise a company off-site is a huge undertaking, on top of all the other day to day responsibilities.  This can create quite a stressful workload and impact your well-being both in and out of the office.

In this ‘How to Organise a Company Off-Site that Pays Off Guide’ we will aim to help you, as an executive PA, to tackle this extremely challenging and stressful task, to organise a company off-site, in a more manageable and proactive fashion. Creating this small guide to help you break down all the tasks in hand to organise a company off-site.  We are here to help 🙂

Before beginning to organise a Company Off-Site it is important to have some clear and specific objectives in place.  Whether on the beach or off the beaten track, understanding the need to kill complacency and connect with your team like never before is wonderful.  This is the value of taking your company off-site to connect your workforce and develop your company culture…but there should be additional driver or purpose. What is the key problem you are trying to solve or objective you hope to meet by organising a company off-site.

Please take some time to discuss the quesitons below with both your senior management team and handful of employees from the company. We suggest creating a company off-site think tank to help you develop the concept and core purpose of the Off-Site.  This will help share the burden of organising the company off-site and also help you delegate core tasks to others.

Company Off-Site Hotels

Choosing the right place for your Company Off-Site


Where are your team members located? (If you work with a remote workforce).

This will help you understand what location would work best for your retreat from a logistics standpoint. What airlines fly direct to the destination from these locations and can you get to the destination in a timely and simple fashion.

Team / Company Size:

This will help you. choose a suitable accommodation option when you organise your company off-site.

Where would you like to go for next year’s off-site?

  • City
  • Beach
  • Mountain
  • Countryside / rural

What kind of hotel would you prefer? (big hotel chains, boutique hotels…) 

  • Chain Hotels
  • Boutique Hotels
  • Country House
  • Camping
  • Other….

What kind of rooms do you request? (single / double / twin)

  • Single
  • Double
  • Twin

Opting to share rooms will bring down the price of the off-site in quite substantially.

Company Off-Site

Choose the right time for your company Off-Site to help take people out of the Status Quo


What values and beliefs define your brand?

(Without a clear strategy and purpose, your most valued asset, your team can very easily start working for work sake). 

Please state your top 3 reasons to celebrate at your company off-site:




On a level of 1 to 10 how well do you know your colleagues? 


What would you consider the 3 most important focuses for your company off-site? 

  • Fun
  • Relaxation
  • Team Work / Team Building
  • Adrenaline
  • Leadership
  • Team Bonding
  • Networking
  • Motivation
  • Development of Trust
  • Creative / Hands On
Company Off-Site Facilitation

Choosing the right facilitator for your Company Off-Site can make a huge difference.


What would you consider the primary focus for the company off-site?  Please highlight 3.

(Keep your purpose realistic. You might have large goals that cannot be accomplished within one retreat. Prioritise your needs and desires).

  • Celebrate great performance
  • Get out of your comfort zone.
  • Support managing change
  • Improve communication
  • Enhance the Company’s culture
  • Opportunity to innovate
  • Alignment of Mission and Vision!
  • Unite a global/remote workforce
  • Refine / Define Values
  • Escape routine
  • Incorporate a new way of working 
  • Evoke a behavior change
  • Leadership / Personal Development
  • A shared experience
  • Simply to have fun!

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Do you need a meeting space and what is the ideal room set up? 

  • Cabaret / Banquet
  • Theatre
  • U Shape 
  • Classroom

Do you require breakout spaces – if so how many?

What past activities have you experienced- what has worked and not worked?

Are you interested to incorporate a facilitator into your Company Off-Site?  Yes or No. 

(Our trainers, serve as a neutral group facilitator, and help disrupt your thinking by asking you questions that you might not have thought of independently. They help you identify, prioritise and resolve your key objectives as well ensure you stick to the pre-arranged agenda. Our Trainers and Trust Architects can also take the majority of this work away from your hands to organise a company off-site that pays off.)

Facilitators also help to empower the introverts in the group to have a say.  There are many meeting methods and tools to aid a more democratic and balanced approach to meetings. Asking each individual in the group to summarise their own thoughts on post-it notes, then place them on the board is a great way to encourage those who are less confident to ‘voice’ their opinion. 

This highlights the benefit of recruiting an independent meeting facilitator to host the retreat. It ensures that the CEO or confident extroverts, within the team, do not hog the microphone.  Talking of microphones…CatchBox is a great throwable microphone that encourages great interactivity within a meeting.

Company Off-Site activities

Choosing the right activities to incorporate in to your Off-Site helps create stronger connections


What are the 3 must-haves to ensure you have a successful, productive and enjoyable company off-site? 

  • Scheduled programme
  • Downtime with colleagues or own
  • Great hotel 
  • Destination
  • Limited travel time
  • Informative guest speaker
  • External facilitator 
  • Time to explore the destination
  • External activities
  • Great celebratory Gala Dinner
  • High standard of hotel room
  • Something different
  • Other: 

If you had one free hour each day of the company off-site, how would you use it? 

Choose a type of experience you would MOST like to incorporate into the company off-site – Highlight up to 3. 

  • Culinary/gastronomic
  • Exploration / City Rally
  • Digital Detox 
  • Creative Exercise 
  • Active (Early morning run)
  • Relaxation / Spa
  • Team Work / Survival
  • Competitive Activities / Olympics / Sporting Competition
  • Adrenaline / Karting / Wind Tunnel
  • CSR Programme 
  • Trust Building / High Ropes
  • Networking / Local site visit
  • Informative Workshops with Key Person of Influence
  • Motivational speaker 
  • Attend an event (cultural, sporting, concert etc)
Company Off-Site themes

Create a theme for the Off-Site that drives engagement

How to get everyone to engage at your company off-site?

The most important understanding when you have your team at a company off-site is to leave titles at the door.  Many company off-sites aim to inspire bottom-up innovation, where staff members on the front line can voice their opinion and have an opportunity to share ideas that would help solve the particular objective in question.

Planning for the next company off-site!

  • Debrief to ensure the next one is better
  • Gives everyone something to look forward to
  • Set the date

This will help retain and attract talent – your most precious commodity (apart from time)!

We can help you tailor a company 0ff-site that pays off:

If this seems all too much to manage on top of your daily workload then we are are here to help. At Travel Out There we do not believe in selling bespoke packages or off the shelf experiences. We like to give our clients exciting ideas and inspirational concepts that we then work closely with you to tailor make a company off-site to your exact needs and requirements. We specialize in creating and forming unique Company Off-Sites, please do not hesitate to contact us should you require any further information.

Company Off-Sites that pay off

A happy workforce is a connected one. This is your ROI for a company Off-Site.