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How To Run An Awesome Company Offsite

Corporate offsites are back in vogue post covid.

And so they should be, as run well, they can be incredibly productive.

But unfortunately, most are not run well, and the opportunities they could bring are quite literally left on the conference room tables.

So having just completed a very successful offsite with Crossfin at the Arabella Hotel in Kleinmond, I thought it helpful to share a few ideas on how to make sure your next event goes as well as ours did.

The Crossfin Armada Group Photo - Arabella Country Estate, Hermanus

(If you are organising an event and want to bounce a few ideas around, drop me a note.)

1. Be Clear About The Goal Of The Event

Sounds obvious, but the reality is that most offsites are not planned with a clear goal in mind.

So it's not surprising that most events are somewhat formulaic and therefore, indistinguishable from any other offsite.

Turn up, keynote, keynote, break, keynote, lunch etc. etc.


As with most things in life, the clearer your goal, the better the planning and execution will be.

So it's worth taking the time to brainstorm with your colleagues what benefits and outcomes you are expecting, both immediately after the offsite and over the following months.

Notes from the Crossfin offsite planning session
I have pages and pages of A2 scribbles from brainstorming with Crossfin's co-founders Anton Gaylard and Dean Sparrow for their annual offsite. Turns out the time was well spent!

For Crossfin's event, co-founders Anton Gaylard and Dean Sparrow were clear from the start that they wanted to use the event to increase the potential for collaboration across their portfolio of investee companies.

2. Support Your Goals With Objectives And Key Results

The best companies use OKR's to design and execute strategies, and OKR's will be equally effective in helping you design and execute a great offsite.

Here is an example that I hope gives context.

Offsite Objective 1 - Catalyse the development of a culture of Helpfulness across the group

KR 1 - Each attendee is expected to hand out at least 30 baseball-style personal profile cards (skills, interests, personality profile, position, etc.), to new contacts, during the conference to facilitate introductions.

KR 2 - 60% of attendees can demonstrate they spent 10% (or more) time supporting colleagues outside of their business unit within 3 months of the conference ending.

When I read OKR's like this one, I'm already dreaming up ideas about how to turn these target outcomes into reality.

And that is the power of OKR's.

Having as few as three or four OKR's will make an immense difference in helping you and your team ask all the right questions during the planning phase.

Questions like:

- How could I use the physical environment to break down social barriers and catalyse conversations?

- What types of exercises and activities will generate the best ideas?

- How can we make sure these ideas are captured and converted into executable strategies?

- Which topics, experts and speakers would be good launch pads for further debate?

If you want to learn more about how OKR's differ from KPI's and how to create them, I'd recommend you check out What Matters.

3. Use Scrum

An offsite cannot be managed by one or two people. It really is a group effort. So use project management frameworks like Scrum.

That way, you will ensure (to name just a few benefits)...

- short focused daily standups

- clear recording of who's doing what, by when

- team roles are defined

- you engender a culture of trust and honesty, where people shout out when they need help.

If you want to learn more about using scrum, I'd recommend Scrum, The Art Of Doing Twice The Work In half The Time.

4. Pick your best team (and reward them appropriately)

Organising an ordinary (boring) offsite is easy.

Organising an incredible offsite that really delivers value is hard.

So make sure you pick your best people and reward them financially, emotionally and career-wise.

Being part of the organising team should be seen as being a potential career launch pad, not something to leave to an external events team.

5. Ensure diversity in your organising team

Every attendee at your event will be unique.

Unique based on their age, sex, seniority, interests, race etc. etc.

Unique based on their personality.

Unique based on their role within the company.

All these differences need to be considered by the organising team.

The easiest way to make sure that you don't fall into the trap of designing an offsite that only appeals to a few, is to make sure you have as much input from as diverse a set of people as you can.

And that likely includes input from people outside of your organisation.

I'd also suggest you focus on getting significant input from the more junior within your ranks. They'll typically give better insights into how to develop something that will appeal to all.

And if what they concoct makes your c-suite slightly uncomfortable....your probably heading down the right lines.

6. Don't cram too much in

Offsites are expensive and infrequent, so it's easy to try and cram in as much as possible.


The worst offsites are always the ones that are stuffed with content.

Too many speakers and activities will mean your attendees switch off.

A 09:00 start / 16:00 finish is absolutely perfect.

And if you decide 09:30 to 15:30 works better, go for it.

I would have fallen into this trap at Crossfin's offsite if it wasn't for Anton's consistent reminders that "less is more".

This is certainly a lesson I'll take into future events.

7. Make The Lunches More Snack Than Sit-Down

If you want to kill any possibility of productive discourse in your afternoon sessions, offer a multi-course sit-down lunch.

If you still want activity and alert minds in your afternoon sessions, work on developing a menu of healthy canape-styled foods with plenty of nuts, fruits and vegetables.

Photo by Sasha • Stories on Unsplash - Not perhaps the best photo I could have chosen to stress this point as I'm sure I can see some chocolate deserts on this slate board. Still, I think you get the idea?

8. Minimise Powerpoint And Ban Presentations With Text

Much as I hate PowerPoint, it can still be a powerful visual aid if used properly at your conference.

But the problem is most presenters don't use it properly.

They cram their decks with slide after slide of tables and numbers and text.

Don't do that. Or rather don't allow your presenters to do that.

Challenge anyone that has asked to use PowerPoint to only prepare slides with pictures, videos or sounds.

You want the audience to listen to the speaker, not read the powerpoint, so any presentation material must reinforce the speaker's points and/or provide visual cues to help attendees remember the key messages.

(C-level executives will find the shift from presenting numbers and words to engaging stories and messages particularly challenging - Good luck)

Mmusi Maimane's keynote used the perfect number of slides. Just this one showing in the picture.

9. Manage Time Ruthlessly

From setting the agenda timings to ensuring speakers stick to the clock, make sure that every session finishes early.

There is nothing worse than watching a presenter or moderator try to cram in one last point of discussion to make sure they use their full slot.

If the Q&A, keynote or discussion hits a natural pause five or ten minutes before the prescribed endpoint, call it.

There is nothing wrong with having longer breaks because sessions finish early.

Equally important is making sure the attendees return to their seats punctually.

The reality is you will need to herd your attendees to return to their seats like sheep if you want to get going on time.

So make sure you have an army of herders who will start corraling people back into their seats at least 5 minutes before your prescribed start times.

One trick if your AV allows is quite simply to make it impossible for them to speak during the break by drowning them out with music!!

10. Plan The 'Fun' Activities With Science And Precision

Remember, one of the most important benefits of an offsite is harnessing the crowd's power.

Bringing people together offers the opportunity to create new business networks, curate new ideas and ultimately lay the foundation for new ways to boost profits and solve problems. It's also a great launchpad for improving your company's culture.

If you are offering golf, spa's, dinners, entertainment or any other typical 'fun' activity, design them carefully so that the conversations keep running and all of your attendees remain comfortably engaged.

The worst outcome, which you'll have to work hard to avoid at all costs, is that the existing cliques become even more cliquey.

The golden rule here is not to give your attendees too many choices as to where they should be and who they should be with during the conference if you want to keep the conversations rolling.

Dale Gaylard crafted beautiful post-event experiences. This photo was taken at the Benguela Cove Lagoon Wine Estate, which provided the perfect environment for more conversation and relationship building.

11. Ensure regular periods of silence and self-reflection

This may again seem counterintuitive, but you need to enforce periods where attendees have to be silent and reflective.

Perhaps you do this by asking them to read something, which is then followed by a written exercise.

Maybe it's an online survey. (I recommend Slido here).

Giving your audience time to 'think' is perhaps one of the most productive things you can do at an offsite.

Consider this...

When else are you going to get a chance to get your leadership team to reflect on the same topic, at the same time in a way that opens up the opportunity to discuss their thoughts on mass?


So make sure there are periods for reflection and choose the right music and environment so the ability to reflect is amplified.

12. Make the keynotes short and the debates long

I am regularly paid to present at conferences on leadership, strategy and culture.

And my clients typically expect me to present for 30 to 40 minutes, with 20 min of Q&A, before heading into the break.

I believe a better model is to keep the presentations short and focus on increasing the time made available for conversation and debate.

There are a number of ways to do this, but I have found from experience that the following work really well:

1. A fireside conversation with an expert

I particularly like this format as I feel you can extract even more value from your guest than if it was a standard keynote.

And I think the format is far more engaging for audiences than a standard keynote, especially if the moderator brings the audience into the discussion early on.

Here Roger Grobler is explaining how companies that use data-led decisioning have a massive advantage (and why most companies fail to apply data-led principles)

2. A well-worked panel discussion

If I had the choice, I'd pick one-on-one fireside above panels, because they are easier to moderate.

But panel discussions can still be effective mediums, especially if you apply this one golden rule....

Do not allow every panellist to talk to every point.

Audience questions being moderated by yours truly Colin Iles and answered by special guests Jan Pilbauer (BankservAfrica), Matthew Blewett (Multiply Invest) Paul Edwards (Vantage Pay) and Muzaffar Khokhar (Unity Digital)

I prefer listening to nails on a chalkboard to a panel session where every panellist is given the opportunity to chip in on every question.

If you want it to flow, make sure you have planned in advance how you want to introduce the different themes and how you will bring each of the panelists in at the appropriate time.

As a final point, if you are moderating a panel discussion, don't be afraid to use humour to keep your panellists in line, particularly when you need to cut the conversation to move on to the next theme.

3. Co-presenting on a topic

In this format, you share the stage, which gives you the opportunity to have a much more interactive (and I think more engaging) session.

In this example, I'm co-presenting with Henri Zeitsmann from AWS.

Terrible photo, but co-presenting with Henri Zietsman (AWS) about the techniques the worlds fastest growing companies added real depth to the keynote.

In this session, we were talking about the attributes of exponential organisations, which were so well articulated in Salim Ismail's book of the same name.

I'd introduce an organisational theory or concept, and Henri would provide a practitioner's viewpoint.

This type of tag-teaming worked well as it allowed for discourse about whether the ideas being discussed were being applied at AWS and/or whether they could be applied at the companies being represented within the rooms.

Those moments where your co-speaker (or the audience) fundamentally disagrees with something you've suggested are perhaps the best of all.

(I always feel that I learn more when there is some healthy disagreement as it forces you to think more deeply about the topic in hand.)

13. [ ? ]

What else do you think is needed to manage a great offsite?

I'd love to hear what you think and add as many of your ideas to this post as possible.


I hope you found some of these suggestions helpful.

Many of these ideas were born out of the Crossfin conference.

So I must thank Anton, Dean and the attendees for allowing me to share back these ideas with you.

But I must also thank Dale Gaylard.

While I sat on stage interviewing cool people about cool things, Dale was working tirelessly behind the scenes to organise the venue, the after-parties, the food and drinks, the av, the transport, the accommodation and a million and one other details that have to be right to make an event like this just work. Her orchestration was mission-critical. Thank you Dale 🙏.

If you want support for your next offsite, do drop Dale an email. You can reach her at


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