Reflections of our 2018 Hi5 Retreat

We just returned from our 2018 retreat and I thought I would share some helpful insights from our 2nd retreat in our 3rd year of existence.
Reflections of our 2018 Hi5 Retreat
Gary Willmott
I’m not writing a post for a post’s sake — for the first time in a while it felt like we achieved something that felt meaningful and helped us steer the team in the right direction.


We had our retreat in a remote little town on the West Coast of South Africa, called Elands bay.
Why Elands? There is nothing to do besides relax, connect and surf (yes, 1/2 of our team surfs).
Being involved in a fast growing startup, we don’t often get to connect and I wanted a place where we could really get to know each other and not be in a town where there are loads of shops, activities & distractions.

Day 1: Friday

We took the day off away from the office and took a slow drive (about 2 hours), stopping off at the harbour when we arrived, then settled in. We took a long stroll to embrace the sunset, kicked the weekend off with a burger braai (that’s a BBQ if you are not South African) and jammed some ukelele covers until the board games came out. 🤓

Hi5 Retreat 2018
Hi5 Retreat 2018
It’s also important to bring your dogs with :D
Hi5 Retreat 2018
Make sure to provide lots of reading material and vibe.
Hi5 Retreat 2018
Hi5 Retreat 2018

Day 2: Saturday

After sleeping in and having breakfast, we kicked off our planning session for the next 6 months. We chose the morning because we knew that 40ºC weather was on the way. ☀


I’ve been involved in loads of leadership and coaching frameworks, but to be honest I find most of them laborious and more administrative than effective.

Hence, we chose the V2MOM framework, which Marc Benioff established at Salesforce. They’ve been using it since 1999 and it works great for every phase in the lifecycle of an organisation. These are the basic questions we asked each other and voted up as a team:

1. VISION (What do you want?)

2. VALUES (What’s important about it?)

3. METHODS (How do you get it?)

4. OBSTACLES (What might stand in the way?)

5. MEASURES (How will you know when you have it?)

We all wrote down our interpretations on each of these points and voted them up with sticky notes.

Hi5 Retreat 2018
Going analogue!

This helped us realise that we have various methods, obstacles and measures. We honed these and then clarified our goals in Hi5 for the next 6 months. This was really helpful as most of us have been very T-Shaped, however now that our team has doubled in size, we can divide, focus and conquer.

We ascertained that we will need to double our team for next year, so if you’re looking to join, please take a look at the positions available.


We clarified and fine-tuned our values, which are listed on

Hi5 Retreat 2018

  • You are always learning and trying out new things that help you become better within your career and as a person.
  • You are always looking at better ways to help people grow within companies.
  • You reflect and measure on what you have done in the past, so that you can do better in the future.

  • You make the most with what you have and the situation you are in.
  • You strive to approach things in a positive and optimistic way.
  • You avoid criticising team members or users.
  • You go out of your way to make others successful.

  • You are more focused on output and results than hours and process.
  • You would rather ask for forgiveness than for permission.

  • You understand that nobody knows what’s best for Hi5 more than our customers; it’s best to keep shipping to them first before having our own perceptions.
  • The customer isn’t always right — they don’t need features, they need solutions. Always ask why and look at the “Jobs the be done”.

Have fun and be human
  • Never forget to enjoy your job!
  • There is always time to give a Hi5 for a job well done.
  • Work to live, don’t live to work.
  • Take a break when you need it. 🏄 ⚽ 🕹️ 📖 🎹 🎸

Mid-morning break

After our first session, we took a mid-morning break to pick some mussels from the rocks for our evening starter dish.

Hi5 Retreat 2018
Harvesting mussels at the source.
Hi5 Retreat 2018

Client feedback

Before the retreat we sent out a simple survey to our clients asking simple questions like what they like and don’t like about Hi5. We were really surprised with the response & feedback we received, as well as the effort that our customers put into their feedback.

Hi5 Customer responses
Customers responses
Hi5 customer responses
Customers responses
Hi5 customer responses
A couple of comments that stood out in the survey.

Dream about an “11 Star Experience”

We then discussed what an “11 Star Experience”  would be for any users on Hi5.
This is based on Brian Chesky’s discussion with Reid Hoffman on Masters of Scale, you can listen to the whole episode here. It comes down to this, If you want to build something that’s truly viral you have to create a total mind-blowing experience that you would tell everyone about.

We all came up with ideas at different stages and voted them up. This was pretty fun and it was great to think creatively and dream of something that could really help make the workplace simple in the future.

Hi5 Retreat 2018
Don’t forget to serve snacks and provide play dough to keep fidgeters happy ;)

Day 3: Sunday

The surf was flat, yet we still found some things to do. We ended up exploring the nearby fort and ancient caves with rock paintings. We also did a before & after experiment with coins on railroad tracks. 👀

Hi5 Retreat 2018
If we don’t take selfies, how will people know?
Hi5 Retreat 2018
It seems like there were Hi5's 1000’s of years ago?
Hi5 Retreat 2018
Before — money useful for buying things
Hi5 Retreat 2018
After — great souvenirs

End off

There were late nights of eating together, talking rubbish, cracking jokes, playing games, staring at the stars & getting deep.

Hi5 Retreat 2018

What I learnt?

I always saw retreats as a nice-to-have when building a company, but I’ve realised after this trip that it’s really a need-to-have. Even more so, it’s important to be intentional with what you would like the team to get out of the time away and then plan around that.

What I would have done differently?

Three days almost wasn’t enough! I think I would have preferred to go on for 4–5 days and split the sessions up. There are a lot of implementational items which we still need to break down & agree upon.

I hope this helped you in some way. If you’ve ever run a retreat that’s been successful, let us know! Keen to hear your feedback.