How to Run a Great Business Strategy Day

If you’ve been in business for more than five minutes, I can guarantee you’ve had a terrible strategy day experience – all talk, no action, and the highlight of the day was the mediocre muffins at morning tea.

You deserve better. Your team and your customers deserve a business that knows where it’s going, and why, and most importantly how it’s going to get there.

You need to run a great strategy day. An amazing strategy day. The kind of strategy day that your team will talk about with reverence for years to come – “Do you remember the Brisbane Powerhouse strategy session we had in 2024? Now THAT was a good day.”

Here are the six steps to make a great business strategy day happen.


Not all strategy days – also commonly referred to as team offsites, strategic retreats, or (though I shudder at the term) team building days – are created equal. There are several different outcomes you may be seeking, so you need to be clear about your specific purpose before the day so everyone comes ready to focus appropriately.

The most common strategy day purposes I see are:

  • Vent – We sometimes call this The Good, The Bad, and the Ugly. It’s not about solving the world’s problems, it’s about identifying what’s really going on in your business and openly airing any concerns so a way forward can be found that doesn’t sweep them under the carpet.
  • Brainstorm – You have some general thoughts and questions, but not yet any solutions. Open up to input from the partners or team to uncover all your options and opportunities.
  • Discussion – You have some specific ideas, and are looking for a focussed discussion about what they would look like in practice in your business.
  • Present – Either presenting recommendations or board decisions, this may include some discussion but most of the strategic thinking has already been done by a project team or business leader. Make sure said team or leader is ready to present!
  • Decide – Often linked to the Presentation, this asks the partnership or leadership team to make key decisions. No more sitting on the fence – are we going to do this or not?
  • Team Building – If you only want a team building day, do it well and don’t let strategy get in the way. But just so you know – if your culture is in dire straits and your team members hate coming in to work each day, even the best team building session is only putting lipstick on a pig.

Especially if you have a full day or a two-day retreat, you may want to set a different purpose for different sessions. For example, you may start by Presenting some recommendations; then opening up a Brainstorming session; then bringing it all together to make some key strategic Decisions; then hitting the golf course or Aquaduck for the team building component.

Just communicate the shift, and don’t blur the purpose.

You do NOT want to be deciding strategy on the Aquaduck.


Having the right people in the room for the conversations you want to have is critical, and again you may split the day – for example, Directors / Leadership team in the morning, and a wider group in the afternoon.

If you have multiple shareholders, I would encourage you as a group (possibly with your GM / Ops Manager if applicable) to be running some kind of strategy session as a small group at least twice a year.

Honestly, I find the most valuable strategy days are those where the directors give themselves the luxury of a whole day or two out of the office without the rest of the team around. There will be plenty of time to communicate with them later – this is your opportunity to lead and go deep into the parts of the business that really energise you.

If you do choose to include your team, a maximum group size of 12-15 is optimal for running a great strategy day. In my experience, willingness to contribute to a discussion tapers off dramatically once you have a group of 16 or more people. The only exception I would make is if your entire business is between 15 and 30 team members – make sure your plans involve plenty of small group / table activities to encourage contribution, but seek to involve everyone.

If you have a larger business, you may want to invite a cross-section of the different departments, to prevent the ‘Us versus Them’ mentality that is sometimes created between Sales / Technical / Admin / Management teams. Look for people who:

  • Have experience and perspective about both their functional area and the overall business;
  • Are outspoken, so will be willing to contribute on the day and represent their absent colleagues strongly;
  • Fit your business culture, so they don’t push strategic decisions in a direction that doesn’t align with your overall purpose.

If you want team members to prepare anything, including having discussions with their colleagues who won’t be present on that day to see if there are any issues or opportunities worth discussing, be sure to give them plenty of notice.


A great coaching technique is to start each session by asking the client what’s on their mind. This is a TERRIBLE approach to running a great strategy day!

You need to plan ahead, and distribute the agenda to every attendee at least a week in advance. This is partly to help them prepare, but more importantly it demonstrates that the strategy day has been planned and that you are organised. This gives your attendees increased confidence in the value of the day – it’s not just something that’s been slapped together and will be very quickly forgotten.

If you do run quarterly, six-monthly, or annual business strategy days – as many of my clients do – you may develop a regular agenda that keeps them consistent. It’s still a useful exercise to circulate this a week or two beforehand.

If you have never run a strategy day before, you may be looking for a business strategy day template agenda. And you’re in luck: I have outlined a broad agenda in this video and article, while also including specifics in this series designed to help businesses at different sizes plan their ongoing strategy.

These are starting points. Just as I walk through these agendas with my small business coaching clients to personalise them, so too you may want to add or remove certain sections that are less relevant for your business today.

You will need to add times to the sessions, and be sure to include sufficient breaks throughout.


There are two key roles that are imperative for any successful business strategy day – the Documenter and the Facilitator.

The Documenter’s role is to take notes. Agree with them in advance whether these are detailed, formal minutes or (my personal preference outside of a Board environment) focused just on a specific list of agreements and actions. Having a laptop or tablet they can type directly into will save time afterwards. And make sure you communicate with this person whether you want them to contribute in the discussion or not.

The Documenter is also responsible for distributing these notes afterwards – perhaps to the business owner or CEO for review first, and then to all attendees or the whole business in a timely manner.

The Facilitator’s role is to manage the energy of the group during the day, which includes obvious elements like sticking to the agenda and timing, as well as more nuanced leadership skills like ensuring everyone’s voice is heard and identifying when a breakthrough is imminent and guiding the team in that direction.

Is it worth paying a business coach to run your strategy day? This depends on the experience of you as a business owner, and also the purpose of the day (an experienced facilitator will help with making key decisions, for example, and will often be able to bring their own frameworks to accelerate the discussion for a better outcome).

Don’t be afraid to invest in this role. As a business owner, you need to be part of the discussion and decision-making at your strategy day. And that’s difficult to do when you’re managing the energy of every participant from the front of the room. Expert facilitators may cost you anything from $1,500 to $5,000 per day – if you’re making decisions about strategy for a multi-million dollar business, that’s a very small price to pay to make sure it’s done well and you don’t have to repeat this exercise again in a short while.


Sometimes it’s necessary to take the team away from your office to maximise the benefit of your strategy day – they will be better able to think ‘big picture’ if they’re not surrounded by everyday décor, and they’re not running back to their desks to check emails and make phone calls at every break.

If you do hire an external room for the day, make sure it has plenty of natural light and a reasonably high ceiling. Both have been proven to improve strategy day outcomes.

This can be as fancy, or not, as you choose. My team has run strategy days for clients on the beachfront of Moreton Island, and at the Queen’s Arms Hotel before the latest renovation.

If parking at the location is going to be difficult, be sure to communicate this with the team beforehand and possibly arrange some carpooling from the office with plenty of time to grab a coffee at the venue and start the day.

Oh, and on the topic of coffee … I’m not the only one who loves a caffeine jolt to kick off a great strategy day, so check with the venue that this is available. There are some awesome meeting venues, like the Brisbane Powerhouse, that don’t have coffee available nearby until later in the day … not a good start for those who need (or like, or are just expecting) a morning fix.

Jacob Aldridge facilitating a group strategy session


Lastly, you need to remember that a great strategy day is part of an ongoing business process, and it doesn’t stop when you and the team call it a day.

Immediately afterwards, you may choose to organise some drinks or a team dinner. These can be a practical way for the team to unwind from a purposeful day. If you want the conversation to continue – or plan a working dinner mid-way through a two-day strategic offsite – be sure to communicate that so expectations are clear.

Within two weeks, the Documenter needs to circulate the agreements and actions from the strategy day. If these already have timeframes and responsibilities assigned, then your business can move forward with those actions.

If not – and in my experience, they usually won’t – then within 2-4 weeks of the strategy day you need to schedule a follow-up meeting in your office. I recommend scheduling this before the actual strategy day – again, to demonstrate to the team how organised and committed to this process you are.

At this meeting, you want to shift the strategic decisions into implementation mode.

  • What are the key steps?
  • Who is responsible for each one? (Only one person can take responsibility, though they may have several team members helping them to make it happen)
  • When do you expect that step to be completed?

By having this follow-up meeting in your office, you have demonstrated that the offsite strategy day has been brought back into the day-to-day operations of your business. It’s an important emotional step in ensuring strategy turns to implementation.

And ultimately, it’s that implementation that determines whether you had a great strategy day … or not.

If you have run strategy days in your business in the past which have failed to live up to expectations – either on the day, or turning ideas into results afterwards – you may want to chat to our me and our strategic advisory team about how we can help you change that outcome in the future.

Participants at a Group Coaching Workshop

Related Posts

Leave a Reply

Most Popular Posts