January 19, 2023

How to run a strategy day for a software company

Last week, Moonward did something a little different. A few of our key members from the leadership team went away for a long weekend for a strategy day. The motivation behind it was to take us out of the day-to-day and put us into a place to do some solid planning for 2023. Here at Moonward we are in the business of big hairy ambitious overachieving goals, for both our team and our clients. None of our success comes through luck or wishful thinking, instead it comes from hard work, passion and continuous commitment to systemisation. 

At Moonward, we have never hosted a strategy day on this scale before, usually it is just myself and the other Moonward owner chatting over a lunch. But as our team has grown and layers have been introduced, we recognised the need and importance of getting our growing leadership team on board to help us execute. 

At the end of the day, team work makes the dream work and none of us are smarter than all of us together.

If you are thinking about hosting your own full day strategy session, here is how we do it at Moonward. 

Everyone gathered, ready to begin the session.

A few things to think about before you lock in your strategy day

First of all, a few establishing points for you to consider before you jump into the fun stuff.

Size does matter

Even though I am young (27, yikes), I am fortunate enough to have been exposed to alot of business situations and sizes. 

I have been a cog in a team of hundreds, I have been the other half of a team of two. I went to a previous leadership retreat where at least forty people attended, and of course I have been to planning sessions where it is essentially me and one other person disagreeing with each other the entire way. What this has taught me, in the context of hosting a strategy day/ leadership retreat is size does matter. 

If you have too many voices in the mix (more than eight), really good productive points will become lost in the noise. On the other hand, if there are not enough people involved (less than four) the small group can lack depth and easily become swayed by the loudest voice in the room. 

I really believe that the sweet spot for a productive planning session is five to eight people. Now, that might seem small, and it is, deliberately. Pick your strongest players, the people you feel have the biggest width of knowledge over their area of the business. This individual could be the lead of their department or someone who has an excellent understanding of the systems, such as business development. 

Make sure you curate this group of people very carefully before you extend the invites.

Pick a location

Just like in Real Estate, location is everything. 

I would definitely recommend doing a few nights away at a location outside of your city, literally it’s in the name, retreat. It doesn’t have to be crazy extravagant, you don’t have to all jump on a plane or go to a special location you would prefer to go with your husband or wife - it just has to be somewhere else. 

For our Moonward Leadership Getaway we went away to Maleny in the beautiful Sunshine Coast Hinterlands. We hired a big secluded property through Airbnb. We picked this house because it had plenty of outdoor spaces to sit and collaborate with each other. It also had a pool and a little farm which acted as a much needed distraction during our breaks. 

Another thing to consider is going to a location that is offsite means you will need to think about how you are going to feed and house all these people, this can definitely up the price of a retreat but I can guarantee if done right, the ROI will be huge.

Andrew feeding the animals. While Anthony looks on.

Create an agenda for the days you will be away

Don’t just create an agenda for the strategy day itself, instead create an agenda for the entirety of the leadership retreat. Factoring in time for dinner and drinks together is just as important as the planning itself. 

When your team members are taking time away from friends and family to spend a few days with you, you don’t want them to feel like any of their time was wasted. 

You also want it to be memorable. You want them to look back when they are actually executing the plan and remember the ‘why’.

Plan to succeed

This is going to be either a huge investment into the direction of your business, or a huge expense with no outcomes. Do not expect to just show up on the day and have great things happen. Plan, plan, plan. 

Give me six hours to chop down a tree and I will spend four hours sharpening the axe - Abraham Lincoln.

The strategy day itself

Ok, so now we have a few things in place to ensure the leadership retreat is heading in the right direction, let’s get into the actual strategy day.

What you will need: 

- A3 sized paper that you can draw a few diagrams on

- A pen for everyone

- A thick marker pen for you to draw with

- Post it notes for everyone

- A bluetooth speaker to cut the silence and lighten the mood

- Snacks

- Refreshments

- A host (this could be you) with a great attitude

Set the rules

Of course, you would hope that your culture exhibits these sorts of qualities in the team already, but it is always good to loosen everyone up and rattle off a few establishing rules. These are the rules we used at Moonward.

What we don’t want

- To immediately start talking about our issues and challenges with no intention of finding solutions (there is a time for this, we want to move forward)

- Talking over each other or the loudest/ most extroverted speaking the most

- Solutions to be talked about at random, before we really know what the core issues are

- Different issues are being talked about at any one time, we want to focus on one thing at a time

What do we want

- Fresh minds

- Anyone who is participating in this discussion to always keep the business outcomes at the front of their minds

- Everyone to have the opportunity to speak

Starting point - The Mountain Climber

This is my favourite place to start. Print off this picture below, or draw it up on one of your pieces of A3 paper with your black marker. Give everyone a stack of post-it notes and a pen.

The Mountain Climber represents your business. What you will identify in this exercise are the things that your business is doing well, and are pushing you forward up the mountain (the wind at your back), and what are the negatives that keep pulling you down the mountain (the rockfall at your feet).

The Mountain Climber with the wind at his back and the rocks at his feet.

Turn the tunes up and give your team five minutes to write as many points down on their post-it notes. Instruct them to stick their post in notes either below or above the Mountain Climber, depending on whether they are positive or negative things. Draw a line through the paper if it makes it easier for people to see where the Mountain Climber is. 

At the end of this, your paper should look something like this.

The Mountain Climber chart example.


Now that you have all your post in notes, it’s time to categorise them according to what they relate to, such as Team Culture or The Office. If you have any post-it notes that are double-ups, shelve the double-up so you don’t have thousands of post-it notes flying around.

Placing our ideas on the table.


Dot Voting

Now that we have all our issues laid out, we can vote on what items are the most important. Take your black marker pen and pass it around. Every team member is allowed five black dots each to draw on an individual post-it note. Items that are the most important will gather the most dots, and items considered less important will receive no dots and can be shelved. 

During our Moonward strategy day, we addressed every post-it note, even if it only received one dot. Items with one dot are generally easier to work through and will have quick-fire solutions. 

Although you will most likely eliminate all the positive stuff (the wind that is pushing the Mountain Climber up the mountain) during this phase, it’s important to also acknowledge and double down on those things. At the end of the day, these are the things that people really enjoy about your business, and you cannot lose sight of this.

An example of prioritising sticky notes.


The goal for this next phase is to create solutions to the prioritised challenges. You will need to change the narrative on a few of these post-it notes, for example, someone might have jotted down, ‘the office is too loud.’ You now need to turn these issues into opportunistic questions, such as ‘how are we going to reduce the noise in the office for people who prefer quiet?’

Start by having an open discussion, and when a solution is mentioned, write it down and attach it to the post-it note. At the end of each of the points you should have an actionable solution for each of them that the team agrees on. 

Some of our ideas.

As a heads up, this will be the chunkiest part of the session. During our Moonward strategy day this conversation went well into the evening.


We have now gone through the top prioritised challenges and their accompanying solutions. Now we need to create a system around what solutions we will tackle first based on the effort to implement and the impact on our team or clients. 

Take another piece of A3 paper and your black marker to draw this diagram up.

An example of a commit chart.

One person will do the placing of solutions on the paper and everyone else will direct whether a solution will go higher or lower, left or right.

Once all our solutions are on the board, write down the following so the team understands what needs to be done now and what can be made into a project. It’s important you don’t reveal this last part of the session until last, otherwise team members will become emotionally attached to points they are extremely passionate about and weigh them higher than others, when other members of the team do not.

An example of a filled commit chart.

Well there you have it, now you have all the pieces. Last thing to do today is write down all your solutions according to department (Design, Development) and correctly label whether they need to be done now, made into a project, made into a task or ignored (for now).

Now have some fun, make some food together, have a few drinks and play some games together. It’s been a hard hitting day that has required alot of brain power. Come together again as a team and celebrate the good work you did.

Now the hard work

No planning is worthwhile if you cannot execute. 

“Plan your execution. Execute your plan.” Anonymous

When you come back from your planning session, set up recurring meetings with the team that attended the leadership retreat and create a system to execute the solutions. 

At Moonward, this team has weekly meetings and a shared project management system where we can all track the progress of our strategy day. Everyone has a series of tasks to work through during the year, and every week we hold each other accountable to them. 

No matter what you do, the greater team is going to think you just went away on a holiday to drink and have some fun, the way you can showcase the value to your team is by making real change in the business, right away. 

All the best!

Lachy planning, while Anthony poses.

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