How to Run a Strategic Retreat

Want a way to inject new ideas into your business, clarify the direction forward, motivate and get buy-in from staff, and have a bonding experience with your team? Running a strategic retreat can achieve all of that!

At the IT support business I was involved with, we ran an annual “Strategic Retreat”. This was never intended to be a regular occurrence but after the success of the first one, the team was hooked.

But before you go off booking expensive venues, do a little planning time to make sure you’ve set it up for success. Here’s exactly how we ran ours…

Set the Theme

Don’t wait until you’re sitting around a conference table with a blank whiteboard in front of you to start brainstorming. Although you want the ideas to be free-flowing, you need to give them some direction. So decide upfront what the pressing issues are for your business. Phrase these as a few questions. (Sometimes figuring out the right question is the most important part of finding the solution.) The question/s can and should be fairly broad but should give direction to your team’s thinking.

For instance, one year our questions were;

• How can we attract more customers?
• How can we provide even more value to our current customers?
• How can we make <business name> the best place to work?

Get Your Staff to Do Some Pre-Thinking!

In my opinion, it’s a good idea to include as many staff as possible in your strategic retreat. The benefits are not only more ideas and improved thinking, but a huge boost to morale and buy-in. However, it definitely should not be viewed as a free-ride or junket trip!  To solve this conundrum, we put up some hurdles for staff before they would be considered for the strategic retreat.

They simply had to do some thinking and submit their ideas as answers to your questions (above) in writing. Our staff were very young, so we were fine with dot point ideas and didn’t really screen based on the quality of ideas (but you may need to depending on your team size). This got everyone doing some independent thinking, incorporating different viewpoints, and gave us a great starting point for the actual retreat.

Giving yourself and your team some time to think over these questions can help their ideas marinate and develop. Remind everyone to devote some real time to thinking laterally about possible solutions.

Choose a Suitable Venue

A venue away from the office environment is ideal as it helps to get people thinking in different ways (and can also change the dynamics between staff of different levels). We opted to utilise fairly low-cost conference centres and had everyone stay for a weekend – usually in winter (out of wedding season). When we were smaller, we’ve also run them at a friend or family member’s holiday house too. Depending on your budget, you may only be able to do one day – this is still worthwhile as you can achieve a lot in one day.

Our format was to arrive on the Friday night, settle in, and then have a casual dinner together (with not too many drinks). We had a full day on the Saturday, and then we’d do something a bit different on the Saturday night (like play “How to Host a Murder”). We’d also tend to have a few more drinks and make it a very social and fun experience for everyone – something to remember. On Sunday, we’d be back at it for the second half of the program.

Set the Tone

At the start of your workshop, it’s a good idea to give everyone a little pep talk. Discuss the vision of your business, talk about the background of the business (how and why you started it), the last year (what worked, what didn’t), and finally, make sure you thank everyone wholeheartedly for coming and contributing to the future of the business. Let them know it means a lot to you and that you’re optimistic that lots of good things will develop as a result of this strategic retreat.

You should also explain the format for the Strategic Retreat. If you’re following this format it will be;

• Present everyone’s ideas
• Brainstorm new ideas
• Group and sort
• Prioritise
• Set Up Initiatives

Also, and it’s been said a million times before, you really want to make sure that everyone feels like their ideas are valued. Set up some ground rules for the duration of the retreat. These could be something like;

• There are no dumb ideas – during brainstorming let’s focus on quantity rather than quality
• There are no dumb questions – if you don’t understand something, chances are someone else doesn’t either
• Keep the discussions central – no side discussions
• Stay focussed on the objectives and the agenda (we will need to keep moving so let’s not get sidetracked)
• Participate honestly and candidly – bring your best thinking and give your all

Go Over Everyone’s Ideas

Once you’re into the actual Strategic Retreat, and have set the tone, you can start by simply going over everyone’s ideas that they submitted prior to the retreat. It’s a good idea to have these already summarised and in dot point form (perhaps in a powerpoint presentation), this way no ideas get skimmed over or left out. You can then ask the contributor to elaborate on their thinking.

You should also have some ideas that you’ve contributed yourself and explain them (just like the other team members).

As you go, you should capture these ideas – either on a whiteboard, using large post-it notes, or electronically (if you’re using a projector).

Depending on how many people you have along, this part of the process may take some time – perhaps half a day.

Brainstorm New Ideas

During the last process, you may have come up with some new ideas which should have been captured as well, but make sure you also leave time to do a bit more group brainstorming at the end of this session. Hearing other people’s ideas may spark something new, or an extension of someone else’s idea.

Group and Sort

Now starts the hard part! Of all the ideas you have, think about which would go together as a project or initiative that can be actioned? Start putting potential projects together. Practically, this is easiest if you’ve opted to capture your ideas using post-it notes. Simply move the different ideas around into different groups and then give that “project” a rough working name. For instance, these could be things like; Improve Website Usability, Develop Customer Guarantee, Boost Sales Team, or Add New Product Line. At this time, don’t worry about how feasible these are.

Prioritise, Prioritise, Prioritise

And now it gets really hard! Looking at all of the potential projects you now have on the table, you need to think about which projects you should actually embark on.

There is a system for how I like to prioritise, but as this post is getting long, I’ll explain that in depth in a post dedicated to prioritising projects. (Make sure you’re signed up to receive our emails so that you’re notified.)

Set up Initiatives

So, now that you’ve decided which projects you’ll embark on, you need to set up a system for actually getting them done. You could just take this all on yourself, but then you’ll lose some of the commitment and buy-in from your team. The ideal thing to do is to set up “Initiatives” or “Projects”. Try to resist the temptation to embark on too many initiatives. By opting for fewer, there’s a greater chance that each will get finished.

Each initiative should have a leader and several team members (preferably ones that were passionate about this idea and whose expertise and skills will help make this happen).

Once the initiative teams are formed, you can start fleshing out the details. Start with headings such as;

• Objective
• Success Criteria
• Milestones and Dates
• Steps (encourage the team to be as detailed as possible, especially about the first few steps)

Wrap up your Strategic Retreat by thanking everyone again, and summarising where you started and the upcoming initiatives you now have on the table. Let them know how excited you are to see these initiatives unfold.

Back at the Office

The last thing to add here is to make sure that these initiatives actually get the attention they deserve once the day-to-day busyness sets in. Encourage each initiative team leader to set weekly meetings with their team and focus on the speed of moving forward. Have a weekly meeting with the initiative team leaders where they are expected to report their progress to you.

If your team is very small and there is only a handful of you, perhaps each person has one or two initiatives they are responsible for. Again, have the weekly meeting where you discuss progress and resolve any obstacles they might face in getting it done.

Have you ever run or been part of a Strategic Retreat? Did it achieve its objectives? Why or why not?

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