How to run a strategy and design day

Every six months our team gets together to reflect on where we’ve been and where we are going. This type of activity is extremely important, even for the healthiest of teams.

Example of the types of postits we post ‘Live your best life’

The benefit:

• Strategy days defibrillate your team’s heart and prevents it from stagnating. You want to constantly inspect, adapt, grow, evolve and measure your team, just as much as you evolve your sprints, products and services.
• If your team creates its own strategy they will be more likely to own and execute it. People like to be part of a change movement, over being mandated that a change needs to occur.
• Your team will connect through ideas, aspirations and challenges. This is extremely important as your team grows. You want to fast track the ‘getting to know you’ phase, as it can slow down productivity and disrupt the beautiful culture that you’ve been growing.
• By collaborating on professional development plans your team can leverage diverse skillsets and support each other to grow. Everyone has different strengths and weaknesses — use them to your advantage.

This might sound very airy-fairy, but strategy days are good business. If you’ve ever worked within a team that didn’t get along, or you’ve had to replace an unhappy team member, you will know how expensive and disruptive these things can be.

What type of strategy are you wanting to set — long or short term?

When it comes to setting a strategy or goal there are two things to take into consideration — are you setting finite or infinite goals? I’d recommend reading Simon Sinek’s book The Infinite Game for a deeper understanding of the two.

The TLDRs (too long didn’t read) of it all:

1. Finite games, like football or chess, have known players, fixed rules, and a clear endpoint. The winners and losers are easily identified.
2. Infinite games, like business or politics or life itself, the players come and go, the rules are changeable, and there is no defined endpoint. There are no winners or losers in an infinite game, there is only ahead and behind.

We had a defined timeframe and ‘players’ so the types of goals we were looking for were finite. We stayed away from infinite goals like … be more awesome, have the largest team, have the coolest projects, be the best.

North Stars

Our finite goals do feed into our infinite goals — which have already been set. All teams need a North Star, something to sail towards. You may never get there and you may change course, should the seas change, but a team without a reason can start to feel demotivated and you will most certainly lose your way. 🧭

So what does a Strategy and Design team do for their own strategy and design? We do the same as most teams…we just add a little bit of spice. 🧂

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Let’s get into it

What does a good Strategy and Design Planning Day look like and how long should it take?

What an awesome team looks like.

Timeframe

How long is based on what you’d like to achieve and the tasks you need to do to achieve them. I wouldn’t recommend working backwards from a timeframe and filling time. We knew our goals, came up with activities, and identified how much time we would need. We added it all together and added in some buffer — the end result was 4 hours. These things don’t need to be done in one chunk. If you are short on time or energy you can break it up.

Also, this is the first step. Our real timeframe was 6 months. We check in and track how we are doing regularly. You don’t want to do these things once and then let them fall away. This is bad for two reasons:

1. All that hard work was for nothing.
2. The next time you do this activity people will be less responsive.

It’s better to do nothing than to do something and then not follow through.

Goals

Our goal was to create list of actions that could be completed in six months, that resolve some of the things that are holding us back, implement some of the things that will make us more awesome, and grow us as individuals. The list of actions needed to feed into and serve our Infinite Game.

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The Warm Up

First, we put fuel in the ol’ tanks with Lunch and Bubble Teas. Bubble Teas are fun, delightful, and chilled….just like us. Wink.

The team warms up and breaks the ice.

Second, we played two icebreakers. We all know and trust each other. We also have a culture of feedback and transparency, so we generally don’t need to ‘break the ice’, but we do love a good laugh and that’s exactly what our icebreakers did.

Icebreaker 1: Collaboration Portraits

What a collaborative portrait looks like.

How:

1. We all put our name on a piece of paper and draw the shape of our own head — using our opposite hand. Then we pass to the left.
2. Then we drew the nose of the person to our right and then pass to the left.
3. We continue doing this until everyone has had a turn contributing to the portrait and your portrait returns back to you.
4. The end results are hilarious and this picture is now your portrait for the rest of the day. Oh boi.

Why:

Drawing each other further developed our individual connections with one another, while quickly drawing with your opposite hand teaches you to embrace the imperfect.

Requirements: Just pens and paper.

Icebreaker 2: Pick a Topic

How:

1. We were dealt four cards. Each card had a question on it that we had to answer.
2. We give everyone 4 cards so they can have options — We don’t want anyone answering questions they don’t feel comfortable answering.
3. We all take turns answering questions.

Why: Sharing our stories and hearing the stories of others helps create a trusted, safe environment so that we can bring our full selves to everything we do. We wouldn’t recommend this activity for teams who don’t work together often.

Requirements: We used the ‘What’s your story?’ set by Corban & Blair. There are plenty of icebreaker cards available online or you could create your own.

Why two icebreakers you ask? You can do one, but as I said, we like to add a bit of spice.

Divergent & Convergent Thinking:

Next Cornel ran a retro. You may have seen or done the sailboat retro before — it is a fine retro, but when you’ve done as many retros as we have….you want to mix things up. Some popular themes: The Witcher, Mario Cart, Zombie Apocalypse, Harry Potter, and American Football. The outcomes are similar to the sailboat, but the experiences are always fun and memorable.

Cornel running a spicy retro.

This year’s theme was online shopping, more specifically ASOS. Stay with me.

1. Cornel created ASOS themed titles and stuck them on our windows — first world problems, we don’t have large enough whiteboards or walls in the room we were in. It does prove that any room can be a collaboration space.
2. We were all given 5 minutes to jot down responses and ideas for each of the themed titles.
3. What’s on Sale / Aka — What do we love about the team, our projects, our work etc?
4. What did we keep / Aka — What do we want to continue doing?
5. What do we return / Aka — What don’t we love about the team, our projects, our work etc?
6. What are we adding to our cart / Aka — What are the actions for the next 6 months? These are a mix of outputs from the previous areas.
7. We then divided the actions amongst ourselves and individually or collaboratively make those things happen. E.g Morgan is responsible for creating a skills sharing program, I’m responsible for creating a remote working day at a cool location, and Josh is responsible for running a North Star workshop — to name a few of our activities.
8. All of the actions will be rolled out over the coming weeks. We will check in on how we are doing as we go and at our next planning day.

Our Individual Purpose

Josh facilitates our individual purpose.

For the last activity of the day (facilitated by Josh), and taking the ASOS theme one step further, we each created our “Profile” pages. Loosely inspired by the Ikigai philosophy (Japanese for a “reason for being”), this helped us define our personal perspectives and goals. The questions we answered were: ‘What are you good at?’, ‘What do you love?’, and ‘What you’re not so good at?’.

By individually reflecting on these questions and then discussing our answers with the team, we achieved two things:

1. We get a better understanding of our team members’ strengths, weaknesses, skills, and passions;
2. We created a short mission statement; aligning the things that each of us love doing, to what the team needs (these were actions that came out of the first half of our workshop).

With our individual missions in hand; everyone feeling empowered to chase their personal goals, and a list of items the team wished to action, we set off to improve and refine our team.

In conclusion

When did your team last come together, shared a meal, and candidly talked shop? With the right balance of thought provoking questions and fun, in about 4 hours, you can (re)fill your cart with passion and direction. And don’t forget to inspect and adjust your goals in 6 months!