Is tactical work overloading your team? Do you need to stop and think about improving your skills and processes? Do you want to overcome your team's barriers and think bigger?

Developing a strategy isn’t something you can rush. We know this because we tried and we failed. It's impossible to think about strategy in a one-hour meeting squeezed in the middle of a busy day. We tried to find a balance, dedicating 30 percent of our sprint to strategic topics. Yet, in every single sprint, a higher priority strategic task would take over that allocated time. It just wasn’t going to work for us. To work on strategy, we needed to focus!

So we tried a crazy idea; we decided to plan an entire day to focus on strategy. We would work on nothing else. And to our surprise, it worked! This is a story about how my team found a simple solution to deal with these problems. Every two weeks, the whole team dedicates a full day to strategy. We call it, the Strategy Day.

Focus on strategy, nothing else.

We Don’t Have Time for That!

You might think that you can’t afford to dedicate a full day of your team’s time to strategy. It probably seems like a huge sacrifice, but let me frame it like this: what’s the impact on your team’s work of, say, a national holiday? Not much, right? Think of a strategy day in the same way, except your team will actually work on stuff that matters. If you do this every two weeks, it represents 10 percent of your team’s time. Also, consider the cost of not working on strategy...

So You Want to Do a Strategy Day

Here’s what you’ll need to do first and foremost:

  • Pick a topic: We keep a prioritized list of topics in our backlog.
  • Set a date: Pick a day and reserve a room in your office or a place outside where your team can work together. Be sure to have a whiteboard that people can write on.
  • Cancel or reschedule everything else: The entire team should cancel or postpone any other meetings on that day. You want to have everyone focused and in the space working.
  • Reserve the time: Include the day in your team’s schedule. We treat this day like a holiday; the time can’t be renegotiated for something else.
  • Bring your work tools: Paper, pens, pencils, post-its, computers, etc.
  • Bring healthy (and not so healthy) food and drinks: don’t forget that you all need to survive the day.
  • Bring a timer: You will be on a tight schedule.
  • Select a facilitator for the session: A few tasks need to be done in preparation (we’ll detail them below). There’s no big overhead, so the facilitator may also participate in the session.

What You Won’t Need

As I said, it’s a one-day event, so, there is no need to prepare (besides gathering the items listed above and scheduling the event)! Think of this as your one-day project: on this day you will discover the problem, gather all the information you need, make a plan, execute the plan, and wrap up. All in just one day!

This is how you might feel when you are about to start strategy days.

The Morning

It’s the morning of the strategy day, and your team meets in the room you booked. It’s time to kick off the day.

9:00–10:45 - Share context. Lay out everything that you have on the topic of the session. The team will have a lot to say. The facilitator should take notes about everything that may be relevant; this will help you later. During this stage, everyone should participate—there is no critique, no judgment—you want to get the most information possible.

Invite your manager to share context with you. Managers are always busy, but they do have a lot to share, so bring them into the session! If the topic that’s being addressed is something your manager is really interested in, consider inviting them for the whole day.

The facilitator gets to write a lot!

10:45–11:00 - Take a break.

11:00–11:30 - Define what you want to focus on. What are your goals for this session? Be sure to write a goal on the board and keep it visible throughout the session.

11:30–12:00 - Draft a plan for the rest of the day. How are you going to reach that goal? Start detailing how you will get there. You need a plan!

A draft of a plan for strategy day.

After we’ve decided on a focus, here’s how we plan the rest of our strategy days:

1. Define the tasks. First, define tasks in collaboration with the team; these tasks are the way to reach your goal.

2. Split up the team. Next, assign tasks to each of your team members. If your team is small, the work can be done individually. If your team is larger, you can have teams of two deal with each task. Estimate with each subteam how much time each task will take (in minutes).

3. Work on tasks, then share and record. Always save some time for the teams to share their work and gather feedback. Try to take no more than an hour for this.

4. Wrap up the session. Save 30 minutes at the end of the day for this. Identify what went well, and what can be improved.

If at the beginning you were hesitant in dedicating a full day to strategy, by now you’ll probably be wondering where all the time is going. If you don’t think you can cover everything, don’t worry. You don’t have to do it all in one day. Prioritize what matters and what is really necessary. Reserve some topics, and solve them in the next strategy day or in a follow-up meeting.

And… half of the day is gone!

Time flies, keep on schedule.

The first few times we did this, we were surprised by how quick the morning went. However, the work you do in the morning is the key to focused and productive work in the afternoon. At this stage, you have a plan and your team is committed to getting the job done. You have essentially created alignment, and everyone is now in the zone with what you are trying to solve. Embrace the risk of failing. You might end up with nothing useful, but at least you tried, and most importantly, you tried it while keeping the risk and impact low.

12:00–13:00 - Go and have lunch. You are halfway there.

It’s time for lunch. A full day doesn’t seem excessive, does it?

The Afternoon

13:00–13:15 - A quick recap of the goals and the plan. It’s time to start putting the plan into action. Each team or individual is responsible for registering their outputs to a shareable medium. We used Google Slides for this.

13:15–17:00 - Stick to the plan! The facilitator sets the timer and keeps everyone on track with their time estimates. It’s important that the facilitator keeps everyone on schedule, otherwise, the group won't stay on track and reach the goals. The pressure of time helps keep everyone in the group focused, moving from task to task, and not rambling over the details.

Our beloved timer.

Keep the room as quiet as possible. Remember, focus is essential. Everyone should talk only about the work at hand. If a team needs to discuss something that may be disruptive, they should move to another room.

We do a lot of group exercises with post-its.

When sharing outputs, be careful to facilitate the discussions and avoid diving too deep into details. If there is a topic that needs further discussion after the session, consider having a section on your whiteboard to take note of these topics. The “parking lot” section, as we like to call it, is where you write this stuff down so you don’t lose it. You have to know when to stop.

A team member, working remotely and sharing her work with us, and a pink swan.

17:00–17:30 - Feedback. Now is the time to gather what worked and what didn’t. Everyone should grab a few post-its and take five minutes to write down three positive things and three ideas that could improve the session. When the time is up, everyone gets two minutes to explain their choices. Again, the timer is your friend until the very end!

Gathering feedback on the session

Keep the GOOD STUFF post-its; work on the TO IMPROVE post-its before the next session.

Well, Did it Work?

Well, in a nutshell, yes, it did!

Here are a few examples of topics that we explored during our strategy days and that would have been in our backlog for a long time before ever getting tackled, if ever:

  • Setting up a new initiative to start the roadmap of our product.
  • Checking the state of the UX and Product Design specific programs in R&D and defining next steps.
  • Understanding and identifying the struggles of first-time users of our product.
  • Drafting our product vision and looking at how we evolve as a team in an R&D department that is growing rapidly. We split this one into two sessions, and our manager was involved in both days.
  • Writing articles about what we do (this article was envisioned and drafted on that strategy day, along with six others).
  • Planning the team’s participation and activities in the OutSystems Worldwide Developer Conference.
Our awesome booth at the OutSystems Worldwide Developer Conference with plenty of activities. We planned the booth on one of our strategy days.

What About Impact?

The strategy days changed how we do things on the Product Design team. Working together is highly rewarding, and it’s also the best thing you can do to improve team focus. It’s worked for us; thanks to strategy days, we are a stronger, more unified team. On strategy days, we get to try things outside of our daily work and think strategically on a higher level. This kind of activity impacts our team’s maturity: the process of understanding a problem, coming up with a plan, executing it, and actually seeing results in just one day provides a lot of pragmatism experience. Plus, everyone gets a chance to think strategy along with their managers. Last but not least, we have delivered some awesome outputs with little impact on the tactical stuff or our day-to-day work.

There’s always a lesson in failing. Here’s what we’ve learned by failing:

  • Snacks and breaks are REALLY important to keep the flow and energy (and the peace).
  • Keep the goals visible throughout the session
  • Act on the feedback from previous sessions.
  • Always work with the timer; never do open discussions without the timer!
  • Some sessions need a follow-up meeting to wrap up all the loose ends. Typically we add a small task into our backlog and allocate it to a team member to complete after the session.
  • As the team scales, this becomes more challenging. If your team has more than seven people, consider splitting the team into two separate sessions.

Are you ready to adopt a strategy day? Let me know!