4 Questions Every Strategy Retreat Should Answer

You have an upcoming team strategy retreat but don’t have an agenda yet.

Don’t worry; I’ve got you covered!

You want to make it valuable, worthwhile, and productive, but you’ve never run a strategy retreat.

Don’t worry; I’ve got you covered!

Several years ago, I was elected to the board of the National Speakers Association in NYC. As we approached our board strategy retreat, I took some time to talk one-on-one with each board member to learn about their vision and plan for the year.

Through these conversations, I realized we didn’t have a clear vision or plan as a team. Everyone said something different, and our team was all over the place.

I knew the only way we were going to walk away from the upcoming strategy retreat feeling aligned was if we tackled these four questions at the retreat: 

  • Where are we going? 
  • What are we going to do? 
  • Who is going to do it? 
  • When are we going to do it?

Sounds simple, right? Even though the questions may sound simple, getting the answers aligned as a team is much more complicated than you might think.

Breaking Down Each Question:

Where are we going?

Imagine you are standing at the base of three mountains with your team. You can see the peak of each mountain, and your team looks at you and says, “Well, boss, which mountain are we going to climb?” This is the big picture, the final destination. This answers the question, “Where are we going over this next period of time?”

You are plugging in GPS coordinates for your team by picking a mountain peak. The retreat I was a part of for the National Speaker’s Association was to plan for the whole year. Other groups will do 3 or 6 months. The answer to this question is based on where you are going over the next period of time, which is usually one year, six months, or three months. The team is looking to its leader for guidance here. Are we trying to launch a new product this quarter? Are we focusing on sales growth? Or are we focusing on reducing expenses and streamlining our operations? By answering this question, you and your team will have a clear framework to answer the next question.

What are we going to do?

Our team has a Google Excel file called “The Big Brainstorm Bucket.” The idea of this file is that anytime someone comes up with an idea to help improve or grow the company, it goes on this document, and they know that during the “What are we going to do?” part of the strategy retreat, it will get thrown up as an option for us to do. I’ll admit it also has a bunch of “are we really considering this” type of ideas too.

Our brainstorm doc has some very tangible ideas, such as cleaning up our CRM and removing all duplicates, to crazy, wild ideas like getting Swift Kick accredited for continuous learning credits in higher ed. The point of our Big Brainstorm Bucket is that every idea on the list will get a chance to happen at each strategy retreat. Most never do.

There are three steps to filtering the list down to what we will actually do.

The first step is to have each person in your group individually pick which ideas from the list they think work well with the answer to the first question, “Where are we going?”

The second step is to reveal the answers. Any idea above the majority of votes automatically goes on to the next round, and an idea with less than that gets a 2-minute debate to see if the group changes their mind and is willing to move it on to the next round.

The third step can take a while because you will discuss each idea in depth to determine its place on The Veto Matrix.

What’s the Veto Matrix, you ask?

The Veto Matrix is a four-part chat based on two criteria… On the y-axis, you ask how much value this idea will give the organization. On the x-axis, you ask how many resources (time, money, and effort) it will take to implement this idea.

Once you discuss and plot each idea on The Veto Matrix, it’s time to filter things down again. Items in the lower left corner should be delayed. They should be returned to the brainstorm list for review at a future retreat. Items in the lower right only do if time allows for them. So, keep them on the list for now. The items in the upper right should be done. They are higher-value and low-resource activities, so they are no-brainers. Items in the upper left corner should be discussed again and filtered down because you must be very selective about your choice. These projects will take up the bulk of your time. Our team usually has ten items in this box, but afterward, we’ll filter out at least six because we know we won’t have time to do them this quarter.

Once you have gone through each box, you are done with “What should we do?” And it’s time to move on to “Who is going to do it?”

Who is going to do it?

By now, every item left is something that you and the team should be okay with doing because it fits perfectly with the answer to your first question, ” Where are we going?”

But that’s still not enough because there is still one final filter: ” Who is going to do it?” Every task and project needs a champion. And someone should only be the champion if they can say yes to these three questions: Does this project fit within the wheelhouse of my role? Am I excited to do this project, and/or know I need to do it for the company’s sake? Do I have time to do this project? If they say yes to all three, they will put their name next to the project. That’s how you answer the question, “Who is going to do it?”

Our team takes this one step further. We map out roughly how many extra hours we must allocate to new projects for the next quarter using a simple math calculation. First, we find out how many work hours are in the quarter. Then, we subtract how many hours we spend caring for our regular daily/weekly/monthly work. Then, we subtract how many hours will be used for personal trips, holidays, or events like conferences. The final number is how many hours we have for the quarter to allocate to new projects.

Once everyone has gone through the list of possible projects left and put their name next to the ones they are going to work on or lead, it’s time to move on to the last and final question.

When are we going to do it?

If your strategy retreat is to set your team up for the next three months or quarters, then the answer to this question is what week or weeks we are going to work on each project.

To do this, first, each person should map out what their quarter looks like week by week. Some weeks will already be jam-packed because of pre-planned events, conferences, or holidays. Knowing this beforehand is good so you don’t put all your projects on those weeks.

Have your team review each of their projects and slowly place them into the week or weeks they plan to work on them.

Some projects will require coordinating schedules between everyone involved so that the weeks chosen will work for everyone.

Once every project is assigned a specific week or weeks, it should be transferred into your team’s preferred project management system, such as Asana.

And there you have it! Your roadmap for a strategy retreat that doesn’t just go in circles but actually takes you somewhere.

Recapping the 4 Key Questions That Will Revolutionize Your Retreat:

Where Are We Going? – This is where you choose your mountain to climb. Set your big-picture goal and align your team’s compass toward that peak.

What Are We Going To Do? – In the brainstorming and filtering stage, you turn ideas into actionable plans. Remember, it’s not just about dreaming big; it’s about being smart with The Veto Matrix.

Who Is Going To Do It? – Here, you assign champions for each task. It’s all about matching projects with passion, expertise, and bandwidth. If it’s not a resounding yes to the three questions, it’s a no.

When Are We Going To Do It? – Schedule it out. Allocate your team’s time wisely, considering pre-planned events and individual capacities. It’s about making every week count.

Remember, a strategy retreat is more than just a meeting; it’s a launchpad for your team’s success. It’s where clarity meets action.

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