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Design & Execute Your Best Strategic Thinking Session Ever


It’s go time!

You’ve done your pre-planning and preparation. Your participants have done their pre-work. You’ve conducted customer interviews and market research.

Let’s take all those valuable inputs from the prep phase and put them towards the creation phase of your strategic thinking process. And, yes, we use the term “thinking,” not “planning.” That’s because we can't really plan for the future, we can only prepare for it.

In a rapidly changing world, we have no idea what's coming next or what new challenges might arise. Plans might change, but flexible and adaptable strategic priorities can pivot as circumstances shift and opportunities arise.

Who to include

You need the right mix of people in the room for a great strategic thinking session.

Make sure everyone who was involved in pre-planning is involved. And ensure the key people responsible for executing and measuring the strategy moving forward are there, too. Who do you need to engage to create commitment and increase the likelihood of follow-through when implementing?

Don’t keep the guest list confined to your leadership team. Go for a diagonal cross-section of your organization that cuts across departments and units and encompasses various levels of management right down to your frontline staff. It’s messier, but ultimately, this diversity will result in better strategy, more buy-in, and higher ownership in the final output.

If you’ve got a large group, break out into small groups that report back to the whole, so everybody is a part of the conversation. If the group gets too big, it will feel too much like public speaking, and some people will stay silent. Make sure it feels like a conversation, not a public address.

Session structure

Strategic thinking is hard, tiring work. It’s essential to design your sessions with people’s energy levels in mind to maximize their input and not drain their batteries.

We find partial day sessions (roughly 6 hours) provide enough time for rich discussion without depleting everyone. Along with ensuring you get the best out of your participants, it’s enough to build in some unstructured social time before and after the official schedule for participants to connect and share ideas. (When we lead virtual strategy creation conversations, we typically break the process into even smaller, bite-sized sessions of 2-3 hours.)

Set the scene

Kick things off with a review of your current state. This is where you share your people’s SWOT responses, customer interview intel, and market research.

This foundational information will inform the conversations to come.

Define Your Purpose

A purpose-driven strategy allows people to think more broadly about the value you deliver, to keep the focus high-level and even aspirational. Spend some time near the beginning of your strategy thinking session discussing what your organization truly provides.

For instance, if you're a steel maker, instead of getting locked into the idea that “we make steel,” encourage participants to think about the real value you deliver, such as “we provide the resources people need to make things.”


From here, invite participants to start to share their impressions from the research. Some general questions to kick off the discussion:

  • What markets are growing, and which are shrinking?

  • Where are our growth opportunities?

  • What differentiates us?

  • What target markets do we want to be in?

  • Where should we consider reinvesting?

Initially, you want to be as open as possible (don’t worry, you’ll converge later). These wide-ranging, divergent conversations make space for big ideas to bubble up.


Once you’ve got a lot of great ideas generated, it’s time to focus.

Ultimately, your aspirations and the opportunities you’ll pursue must align with your resources. If there’s a huge opportunity you can't take advantage of because you just don't have the human or financial capital to access it, it’s not strategic, it’s just wishful thinking.

To keep the discussion broad yet focused, remind participants to consider a few key questions:

  • How can we create unique value?

  • Do we have, or can we develop the right competencies?

  • Is this the best use of our capital? (Intellectual, human, financial, etc.)

Encourage dissent

Universal head-nodding is the worst thing you can see at a strategic thinking session.

There should be a lot of different opinions. Don’t shy away from respectful conflict. You want to have the most open, wide-ranging conversation possible to get at the deep work of making choices and articulating priorities.

The biggest mistake most organizations make in strategic thinking is not challenging the assumptions, beliefs, and perceptions that made them successful and underlay their current strategy. In Stall Points, Matthew S. Olson and Derek van Bever write, “you must continually articulate and stress-test the assumptions underlying your strategy because it is the assumptions that you believe the most deeply or that you have held as true for the longest time that are likely to prove your undoing.”

Pivot to execution

Now, it’s time to talk about how to get from strategy to results, to connect the dots between where you are and where you want to go.

Based on the discussions you’ve had so far, list the top three to five strategic goals that have emerged. These should be specific. They might relate to things like market share, profitability, total revenue, product development, or service levels.

Next, ask yourselves: what are we going to do to attain these?

List five to seven broad actions to drive those strategic goals. For each, you’ll need a scorecard. What indicators will you want to track to know if you’re effectively executing your strategy?

From each of those five seven actions, list three to five projects, creating a portfolio of potential initiatives. Prioritize and sequence the projects, whittling the list down to the highest impact projects you'll undertake.

Congratulations! You’ve now got a solid strategy to drive your organization forward.

Next up in our Stages of Strategic Thinking series, we will be sharing posts on:

  • Execute: Actioning your strategy to make it real

  • Measure: Calibrating results against projected goals

  • Top tools: A roundup of our favorite strategic thinking tools

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