Strategy Sessions That Work

Strategy Sessions That Work

  • Colleen Murray Colleen Murray
  • Lauren Magrisso Lauren Magrisso
  • June 24, 2022

Every team needs to make sure they’re aligned on the best way forward. A great executive offsite or strategy session can be a critical tool for business success. What makes for a great offsite?

In times of rapid change, it’s important for leaders to align quickly on objectives and actions. Business simply moves too fast for different functions to go off on their own for extended periods of time without checking in. In most healthy organizations, we see leaders coming together for a strategy session at least once a year, and often once a quarter. These sessions give decision makers a chance to step back, share some perspective on what’s going on with the business, and get aligned on how to move forward.

Successfully executed, a strategy session can be a transformative experience. It becomes a chance for every member of a leadership team to offer insights about what’s going on with the business, contribute ideas about how to solve the challenges that the company faces, and ensure that the organization moves forward together. When executed poorly, however, these sorts of off-sites and retreats devolve into tedious PowerPoint shows where real issues aren’t addressed, new options aren’t put on the table, and real alignment doesn’t happen. At their best, executive strategy sessions are an effective vehicle for driving change. At their worst, they’re an annoying waste of time. The results aren’t a matter of luck. A few simple techniques can help any leadership team looking to have a successful session, stack the deck in their favor.

1. Set the challenge in advance.

Organizations significantly increase their likelihood of success when they have clear challenges to focus on. Perhaps growth has stalled and new opportunities need to be identified. Perhaps a new competitor has entered the market, disrupting the existing business model. Perhaps costs are way out of line and demand hasn’t increased like originally projected. Every business has multiple challenges. However, most businesses have one or two challenges that are the most important. Success depends on focusing the collective energy of the company on tackling those problems first.

That said, it can be surprisingly difficult for a leadership team to clarify important challenges in real time. All too many teams are comprised of people who are excellent at solving problems, but less adept at defining them. What’s more, the view can look different depending on where you sit. Finance leaders can see that spending is out of control, while R&D managers see the need to invest in a long-term pipeline. Too many sessions fail because teams either burn up their time trying to figure out what the problem actually is, or trying to argue about the relative merit of alternatives that are the solutions to very different problems.

You can make the most of a strategy session by defining the challenge in advance. Don’t do it in the meeting. Have a smaller team spend a little time analyzing ‘voice of the customer’ information, competitor trends and financial performance data to get to a clear and succinct problem definition. Conduct a round of stakeholder interviews to get input from different parts of the business. If possible, run an internal survey to ask employees what they think the most pressing challenges are. In our work, Jump has found it useful to employ a diagnostic tool to aid leaders in getting a sense for what their own managers think matters most. Individual opinions can vary greatly. But there’s usually tremendous wisdom in a company’s collective intelligence. The time you spend together as a leadership team is precious. Don’t waste a minute of it trying to define the problem. Set the challenge in advance.

2. Include both deciders and disruptors.

When planning a strategy session, the biggest decision a leader makes is who’s in the room. It’s critical to get the key decision makers, namely the folks who’ll be on the hook for taking initiatives forward. At the same time, it’s critical to include the voices of anyone who can help the team evolve its thinking and get to the very best answers.

Many session planners decide on attendance by resorting to hierarchy. Participation is determined by identifying business leader’s direct reports. Others determine participation by level, by who is an SVP and who isn’t. Meeting organizers can feel compelled to include everyone at a particular level of seniority, so that no one feels left out. As participant head count rises, the meeting quickly becomes unwieldy, turning participants into spectators. Of course, org charts are a reflection of the business’s key decision makers in the broadest sense. But they can’t be counted on to reflect who the right people will be to rally around a particular strategic challenge.

Who should come? Start with primary business leaders. While that may sound obvious, we’ve encountered the occasional exec who tried to delegate away their own participation in the meeting. Leaders matter. If a pressing crisis arises that prevents the business leader from attending… reschedule the meeting. With the business leader on board, include those direct reports who will be required to execute on any plan that results. Leave out direct reports who won’t be on the hook for implementation, either because they run a peripheral group or an unrelated support function. The most effective sessions have fewer than fifteen people. Organizers will, of course, need to thoughtfully communicate their logic of who’s included and why to both participants and non-participants. Communication to those not invited will be much easier if there are other sessions being held that would be a better use of their time.

Once key decision makers have been identified, planners can break out of the hierarchy. Go beyond decision makers to include people who’ll disrupt the conventional wisdom. Are there individuals one or two levels down from the exec team who will need to personally drive downstream initiatives? Include them. Are there a few individuals who are closer to the problem or who can otherwise push the team’s thinking? Invite them as well. The inclusion of valued outsiders to the core team can transform a conversation. And yet, many executive teams leave them out. We’ve seen consumer packaged goods teams that attempted to craft a Hispanic marketing strategy, but failed to bring in Latinos from their own company, consumer electronics execs who were discussing social media without any digital natives present, and beauty products retailers who had no women in the room. It’s certainly concerning when greater diversity isn’t present in the basic org chart. It’s suicidal when that diversity isn’t included in crucial conversations. There’s no good excuse for not including “outside” voices that are still inside the company. It’s simply too easy to not do. Those voices will help push the conversation, and disrupt old ways of thinking. To ensure you get both broad input and direct accountability, include both deciders and disruptors.

3. Find a hybrid facilitator.

The quality of any good meeting is dependent on the facilitator. A trained and competent moderator knows how to bring out different voices, push the team’s thinking, and ensure clear alignment. That’s a skill that most of us don’t have, if only because we don’t do it every day. Moreover, even leaders with effective meeting facilitation chops can stumble when trying to facilitate their own team. That’s because you can’t be responsible for effectively bringing out different voices while offering your opinion. The game breaks down when the quarterback tries be the referee as well. Get an outside moderator.

Of course, we’ve all been in meetings where an outside facilitator was unable to get the job done. Voices get heard, ideas are put out there, but the decisions aren’t made. That’s because too many professional moderators seem to lack the business acumen needed to bring a team to a satisfactory conclusion. Facilitation isn’t just about writing on the white board or telling everyone when to break for lunch. Nor is it about simply team building. It’s about getting the business to make the best decisions possible. A strategy reached by groupthink may not actually lead you down the right path.

The best facilitators know how to push the thinking forward. And they know what good strategy looks like. In short, they’re not just meeting facilitators; they’re strategists who know how to run meetings. This kind of hybrid strategist/facilitator will make sure you’ve considered analogous players, competitors and the forces affecting your industry. They’re aware of industry practices. They’ll encourage you to come up with multiple options, challenge your frames and consistently reference what success looks like for your organization. They can identify seemingly good ideas that actually have a high chance of failure. Of course, they’ll get the team aligned. But they’ll also make sure that the team is aligned on the best decision possible. When evaluating potential moderators, ensure that you’re finding someone with the necessary business acumen to do the job. Hire a hybrid facilitator.

4. Get people leaning forward, not back.

Execs are busy people. The time that they spend together should be of the highest possible value. The goal of any strategy session should be to work together to push the thinking forward: to come up with new possibilities, evaluate different options and make real commitments for moving forward. If the goal is simply to give meeting updates or share information, that’s probably best done offline or via email. Of course, sharing information isn’t the same thing as buying into it. Most people simply don’t get on board with an idea if it’s presented to them. Real commitment happens when people act as co-creators of the solution.

Strategy sessions fail when they’re reduced to a daylong series of PowerPoint presentations. People start to lean back like they’re watching a show. They may even zone out or start multitasking. When they do engage, it can be in the role of a critic rather than a co-creator, as if their job was to poke holes in an idea, rather than come up with a better one. Worse yet, studies show that people’s ability to simply retain what’s presented maxes out after about ninety minutes. Sitting still and talking at a group will only retain their attention for a short period of time.

The creation of great strategic action requires people to be active participants, not a passive audience. Make the meeting a work session, not a presentation. Design the day to eliminate any time spent staring at a slideshow. If information needs to be shared, make it a pre-read. Get people in the same room, not dialing in by phone or video. Limit the amount of time that people spend just talking at each other. Instead, get them to roll up their sleeves, move around the room, write up their ideas and engage with the content. The goal is to design an experience that gets people to lean forward and create, not lean back and critique.

5. Force choices, ideas and actions.

Any strategic conversation will demand some degree of abstraction and generalization. It’s important that teams are using a strategy session to truly step out beyond the demands of the day to day. Without that kind of big picture thinking, you can end up having detailed conversations about how to rearrange the deck chairs on the Titanic.

Even the smartest execs can struggle with thinking about ideas in the abstract. Many folks get frustrated when the conversation feels overly academic. The implicit pressure to seek alignment can encourage individuals to speak in broad generalities that mask real differences of opinion. Left to their own devices, even some of the best teams can end up offering up platitudes that sound more like a U.N. charter than a strategic plan. Alternatively, action-oriented leaders may feel the urge to leap on the first concrete idea they can think of.

Rather than talking about an issue in the abstract, ask participants to generate examples of how this issue manifests. Then encourage them to notice patterns in the examples they cited. Quickly follow up those observations with a call for multiple possible solutions. Finally, select the solutions that will be the easiest to implement while having the biggest likely impact. Most successful decision makers are incredibly concrete and have a bias for action. Effective sessions force choices, produce multiple ideas and commit to real action.

A Successful Session

The late business professor and guru Peter Drucker once remarked that “Culture eats strategy for breakfast.” The best laid plans are often overtaken by what actually happens on the ground. While experience certainly seems to bear this out, it’s important to note that you don’t have to pick between the two. Strategy and culture should work together. And, done right, a strategy session can be an effective tool for both. A great strategy session can help leaders to step back and imagine bold, new alternatives. Simultaneously, it can be a way to strengthen the team and the first step to shifting a culture. Great sessions should be energizing. They should be insightful. And they should leave participants amazed about how quickly they were able to get to clarity.

Whether you are hoping to change direction, ramp up an existing initiative or looking for a new path forward, a great strategy session has the ability to harness the power of your people and move your organization to the next level. Success comes when teams focus on the right questions, engage people to come up with great solutions and test their ideas through experimentation. Great strategy is never the product of a single moment in time, but the hundreds of decisions that follow. Set up your sessions to enable better decision-making and move your business forward.

Colleen Murray


Colleen works with executives through large-scale transformations: reinventing businesses and unlocking new markets. Her experience has crossed a number of industries, including consumer electronics, digital entertainment, consumer packaged goods, and office environments.

Lauren Magrisso


Lauren brings an expertise at the intersection of social research, design and business strategy. She has helped some of the world’s most admired companies tackle critical challenges, from climate-beneficial product strategies to the future of retail.