Helping Groups Be More Strategic

Practical tips to help build the capacity and capability of any group to have more strategic discussions and make more strategic decisions.

Approximate reading time: 10 minutes to skim; 15+ to contemplate and apply.

Note: In writing this essay, it quickly became apparent I could fill a monograph. To keep it to the length of a magazine feature article, I intentionally chose a limited mix of key principles and a few practical examples to guide your efforts.

To calibrate your expectations, think of the content like a small plates or tapas experience: you get a variety of tastes to savor that hopefully leave you sated at the end of the meal (essay) even if you might have desired an entrée-sized portion of some.

A strategic planning meeting that lacks strategic thinkers?

Run for the exits.  I kid.  Slightly.

Obviously this is a situation to avoid. Those invited to participate in a strategy development session should possess the mindset, skills, and knowledge appropriate for the work that is required.  What does that look like?  What does good strategy look like? 

Ultimately you need to answer that question yourself, but here is some of the thinking that I regularly draw on (and often share with session participants)

In some cases, however, an existing entity (often the board of directors, a specific committee, or the management team) automatically is tasked with strategic planning.  Let’s assume can’t change the composition of participants in the strategic planning session that you need to design and facilitate and you also are aware they may not be the best at strategic thinking.  What can you do?

I look to three areas—Participants, Preparation, and Process—where session design and facilitation can increase the likelihood of strategic thinking and choices occurring regardless of the people involved.

Here are a few of the key considerations I usually explore for each area to inform my strategic planning session design and facilitation.


learning about the participants convening for the strategy work

Answering the following questions almost always yields useful insights to inform design and facilitation choices.

  • Drawing on the strengths-based management work of Gallup, what strengths might each participant contribute to the strategy work?  What weaknesses might they need to manage around?

  • In terms of strengths and weaknesses, what is the aggregate profile of the strategic planning session participants?

  • What experience(s) and relationships might inform individuals’ contributions to the work?

  • What potential biases or existing assumptions might participants possess?

  • How are they likely to engage in the actual strategy conversations?  Creative or analytical?  Big picture or details?  Extroverted or introverted?  Et al.

To gather this information, I often survey or interview participants in advance and then share a summary of it prior to the session(s) for everyone to review.

You also can gather it quickly at the onset of the session (be it onsite or online) using polling, a human graph exercise (physical if online, using the annotation tool if virtual), or an icebreaker or priming activity that surfaces the information.

Remember, facilitation is about making it easier to achieve the desired results. So regardless of when or how I surface the participant information, I almost always engage them in a discussion around the findings.  I draw from the following questions (among others) depending on the timing of that discussion.

  • What would make it easier for you individually (or the group collectively) to engage in strategic thinking and decision-making? 

  • How might you need to engage with each other in order to produce the desired results? What might make that easier?

  • What might you need from me as a facilitator during the session?

  • What other perspectives or voices might we want to draw on to inform the discussions and decisions?

  • What advance preparation might accelerate efforts once we convene?

I find this type of collaborative conversation with participants reduces the odds that I end up in an adversarial role with them during the actual discussions. 

Anyone can, and everyone should, make facilitative contributions during discussions and decisions, not just me as facilitator. Enlisting participants in examining the group’s composition and its potential implications increases the likelihood that they will.



the data, perspectives, and pre-work participants engage with in advance to accelerate discussions and decisions during the strategic planning session(s)

While particularly useful for a group lacking some strategic thinking capability, even the most well-qualified strategic thinking group can benefit from engaging with pre-work that includes perspectives other than those represented among the planning session’s participants. 

Here are some common pre-work options that can help expand participants’ awareness of relevant trends, as well as what might be desirable to pursue:

  • Surveys of relevant stakeholders

  • Thought-provoking articles on key strategic issues

  • Case studies of how others have handled analogous situations

  • Field trips (physical or virtual) that expose participants to others doing interesting work in relevant areas or who have embraced new thinking or technologies

  • Interviews with select thought leaders who can expand session participants’ ideas of what might be desirable and/or doable

  • Relevant historical trends and milestones for the organization

  • Data regarding external trends and forces

Your preparation approach should allow time for participants to review all of this pre-work and to distill their perceptions and takeaways prior to the actual session.   Because the volume of information may be overwhelming,  provide some basic structure to make it easier for them to do discern what stands out for them:

  • a few categories in which to capture takeaways

  • a handful of questions to prompt their thinking, or

  • a couple of unfinished stems/prompts for them to complete

After aggregating and distributing the distilled takeaways, engage participants in identifying the key ideas, insights, or questions that the actual session should explore, asking: Based on the identified takeaways from the pre-work, what questions, issues, or discussion items should the agenda include?*

What if you are unable to facilitate such a discussion in advance?

  • Have participants post their takeaways and invite them to answer the agenda-building question noted previously.*

  • Review all their submissions, draft an agenda, and share it for comments and suggested refinements, typically using Google Docs or a similar tool that allows everyone to see all feedback.

  • Draft the final agenda.

Finally, while far from ideal, you can do these steps and collaboratively build the agenda at the onset of the actual session.  However, doing so uses up valuable time, energy, and brainpower that are better directed toward the actual strategic discussions.


the tools, techniques, formats, et al, that you select that will make it easier for the participants to engage in strategic thinking and decision-making

Crafting questions

The framing and language used for the agenda’s key issues and questions can significantly enhance or impede the strategic discussions and decisions that result.  Crafting a handful of core questions that are a catalyst for inspired thinking and conversation is more art than science, but author Warren Berger and the renowned innovation consultancy IDEO provide some key advice. 

The first draft of any questions or issues framing often is pretty average.  Spend some time editing and playing with the language to produce a more inspiring result.  Check the improved questions for any potential biases in framing the issue and evaluate them against Warren Berger’s definition of a more beautiful question. An additional resource worth examining is the ChangeThis article: Active Inquiry: The Most Important AI for Our Future.

Stretching the thinking: using norms and agreements

If not carefully designed and facilitated, a strategic planning session lacking strong strategic thinkers can easily devolve into a tug-of-war between participants and a facilitator who is trying to enact greater strategic deliberations. 

Whenever possible we want to develop some shared norms and agreements which help participants hold themselves accountable for the strategic level of their efforts, instead of turning into the enforcer ourselves as facilitator.  Have participants develop a handful of self-assessment questions they can use to evaluate their discussions and decisions as they unfold such as:

  • Have we thoughtfully considered all the perspectives relevant to the issue we’re discussing?

  • Are we drawing appropriately on data about existing conditions and future trends?

  • What, if any, biases or assumptions may be limiting our thinking?

  • What are alternative assumptions we could consider to produce different strategic options?

  • Is our thinking sufficiently strategic?

  • Have we got ourselves into the weeds on this question/issue?

Post these questions and explicitly invite participants to introduce them—and do so yourself—during discussions to help produce the most strategic thinking. 

I sometimes ask participants to volunteer to be the conscience for one of the questions we generate, assuming the most responsibility for thinking about it and introducing it when necessary.  This helps distribute ownership for the quality of our thinking among all participants and can make it easier for people to introduce a question.

A few other simple tools and techniques for eliciting more strategic thinking:

Groups often stall when brainstorming ideas or identifying strategic possibilities.  Here are a few simple tools I often use to recharge participants and their thinking.

Abstraction (Zoom)

Sivasailam Thiagarajan’s ZOOM technique © rests on a simple concept: increase the abstraction of a question to generate more possibilities.  Here is one example he offers to illustrate the technique:

  • Original question: In what ways might we sell books to professionals on the Internet?

  • Question at the next higher level: In what ways might we sell books on the Internet?

  • Question at the next higher level: In what ways might we sell things on the Internet?

  • Question at the next higher level: In what ways might we sell things?

  • Question at the next higher level: In what ways might we persuade and influence others?

The additional insights gained from broadening the question can then be discussed in a narrowing fashion, moving back toward the original question posed.

Zoom Out and Zoom In

Similar in spirit to Thiagi is John Hagel and John Seely Brown’s Zooming Out and In.  it is a simple way to broaden people’s thinking about the future before then inviting them to do some more tactical level work.  Here are sample questions for each.

Zoom out
What do our environmental scanning efforts suggest
our profession and the market might look like 10 to 20 years from now?

What kind of organization will we need to be then in order to be successful? What changes are required?

Zoom In

What are a few initiatives we could pursue in the next 6-12 months that would most accelerate our transition to becoming that kind of organization?

What metrics could help us understand how successful these initiatives are?

Zoom Out and Zoom In is an approach from John Seely Brown and John Hagel, Deloitte Center for the Edge.


Storytelling has long been used to inspire new thinking or to describe a future people might find difficult to imagine.  As part of your session you could ask individuals (or pairs, trios, or quartets) to craft a simple story telling the tale of a strategic choice in action at some point in the future. Once all stories are shared (posted in writing or read verbally), facilitated discussion can focus on the desirable elements in each story that people want to explore further.

This exercise often works well as a way to “clear the mind” and produce some initial distillations after lengthy discussions have ensured.  Think of it as a palate cleanser to prepare for additional discussions and deliberations.

For some, “tell me a story” can sometimes be too ambiguous an instruction so consider creating a simple template with a few leading phrases that people can complete in order to create their story.

Drawing Out Hunches

People are often nervous about how people might react if they share thoughts not fully formed or “half-basked” ideas.  Yet we know that creative insights and innovative solutions often result from the connections that such sharing sparks in others.

To make it easier to do so, I often show this four-minute animated video highlighting concepts from Steven Johnson’s book Where Good Ideas Come FromIt illustrates the power of sharing hunches and connecting diverse and separate ideas.

I then invite individuals to note one or more hunches related to a strategic question or direction, one per large index card.  All cards are then posted for people to silently read and we do a rapid read and review in which people read and pass cards clockwise until all cards have been read by all participants.  Open facilitated discussion follows wither approach.


A Wild Card Idea: Real-Time Reactors

In many traditional strategic processes a small group convenes and drafts a plan, later shares it for feedback, and then often reconvenes (sometimes months later) for revisions.  Groups looking to condense that timeframe (and likely improve on the initial draft) might wish to consider what I call “real-time reactors.”

What is the role of real-time reactors?

Reactors are invited individuals who agree to provide feedback to the strategic planning group’s real-time output at a pre-determined point during the actual planning session/conversations (such as mid-day or end of day one of a multiple day planning retreat).

Who are real-time reactors?

In working with a planning group to determine whose reactions to seek, I usually pose this question: Whose real-time feedback on draft output might be most helpful to producing the most strategic direction and decisions?

The responses to this question usually reflect individuals belonging to one or more of the following categories:

  • knowledgeable individuals (both internal and external to the organization) you invite to perform this role

  • everyone with certain functional roles in an organization (i.e. everyone in a management position or all committee and task force chairs),

  • everyone who meets a certain demographic (i.e., new customer within the last 12 months, new employees within the last 12 months; and/or

  • respondents to an open call for anyone interested in offering feedback

How are real-time reactors engaged?

Using Reactors can seem logistically challenging, but it really is quite simple.  I commonly have the strategic planning group type up a one- or two-page summary of its work so far in a session and post it online at a predetermined time (i.e., during the lunch break). 

Reactors—who know this will occur—review the output and react to specific questions the group poses (usually done in a combo of a few polling questions and a few open-ended survey questions).

How does the planning group use the feedback gathered?

When the planning participants reconvene, Reactor feedback is reviewed and discussed.  In some cases, it might be useful for the strategy session participants to actually speak with select Reactors (i.e., key customers or stakeholders, association past presidents, etc.) and engage in some conversation about their perceptions of the group’s work.

I find planning session participants often reference and apply Reactor feedback as the strategy discussions continue.

Bottom line?

Any strategy effort benefits from including diverse perspectives that can inform participant discussions and decisions, exposing them to relevant historical and current data, evolving trends and other environmental scanning insights about possible futures, and diverse stakeholder perspectives that participants themselves may not actually hold.  This is particularly true when those involved in developing strategy may be less experienced or gifted in doing so.

© Facilitate Better and Jeffrey Cufaude, 2021. All rights reserved.

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