What You Can Do [2]: Liberating Strategy SuperAntiFragilisticExpialidociously

Keith McCandless
8 min readSep 11, 2022


By Keith McCandless and friends

This work requires courage to examine “what is sweet in life and what is terrible, and then go out undeterred, to meet what is to come.” [McCandless, Pericles]

PART 2 introduces practical steps that are effective for liberating strategy in a wide range of organizations and settings. It features portions of the Strategy Knotworking approach. See Part 1 for a review of the theory, logic and complex dynamics associated with antifragile and more of both strategies [See Figure 1]. Five general recommendations for applications are followed in Part 3 by colleagues sharing their experience in business and ecosystem regeneration.

What You Can Do: Top Five Recommendations

Below is a short list of favorite approaches I am currently using to liberate more antifragile thinking and “speculative exploration of multiple peaks.” Each can stand alone and together they can be more powerful.

1. Use Liberating Structures To Invite More Distributed and Diverse Interactions

The first and most important action you can take is to invite more people and unusual suspects into your planning efforts. LS is an antifragile way to operate because it distributes power to local participants and connects informal networks. Even when connections are loose, people closest to the action who share a purpose will be the most productive participants. Unusual suspects may include customers, suppliers, students, citizens, people outside your functional role, and people with more and less formal power in your domain or context. Reach far, reach wide. LS is an operating system designed for shaping the future with everybody every day.

Action: one simple way to get started is to use online video conferencing to connect people and generate insights in far flung local settings. For example, the open questions below can be posed to a diverse group who share answers in Chat. Each individual draws on their own unique experience when answering. When inviting participants, try to abandon the organization chart and focus on your organization as a network of relationships and an untapped source of social capital.

“Given our purpose to ____ ____ ____ [e.g., end suffering from diseases for which we have treatments], please complete the following sentence # 1…. [1 minute pause to compose a sentence]; Now # 2…”; Now # 3… -10.”

  1. An event that has opened a new door for us is…
  2. If all our services / products disappeared last night, I would bring back…
  3. A new partner or opportunity I see in our local area is…
  4. A project or product I see advancing our strategy is…
  5. Two activities that might be productively combined are…
  6. A common sense next strategic move is…
  7. An absurd idea that just might help us is…
  8. A bold yet pragmatic strategy or tactic is…
  9. A strategy that would cost almost nothing and could be tested next week is…
  10. What seems possible now that we have shared ideas is…

Participants see each others’ answers. Stories are told about novel strategies put into play. Possibilities are generated where none seemed to exist before. Participants ask each other questions and offer peer support that generates curiosity. People who play brokering and connecting roles in the network will spread new ideas across boundaries. You have invited everyone who cares about your purpose to join in strategy making while developing distributed capabilities (i.e., collective muscles that gain from addressing disorder and challenge).

2. Iterate, Iterate, Iterate To Generate Depth, Novelty and Momentum

Counterintuitively, repetition can generate novel strategies. I recommend asking group members: “Can we dig deeper or reach higher by repeating the last activity? What is possible now that we have generated this set of ideas/actions? Is there a novel idea that re-combines what we already know about this challenge?” Multiple small groups are iterating simultaneously in a distributed search for effective strategies. This may seem redundant or inefficient if you did not embrace the creative power of small-scale decentralized interactions for searching out more effective strategies.

  • Action: Repeating 1–2–4-All with creative twists is often a great idea. Also, using different LS with similar purposes back to back can be productive. For example, 9 Whys and Drawing Together complement each other when you are clarifying and deepening your purpose. In succession, invite groups of people with distinct and diverse experience into a User Experience Fishbowl exploring the same topic (e.g., users then designers then suppliers). Similar to LS TRIZ with three segments of 1–2–4-All, repeating the use of a single LS through multiple lenses can be a very productive way to generate, sift, and sort more options.

3. Face Down Critical Uncertainties

Third, spend time imagining and describing how to face up to Critical Uncertainties in your future. Detail how you would pursue your purpose and operate successfully in an extreme range of operating realities. This engages the whole group in playfully imagining future scenarios.

Action: 1) identify the two top unpredictable dynamics that could put you out of business; 2) invest time exploring what investments and divestments would help you operate successfully in each of these futures. Focus on the most extreme conditions you can imagine; then strategize with your more inclusive and distributed group of participants. Creating seriously~playful conditions for doing this work is important. Imagination is stifled by fear… so bring lightness to the party.

For example, Figure 3 illustrates two typical critical uncertainties recent clients have identified. Relative access to capital ($$$$ / ¢¢) and the degree of disruption and dislocation arising from climate, political-economic, and epidemiologic health challenges.

Figure 3: Two factors (access to $ and disruptions/dislocations) that threaten the ability to operate successfully are combined on a continuum to create four quadrants. Each quadrant represents a plausible yet unpredictable future that disrupts or puts stress on an organization. In turn, each quadrant calls out for distinct strategies.

With a four quadrant grid established, participants are invited to create titles and events that bring unique future operating challenges to life. Then, in small groups, suggestions for strategies that would help make progress are generated. Both investment and divestment options are specified. A range of conventional and antifragile strategies are encouraged. No holds barred. All quadrants 2–3–4 can generate novel strategies with # 4 generating the most with antifragile twists.

4. Cultivate Relationship Patterns That Generate Surprising Value

Fourth, focus on relationship patterns that generate new sources of value. More generative patterns uncover adjacent possibilities and exponential growth options in every day interactions. The idea comes from biological sciences: new possibilities for biodiversity tend to expand as you explore them. For example, novel combinations of proteins in DNA open up as you add other new combinations–life keeps expanding into the adjacent possible. In organizations, the boundaries of what is possible grow as you explore them.

Action: Use the Generative Relationships STAR with group members, key partners, team members, and across functional groups [see Figure 4]. The approach invites group members to identify the current status of four attributes that “produce new sources of value that cannot be foreseen in advance.” The focus shifts to more liberating group interaction patterns rather than developing the expertise of individual participants.

Figure 4: Generative Relationship STAR invites each individual and the group to assess the degree of S, T, A and R present in their interaction pattern. With this simple assessment in hand, group members make decisions to improve their generative potential. Decisions may include adding more diverse participants, listening more carefully, focusing on action projects, or revisiting the purpose or reason for the group to exist.

5. Act, Plan, and Evaluate Iteratively and Periodically

Fifth, make it routine to evaluate the dynamic interplay of strategy and results as the work proceeds over months and years. Reconnect the planners, the doers, the entrepreneurs, and evaluators. Periodically, use a visual portfolio management approach to develop more strategic thinking, deeper engagement, and more transparent evaluation into the fabric of the work with your group.

  • Action: use Ecocycle Planning on a routine basis to identify activities or relationships that can be cultivated, combined, or repurposed to generate new sources of value [see Figures 5 and 6]. Some may generate exponential growth. Attention to the Ecocycle’s back loop–the Creative Destruction (release or making space phase) and Gestation (exploration phase) activities–will generate more productive possibilities. Managing the backlog and increased flow of new options can be facilitated with a reverse kanban method. With the Ecocycle, managing strategy proceeds as a gradual, networked process in which hunches are explored and combined across formal boundaries and diverse functions.
Figure 5: Ecocycle Planning invites a group to view, prioritize, and update strategies (both activities and relationships) using four developmental phases: birth, maturity, creative destruction, and gestation. Most portfolio management approaches do not include creative destruction and gestation phases. Managing these complex elements together with a diverse group can generate adaptive strategies that match the complexity of challenges in play.
Figure 6: Antifragile strategies arise where there is open space to explore novel ideas and recombine elements that are already working. Attention to the Ecocycle’s back loop–the Creative Destruction (release or making space phase) and Gestation (exploration phase) activities–can generate more productive options for exponential growth.

Summing Up

With these five approaches, the exploration can become as serious as it is playful. LS is based on a hunch that it becomes possible to design interaction with a high degree of variability at the micro-scale (experienced as imaginative play) while retaining meta stability at the macro-scale (experienced as useful or exponential results). [see More Magic, Less Mystery: Sustaining Creative Adaptability with Liberating Structures]

If you are co-leading, I recommend paying close attention to the composition of micro-organizing elements. Each activity should be linked to purpose and the process should be guided by minimum specifications that maximize participation. As a result, participants will have more freedom and more responsibility to shape strategy.

Field Stories: Part 3

Coming in Part 3: luminaries in complexity-inspired strategy Johannes Schartau, Nancy White, Larry McEvoy (MD), and Michael Arena) share field stories illustrating how liberating strategy takes shape in different domains.

Johannes Schartau, Agile Consultant, Hamburg Germany. Tying and Retying Strategic Threads

Nancy White, Full Circle, Seattle, USA. Knotworking Across

Larry McEvoy, MD, Montana, USA. How Biology Does Strategy

Michael Arena, Connected Commons, USA. Follow the Energy

Learning Resources

McCandless, Keith and Schartau, Johannes (2018), Liberating Strategy: Surprise and Serendipity Put To Work (Medium)

Lipmanowicz, Henri and McCandless, Keith (2013). The Surprising Power of Liberating Structures: Simple Rules to Unleash A Culture of Innovation. Seattle, WA: Liberating Structures Press

McEvoy, Larry, MD. (2021). Epidemic Leadership: How to Lead Infectiously in the Era of Big Problems (John Wiley and Sons, publisher)

Arena, Michael and Uhl-Bien, Mary (2016). Complexity Leadership Theory: Shifting from Human Capital to Social Capital, People + Strategy

White, Nancy. (2018) Adaptive Strategy Development and Facilitating Strategic Planning in Complex Contexts , Full Circle blog

  • Video [10 minutes] describing the Strategy Knotworking approach by an international NGO serving activists and communities working to end violent conflict and tyranny everywhere in the world https://vimeo.com/693378067/0187842d67
  • Credits: LS icons by Lesley Jacobs; photos by Keith McCandless
  • Editorial magic provided by Nancy White and Leslie Stephen
Keith McCandless is the co-developer of Liberating Structures and co-author of The Surprising Power of Liberating Structures: Simple Rules to Unleash A Culture of Innovation (2013).



Keith McCandless

Keith is co-developer of Liberating Structures and co-author of the book The Surprising Power of Liberating Structures ...