Anguish, heartbreak, and fear, the declaration of “if you’re not with me then you’re my enemy.” This is the final confrontation of Star Wars: Revenge of the Sith between Anakin Skywalker and Obi-Wan Kenobi. While your leadership team is likely not engaging in literal battles over your strategic management process, many arts leaders see heated battles between cynics and believers while implementing new strategic initiatives.

The potential solution to “Bring Balance to the Force” within our organizations is to engage the cynic in the process from the beginning. For too long the field has regarded the cynics among us as individuals who somehow get delight from obstructing new strategic management processes. In reality, they are just individuals who want the best possible outcome and need adequate information before moving confidently in a new direction. Due to this, the cynic has the potential to be one of an organization's most useful perspectives and most powerful advocates for new initiatives, if they are properly engaged in the strategic process. This article explores potential suggestions for engaging this archetype and suggests how they are a powerful resource to the strategic process.



“Scratch the surface of most cynics and you find a frustrated idealist — someone who made the mistake of converting his ideals into expectations.”Peter Senge

1.    Connect them to the Why

In his TED talk “How great leaders inspire action”, Simon Sinek asserts that “the inspired organizations -- regardless of their size, regardless of their industry -- all think, act and communicate from the inside out.” The not-for-profit world knows this, as our entire model is built on people putting their resources (time, money, social capital, political power, etc.) in support of a different future. This is wonderful, but often the “inside-out” approach feels overly emotional or “touchy-feely” for most cynics and they may find it hard to connect to the mission amid the work of delivering on program outputs. Even so, there is a reason why the cynics do the work they do, and making time to openly discuss the mission, the underlying assumptions of the mission, and the spoken and implicit organizational values can activate and engage even the most cynical among us.

“We can be skeptical -- demanding evidence before we believe in people -- but hopeful knowing they can change for the better.”Jamil Zaki

2.    Ask them what Risks they see and Ask for Evidence

While cynics appear in every department and leadership level of an organization, they often find themselves overly consumed with the “how” of new strategic plans. This makes them terrific risk mitigators and inspired creative problem-solvers, but it can also lead to too-narrow thinking and missed opportunities for strategic innovation. When implementing a strategic process, instead of trying to keep the cynics from the nuts and bolts of the proposed program, engage them directly in identifying the more complex elements of the environmental scan or SWOT analysis. The key to this strategy is to ask the cynic for evidence to back up the risks they see in elements of the proposed strategic processes. By asking the cynic to fully exhaust everything that could go wrong and requiring that the points remain evidence-based this strategy offers a robust risk assessment for the proposed initiative and sets the stage for future adaptive thinking and mobility.

“A cynic, after all, is a passionate person who does not want to be disappointed again.” - Rosamund Stone Zander & Benjamin Zander, The Art of Possibility: Transforming Professional and Personal Life

3.    Keep Goals “SMART”

At the end of the day, many cynics don’t support new initiatives or won’t engage in new strategies simply because there are too many unknown factors. Again this provides an opportunity for organizations to get as specific as possible with their objectives as possible by creating “SMART” goals, or objectives that are specific, measurable, achievable, irrelevant, and time-specific. Employing this model of goal development builds the required resource allocation, timeline, expectation, and accountability into the strategy, quelling some of the potential anxiety or frustration. By specifically outlining the building blocks into digestible goals as many factors as possible are defined, cynics can see how their skills and strengths fit into the new strategy.

4. Hold space for emotions & ease distractions

Change is scary for everyone, and sometimes more so for the cynic in the group. It is important to remember this when embarking on strategic processes and plan for emotions to bubble up in this process. People are not robots analyzing likeliness data, but living through challenges in the moment.  Fear, scarcity mindset, personal circumstances, macro-level trends, systemic injustices, and cultural norms are all at play in the conversations surrounding strategic processes. By acknowledging and naming these factors before implementing the new strategies, arts leaders create space for the emotions, external factors, and expectations to be released, setting the strategy up for success.

At the end of the day, even the most cynical among not-for-profit arts leaders believe in the mission and importance of what we do every day. If they did not then they would have left long ago. Often these individuals’ wariness was hard-earned through difficult circumstances and decisions made beyond their control. Instead of fighting against their nature and ignoring their concerns, it only benefits organizations to actively engage them and leverage their unique perspectives to fortify strategic processes. Doing so, hopefully, will lead organizations away from a reality where various stakeholders are engaged in battle on a lava field as we embody Yoda’s advice of “out of acceptance comes wisdom” and “bring balance to the Force.”

Written by Ashley Cooper, a graduate student in the M.F.A. in Theatre - Arts Leadership program at Virginia Tech.