In a recent meeting where board members and the CEO were grappling with an array of challenging issues, the conversation took a turn. Tensions were running high, and time was running short. Let’s just say it got spicy in that room. Under the guise of “I’m the only one who can see what’s happening here,” a member jerked the discussion from something generative and shut everything down.
I recognized the pattern: cynicism masquerading as wisdom or insight.
Don’t get me wrong—I’m a regular skeptic and encourage healthy skepticism; it saves us from going down the wrong path. But there’s a steep price to pay when cynicism looks like leadership.
As futurist Kevin Kelly puts it: “Cynicism is easy. An optimist creates something. A cynic just waits to be proven right.”
When cynicism becomes the enemy of possibility
Cynicism is safe. It’s risk-averse. It’s the sideline commentator who never steps on the field. It finds its way into our polished PowerPoints, strategic plans, and hiring decisions.
But what we need now isn’t more cynicism. It’s courage. Courage that comes from hope.
Wait… hope? I’m not talking about toking on the “hopium” pipe.
We’ve all heard the cliché: “Hope is not a strategy.” And that’s right. Hope, without practical grounding, invites cynicism.
But here’s the nuance: hope is the spirit that fuels strategy. Without hope, strategy has no aim. There’s no reason to pursue something better.
The journalist and activist Gloria Steinem said: “Without leaps of imagination, or dreaming, we lose the excitement of possibilities. Dreaming, after all, is a form of planning.”
Finding the middle path: Four practical steps
So how do we rise above the false choice between cynicism and blind hope? Here are four practices:
1. Call out cynicism when you hear it
Instead of letting “We’ve always done it this way” end a conversation, use appreciative inquiry (AI) to redirect energy toward what’s possible. Pioneered by David Cooperrider, this kind of AI is rooted in asking strengths-based, possibility-oriented questions.
When cynicism surfaces, reframe using appreciative inquiry:
- “What conditions would need to be true for this to work?”
- “What’s changed in our environment that might make this idea possible now?”
2. Embed structured visioning into regular team rhythms
Many teams get stuck in familiar patterns: task-oriented meetings or typecast grooves where one person is always the dreamer and another plays the role of devil’s advocate. To counter these patterns, leaders can deliberately design time for “strategic dreaming.”
Try this:
- Incorporate Liberating Structures, such as “What, So What, Now What?” or “Five Whys,” to create collective meaning and strategic insight.
- Get everyone on the same side of the table. Instead of a debate between the dreamers and the devil’s advocates, divide a meeting into time blocks: one block when everyone considers all possibilities and another when everyone pokes holes.
- Host quarterly, 1-hour “Futures Labs” sessions to explore:
- “If we were starting from scratch, what would we do?” or
- “What would this look like if it succeeded beyond our wildest dreams?”
3. Reframe governance around purpose and participation
An oldie, but a goodie is the Governance as Leadership framework, which emphasizes that effective boards operate in three modes: fiduciary (oversight), strategic (planning), and generative (sense-making and purpose). Most boards over-index on the first two and neglect the third.
I’ve seen boards become unstoppable forces for good when they embrace the idea that great minds think differently.
Boards operating in a generative mode build stronger trust with staff, make better decisions, and stay more closely aligned with their core purpose.
Try this:
- Cultivate different points of view through penetrating questions:
- Who sees this situation differently? What are we missing?
- What is the best possible outcome? What is the worst-case scenario?
- What is the next question we should discuss?
- Disrupt old habits: Shift 50-60% of board meeting time to generative thinking instead of report-outs.
Now what?
Each of these practices is a small act of cultural leadership. Together, they shift organizations from guarded to generative, from reactive to resilient, from cynical to strategic.
They don’t just fight cynicism—they build its antidote: shared practices of hope-rooted, strategic action.
As Seth Godin writes, “The future belongs to those who care.” Hope is not naïve. It’s an act of leadership, friends!
