The Conversations We're Avoiding (And Why That's Where Clarity Lives)
- Deepa Mirchandani
- Jul 21
- 4 min read
A mid-year provocation for leaders navigating uncertain times.
Six months in, and the world feels more complex than ever. Political landscapes shift beneath our feet, funding streams narrow or disappear entirely, and the systemic challenges we're working to address seem to multiply faster than our capacity to respond. It's tempting to hunker down, wait for clarity, stick to what's worked before or cut our (presumed) losses and divest.
But what if the conversations we're avoiding in these uncertain times are exactly the ones we need to be having?
The Comfort of Familiar Discussions
I've been noticing a pattern in my conversations with social impact leaders lately. We're having the same discussions we had six months ago; about funding pressures, about scaling challenges, about stakeholder tensions. Important conversations, certainly, but ones that feel stuck in familiar grooves.
Meanwhile, the conversations that might actually shift something - the ones about fundamental assumptions, about what success really looks like in this landscape, about the tensions we're not ready to name, those remain at the edges of our awareness and seemingly just beyond our reach.
There's something about uncertainty that makes us grasp for the familiar. We return to known frameworks, trusted advisors and predictable patterns of thinking. It's human nature. It's also where transformation goes to die.
The Questions Hiding in Plain Sight
What would it mean to lean into the discomfort of not knowing? To design conversations that help us think beyond the frameworks that brought us this far? These are also some of the explorations that I’ve been having with bold leaders who want to step into so they can step out of being stuck and frustrated with the status quo.
In my work developing what I call "conversation architecture”, the intentional design of dialogue that moves us beyond recurring discussions to clearer action, I've learned that the most meaningful conversations often emerge when we stop trying to solve problems and start exploring the assumptions beneath them.
Some of the questions you might be avoiding include:
What if the way we've been measuring impact is part of what's keeping us stuck and holding us back?
Which of our strategies are we continuing because they feel safe rather than because they're still effective?
What conversations are we not having with our funders, our communities, our own teams because we're afraid of the answers?
How might this period of uncertainty actually be revealing possibilities we couldn't see before?
Beyond the Usual Suspects
When facing strategic uncertainty, we naturally reach for familiar tools; analysis, planning, stakeholder consultation. These remain essential, but the question becomes: how do we use them in ways that actually surface new possibilities rather than confirming what we already think we know? Often our planning processes reinforce existing assumptions, our analysis asks the same questions in the same ways, and our stakeholder consultation seeks validation rather than genuine exploration of different perspectives.
What's needed isn't necessarily different tools, but a different quality of engagement - conversations that create space for productive discomfort, that welcome diverse perspectives rather than seeking premature consensus, that explore tensions rather than avoiding them or resolving them too quickly.
This isn't about having better meetings (though that might be a byproduct), it’s about designing the conditions where fresh thinking becomes possible and getting into the heart of the complexities the way to do it.
The Practice of Strategic Dialogue
Creating these conditions requires what I've come to understand as conversation architecture - the conscious design of how we engage with complexity. It means moving beyond the predictable patterns of problem-identification, option-analysis, recommendation towards something more exploratory and emergent.
It means creating what we call "conducive containers”. The spaces where people feel both stretched and supported enough to think beyond familiar territory. It means skilled questioning that unlocks rather than interrogates. It means holding space for the contradictions and paradoxes that living systems actually contain. Most importantly, it means having the courage to step into conversations where we don't know the outcome in advance and being okay with the fact that it may take a few iterations to get to where we need to be.
An Invitation to Uncertainty
As we move into the second half of the year, I want to offer a different kind of strategic planning question: What conversations have you been avoiding because the stakes feel too high or the uncertainty too great? Those avoided conversations - that's where your next clear step might be waiting.
But what about the conversations we have with ourselves? The half way mark of the year, and the summer (in the western hemisphere) offers a natural pause, a chance to examine our own assumptions before the seasons change and momentum picks up again. Sometimes the most important questions aren't the ones we ask our teams, but the ones we avoid asking ourselves: What am I taking for granted? Which beliefs about our work am I holding onto because they feel safe rather than because they're still effective? What would I do if I truly believed change was possible?
The world doesn't need more leaders who have all the answers. It needs leaders who know how to create the conversations that help us discover what action to take together.
What if uncertainty isn't the problem to be solved, but the invitation to act differently?
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If you're ready to explore what strategic clarity might look like through designed conversation, I'd be curious to hear what you're grappling with. Sometimes the conversations that change everything start with a simple question: What if there's a different way to think about this?
