Pain By Design: Why Discomfort Is Curriculum, Not Problem
Lesson 11 of 25 from podcast conversations with leaders who leave the world better than they found it
Kwasi Adi-Dako runs educational programs that bring together young people from 23 different African countries. He could design for smooth sailing—create environments where everyone gets along and conflict is minimized.
Instead, he does the opposite.
He deliberately creates challenges that push people to their edges. Assignments that force different perspectives into collision. Scenarios where there's no easy answer and someone's going to be uncomfortable.
"Play becomes the foundation for learning how to navigate conflict, build empathy, and grow courage," he told me.
In Kwasi's classroom, discomfort isn't something to manage away. It's curriculum.
And organizations desperately need to learn this lesson.
The Problem With Comfort
Most organizations optimize for comfort. Not deliberately—nobody says "let's make sure we never have difficult conversations." But through accumulated habits and unstated norms, we create cultures where discomfort signals something's wrong.
Someone raises a challenging question in a meeting, and the room gets tense. That tension feels bad, so someone smooths it over. We move on. The question doesn't get answered.
A team member points out that a strategic decision doesn't make sense. Leadership gets defensive. The team member learns to keep concerns quiet.
Two departments have different approaches and need to work it out. Rather than having the friction that would resolve it, they just avoid each other.
We treat discomfort as dysfunction. Something to eliminate through better communication, clearer processes, stronger culture.
But what if discomfort isn't the problem? What if avoiding it is?
When Comfort Becomes Stagnation
Organizations that optimize for comfort eventually stagnate.
They stop having the conversations that would challenge assumptions. They stop making the pivots that would serve the mission better because pivoting is uncomfortable. They stop growing because growth requires moving through discomfort.
Here’s some examples:
A founder knows their original theory of change isn't working anymore. But admitting that feels like betraying the vision. So they keep doing what isn't working because changing is too uncomfortable.
A leadership team sees that two programs are competing for resources and neither is thriving. But having the conversation about which one to sunset means disappointing people. So they keep both limping along.
A board knows the executive director isn't the right fit anymore. But the conversation about transition is awkward and difficult. So they avoid it, and the organization suffers.
Comfort isn't neutral. When you choose comfort over truth, you choose stagnation over growth.
What Productive Discomfort Looks Like
Kwasi's work shows what happens when you design for productive discomfort instead of avoiding it:
Students learn to navigate conflict because they practice it in structured ways. The discomfort isn't chaos—it's designed.
Empathy develops not through workshops on empathy but through genuine encounters with perspectives that challenge your own.
Courage builds through repeated experience of discomfort that doesn't destroy you. You learn that you can handle hard things.
The same principles apply to organizational life.
Productive discomfort looks like:
Having the conversation about strategic misalignment rather than pretending everything's fine
Naming that this partnership isn't working instead of letting it drain resources
Acknowledging that this approach isn't achieving impact even though we've invested two years in it
Confronting the behavior that's damaging team dynamics instead of working around it
These conversations feel uncomfortable. That discomfort is information that something important is at stake.
The Conversation Your Team Is Avoiding
I'd bet there's at least one important conversation your leadership team is avoiding right now.
Maybe it's about:
A strategic direction that isn't working
A team member whose performance is struggling
A partnership that's become more burden than benefit
A founder who needs to transition but nobody wants to say it
A program that should close but people are attached to it
You know what the conversation is. Everyone on your team knows. But nobody's having it.
Why?
Because it's uncomfortable. Because someone might get defensive. Because there's no easy answer. Because relationships might get strained. Because it's easier to just keep going than to disrupt.
But that avoidance has costs:
Strategy stalls because you can't make clear decisions when you're not honestly discussing reality.
Trust erodes because people can see the truth isn't being spoken, and that makes everything feel unsafe.
Problems compound because issues that could be addressed early become crises when they're avoided long enough.
Capacity drains because managing around the unspoken truth takes more energy than just addressing it.
How To Design For Productive Discomfort
Kwasi doesn't just throw students into conflict and hope for the best. He designs structure around the discomfort.
The same approach works for organizations:
First: Name what's at stake. "We need to have a conversation about [X] because avoiding it is costing us [specific consequences]."
Second: Create container. Set aside dedicated time. Make it clear this is the purpose of the meeting. Don't ambush people with hard conversations.
Third: Establish desired outcome. "By the end of this conversation, we need to [make a decision / surface different perspectives / identify next steps]." Discomfort with direction is productive. Discomfort without direction is just painful.
Fourth: Name the discomfort. "This is going to be uncomfortable. That's okay. The discomfort means we're talking about something that matters."
Fifth: Stay with it. Don't let someone smooth over the tension before you've actually worked through it. Resist the urge to move on before you've resolved anything.
Sixth: Acknowledge courage. Having hard conversations takes courage. Name that. Appreciate people for showing up to discomfort.
The Exercise That Surfaces Avoidance
Here's something you can do in your next leadership team meeting:
Ask: "What conversation are we avoiding?"
Give people two minutes to write privately. Then share.
My guess is you'll see patterns. Multiple people will identify the same unspoken conversation.
Once it's named, you can't un-name it. Now you have a choice: continue avoiding or schedule the conversation.
If you schedule it, use the structure above. Create container. Establish outcome. Name the discomfort. Stay with it.
If you avoid it, at least you're doing it consciously. At least everyone knows that's what you're choosing.
Why This Matters For Mission-Driven Work
Mission-driven work is inherently uncomfortable. We're trying to change systems that don't want to change. We're confronting problems that are complex and don't have easy answers. We're working with limited resources to achieve ambitious goals.
Discomfort is built into the work.
When we optimize organizational culture for comfort, we're optimizing away from our mission.
We can't transform systems while avoiding uncomfortable conversations in our own organizations. We can't build courage in the communities we serve if we're not practicing it ourselves.
Kwasi's insight is that discomfort is where learning happens. Not despite the discomfort—because of it.
Organizations that embrace this grow. They have the hard conversations. They make the difficult pivots. They stay in productive tension long enough to find breakthrough solutions.
Organizations that avoid discomfort stagnate. They keep doing what feels safe even when it stops working. They sacrifice impact on the altar of comfort.
Permission To Be Uncomfortable
One of the most valuable things leadership can do is give teams permission to be uncomfortable.
Not punishing discomfort. Not creating unnecessary discomfort. But not optimizing it away either.
When hard topics come up, resist the urge to smooth them over. Stay with the discomfort. See what's on the other side of it.
When conflict emerges, don't immediately try to resolve it. Explore it. Understand what it's revealing.
When someone raises a challenging question, don't deflect. Sit with it. Let the room be uncomfortable while you really think about the answer.
Model that discomfort doesn't mean failure. It means you're working on something that matters.
The conversations you're avoiding are probably the ones that matter most.
Schedule one this month.
Yes, it will be uncomfortable.
That's how you know it's important.
This is lesson 11 in a 25-part series exploring insights from podcast conversations with leaders who leave the world better than they found it.
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