The Conversations Leaders Struggle to Have (and Why They Matter)

The Conversations Leaders Struggle to Have (and Why They Matter)

One of the most difficult parts of being a leader isn’t just making decisions—it’s making them with incomplete information, while navigating the conversations you need, want, and avoid.

We make decisions based on the conversations we have, the ones we want to have, and—perhaps most importantly—the ones we don’t have. The struggle lies in knowing which ones to lean into and which ones are holding us back.

A reader of Strategy to Action put it best:

“I think it’s about learning to live and act with uncertainty.”

That’s the real challenge: making bold moves while knowing you’ll never have perfect clarity.

The Three Types of Conversations That Shape a Leader’s Journey

1. The Conversations We Have

These are the ones that drive our day-to-day—discussions with our team, investors, customers, and advisors. They feel productive because they move things forward, but they’re often reactive.

Leaders get stuck here when they operate only within the conversations that are easy to have. They stay in execution mode, talking about tasks and deliverables rather than the deeper strategic questions:

• Are we still solving the right problem?
• What would failure look like in six months?
• What’s the hard truth we’re ignoring?

If the conversations you have aren’t challenging your assumptions, you’re running on autopilot.

2. The Conversations We Want to Have

These are the ones we know could change things but hesitate to start. Maybe it’s a tough talk with a co-leader about their role, a hard decision about firing a key team member, or an investor discussion you’ve been avoiding.

Wanting to have a conversation but not initiating it is often a sign of fear—fear of conflict, fear of looking foolish, fear of making the wrong call. But waiting for the “perfect moment” is a trap.

Uncertainty is always present. The best leaders lean into these conversations early, knowing clarity comes from conversation, not before it.

3. The Conversations We Don’t Have

These are the silent killers—the unspoken issues that compound over time. Leaders often avoid them because they feel risky, uncomfortable, or emotionally loaded.

• A key hire isn’t working out, but you keep hoping they’ll improve.
• A major customer relationship is shaky, but you avoid addressing it head-on.
• You’re burning out, but you don’t talk to anyone about it.

Avoidance doesn’t eliminate uncertainty; it just delays the inevitable. These are the conversations that separate reactive leaders from resilient ones.

The Leader’s Real Job: Making Uncertainty Work for You

As a leader, you will never have all the answers. The goal isn’t to eliminate uncertainty—it’s to build the courage and discipline to act despite it.

Here’s how to do that:

1. Start before you’re ready. If you’re waiting for total clarity before having a hard conversation, you’ll wait forever. Start with a small question: What’s the worst that could happen?
2. Make space for real dialogue. Not every conversation should be transactional. Schedule time with your team and advisors to explore the bigger questions.
3. Ask what you’re avoiding. Regularly check in with yourself: What conversation am I not having that I should be? That’s usually the one that matters most.

Your Business is Built on Conversations

Everything you’re building comes down to the conversations you have, want to have, and don’t have. If you want to lead with impact, you need to start having better ones—starting today.

What’s one conversation you’ve been avoiding?

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In all that we do, let us seek wisdom, discipline, courage & justice.

Be well,

Keita