Step 3: Strategic Conversations

"Better Work" Series: (5 of 5)

Most leaders aren’t short on ideas. They’re drowning in them.

You know what you need to do, but can’t bring yourself to do it. 

That gap? Strategic conversations.

I’m not talking about communication skills. While that is vital to leadership, this step isn’t about public speaking, active listening, or giving better feedback. I am talking about thinking out loud with a trusted partner or advisor—verbally processing ideas, aligning expectations, staying accountable, and sharpening your own development.

This is what ties the entire “better work” process together and keeps us from running in circles.

The Loneliest Job in the World

In 1962, John F. Kennedy took a quiet walk on the beach near Cape Cod, struggling with the reality of the Cuban Missile Crisis. He had the weight of the world on his shoulders—literally. Nuclear war was on the table. One wrong decision, and millions would die.

History tells us Kennedy made a series of calculated moves that de-escalated the crisis. But he didn’t do it alone. Behind the scenes, he relied on a small, trusted circle of advisors, talking through scenarios, questioning assumptions, and clarifying his own thinking.

That’s what I mean by strategic conversation.

Now, you’re probably not navigating a Cold War standoff (unless your office politics are really bad), but the same principle applies. Leadership is lonely, if you choose for it to be. 

Decisions are high-stakes. Without someone to process with, you get stuck in your own head, second-guessing, overcomplicating, or—worse—doing nothing.

Why Leaders Get Stuck

Without strategic conversations, you’ll run into three problems:

1. Unclear Expectations – Ever had a plan fail because everyone assumed different things? 
2. No Accountability – If no one is holding you to your own commitments and standards, you’ll let them slide. It’s human nature.
3. Stagnant Development – You don’t know what you don’t know. Left unchecked, your blind spots stay blind.

What a Strategic Conversation Looks Like

A good strategic conversation isn’t a meeting. It’s not a status update or a to-do list review. It’s simply thinking out loud; processing problems, refining your direction, gaining new perspective, and getting clear on next steps.

Let’s break it down:

1. Expectations

At one point in my career, I was leading an organization through a massive transition. I thought I was clear on our priorities. Then I sat down with a mentor, and he asked one question:

"If I asked your team, would they say the same thing?"

Lol, nope. Lesson learned. 

Good strategic conversations expose the gap between what you think is happening and what’s actually happening. That’s why you need an outside perspective—someone who’s not inside your daily chaos, who can call out misalignment before it turns into a disaster.

2. Accountability: Someone to Keep You Honest

It’s easy to convince yourself you’re doing everything right—until someone who knows you calls you out.

Accountability starts with you; it’s about having someone who keeps you accountable to what you said you would do, how you said you would do it, and the kind of leader you committed to being.

Be honest: when left to our own devices, we all let things slide. We justify delays, tweak the plan, or shift priorities without realizing we’re moving the goalposts. A good strategic conversation prevents that drift.

• Did you follow through on your commitments, or just stay busy?
• Are you leading the way you said you would, or making excuses?
• Is your team experiencing consistency, or feeling the ripple effects of your inconsistency?

This isn’t about pressure; it’s about integrity. You need someone who will hold up a mirror and ask, “Is this really what you committed to?” Not to judge, but to make sure you’re staying aligned with the standard you set for yourself.

Because the best leaders don’t just hold others accountable. They make sure someone is holding them accountable, and let their team observe that standard.

3. Development

Want to know the fastest way to find your leadership blind spots? Talk to someone who won’t just nod along. That ain't anyone your team btw.

Legendary investor Charlie Munger once said, “The best thing a human being can do is help another human being know more.” That’s the power of strategic conversations. You don’t just process your thinking—you get exposed to new ways of seeing the problem.

• Are you playing the same game you were last year?
• Are you solving surface problems instead of root issues?
• What’s the biggest risk you haven’t considered?

Without these conversations, you’ll default to what’s comfortable—and comfortable rarely leads to growth.

How to Build This Into Your Work

Most leaders don’t lack intelligence. They lack objective thought partnership. You need a source of strategic conversations, not just spontaneous chats that reassure your ego and insecurities. Here’s how:

1. Find the Right Person – This isn’t your best friend or a yes-man. It’s someone who can challenge you, think critically, and call you out when needed.
2. Prioritize Frequency – Thinking time isn’t “extra.” It’s necessary. Block it off, protect it, and make it part of your rhythm.
3. Use a Framework – Start with expectations, check accountability, and explore development. Ask better questions, get better results.

The Bridge to Better Work

The best way to stop spinning your wheels is to get out of your head. Find the right person. Think out loud. Build strategic conversations into your workflow.

Because the best leaders don’t just work harder. 

They think smarter.

And they don’t do it alone.

Better Work: The Full Picture

Better work doesn’t just happen—it’s built. And the leaders who build it aren’t guessing. They have a system that turns vision into reality.

Three steps to creating better work:

Clarity – Get your objectives, structure, and process out of your head and onto paper. A plan isn’t real until it’s written down.

Calendar – Proactively set the four core events that drive your objectives into action. If it’s not scheduled, it won’t happen.

Conversations – Stay honest, accountable, and keep developing with someone who won’t let you off the hook. No fluff, no excuses—just real progress.

If you’re navigating big decisions, feeling stretched too thin, or want a better system for how you work, let’s talk.

🔹 20-Minute Discovery Call – Let’s see if we’re a fit. No pressure, just clarity.

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