INSIGHTS FOR GROWTH

We tell ourselves we're waiting for the right moment. That we need more information. That it's "not the right time." But usually, we're just afraid.

If I could give leaders one question to use in every important conversation, it would be this: “What else?” Not complicated. Not clever. But remarkably powerful.

For years, leadership meant having all the answers. Projecting confidence. Never showing doubt. Keeping your struggles to yourself. But here's what research — and experience — keeps showing: vulnerability isn't weakness. It's the foundation of trust.

Hard conversations don't have to be harsh. In fact, the best hard conversations often strengthen relationships rather than damage them.

Care. We sometimes avoid hard conversations because we “care too much” to hurt someone. But that’s not care. That’s comfort.

Clarity. We often soften hard messages to be “kind.” We hedge. We hint. We hope they get it. But clear is kind. Unclear is unkind.

Honesty. We often treat honesty and kindness as competing values. As if we have to choose. But honesty without kindness is cruelty. It’s using truth as a weapon.

Courage. There’s probably a conversation you’ve been putting off. The feedback you need to give. The boundary you need to set. The truth you need to speak. We tell ourselves we’re waiting for the right moment. But here’s the thing: there’s no right moment. There’s only the cost of waiting — and it’s almost always higher than we think. The conversation you’re avoiding is usually the one you need to have. Not because it will be easy.

Wisdom. This week we’ve explored questions, curiosity, discovery, and depth. They all lead here: wisdom. Wisdom isn’t having all the answers. It’s knowing that the first answer is almost never the real one — and having the patience to keep asking. The wisest leaders I’ve worked with aren’t the ones who’ve figured everything out. They’re the ones who stay curious about what they might be missing. Who ask “what else?” when everyone else has moved on.

Depth. It’s tempting to stay on the surface. It’s faster. Safer. More comfortable. But in coaching, I’ve learned: the presenting issue is rarely the real issue. The real one lives underneath — beneath the first response, beneath the obvious explanation, beneath what everyone already agrees on. Go deeper, not wider. One good question, followed through, reveals more than ten surface-level ones. Where in your life would going deeper serve you right now?

Discovery. We think questions lead to answers. And sometimes they do. But the best questions? They lead to better questions. In coaching, I call this “following the thread.” Someone brings me a problem about their team’s performance. I ask what they think is driving it. Their answer reveals a deeper question about trust. That question reveals one about their own leadership pattern. And that’s where the real work starts. The right question doesn’t close a door. It opens three

There’s a moment in every leader’s development where the skill that got them promoted becomes the habit that holds them back. Having answers.