“Difficult conversations” are a problem at virtually every level in every organization. They were a big problem in my life, too, until I had two realizations that changed the way I lead and communicate: kind is better than nice, and meaning must be mindful.
I used to think being nice was the same thing as being kind. It isn’t. Nice and kind may look similar on the surface, but they come from very different places, and they produce very different results.
In this 2:38 video, I share the two realizations that gave my leadership, my difficult conversations, and my influence in the world a massive lift.
Nice tries to avoid discomfort
Nice wants everyone to feel good right now. Nice softens the message until the message disappears. Nice says yes when the truthful answer is no. Nice postpones a conversation because we don’t want someone to be upset with us.
That can look generous, but it’s often more about protecting ourselves than serving the other person. We don’t want to feel awkward. We don’t want to be disliked. We don’t want to sit in the tension that honest leadership sometimes requires.
Nice asks, “How do I keep this comfortable?” Kind asks, “What would genuinely serve this person and this situation?”
Why I say nice can be disgusting
That’s intentionally provocative. I don’t mean ordinary warmth, courtesy, or friendliness. Those things are wonderful. I mean the kind of “nice” that masquerades as care while allowing a problem to grow.
If someone on your team is struggling and you refuse to tell them clearly, you may spare them discomfort today while costing them growth, trust, or even their job later. If a decision is wrong for the organization and you stay silent to keep the room pleasant, the pleasant moment can become an expensive problem.
Kindness is willing to risk temporary discomfort in service of a better outcome. It tells the truth without making the other person wrong. It respects people enough to trust that they can hear something real.
Meaning must be mindful
Facts happen. Then our brains make meaning out of them, often instantly.
Someone interrupts you and you decide they don’t respect you. A colleague misses a deadline and you decide they don’t care. A leader questions your recommendation and you decide they don’t trust your expertise. Any of those interpretations might be true. They also might not be.
When we treat the first meaning our brain produces as an unquestionable fact, we walk into the conversation ready to defend ourselves against a story the other person may not even know exists.
A more useful approach sounds like this:
“Here’s what I noticed. Here’s the impact it had. Here’s the meaning I started to make from it. Before I assume that meaning is true, will you help me understand what was happening?”
That’s direct. It’s also curious. It lets you tell the truth while leaving room for another human being’s reality.
Relax into the present
Many difficult conversations become even more difficult because we’re not actually in the conversation. We’re replaying the last three times this happened, rehearsing the argument we expect to have, or imagining everything that could go wrong.
Come back to the person in front of you. Listen to what they’re actually saying, not only to what you feared they would say. You can be prepared without being preloaded.
Presence makes it possible to respond instead of merely react. And when you’re present, the other person has a much better chance of becoming present, too.
A practical way to have the kind conversation
- Get clear about your intention. Are you trying to win, punish, relieve your own frustration, or create a better result? Your intention will come through, whether you name it or not.
- Separate what happened from the meaning you made. Lead with what you observed. Own your interpretation instead of presenting it as objective truth.
- Say the important thing clearly. Don’t make the other person decode a message hidden inside six layers of politeness.
- Stay curious. Ask what you may be missing. Listen for new information, not merely for your turn to speak.
- Make room for discomfort. A conversation can be uncomfortable and still be respectful, productive, and kind.
- Agree on what happens next. Clarity is kinder than leaving both people with different interpretations of the conversation.
Kindness isn’t weakness
Kindness doesn’t mean becoming vague, passive, or endlessly accommodating. It doesn’t mean abandoning standards or pretending poor performance is acceptable. And it certainly doesn’t mean becoming someone other than yourself.
Kindness is truth with humanity. It’s clarity without cruelty. It’s the willingness to care about the person and the outcome at the same time.
That combination builds trust. People may not enjoy every difficult conversation with you, but they can come to trust that you’ll be honest, that you’ll listen, and that you won’t use honesty as an excuse to diminish them.
The leadership question
The next time you’re tempted to avoid a conversation, ask yourself:
Am I being kind, or am I being nice because I’m trying to escape discomfort?
You don’t need to become harsh. You don’t need a performance trick. You need to bring the truth, your care for the other person, and your attention into the same room.
That’s when a difficult conversation can become an act of leadership.
Make consequential conversations clearer, more human, and more effective.
Executive Speaking Success helps accomplished leaders communicate with clarity, trust, and influence when the stakes are high.
