I’ve worked with a lot of leaders preparing for a difficult conversation, and I can usually tell quickly whether they are preparing to have a conversation or preparing to win an argument. While the words may sound similar, the intent and how it feels to everyone involved are completely different.
Winning Is a Solo Sport
Walking in ready to make your case, land your point, and leave having been proven right isn’t preparation. It’s keeping score on something that should never be a competition. If you treat a difficult conversation like a debate or challenge to win, and if you are good at debating or overpowering (two different things), you will probably win.
You may make your point, hold your ground, and walk out having said everything you came to say. The problem is what you may trade for your win because this is also one of the fastest ways to lose people’s trust, respect, and loyalty.
If you walk into every hard conversation certain of the outcome before it starts, you’re not working toward a solution. You’re delivering a verdict and calling it dialogue. And people can tell the difference.
What Winning Actually Costs
The cost of winning isn’t always obvious in the moment. It shows up as a quiet withdrawal. The other person stops pushing back, stops volunteering their real opinion, and starts telling you what you want to hear because it’s more efficient than being overruled again.
I remember experiencing this early in my career. The team I worked on went from a dynamic, curious department with a great leader to a leader who was only interested in listening to his own point of view, or that of anyone with more seniority. The team quickly figured out it was his way or no way, so we stopped being creative and stopped offering ideas. We quickly became a department whose messaging and work all sounded the same. And we also became a department with high turnover.
When someone is in a “conversation” where they feel they don’t have a voice, there’s a good chance they will stay quiet and appear to capitulate. But that compliance is not the same as ongoing future commitment. They may agree in the room and then become more quiet and have a significant reduction in their energy and eagerness to give their all… not to mention a reduction in their trust and respect for you and the organization.
This means you may feel you have won in the short term and then notice what has been lost – perhaps much too late — when the person resigns. It is a version of the old warning: “Win the battle but lose the war.”
That’s not a relationship or your team getting stronger. It’s about losing traction until the only voice left in the room is yours.
A Different Scoreboard
If winning isn’t the goal, what is?
When I’m working with or coaching leaders, I ask them to check four things after any difficult or crucial conversation. Instead of asking if they made their point, I ask:
- Do you and the other person understand each other better than you did an hour ago?
- Are you and the other person more able to work together tomorrow than you were yesterday?
- Did you learn something in that conversation you didn’t expect to?
- Did you thank the other person for their time?
Note: This last question is not specifically an outcome question – it is a very important politeness and culture-building check.
If the answers are yes, the conversation worked — regardless of who was technically right, and regardless of whether you got the exact outcome you walked in wanting / expecting. If the answer to any of these questions is no, the conversation may not have been a success… and/or you still need to do some work on the issue and your relationship.
In many cases, looking for four yeses to the questions above will change how you prepare. Yes, you want to be crystal clear about your points. And no, you don’t want to memorize every line of what you will say. This is a conversation not a theatre production.
If you want the conversation to go well for both of you, you have to approach the conversation being authentic, honest, a bit vulnerable, and knowing that you are willing and able listen and share… not only tell. And then, you must be ready to change your perspective, to learn, and to understand something differently by the end of the conversation. That’s a much harder thing to prepare for, and a much more useful one.
Humility Is the Red Seal
Well… not really the Red Seal, but like it in symbolism.
The Red Seal in Canada is a trades skills term and a sign of quality. A Red Seal is a professional endorsement for skilled tradespeople that proves their skills match an exceptionally high national standard. The Red Seal applies symbolically here because humility is a critical skill we all need… and we all owe it to ourselves to develop.
Part of being humble is being authentic, patient, and kind… rather than just defending a position requires being open to updating your view in the middle of the conversation, not just at the end once you’ve run out of arguments. That’s uncomfortable. It also happens to be the difference between a leader who resolves conflict and builds team culture and one who just outlasts conflict… but might be left standing alone, even among their so-called team.
Humility also requires us to be confident in ourselves — confident enough to not always have to be right, and confident enough to stand our ground when we know our values and morals are right. This is a balance that’s easy to get wrong in both directions. Some leaders hear “be humble” and quietly fold every time there’s friction and call it collaboration. Others hold their ground on everything and call it integrity. Neither one is likely the right solution – rarely is the answer we give up everything or we get it all. Which leads us to perhaps the best three questions to ask. They are, “What is this costing?” “Who is it costing?” and “What will be the long-term impact?”
A safe environment will let us share our position, but we also have to recognize just because we may think we are correct, it doesn’t always mean ours will be the solution. Sometimes, bureaucracy wins. Sometimes there’s context two or three levels above us that we don’t have. Knowing the difference between “I’m right and this matters” and “I’m right and I’m going to let this go” is its own leadership skill — and arguably harder than the humility itself.
The Real Measure of Success
A “won” conversation usually feels like relief — you got through it, you made your point, it’s over. But relief and progress aren’t the same thing.
I’d rather leaders walk out of a difficult conversation having strengthened the relationship as their top goal. If there’s more trust at the end than there was at the beginning, even if the topic itself was hard, I would count that as a win. Trust will last far longer… years and years even than any one issue that you resolved. For example, I still remember and respect great leaders I worked with from years ago. And, if they called me up today I would still trust them.
That’s not a soft compromise on accountability. It’s the opposite. Relationships strong enough to survive honesty are the only ones capable of sustaining real accountability over time. You can’t hold people to a high standard in a relationship they don’t trust — and knowing how to hold that standard without losing the relationship is a skill leaders can build, not a trait some are simply born with.
This is the thread that runs through everything I teach about difficult conversations: they’re not conflict to be managed, won, or survived. Done well, they’re built on respect, funded by trust made in advance, and measured by whether the relationship comes out stronger than it went in.
If your team is ready to think about difficult conversations this way, that’s exactly what I work on with leaders in my keynotes and workshops.
Contact me anytime to bring this to your organization.