Why You Don’t Want to WIN a Difficult Conversation

Everybody wants to win.

Some people are more compelled to win than others, but the reality is—there is an underlying competitive dynamic inherent to most of the situations we face. It’s even in our difficult conversations.

That’s not all that is present. Another dynamic inherent to most hard conversations—the hardwired need to avoid conflict.

The desire to win and the bent to avoid conflict at all costs do not ‘play nice’ with one another in difficult conversations. Let me explain why.

Whenever we are thrust into a difficult conversation, it doesn’t feel good. Tensions run high, strong emotion is expressed, and we want to get out of the conversation as quickly as possible.

Our emotions scream to our brain—come up with a ‘brilliant insight’ that will cause the ‘opposing’ party to listen, chill out, and back out of the conversation.

It may not seem like avoidance, but that is basically what we are doing when we take the easy way out.

We tell ourselves, “Once they hear what I have to say, they will understand why the way they are responding is irrational and we can be done with this ridiculous conversation!

Have you ever noticed that this tactic rarely, if ever, works? And if sharing our ‘perfectly logical’ perspective doesn’t seem to calm the other person down (perhaps even incenses them further) we often resort to trying again, just with a different form of the same argument. We present our logic repeatedly, each time with a little less tact.

Shouting to be heard isn’t winning. A defensive posture that refuses to empathize with the other party isn’t winning.

In fact, even if the person fully listened and changed their perspective, if they left feeling ‘put in their place’—you haven’t really won the conversation.

You may THINK that you have won the conversation, because you appear to have won the argument, but in reality— you’ve just lost.

The hardest part? Not only did you miss the goal of the conversation, without radical amends, you may have lost the relationship as well.

The good news—it doesn’t have to be this way. You can emerge from difficult conversations and intense conflict with a strong relationship intact. You can even come out of it with your

relationship stronger than when you began.

Impossible? Absolutely not. In fact, I’ve seen it accomplished over the last 25 years in businesses across the country. How, you might wonder?

Start with the end in mind. Ask yourself, what is the goal of this conversation?

Think about the co-worker you are consistently at odds with. Do you want to work with that person more effectively in the future? What’s the alternative…making your life at work increasingly miserable by having to recall all the difficult moments that keep compiling without resolution?

How about your spouse or another other close family member? Do you want to have any kind of relationship with that person in the months and years to come? Of course, you do. These are the questions we need to ask ourselves before heading into a difficult conversation with a mindset to ‘win.’

Instead, we can frame the conversation to be about real listening (crosslink), genuine understanding (even if we don’t agree), and a resolution that benefits both parties moving forward.

Attempting a conversation without trying to ‘win’ is a counter- intuitive thought process in so many ways. So much in our culture is geared towards winning the race, beating the other team down the field, or out jockeying our competition in the market.

However, bringing that “win at any cost” mindset into a difficult conversation is incredibly dangerous.

Instead, take the mindset that the goal of the conversation—the

touchdown, the finish line, the home run—is to strengthen this relationship by looking for a win-win solution.

We can focus on finding legitimate action steps both parties can take to strengthen the working or familial relationship in the future.

Sure, we can put the other person in their place with our sharp wit or commanding intellect, but our ‘win’ will leave a wake of strained relationships.

Think about a time when someone belittled you for the sake of winning an argument? How did it make you feel? Did it strengthen or weaken your relationship with that person?

You want to be heard and thoroughly understood—so does the other party.

When you decide to have the conversation WITH the other party, instead of AT the other party, you will be accomplishing your goal.

You are out to gather puzzle pieces of understanding, process genuine emotions, insecurities, perspectives, and come to a genuine resolution that helps all parties involved.

You want to practice being tentative in your language. Try phrases like,

“Is it possible that you may have…”

“What I hear you saying is that I may have…”

“Help me understand how that made you feel…”

This invites participation, encourages genuine process, and helps build a stronger bridge for even more vulnerable sharing and communication in the future.

‘Winning’ through dominating debate may seem easier and quicker than pursuing understanding and trying to find something you can both agree on—but what is the actual cost?

Taking the time to work towards win-win solutions may be harder and take longer, but it will yield genuine results that lead to radical breakthroughs in the relationship. Not only can this transform relationships, it has the potential to transform the business you are working to build together.

Every time you engage the difficult conversation with a genuine resolve to see both parties win, you make a deposit of trust into that critical relationship.

Think about how long it takes engineers to design, construct, and test out a major highway bridge. That bridge is built specifically to carry the weight of the load that will go across it every day. It is fiercely and continually tested to accomplish what it was designed to do.

With practice, you can start to view every difficult conversation as an opportunity to strengthen the relational bridge—allowing for it to carry even more weight in the future.

What loads are your relationships at work going to carry together? What about the weight of raising a family or dealing with the inevitable ups and downs of life?

Those relational ‘bridges’ must be strong enough to carry serious weight. They need the ability to carry the weight of greater and greater challenges—pressing through them and strengthening the ties that bind even further.

It is possible to strengthen the relationship by working through the conversation together, instead of merely inflicting your view point on the other party.

Will it take more time? Yes and no.

Yes, you are taking the time to really hear each other out, come to understanding, and find genuine routes forward together—but think about how long it will take to build relational equity with people you are simply inflicting your view point on to ‘win’ the conversation? The value is evident.

Winning an argument is not what success in difficult conversations looks like.

Coming through the conversation to a place of ‘win-win dialogue’ will build the relationship and cause you to be someone others feel confident in. People will trust you to help them work through the inevitable challenges that will come down the road.

It isn’t all about winning. Sometimes, the best way forward is the least intuitive—but the reward is worth the effort.


Want to become more effective at handling difficult conversations in your life?

Sometimes our conversations don’t play out that well, run off the rails, and people leave feeling demoralized or belittled. We know what it’s like to walk away from a conversation that we are still carrying hours, days, or even years later.

That is why we’ve created this FREE resource entitled 9 Reasons Why Difficult Conversations Are So Hard (and what to do about them) It will help you start to navigate even the most challenging discussions. Click here to download the guide now!

Related Posts

Why You Don’t Want to WIN a Difficult Conversation

Send this to a friend