Tips  on spiritual growth, emotional health, and relational healing.


10 Ways to Make Your Next Tough Conversation a Win for Everyone

Sep 5, 2017

Someone once said what you want is on the other side of a conversation you’re afraid or unwilling to have.

Whoever it was, I think they’re correct.

tough conversation two people talking over coffee

We Avoid Tough Conversations

Many of us are avoiding a conversation today. It may be with our significant other, our parents, a boss, a co-worker, or a friend. We avoid these kinds of conversations because we know the risk involved. We’ve experienced too many tough conversations which have ended up as dumpster fires. And we’re hoping by kicking the proverbial can down the road, the problem might fix itself or go away.

Here’s the thing, though. By not having the tough conversation, we’re throwing away a chance at a breakthrough in that relationship.

When I think about my best relationships, we share loyalty, trust, and intimacy because we’ve had tough conversations, not because we’ve avoided them. You get to a good spot with a boss or a spouse or a friend as a result of having tough conversations.

10 Ways to Make Tough Conversations a Win for Everyone

I sat down recently and listed ten steps I feel greatly increase the likelihood a tough conversation will go well. I’d be lying if I said that practice these perfectly – my wife and my staff would be able to find numerous instances where I haven’t. But I do my best to practice these and when I’ve done, I’ve been surprised with outcomes better than my expectations.

Let’s get started!

1. Have the conversation when you’re both at your best (to the best of your ability).

So many of our tough conversations are dead on arrival because we choose to have them when we’re at our worst, not our best. We have more power than we realize, so where possible, let’s choose to not have tough conversations when we’re exhausted, rushed, emotionally vulnerable, or angry. Let’s give these conversations their best chance by being at our best for them!

I totally blew this one recently. The conversation would have been tough regardless but it was doomed to fail by initiating it when myself and the other party weren’t at our best. And I also ignored the next step too!

2. Pick the right place, the right time and the right medium.

To be successful, tough conversations need the right environment. Pick a safe place where all parties can be honest and share openly. It’s super important to give each person time to prepare and to allow the conversation to play out. In-person is preferred, with video conference would be next best bet. At least have this kind of conversation over the phone. Avoid email, text, and any form of Instant Messenger (IM). I know that should go without saying, but these forms leave too much to be misinterpreted. I’m always saddened where I hear stories of tough conversations which failed because of miscommunication due to the wrong medium.

3. Name the elephant in the room.

Admit up front that this is going to be a “crucial conversation.” The other parties need to know you’re aware of how important the next few minutes are for all of you.

Do all you can to convey how important this conversation is to you personally. Share them how you’ve prepared intentionally for the conversation. I recently had a tough conversation with someone and when they realized I not only spent nearly two hours together, but I also had spent hours preparing for the conversation, the person felt more valued.

If you haven’t read it already, I strongly recommend checking out the book, Crucial Conversations: Tools for Talking When the Stakes are High. After reading it, distill the principles into a short list of reminders for easy reference. Bookmark this post and come back to review this list before future conversations.

4. Do your best to create a safe environment.

Tough conversations thrive on honest exchanges. As far as it depends on you, do all you can to create and re-establish safety throughout the conversation. Answer questions like “Will what they say stay in that room? What are you committed to? Do you care about them?” If you have relational credibility with this person/these people, draw on the positive past experiences to remind them of your respect for them and their trust in you. When things get intense, re-center the conversation back to a place of safety.

5. Establish what each party wants to happen in the conversation.

Invite each person to share two or three things they want. Resist the urge to offer judgment here. The goal in this step is to get the agendas out in the open on all sides. If there’s time, also talk about what each party doesn’t want to happen in the conversation. As much as possible, honor the desires of all parties in the rest of the conversation. Mutual respect and honor create a feeling safety.

6. Determine a mutual win.

Based upon step 5 and the wants of each party, seek common ground. Work together to identify one or more mutual wins. Answer the question, “How can this tough conversation progress to a point where each of us consider it a success?” Begin with that agreed-upon win in mind and work together to arrive there together.

7. Reject blame and take ownership.

By admitting fault and making a genuine apology, you’ll diffuse the other person if they’ve come into the meeting hot and ready to attack you. Throughout the meeting, diffuse anger by refusing to blame others.

One of my favorite reads of 2017 is Extreme Ownership: How U.S. Navy SEALs Lead and Win. One of the book’s key themes explores how SEAL leaders own mistakes, even if they weren’t in the room. Even if you want to parcel out responsibility and blame, be a leader and apologize for what happened. Ask for forgiveness. If the other person isn’t ready to forgive, accept their feelings as genuine and request they accept your apology.

Blame is a selfish act and destroys any hope of a win during a tough conversation.

8. Fight to listen well and refuse the temptation to defend yourself.

Crucial conversations often become fights when we seek to defend ourselves, instead of validating and affirming the experience(s) of the other(s). Work hard to keep your focus on listening well. Pay attention to your body language and communicate your engagement with what they are sharing with you. Instead of defending yourself, even if you’re being slandered, accept the criticism and thank them for their honesty.

In some instances, you may be offered an opportunity to provide an alternative timeline or set of facts in order to preserve your job, reputation, or future in some endeavor. However, recognize when that moment is and unless given that opportunity, consider how what you share may be perceived. “Explaining what happened” is often perceived as “becoming defensive” or “avoiding taking responsibility.”

9. Take notes and ask clarifying questions.

I know note-taking is a lost art, but taking notes during an intense conversation communicates that you’re engaged and you’re going to review what you heard later. By writing down the words and feelings of another, you are communicating they have value. Note taking is also pragmatic, as it gives you something to focus your nerves on if you’re worried about the other picking up on your anxiety.

During these tough conversations, clarity is essential. So, seek to understand the other person by asking follow-up questions. Dig deeper and communicate your care for them by leaning in to see things from their perspective.

10. Show the change.

Often, tough conversations fail because the other person(s) doubt our genuine desire to change. This doubt is often based on previous tough conversations where they shared important information with us and we failed to show them any change.

Therefore, immediately put into practice the lessons you learned and act in light of what the other person told you. You can increase the likelihood of success in your next tough conversation by how you handle this one.

Show the other person you’re taking seriously their experience by making changes in the areas where they provided feedback. Even one simple adjustment in short order after your tough conversation can be a game-changer.

Watch out, word will spread about you. Either your reputation will be you refuse feedback or you embrace it. You will either be known as someone who cares about others despite disagreement or you will be known to only care about those who 100% agree with you.

As I said earlier, you can win at future conversations by how you handle your current ones.


Determine Your Future Tomorrow By What You Do Today

I know none of us wake up and look forward to these conversations. (Well, maybe one of you does, but you’re the outlier, for sure.) But these conversations really do determine our future and the future of those we influence.

Tough conversations can create breakthroughs for our leadership and families. They can improve the future of those we influence and love.

Each of us needs other people in our lives who tell us the truth, point out blind spots, and collaborate with us, so we can be more than we would be on our own.

Author and pastor Andy Stanley once noted, “Leaders who refuse to listen will eventually be surrounded by people who have nothing significant to say.”

I don’t know about you, but that sounds like ultimate failure to me.

I’m praying for your next tough conversation. You can do this! (Make sure you enter your email to get my checklist below. I’ll get you ready!)


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