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


Tough Conversations You’re Avoiding

Feb 23, 2016

Spring Break once brought out the worst in me.

My buddies and I were planning an epic road trip. We were going to celebrate Spring Break without killing our checking accounts. We would drive to Northern California and take several trips around the San Francisco Bay area, while crashing at my friend Matt’s parents’ house. Then we would drive down to Vegas and base out of my parents’ house before returning to Phoenix hours before classes resumed.

It was all going well until my buddy Nick got invited and started sharing ideas that ran totally counter to mine. I wasn’t happy with this. He and I got into an argument at one point and things boiled over. I think my exact (screamed) words were, “Nick, this is not your #&*@#$ trip!!!” (insert a specific profanity I would likely get fired for if it came out in a sermon).

tough conversations

Not my finest moment, for sure. Things went downhill from that argument and there was a lot of fence-mending to do before our trip.

Needless to say, I know first hand how difficult tough conversations can be. You know this too. Tough conversations can make or break friendships, marriages, businesses and Spring Break adventures.

I haven’t always done tough conversations well. Even longer after my angry moment with Nick, I’ve avoided, wimped out on and botched difficult talks. But I’ve also learned how essential they are to flourishing relationships and organizations.

I wrote two posts earlier this year for my friends at about the power of tough conversations. Both posts resonated with their audience. Almost all of us have tough conversations we’re avoiding. Whether it’s at work, in our family or with our friends, there are things which are currently unsaid which need to be said.


Several things stop us from having tough conversations.


We ask “what if…?” or “How will I….?” or “why can’t I just….?” Our fears fuel a sense of worry, which becomes a giant roadblock to the chats we need to have. I love how Joyce Meyer defines worry – “making a down payment on a problem you may never have.” In a talk I gave earlier this month, I defined fear as “anxiety based on incomplete evidence.” Fear keeps us quiet, worried about “what if,” “maybe” and “who knows.”


We say, “I’m not someone who does that. ” We excuse the conversation away when we say, “I don’t do confrontation.” Sometimes, we genuinely feel uninformed, “I’m not sure I’d know what to say.” Our insecurity might be exposed if we sat down for a difficult dialogue, so we avoid the danger at all costs.


“Can’t we keep going as is? There’s too much to lose.” Tough conversations are risky. We avoid them because the risk seems too great. The chances of success and future flourishing feel slimmer than the chances of things blowing up in our face. However, we often forget that relationships without risk quickly becoming stale and boring.


“The last time I had one of these kinds of conversations, it didn’t go well. I don’t want that to happen again.” We are prone to project negative results from past experiences into the future. We regret how past tough conversations went, so we avoid the increasing regret in the future. However, we would be wise to remember the research on regret, which says we regret the opportunities we miss far more than the mistakes we make.

In her book, Conversational Intelligence, Judith E. Glaser writes, “In the most extreme cases, when we are faced with situations that stir up highly charged emotional content, most of the tension and drama is actually taking place in our own minds. “


It’s pretty likely we all have a tough conversation on our to-do list and many of us have been allowing the tension and drama in our heads to talk us out of it. If you’ve been avoiding a tough conversation, here’s some simple steps you can take. In fact, these are some steps I am taking this week because of a tough conversation I’m avoiding. We’re in this together!

  • Tell someone else you need to have the conversation and have them hold you accountable. 

Speaking aloud your need to do this will move you forward with more momentum than carrying the burden alone. Also, inviting someone to ask you about it will encourage you to take action.

  • Set a date when you will have the conversation before.

I set a deadline for everything I can in my life. Because if I don’t, I push things down the road to “tomorrow” – a day which never appears on my calendar. Make it reasonable, allowing time for the next two steps. But don’t set it off so far that the pressure is off.

  • Improve your skills in advance.

You may have a legitimate claim to insecurity, so get better before your next conversation. My two posts for include some helpful tools to doing these chats well. I also recommend a book entitled Necessary Endings by Dr. Henry Cloud. Cloud does a masterful job of describing the conversations we avoid, why we avoid them and how we can take the necessary actions.

  • Prepare what you’re going to say AND how you’re going to say it.

No one is surprised when I tell them how relentlessly I prepare for a sermon as a pastor, but we are shocked when someone prepares extensively for a confrontational conversation. Both are important moments, where how we say something often is more important than what we say. Intentional preparation often dials down some of our fear, insecurity, regret and sense of risk.

  • Wait on it until you can be more rational than emotional. 

Ambrose Bierce once said, “Speak when you are angry and you will make the best speech you will ever regret.” Being emotional isn’t bad; in fact, it may be our emotion which helps us discover a new level of courage. However, when we’re all emotion and no reason, we make bad decisions. Even if it’s 51% rational and 49% emotional, make sure you’re in a good place emotionally to have the conversation.

  • Don’t do tough conversations over email, text or Facebook chat.

Seth Godin wrote great wisdom when he posted this short blog in 2011. “When the outcome of a conversation is in doubt, don’t do it by email. And show up in person if you can. The synchronicity of face to face conversation gives you the chance to change your tone in midstream. Ask questions. A great question is usually better than a good answer. And don’t forget–the value of a long pause is difficult to overstate.”

What if what you want is on the other side of a tough conversation you’re afraid of having? I believe our greatest regrets are not the conversations we wish went differently; they’re the ones we wish we had the courage to have in the first place. I’m having a tough conversation before this weekend. I’m praying you’ll be courageous enough to do the same!

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