The Top Objectives to Having Successful Outcomes to Difficult Conversations


Who has felt the pressure to have a difficult conversation lately? Have you had something you needed to tell a member of your team that is underperforming and needing some words of clarity on expectations? Have you needed to tell your spouse something you know they don’t want to hear? Or does your child need some firm words of love on discipline or boundaries in a current situation between the two of you?

I talk on this routinely, because no one ever taught us how to have difficult conversations. And our universities certainly don’t know how to do it because they typically don’t have them. Difficult conversations are often had, that end in complete devastating failure where cutting words get said that were like nails in a coffin.

Our problem is, no one ever taught us how to have difficult conversations typically outside of an awesome minister like ours or a mentor wading in the trenches with you. And if you don’t have either of those two options, then one must take it upon themselves to study up on how to do it. But the big overwhelming key of it all, regardless, is if difficult conversations are avoided, the past will likely look like the future, and minimal real progress will be moving the bus forward. Matter of fact, one will likely take a few step back, rather than forward, by avoiding a difficult conversation. And even more importantly, those that master the art of difficult conversations, will enjoy greater success virtually by whatever tangible or intangible measure one wants to measure.

So now for the keys to having difficult conversations of which I have intentionally observed, absorbed, read, listened to, and failed to deliver at over many years. The top keys to having difficult conversations that help create improved worlds and not destroy worlds in my experience are the following.

  1. Show extreme grace. While you may hold great anger towards the other person, no one is perfect, including you, and you have screwed it up before as well.

  2. Be kind like your momma and grandma always taught you. And show empathy, putting yourself in their shoes to better understand the difficulties they may be having. If we all lived more accordingly to what our mommas and grandmas taught us, I’m certain our world could almost be as perfect as possible.

  3. Deflect inward towards your soul and reflect to them how you have screwed up the same thing over the years showing humility, you are human, and relatability.

  4. Apologize to them for your lack of clarity, or for not talking to them sooner, or for your excessive firmness or candor, maybe even anger shown. Some form of apology to show you not only have a vested interest, but also that you likely aren’t “100% innocent”. As it is my experience in many difficult conversations I have had or I have moderated, that not everyone is 100% innocent.

  5. Forget your lesson teaching mode of thinking, “I’m going to teach them a lesson!” because when a human has this as their objective, the lesson teaching they are going to do in their own head teaches no one. But in the end still leaves you bitter.

  6. If the conversation involves a team member, a client, a student, consider “wearing different hats”. If there is a direct answer, wear the “business owner hat”, but if you truly care for this person, maybe you should also wear the “caring friend hat” or “mentor hat” or “dad hat”. Do this as you preface conversations, because when dealing with people, they need to know “which position” you are coming from on.

  7. Lastly, the most important piece of advice yet. Any time you are going to have a difficult conversation, and know it could get heated or has the potential to “turn south”, before anyone gets started, say this, “We are going to have a difficult conversation, in which you may not like parts of it or may disagree with, but we are going to do this and everyone is going to remain calm, cool, collected, and no one is going to get upset, stupid, or upset and walk out and leave.”

The first time I did this probably over 5 years ago, was a very difficult conversation with a client I won’t go into, but it worked perfect, and they are still a client today. I have recently said this two times in just the last week as well, and I promise you it helps and works every. single. time.

All that being said, I still screw them up, and am not perfect at it. But what I can tell you, if you intentionally work on these 7 objectives every single time, you practice it, you prep for it each time, you apply focus to these 7 points every time, I promise, you will get better at it. Because believe you me, I have more than one former and current employee, a wife, and a kid that would tell you I have screwed it up, but understand, we can all get better at it!

Remember, words create worlds. Words determine direction. Words invite resistance or open hearts. Words convince or deceive. Words cut or heal. Words inspire or discourage. Words make work difficult or enjoyable. Words elevate your status. May God Bless you with intense discernment in those conversations!

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