How to Lead Difficult Conversations

Sometimes, we get to be influential in fun and exciting scenarios like landing a new client or in getting a job promotion, but that’s not always the case.

Often times, we need to be persuasive in difficult situations – like when a person has let you down.

As a leader in your profession, as a parent, or as a friend, you will inevitably want to elicit new and different behaviors from someone who has disappointed you.

This is the kind of conversation most people find uncomfortable and will actively avoid.

And yet, these conversations can create understanding and stronger connections, followed by the change you’re seeking.

Without the ability to step up and guide these conversations, you and the person who disappointed you will be condemned to an endless loop of unmet expectations and heartbreak.

Uncomfortable conversations hold space for the biggest changes.

Give the person who disappointed you the chance to change with a difficult (yet persuasive) conversation.

How to Start A Difficult Conversation After Disappointment

From starting a presentation to leading a meeting, or kicking off a sales call, this first tip is helpful for pretty much any circumstance where you intend to lead a conversation.

This technique is known as pre-framing.

There are many uses for pre-framing. For the context of this article, it simply means giving the other person an outline of the conversation you’re about to have. The beats or guideposts, if you will. This is to give them a heads up about what’s to come.

Here’s an example of what this can look like,

“I’d like for us to talk about what happened. It would be really helpful if both of us can share our perspective on the situation. I’m especially curious to learn what each of us initially thought or were expecting, our experience of the situation, as well as what has happened since. After that, I think we’ll be in a good place to figure out what we could do differently in the future.”

There’s a WHOLE BUNCH of distinctly chosen words in that 4-sentence paragraph. And I’m going to teach you the principles guiding all of them. THEN, I’ll cover each section proposed in this conversational outline – its function and intention.

When you utilize this framework, your next difficult conversation might actually turn out pleasant and rewarding!

The Psychology Behind This Conversation Opener

Starting your difficult conversation with the structure outlined above accomplishes a number of things.

First, by setting up the conversation this way, you are providing some comfort for the person you want to persuade.

They know what to expect. They know what’s coming up. Having this knowledge lets them relax, even if it’s just a little bit.

That incremental relaxation will bring down any of their defense mechanisms that might be kicking in.

Second, it makes the conversation fairer.

Meaning, you walked into the conversation knowing full well what you wanted to say and what you wanted to accomplish. How about we give the other person the same courtesy by giving them just a few moments to gather their thoughts. Yeah, it might not be much, but it is something.

Starting this kind of difficult conversation shouldn’t sound like, “Hey, can we just talk about something?” or “Can we talk about what happened Monday afternoon?”

If you just leave it at that, the other person doesn’t know if you’re disappointed, angry, or really what you want from them at all. And so, their defenses go up and now there’s an added level of tension that you could have avoided.

Lastly, opening the conversation with this structure can help you keep the conversation on track if/when the conversation deviates and gets tangential.

“I know you’re excited to talk about what we can do differently next time, but first let me make sure I have a clear understanding about what you were initially expecting.”

The outline helps you both stay focused, practice restraint, and keep your cool.

You can still have an organic conversation, the outline simply makes sure that it’s not amorphous, and ultimately pointless.

Now, let’s take a closer look at the outline – why certain words are more helpful than others, what each section accomplishes, and how it all leads to a collaborative solution.

Taking Turns

“I’d like for us to talk about what happened. It would be really helpful if both of us can share our perspective on the situation.”

Two important takeaways in these beginning two sentences.

First, notice how you’re eliciting for help, not confronting someone. We all have an innate desire to be helpful. We are social creatures, which means that collaboration is fundamental to our survival.

By asking for help, you are giving the other person power in this conversation – not taking it away.

Second, by saying that both of you will share your perspectives, you’re letting the person who disappointed you know that this will not be a one-sided conversation.

This isn’t chastising. This is problem-solving.

Before, During, After

“…I’m especially curious to learn what each of us initially thought or were expecting, our experience of the situation, as well as what has happened since.…”

There is a reason why we don’t start the conversation by jumping right into the climax of the problem. That’s when emotions were (are) at their highest.

When our emotions are elevated, it’s more difficult to think logically and to problem solve – which is our ultimate intention of this conversation.

You can keep emotions from flaring up too soon (or even at all) by focusing on the events leading up to the issue in question.

Specifically, their expectations. Why? Because this is usually where things fall apart – unclear, miscommunicated, or never-communicated expectations. You can typically sort out the bigger problem by focusing on this first step.

Next, you both will share your experience of the situation.

Take turns. Listen. Don’t interrupt. And repeat what you heard.

“Ok, so if I’m hearing you correctly, it sounds like you were expecting Jeffrey to handle the set-up while you were going to take care of the print materials.”

Repeating back what they said will help you better understand their perspective AND will make them feel heard and validated – which, again, keeps defenses down and cool heads on.

Lastly, the two of you will share what has happened since the disappointing situation. The fallout.

This is important because we don’t always understand the consequences of our actions.

They might not have realized that their actions led to bigger consequences. It’s possible they might not be aware of the fact that penalty charges were incurred because your team didn’t leave the event space in time. They might not know that another department team had to put in extra hours over the weekend to fix the mistake and still meet a deadline.

Don’t mistake ignorance for bad intentions.

Once again, take turns during this section. There might be a ripple effect from the other person’s point of view that you aren’t currently aware of. So, make sure they too get their time to share about the post-event experience.

What We Can Do Differently

“…After that, I think we’ll be in a good place to figure out what we could do differently in the future.”

In order to make this conversation productive, there must be some insight gained so that everyone can do better in the future.

And I do mean everyone …. That means, including you.

By its very nature, relationships include 2 or more people. Which means, every situation involving that relationship has multiple people with multiple perspectives and multiple actions that lead to multiple effects.

Don’t fool yourself into thinking that it’s all them and none of you.

There is some percentage split of responsibility. Whether it’s 50/50 or 90/10, you still bear some form of responsibility.

This difficult conversation is a learning opportunity for them and you.

The focus for the end of the conversation is to set everyone up for success in the future. What changes to our process and/or communication can we make? What can they take responsibility for? What can you take responsibility for? And what can you each of you do differently in the future?

Don’t Forget This Step!

Thank them.

Difficult conversations aren’t just difficult for you. They are difficult for them, too. Give the other person the appreciation they deserve for participating, speaking their mind, listening to you, and helping you find a solution.

Thank them because that was a whole lot of work for both of you.

P.S. Here are a few other ways I can help you increase your influence!

1. Grab a FREE copy of my Mindreader BlueprintIt’s the step by step guide to turning your prospects into enthusiastic clients without slimy techniques, hard selling, or high-pressure pushing.

2. Join me for 1-on-1 Coaching. I love helping my clients clarify their marketing message, improve their sales conversations, increase their client retention rates, and drive their revenues up, ALL by teaching influence language and techniques. Click here for more information and to schedule call!

3. Booking speakers? Your audience will LOVE learning how to be more persuasive in business and in life. Looking for a keynote speaker who jam-packs a speech with practical, how-to content that actually helps professionals be better leaders? Then click here for my speaker kit, which includes a breakdown of my popular programs on positive influential communication.




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