7 Steps To Mastering Difficult Conversations
April 14, 2021
Chrisa Zindros Boyce is the Chief Strategy Officer and Senior Executive Coach at the Handel Group, a renowned executive life coaching company. Her work helps support growing companies and industry conglomerates to design cultures and structures that lead to increased employee retention, engagement and profitability.

The principle we teach people about how to tackle difficult conversations is the difference between grace and wisdom. There has to be a balance for conversations to be effective. Grace is about caring about your audience. It's about meeting people where they are. Grace is about kindness, empathy and compassion. Wisdom, on the other side, is about saying it like it is, straight to the point, no holds barred. Wisdom is about being direct, truthful, and clear. If your grace and wisdom as an approach are imbalanced, it can have negative consequences.

There are grace people and wisdom people. When grace people communicate, they don't get everything out and so walk away feeling not fully expressed. While the person you were communicating with, your audience, walks away unclear about your message. Because grace people don't do the specifics, they say too much in the context of the conversation. They focus on the 'why' - the background and the reasoning - which is the application of grace. But when there's too much of that, and not enough of the content, which is where wisdom comes into play, the point gets lost. So you lose people, because they don't actually understand the takeaways.

Wisdom people go into conversations with blunt, direct, clear direction. And wisdom people leave "dead bodies". You are absolutely clear about what you want to say, but you were not empathetic, you were not compassionate. You likely weren’t kind. “I don't have time to be kind to you, I am busy person.” Your audience is left mad, disappointed and rejected, meaning they can't function. So you have to create a balance of grace and wisdom.

You might notice that sometimes you do grace with some people and wisdom with other people. Maybe at work you do more grace, maybe at home you do more wisdom. You might notice like a an interesting mix. That's normal.

Another rule we give our clients to ensure they aren’t avoiding difficult conversations is the Three Grumble Rule. It gives them an opportunity to have these conversations earlier rather than later. It puts you in control. You’re designing your world and you're keeping yourself in a powerful author-like position; you’re the one in charge, you're feeling proud of who you are, you're in command.

Anytime you complain in your head or express disappointment, frustration, anger, or irritation out loud in relation to a specific person and that happens three times, you need to go have a conversation with that person within 24 hours. That's the rule.

It's super effective. By the third time something or someone's has annoyed you, you've established a pattern with that person and you cannot continue to to let that fester. By applying the Three Grumble Rule, you prevent yourself from having to have these larger, harder conversations. Instead, in the moment, you can use grace and wisdom to say, “Hey, you did something the other day that didn't sit well with me. Can we talk about that so we can get resolved?” It happens much faster, and it's not as scary and you feel more empowered about it.

And finally, regardless of whether it's a big or small difficult conversation, know how to set it up.

  • Ask the person for permission. Give them the heads up that you want to talk to them. You want to make sure it feels safe for them. So you let them know, “Hi, Stacey, I want to have a conversation with you. All is really good, I just want to go over a couple of things that have been getting in the way of our working relationship the last couple of weeks.”
  • Slow down and ensure they are really hearing you. You want to land the person into the why of the conversation. So, “Stacey, I really want us to have an awesome partnership, and have a lot of fun when working together and for me to support you as much as you're supporting me. So I'm having this conversation because I want to make sure we're always doing that together. Does that make sense?”

Notice I said, “Does that make sense?” I pause before I moved on to the next thing, I want to make sure Stacey gets what I'm saying and that she's working with me. Do not try to rush people through everything you want to say or you will lose them. They won’t be able to follow you and you won't get to the end, and the resolution.

  • Set the context. For example: “I'm having this conversation because I want to have a good work relationship. By the way, I've been thinking about saying this to you for the last three months. I haven't because I kind of didn't feel like it. And I didn't think it was my place. And I'm so sorry.” What this does is disarms Stacy. The minute you tell them, “okay, I was scared, I'm sorry,” they soften because you are modeling accountability and humility. They can then model that back for you. Remember, in the conversation you’re role modeling how you want people to be with you.
  • State the core issue. Don't list 18 problems in one conversation. Don't go in there with a long list of all the things in the last seven years you've held against them. Pick one to two items that you want to address in the conversation and know that you're likely going to have to come back to revisit this discussion. Sometimes you can't get it all resolved at once. If you're having performance conversations at work, it usually takes about seven conversations to improve a performance issue with a colleague.

When you give a colleague feedback and they improve, they up their learning curve, but there's always roll back. So you have to go back and have more conversations, reinforce their progress and set them back up for success. You need to be committed to having more than just one of these tricky interactions.

  • Get feedback. Get their side, understand where they're coming from, and be prepared with some questions: What happened on your end? Did I mess up somewhere? Was I not clear?” Get curious. This is how you apply grace, where you don't act like you know all the answers, and you're curious versus critical.
  • Move forward and create a mutual solution. Ask, so how can we move forward? And do you have a proposal for how we might do that? Suggest a monthly check in to ensure the issues get fixed. Don't show up with an: “I don't know how to fix this” attitude. Be ready with a solution that's going to work for you and then be able to negotiate with that person so it's mutual. Then set up a follow up, ending with: “I'm glad we had this conversation, let's follow up in a couple of months to see how this is how this is going.”
  • Script it. When the conversation is big, and you're scared to have it, it helps to script the conversation. Write it out for yourself and practice it. Sometimes I'll even tell my clients to bring it with them, so that they can read from their notes. By the way, people don't find that funny, they find it flattering, like “wow, you really took the time to think about what you want to say to me.” So if you need to script it and bring it with you, go ahead and do it.


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