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The Art of Having Uncomfortable Conversations

Does any of this internal chatter sound familiar?

Ugh. I don’t want to have this conversation. It will be uncomfortable. Uncomfortable for them. Uncomfortable for me.

I’m completely justified in my opinion – and I know I need to provide feedback. Yet, I hate the potential for conflict.

I know what I want. I’m justified in making the request. But I also know it will cause them extra work.

I also know that having the actual conversation isn’t nearly as painful as the current state or the likely future. 

And so, another day slips by without having the conversation we know we need to have.

How do we make them easier?

I have a few ideas for you. 😊

Let’s start here: you are not alone.

Everyone avoids some type of conversation. What conversations are YOU avoiding?

The enneagram provides hints on the conversations different personality types avoid.

Here’s a sampling with possible supporting stories we tell ourselves:

  • Conversations of completion. “We are never done. Let’s keep polishing it or just move on to the next task.” 
  • Requests to others. “I am in service to others here. I don’t even know what I would ask for.” 
  • Resetting agreements or expectations when you are failing. “I cannot be seen as failing. I’ll just double down on effort and find a way to make this look better.” 
  • Conversations of commitment. “I don’t know the outcome or even how we will get there. I can’t commit when there is uncertainty.” 
  • Conversations requiring deeper trust. “Why should I trust them when I’ve been burned so badly before.” 
  • Conversations which deepen personal connection. “Just do your job. We have defined roles. This is a simple transaction. I’ve told you all you need to know.”
  • Conversations with conflict. “It will blow over. I’m good. I don’t want the stress.” 

Did you see yourself in any of these?

Do you have your own type of conversation you are avoiding?

Often people imagine entire conversations before they ever have them. They make up they already know the conversation outcome and then decide they don’t really need to have conversation anyway! I call this conversations with ghosts

Welcome to being human.

Masterful Leaders Lead Through Conversations

Masterful leaders shift from one type of conversation to the next with apparent ease.

Some leaders seem to come to this naturally.

Most of us must learn how.

Masterful leaders are very aware of their strengths and challenges. It is very likely not as effortless for them as you might believe.

Many a great leader ends the day exhausted from their efforts to communicate effectively.

Making conversations look easy isn’t easy.

“Leaders lead through conversations. 

Before you can walk the talk, you must have the talk.”  

Ken Roseboom

The good news is you can learn to “lean in” to the conversations you avoid and be a more successful leader.

There are many tools for becoming better at tough conversations. (There is a link at the end of this article for my tool for preparing for a high impact conversation).

However, the first process is to develop the motivation to have the uncomfortable conversations which will get you more of what you want.

Here’s how to do that.

How to motivate yourself to have uncomfortable conversations in 4 easy steps

1. Recognize the conversations you are delaying, avoiding, or denying.

All change begins with awareness.

I’ll offer three categories of uncomfortable conversations we are putting off.

Delay: Often there is a logical reason for delaying a conversation. You are still gathering data, the time or place isn’t yet available, or it simply isn’t a high priority, yet. This all makes sense and can be entirely appropriate. However, if the conversation has been on the To-Do list for a few days/weeks then maybe some self-motivation is required.

Avoid: These conversations are the focal point. These are the conversations you dread and avoid. It could be the topic, something challenging about the other person, or just a conversation type you avoid (see above list).  Good to know. Move to step 2.

Deny. There is a third category which deserves mention. These are the conversations other people believe are important, but you place little value on them.  They don’t even make your To-Do list. When you deny their importance, you miss leadership opportunities.

2. Name it to tame it.

I don’t know who to give credit for that saying. However, it succinctly describes the experience of gaining power when you name the fear holding you back.

There are quite likely several fears causing your tension about a high-impact conversation.

My suggestion is to actually have fun making your list of fears. Start with a blank sheet of paper and start making a list. Let it flow.

When the paper is nearly full, take a breath and review. Whew!

It’s a bad situation, but not really that bad is it?

3. What’s at risk if you don’t have the conversation?

What is the predictable future? What are the implications to trust, relationship, or the well-being of yourself and others?

Not taking action is an action.

Do you want to live in that predictable future?

4. Are you willing to have the conversation?

This is the step of commitment.

You have considered the possibility of not having the conversation so “No” is a viable and honorable option.

“When “No” is an option, your “Yes” will mean more.” 

Hey Ken, I’m willing to “lean in” to my uncomfortable conversation. But I wish there was an easy to follow, helpful guide to help me plan this conversation and become a better communicator.

I made Coach Ken’s Checklist for High-Impact Conversations for you!

Developing a conversation plan is essential for a high-impact conversation. I invite you to use “Coach Ken’s Checklist for High-Impact Conversations” to develop this plan.

Consistently using the checklist items in this plan will help you:

  • Develop confidence for uncomfortable conversations.
  • Develop your dynamic executive presence.
  • Become more influential and trusted.
  • Create deeper relationships and be more fulfilled.

Get your free copy here: Coach Ken’s Checklist for High-Impact Conversations

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Ken Roseboom

Ken Roseboom is the President of Thinking Partners. He partners with leaders to increase impact, create aligned teams, and deliver better results. He leverages the Alignment process, assessment tools, expert coaching, and years of front line leadership experience to support his clients.
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