How To Master The Art Of Having Difficult Conversations

Most of your problems, in business and life, can be solved with a difficult conversation.

Everyone wants great relationships.

The problem is, most people don’t want to have difficult conversations.

Most people have an aversion to discomfort. So they avoid uncomfortable conversations, even the ones needed to move business and life forward.

The conversations you choose to avoid create limitations in your relationships.

And here’s the thing…

You have a relationship with everything:

• Relationship with your business

• Relationship with your team

• Relationship with your clients

• Relationship with money

• Relationships with family and friends

• Relationship with the world

• Relationship with yourself

Most (if not all) of your problems, can be traced back to a relationship.

Most (if not all) of your problems, can then be solved by having the difficult conversation you are avoiding in that relationship.

• You think you have a performance issue with a team member, but it’s actually a difficult conversation around expectations you’re avoiding.

• You think you have a strategy issue, but it’s actually a difficult conversation to let go of a wrong-fit team member you’re avoiding.

• You think you have a sales issue, but it’s actually a difficult conversation with yourself around money and self-worth you’re avoiding.

• You think you have an intimacy issue with your partner, but it’s actually a difficult conversation around needs you’re avoiding.

Until you have the hard conversations to resolve the relational issues, they will continue to drain you mentally, emotionally, and energetically.

Get good at having uncomfortable conversations.

This is the most undervalued skill in business.

Here are 7 reasons why I think you should get good at hard conversations rather than avoid them.

Why You Should Have Difficult Conversations

1) You take Radical Ownership

Avoiding hard conversations means you’re committed to remaining a victim of the situation.

Leaning into the hard conversation requires taking responsibility, ownership, and leadership.

Radical ownership = being the creator of your life.

2) You turn Conflict into Connection

Communicating feelings and needs in hard conversations creates space for deeper connection and understanding.

3) You process Feelings and Frustrations

Unprocessed feelings and frustrations not only create an energetic drain for you…

It also wreaks havoc on your physical, mental, and emotional body.

4) You heal through Co-Regulation

Self-regulation is only half of the healing game.

We’re relational beings so the other half is healing with others through co-regulation and secure attachments.

This applies to business too. Remember, you also have a relationship with your business, your team, your clients, your money, etc.

5) You rewire Aversion to Discomfort

You avoid difficult conversations to protect yourself from discomfort.

Leaning in despite the discomfort and creating a connection on the other end rewires your irrational fears towards hard conversations.

6) You get Expectations and Requests met

It’s ridiculous to get frustrated over uncommunicated expectations and requests.

Yet, we do this all the time.

Creating space to communicate clearly and understand each other’s expectations, needs, and requests…

Increases the likeliness they get met.

7) You get better at them

Difficult conversations don’t get easier.

You just get better at having them.

“Ok great Colin, so how do I have these difficult conversations?”

Let’s break it down into a tactical step-by-step process.

How To Have Difficult Conversations

Step 1: Prepare

Preparation is the most important and often overlooked step to effective difficult conversations.

Preparing allows you to:

• Organize your thoughts and be intentional (vs reactive)

• Get clear on what your wants and needs

• Regulate any emotional triggers or feelings

Being intentional and clear going into the conversation makes it easier to solve problems, make decisions, and get what you want.

While some hard conversations do happen in the moment, you will be able to prepare for most difficult conversations.

It’s also possible to request some time and space to prepare. That could be as easy as saying:

“I know this is an important matter for you and I want to make sure I’m showing up fully and effectively for you, can we schedule a time to circle back to this matter?”

To prepare for difficult conversations, follow this framework and write out:

• The Facts - what actually happened (objective facts) in this situation?

• Your Story - what are your thoughts and assumptions about the situation?

• Your Feelings - what feelings (or unmet needs) are you experiencing?

• Your Request - what are you wanting from the situation or other person?

Then practice regulating and processing any uncomfortable feelings you’re experiencing.

This allows you to show up to the conversation grounded rather than reactive and emotionally charged.

Step 2: Invite

When you’re ready, invite the other person for a conversation.

Ask if they’re available for a conversation. Don’t demand it from them.

Inviting them to the conversation invites them to take ownership of their own choices.

Demanding a conversation can trigger reactiveness or victimhood.

You can invite them by saying:

“There’s something important I’d like to talk to you about. Is now good or when would be a good time for you?”

The conversation should happen synchronously, in person, or on a video or audio call.

It’s important to see or hear how the other person is showing up emotionally.

Step 3: Frame

To begin the conversation, start by framing it.

This creates safety by preparing the other person instead of surprising them.

Let them know this is going to be a difficult conversation for you, them, or both parties.

You could say:

“I want to start by saying this is going to be a difficult conversation for me (or us). You may feel some anger, frustration, or sadness, and that’s totally ok.”

You want them to know that what they’re going to feel is valid.

When we know what to expect, we can be more mentally and emotionally prepared.

Step 4: Facts

Dive right into the main objective fact or clearly state the difficult situation.

Don’t lead up to it or beat around the bush. Start with the headline so both parties are clear on what this conversation is about.

Then provide brief context with necessary facts.

Step 5: Story or Explanation

Share the story you’re creating or explain the situation from your experience and your feelings.

Keep this brief.

At this point, the other person has likely started to internalize the conversation. They may be experiencing a combination of fear, anger, or sadness. Sometimes even shame or guilt.

Keep it short and to the point.

The purpose of sharing your story or experience is so they can understand where you’re coming from.

Step 6: Feelings

Now is the time to address what they might be feeling.

Ask them for their thoughts and feelings:

“I imagine you’re feeling some fear, anger, or sadness. I’d love to hear from you what your thoughts or feelings are if you’re open to sharing them.”

Now you shut up and listen.

Listen to what they are feeling, not just what they are saying.

Listen to understand, not to justify who’s right or wrong.

Step 7: Seen & Heard

When they’re done sharing their feelings or thoughts, make them feel seen and heard.

This is not about agreeing with what they are feeling or thinking, it’s acknowledging and validating it.

You’re letting them know that you understood and heard them.

You can say:

• “What I heard you say is… am I correct or is there anything else?”

• “Let me make sure I understood you correctly, what I heard you say is…”

Keep going until they are complete and feel heard.

“Thank you for clarifying and sharing, is there anything else?”

Step 8: Resolution & Agreements

Once both sides feel seen and heard, it’s time for resolving or coming to an agreement.

Collaborate on solving the issue or coming up with clear decisions and agreements.

Aim to create the best win-win scenario possible. But also note that not all resolutions or agreements can be an equal win-win.

If you’re letting go of a team member, the decision is already made. The win-win could be offering to be a reference or offering them constructive feedback.

It’s important to close the conversation by confirming the agreements and any next steps.

If the conversation couldn’t be resolved, at least decide on the next steps:

• Schedule another time to continue

• Invite another party to join the conversation

• Set clear boundaries

The ultimate goal is always to end in a deeper connection with clear agreements.

Difficult Conversations Are An Art

Remember these going into hard conversations:

• You are not your thoughts and emotions. They are responses.

• Under everything you do or say is the need to be seen and heard. Same for the other person.

• Curiosity and judgment can't live in the same space. Curiosity always feels more expansive.

• Your intention will not always translate to the impact the other person experiences. The impact you experience is not always a translation of the other person’s intentions.

• It is ridiculous to get frustrated over uncommunicated expectations and needs.

• A regulated nervous system is your greatest tool. You either lead the conversation by default or by design.

Difficult conversations don’t get easier. You just get better at having them.

Putting It In Action

Pick a problem you’re experiencing at work or in life.

Look for the relationship and hard conversation you might be avoiding there.

Follow the process above to prepare for and to have the conversation.

Here are some examples of difficult conversations:

• I’m not feeling supported or acknowledged by you

• I want you to improve your performance

• I want you to change a behavior

• This is not working for me, I need something to change

• I don’t agree with you on this

• I messed up and want to take responsibility

• You messed up and I want you to take responsibility

• I have to let go of you

• I broke an agreement and want to get back into integrity.

• You broke an agreement

Work on one hard conversation at a time.

And watch the amount of energy you free up by clearing the hard conversations that keep you tethered.

There you have it, my framework for having difficult conversations.

Thanks for reading, I hope you found it helpful!

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Your Pal,

Colin

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