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Dreading that difficult conversation? Here’s 5 steps to make a difficult conversation easier.

Young business woman on phone going through the 6 steps you need to take before you have a tough conversation
5-steps-that-make-difficult-conversations-easier

You’re 15 minutes into your morning team Zoom call when a close colleague signs on late, mumbles “sorry”, and eventually settles in. You carry on presenting the report that the two of you were supposed to have created together (bold for emphasis). This isn’t the first time he’s left you ‘hanging’ and you vow to yourself, it’s time to talk! In this article I’ll share 5 STEPS to make difficult conversation easier, and likely more successful.

These are Challenging times

There’s an ambient anxiety in the world right now. Many people are worried about their health, the economy, their jobs. Work routines and work-life balance boundaries changed. This elevated level of stress and anxiety can impact the way people behave.

People may seem more edgy, less focused, or overwhelmed. Some people might even ‘take over’ and you’re thinking ‘dude, back up, I got this’.

If it’s time for that tough talk, here are 5 steps that can help.

5 steps to make a difficult conversation easier

1: Start with you

Before you go ‘take a strip off someone’, start with you. As Daniel Goleman’s research on emotional intelligence shows, the most effective leaders in the world have developed a high degree self-awareness.

We tend to get triggered when we perceive that others ignore or devalue those things that are most important to us. What values expert Scott Bristol Phd. calls our core values.

Ask yourself, ‘what’s up?’ Why am I so frustrated? disappointed, or (fill in the blank?). And what do I really want here?

Here’s a quick way to check-in with yourself, based on what Gervase Bushe in his book Clear Leadership, terms the experience cube.

  • What did I observe (see, hear, experience) that seemed to trigger me?
    • He didn’t apologize for missing our meeting last night.
  • What am I thinking?
    • He’s taking me for granted, he assumes I’ll do the report anyway.
  • What am I feeling?
    • I feel a hurt. Maybe unappreciated.
  • What do I want?
    • to tell him to go to *@%….. actually…to feel respected, or:
    • to keep his promises to me. And if he can’t, let me know.

*Gervase Bushe’s experience cube has much more nuanced and profound distinctions.

Once you’ve stepped through this quick self-assessment, you might decide it’s not that big a deal and just let it go. But if it does feel important, you owe it to yourself to have that conversation.

It’s OK to ask for what you want

Even though someone else may be under stress, it doesn’t mean they’re ‘off the hook’ to deliver on their promises. Whether work related or inter personal, you can still advocate for what you want.

In Malcolm Gladwell’s book BLINK, he shares how our brains have this exquisite ability to perceive a multitude of cues and in a nano second make an accurate interpretation of what’s going on.

The problem is, sometimes our interpretation is corrupted by our own perceptions and we get it wrong. Check out the Ladder of Inference .

If we call them out and it turns out our interpretation was wrong, they might get triggered and their ability to listen goes down. And of course, we want to treat others in a way they feel respected. Here’s what to do:

2: Assume the best

Whether the other person’s intentions were good or not, it can help to assume the best. But wait! Isn’t that still just an interpretation?

When we start by assuming that others have good intentions:

  • We feel empathy which lowers our levels of cortisol and adrenaline.
  • We’re better able to use the executive functions in your brain.
  • The other person is more likely to be open to your conversation.

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What is a More Respectful Interpretation?

Lets say you have a Zoom call at 9 am and a colleague shows up late at 9:20 looking disheveled (interpretation). You could assume that:

  • they don’t think these meetings are important
  • they’re disorganized
  • they don’t respect our time

Some More Respectful Interpretations might be:

  • They were caught on another call resolving an issue on our behalf
  • Maybe they were up late working long hours on a special project
  • Maybe they didn’t realize the meeting started at 9.

While these interpretations may not be accurate either, it allows you to go into your conversation assuming the best.

3: Give them a heads up

Imagine you’re hiking along a trail through a forest when you turn the corner and come face to face with big bear! Fight? Flight? Freeze? That’s what your colleague will do if you ‘spring’ the conversation on them.

big, menacing looking bear in the forest. Not sure whether to Fight Flight or Freeze.
having a tough conversation can be like facing a bear

You could say something like “Hey Jim, I was thinking about that report we were supposed to write together last night, and I wanted to talk with you about it today. When’s the best time?” While this may cause a little bit of anxiety, you’re actually building trust by giving them a heads up.

4: Have the conversation

Here’s an easy, research-backed way to have a difficult conversation. It helps you to stay focused on the issue, make a request, and it’s more likely to leave the other person feeling that they’ve been treated with respect.

It’s called the DEAR model and it’s just 4 simple steps.

  1. DESCRIBE the event in neutral terms. i.e.:
    • ‘We had a meeting scheduled last night to prepare the report and you didn’t come’. instead of
    • ‘You were a total no show and hung me out to dry’.
  2. EXPLAIN the impact on you. Use ā€˜Iā€™ statements. i.e.
    • ‘When you didn’t show up, I felt disappointed and overwhelmed that I’d have to write the report by myself’. instead of
    • You made me feel stressed and invisible
  3. ASK the other person for their experience and intent. It helps us understand their intentions and it can reduce defensiveness. i.e.
    • ‘Can you help me understand why you didn’t make our meeting last night?
    • by the way, tone matters. Try to be authentically curious.
    • then – listen – be curious – you can even double click.
  4. REQUEST what you’d like to have happen in the future?
    • “In the future I’d like you to make it to our meetings so we can work together to create the report”. or
    • “If you do have to miss one of our meetings, I’d like you to call me and let me know before the meeting.’
    • Check for agreement by asking, ‘Will you do that?’
    • If they say no, or start to defend, ask more questions to understand what is getting in the way of meeting your request.
young business woman having a difficult conversation with her male colleague, at a table in an office.
colleagues having a difficult conversations respectfully

5: Say thank you

Whether it’s an employee, colleague, family member, or your boss, these conversations can be uncomfortable. When we say thank you, we’re showing them that we respect their time and their willingness to invest in the relationship. And relationships are so important.

Bringing it all together.

If you’re dreading having to have a difficult conversation, you’re not alone. I hate having these kind of conversations.

My friend Hugh Culver calls it Facing the Tiger. Who wants to face a tiger? It can be tempting to just let it go. So here are a couple of parting thoughts.

We’re constantly interacting with others, talking on cell phones, texts, Zoom, email, slack, in person. We’re roaring between meetings, projects, and family needs. It’s inevitable that we’re going to have interactions that feel like ‘ouch – what was that all about?’.

When these happen, we can check-in with ourselves first, to see how important this is. And then decide if we deal with it at all. It’s a choice.


If the answer is yes:

  1. Start with you – check in with yourself and ask:
    1. what did I see, hear, experience
    2. what am I thinking
    3. how am i feeling
    4. what do I want
  2. Assume the best. What’s a More Respectful Interpretation?
  3. Give them a heads-up
  4. Have the conversation – use the DEAR Model
    1. Describe the event (in neutral terms)
    2. Explain the impact on you (use ‘I’ language)
    3. Ask them for their perspective
    4. Request what you’d like to have happen in the future
  5. Say thank you

During challenges times it can be hard to be the one who is always taking the high road. You have stress too. Yet the world needs more empathy and compassion. When you show that compassion, one person, one conversation at a time, you make a difference.

If found this helpful and you’d like to be kept in the loop, click here for my Resilient Leaders newsletter.

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