Having Tricky Conversations Like a Boss - Point Easy vs. Point Difficult

Most of us avoid tricky conversations. What if we say the wrong thing? What if we make it worse? What if it’s just… awkward? So, we leave it. And for a moment, that feels like the easy option. Until it isn’t.

I worked with a home construction company where we talked about Point Easy vs. Point Difficult, a simple but powerful way to think about performance conversations. Imagine an ideal standard: turning up on-site, tools ready, at 7:30 AM sharp.

One day, someone strolls in at 7:35. Not the end of the world, right? But if you mention it that same day, the conversation is just a gentle nudge. Awkward? Maybe. But manageable.

Now, let it slide.

7:35 becomes 7:45. Then 8:00. Then missed days. The longer you leave it, the bigger the issue gets. What was once a small moment of feedback is now a full-blown “we need to talk” conversation. And worse, everyone’s watching. If lateness goes unchecked, others start pushing the limits too.. Research from Will Felps and colleagues shows that a single toxic employee can drag team performance down by 30-40%, while high performers lift the standard.

How to Have the Conversation

Simon Sinek offers a simple way to structure feedback called FBI Feedback - short for Feeling, Behaviour, Impact. It keeps things clear, fair, and constructive.

• Feeling How did their action make you feel?

• Behaviour What did they do (factually, without judgement)?

• Impact What happened as a result?

Once you understand the structure, the real skill is how you prepare and deliver the conversation so it lands well.

Watch him here describe the approach.

1. Before you start

• Plan it. Write down what you want to say. It helps you collect your thoughts and separate fact from emotion.

• Cool emotions. Wait until the heat has dropped before you speak.

• Practice. Run it past someone you trust if it’s a high-stakes chat.

• Anchor it. People often respond first with defensiveness or denial. Stay calm and restate your intent: you’re there to help, not blame.

• Create a two-way conversation. Feedback isn’t a download. Ask open “how” and “what” questions to understand what’s really going on.

• Use it for good. Don’t save this structure for when something goes wrong. Use it to reinforce great behaviour too — public if positive, private if sensitive.

2. During the conversation

Start by checking in: “Is now a good time?”

Then use the FBI structure to keep the focus on clarity and respect.

• Speak from I, not you: “I felt frustrated when the deadline slipped,” not “You let us down.”

• If you’re unsure how to describe how you feel, try using the Feelings Wheel to find the right words.

• Focus on what you saw or heard, not what you assumed.

• Replace but or however with and — it keeps the message connected rather than defensive.

• Finish by inviting their perspective: “What are your thoughts?” or “How do you see it?”

That’s what turns feedback into a real conversation rather than a lecture.

If you want to go deeper see the following article How to deliver constructive feedback in difficult situations

What Happens If You Don’t

Avoiding tricky conversations might feel easier in the moment, but silence has a cost. It erodes trust, clarity, and performance. Small frustrations grow into bigger issues. People start to fill the gaps with stories. By having the conversation, you model honesty, care, and accountability - the stuff strong teams are built on.