How to Stop Avoiding Difficult Conversations at Work

Right before you have to say something hard, something shifts. Your stomach tightens. Your mind starts bargaining. "I'll handle it next week. It's probably not that big a deal."

That's not procrastination. That's your brain working exactly as designed.

Amy Jacobson, an emotional intelligence specialist and author of The Emotional Intelligence Advantage, explains that our amygdala triggers a fight, flight, or freeze response any time we face an unknown outcome. And what's more unknown than how another person will react when you deliver hard feedback?

"If I could 100% guarantee the person you're about to speak to will be fine with it," Amy said, "it suddenly stops being a difficult conversation. It's just a conversation."

So the first step, says Amy, is recognizing that the avoidance is normal. The second step is learning to override it.

The Difference Between a Difficult Conversation and a Difficult Delivery

Not all hard conversations are the same. Amy draws a useful distinction:

A difficult conversation is one where you still need answers. There's back-and-forth, questions to ask, information to gather. You don't know all the facts yet.

A difficult delivery is when the outcome is already decided. The third warning. The termination. The denial of a promotion. What they say won't change the result. You're not exploring. You're informing.

Most managers treat every hard conversation like a delivery when really it's still a conversation. And that's where things go sideways.

Start With Curiosity, Not an Ammunition Pack

When we're nervous, we over-prepare in the wrong direction. We build a case. We gather examples, metrics, documentation. We walk in ready to prove our point.

Amy calls this the "ammunition pack," and she says it almost always makes the first conversation worse.

In an initial conversation about underperformance, your goal isn't to win. It's to understand. There's a big difference between someone who's struggling because they lack training and someone who genuinely doesn't care. The conversation you need to have with each of those people is completely different.

Amy suggests we start by asking: How are you? How do you feel you're going with your work right now? What do you enjoy most? Is there anything that feels like a drag?

You're listening for the root. Once you hear it, you'll know where to go next.

The Ask, Ask, Tell Framework

When someone isn't owning the problem themselves, Amy recommends a three-part move: Ask, Ask, Tell.

You start by asking open questions to invite self-awareness. Then you ask again, more specifically, to see if they'll identify the gap. If they still don't, you tell. You get factual, specific, and calm.

But here's the key to "tell mode": you detach from the person and describe the role.

"Let's talk about what the expectations are for someone in this role. Here's what we typically see. Here's where your performance currently sits. Does this seem accurate to you?"

That framing removes the sense of personal attack. You're not saying someone is a failure. You're describing a gap between a role and a person, and then working together to close it. Or, in some cases, realizing it can't be closed and the role isn't the right one.

When It's Not Working: The Follow-Up Conversation

If you've had the initial conversation, made a plan together, and nothing has changed, the follow-up is an entirely different kind of meeting.

This one needs a consequence.

Amy is direct about this: if someone has been told four or five times and nothing changes, it's because there's no real cost to not changing. The mind weighs gain vs. loss constantly. If there's no loss attached to the status quo, the status quo stays.

"You have got to come into that conversation in a tell mode, not a conversation mode," she said. "I need you to do this by this date, and if it's not done, here is the consequence."

The consequence doesn't have to be termination. It could be a formal warning. A removal of responsibility. A restructuring of the role. But it has to be real and it has to be followed through.

Everyone Is a Superstar in the Right Role

The most useful reframe Amy offers is this: sometimes an underperformer isn't underperforming because they're incapable. They're in the wrong job.

She described working with a client where a technically brilliant employee had been promoted into a leadership role they didn't want. They were snapping at their team, constantly stressed, grabbing work back instead of delegating. When she sat down with them, one question opened everything: "What do you enjoy most about your job?"

The answer had nothing to do with people.

By having that honest conversation, they were able to restructure the team, put a natural leader in the leadership role, and let the technical expert do what they loved. Both people became higher performers. The team got clarity. And what started as a performance problem turned into an organizational strength.

That's what's possible when you go in with curiosity instead of a verdict.

Keep up with Amy Jacobson

• Website: https://amyjacobson.com.au/

• Book: The Emotional Intelligence Advantage — https://www.amazon.com/Emotional-Intelligence-Advantage-Mastering-Conversations/dp/1394337949

• Free eBook: https://app.box.com/s/0yjaellmagoc8dyceu5bdyndk4uoku6x

• LinkedIn: https://www.linkedin.com/in/amy-jacobson-emotional-intelligence/

• Instagram: https://www.instagram.com/amyjacobson_ei

• Facebook: https://www.facebook.com/findingyoury/

• YouTube: https://www.youtube.com/channel/UC3tV1e6qV8EHqmA7_RFnPTw

The Modern Manager is a leadership podcast for rockstar managers who want to close the gap between knowing what good management is and actually doing it.

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