A Step-by-Step Outline for Starting a Tough Conversation

Let’s say you need to deliver some critical feedback. How do you kick off the conversation?

Maybe you get straight to the point and rip off the band-aid. Just go straight for the jugular.

Alternatively, maybe you start with a simple question, “How are things going?” Your hope is that they bring up the issue and save you a mountain of worry. Obviously they know something is wrong, right?

Critical conversations can be awkward. There’s this giant elephant in the room, and it’s tough to find the right approach to talk about said elephant.

I’m just finishing up Fierce Conversations by Susan Scott. The book provides a structure for having “fierce” conversations, which Scott describes as:

[A conversation] in which we come out from behind ourselves into the conversation and make it real.

In a more practical sense, fierce conversations are those in which we can truthfully attack an issue that’s probably difficult to acknowledge, have an honest conversation, come to a shared understanding, and set some kind of action plan to address the root issue moving forward.

Scott describes the perfect 60-second intro to a fierce conversation. Having flubbed my fair share, I found it to be a helpful template to avoid some of the awkwardness and get into the meat of the conversation.

Common Mistakes in Critical Conversation

“So, how’s it going?” I’m fairly certain I’ve started a critical feedback conversation with some variation of that question in the past. My goal: Hope they bring up the issue so I don’t have to.

Needless to say, trying to shirk responsibility isn’t the recommended approach.

In fact, I’ve probably committed all five of these errors outlined by Scott at some point.

Error #1: Starting with “So, hows it going?”

We start conversations this way because we can’t think of anything better to say, and we want to ease into the discussion. Ultimately though, no one is fooled. The other party probably knows something isn’t going well, and this fake agenda isn’t fooling anyone.

Error #2: Good, bad, good

Hopefully, the idea of the feedback sandwich – sharing positive praise followed by critical feedback and again by positive praise – is no longer common practice. This approach fails for a number of reasons. Most notably, team members begin to cringe whenever we receive praise fearing that the hammer is coming.

Error #3: Too many pillows

Our goal is to soften the message so it’s easier to bear. We think we’re being clear, direct, and thoughtful. The end result is that the other party doesn’t hear what we actually mean. They just hear the sugar-coated version.

This creates an obvious disconnect because I feel I’ve accurately conveyed the issue, but that isn’t the case at all.

Error #4: Scripting the conversation

“She’s going to react poorly to this bit of feedback.”

Our natural tendency is to script the conversation ahead of time and predict how we feel the other person will react. We arm ourselves for the intended backlash.

The downside here is that our thoughts often influence our demeanor so we enter the conversation ready for battle. We need to change our base assumption.

Error #5: Machine gunning issues

Since we didn’t take the time to address issues upfront, they’ve stacked up in our head. Buckle your seat, folks. We’re going to let them have it and unleash all of the issues one by one. Not the best approach.

How Do You Start a Tough Conversation?

If the errors above are how not to start a critical conversation. How should you start? Scott recommends starting with an intro that gets everything out into the open in 60 seconds or less. The perfect intro:

  1. Names the issue. Get the root issue out into the open right away.
  2. Draw on a specific example. Find something that specifically illustrates the impact the behavior had on the team/project/process. Keep it short.
  3. Describe your emotions. Why? Because you’re letting people know that you’re both human and vulnerable.
  4. Clarify the stakes. This is your opportunity to clarify why this is important and the impact the behavior could have if not addressed.
  5. Identify your contribution to the problem. Confront your share of the issue.
  6. Indicate the goal to resolve the issue. Put it plainly. You’re not firing this person. Your goal (as obvious as it might sound) is to resolve the issue.
  7. Invite the other party to respond. Remember, this is just the start of the conversation. It’s not an attack; we’ve just clearly defined an issue that we’re hoping to resolve. Now, we’re looking for input.

Example Time!

Let’s pull all of this together to see what a 60-second intro might look like.

We’ll say we’re addressing a fictitious Tony. He’s constantly interrupting you and other team members during calls and steamrolling your ideas.

Here’s how we might kick off the discussion:

Tony, today I want to talk with you about your communication style and how it’s impacting the team. In our recent team call, for example, you interrupted each person on the team while they were talking and poked holes in ideas before they were even finished. I’m frustrated because I know this likely isn’t your intention, and we’ve worked really hard as a team to foster meaningful conversations. There’s a great deal at stake – two team members have approached me individually because they don’t feel comfortable speaking up in front of the group. That’s not the kind of environment I want to create on the team. I want to resolve this issue with you – the impact your communication style is having on the team. Can you help me understand the issue from your perspective?

Alright – forced conversations like this usually read and feel a bit awkward. That might not translate directly to the actual conversation, but it hits on the main points.

Overall, the goal isn’t for these conversations to feel robotic or read from a script. The seven points above just provide a guide to follow. You can fill in the gaps and tailor the discussion to the particular circumstance.

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