How to start a conversation you're dreading

Wednesday's Daily Briefing post on "Why good leaders embrace the 'cringe moment'" sparked a strong reaction from readers. Several readers wrote in to ask for more advice from Mike Wagner, the Advisory Board's Chief Teaching Officer, who had weighed in with his suggestions.

Reprinted below, see a full transcript of Dan Diamond's interview with Wagner.

Q: Do you agree with the premise of the piece? Basically, is it right to 'lead with the punchline' in a meeting or when managing—especially when the news is negative?

Wagner: We would argue that especially when the news is negative, you should lead with the “bad news first."

People are perceptive and they can tell when something negative is about to be said. To delay the news is to both disrespect your colleagues and damage your own credibility.

Delaying the negative is disrespectful because it takes away the colleague’s opportunity to receive the news, react to it, ask questions—it treats them as fragile and difficult, rather than as a professional who seeks the truth.

Delaying the negative also confuses the message and makes it harder for the listener to understand the leader’s intention—is this a key issue of concern or just a secondary issue being mentioned at the same time as other messages are begin sent? If a leader stumbles through a communication and tries to bury the message, he or she comes across as unsure, doubtful, and inarticulate.

Q: OK, I get it. Leaders shouldn't delay. But to push this idea a bit—I know managers fear demoralizing staff—what about a short positive message at the start of the conversation? Or ending the conversation on a high note? 

Wagner: I know there is an entire theory of the case, espoused by many, that you should say something nice and positive, followed by the negative news, and then wrapped up with another positive comment—the so-called “Sandwich Message." As though somehow, your sandwiching will change the message itself.

It is much better to get to the point, rip off the bandage so-to-speak, and get on with positive interactions, future plans, and action steps that will ultimately prove helpful to the colleague or staff member.

Q: What best practices have you learned around having difficult conversations? Is there other Advisory Board guidance or research that's relevant here?

Wagner: When confronting a staff member with difficult messages, keep the conversation direct and to the point. You should clearly articulate the negative behaviors to be corrected or the negative news to be delivered; explain what would have been acceptable behavior or why the negative decision was necessary, and then explain next steps.


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Q: How does a manager figure out the right next steps after a difficult conversation?

Wagner: Either [explain] what will happen if the negative behavior continues, how the employee can be considered for future opportunities, and/or what the staff member is expected to do in support of the decision.

[Keep it] very simple—negative news, reasons, and next steps.

Q: You make it sound so easy, although I know it isn't.

Wagner: In order to have this type of effective conversation, there are two pitfalls you must avoid.

First, the conversation cannot be a "discovery session" where you are trying to get the facts. You should do that in other conversations and prior to the direct confrontation of the issue.

Your “discovery” conversation can be at 7 AM followed 30 minutes later with your decisions or confrontation. But, you don’t make a “snap judgment” based on facts gleaned in the moment from your colleague or staff member – that comes across as a trap and it undermines your determination and decision making.

Second, you should address no other issues during the conversation. Many staff members will respond with a “fight or flight” response – arguing about the details, or who is at fault, ow that the boss’ observations are incomplete. This simply undermines the decision making process and undermines your authority as a leader. You can always promise to look at confounding factors later and you can promise to resolve complaints the staff member might have at a later time. But not in the main confrontation or difficult conversation.

Q: How important is this skill to being a good leader? Basically, is it possible to be a leader who only deals in positive conversations and hand off these sorts of difficult messages to a lieutenant?

I realize our instinct may say 'of course not,' but I've known leaders who opted for this style—and they've generally been successful.

Wagner: I would argue this skill is extremely important for a good leader to demonstrate.

The concept of a “hatchet man” (or woman) designated to be the bearer of bad news will eventually erode a leader’s credibility. Delivering only good news might make a leader popular and well liked—much like a favorite uncle. But if a leader always defers to someone else to deliver the hard messages, the leader eventually will be marginalized—seen as irrelevant or as only partly in command. 

When times are tough and the challenges are hard, a leader must be able to command respect and loyalty—able to encourage staff to follow even when the leader has asked for great sacrifice. 

Getting a staff member to sacrifice personal gain requires that the leader be seen as transparent—routinely trusted to deliver accurate information, both good and bad. And approachable—open to debate, discussion, and disagreement, even if uncomfortable. And finally, believable—never ignoring, hiding, or glossing over the truth

If a leader delegates the hard conversations to someone else, they will prove to be a person who cannot be trusted and should not be followed in difficult times.


More insights from the Advisory Board

Learn how to deliver the right feedback to motivate your team, get a staffer back on course, and succeed in a difficult conversation with doctors.


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