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What the guides don’t tell you about difficult conversations

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The usual guides to difficult conversations (like this one from HBR) all provide useful tips. What they don’t do is help you figure out what matters most in preparing for them.

What I mean: The usual guides to difficult conversations are all about subject matter, style, knowing your goals, and planning. Most of the guides I’ve run across are intended to help managers communicate better with the people who report to them.

Which isn’t a bad thing, but they’re missing three of the four points of the management compass: your peers, your service recipients (not “internal customers”), and, most important of all, those who sit above you in the corporate hierarchy.

Because they’re focused solely on those you have power over while ignoring those who have power over you, these field guides to management miss two of the most critical differentiators between utter failure and all of the other possible outcomes.

The first is to know your interlocutor.

If you’ll be talking with someone who sweats the details, be prepared to dive in deep. If you’ll be talking with someone who doesn’t sweat the details but does appreciate their importance, focus more on the big picture while preparing to expose just enough of the details to reassure your audience that you have the details covered.

In either case, whatever the difficult subject is you need to cover, plan the conversation so you transition from problem to solution as quickly as you can without creating the impression you’re trying to avoid discussing the problem. You want to make sure the other party understands the problem well enough that your proposed solution is a logical response.

And if you’ll be dealing with someone who sees only the big picture, having neither interest in the details nor an appreciation of their importance? Figure out a big-picture view of the problem and your solution, and stick to them just as well as you can.

Unless, that is, you’re in a negotiation, at which point the details are what justify your estimate of the cost.

Which brings us to another dimension of knowing the person you’ll be talking with: their temperament. You can’t plan a difficult conversation without having a pretty good bead on the other person’s disposition.

If you’re talking with a big-picture executive who is nonetheless patient, you can get away with one of my favorite threats: “You can either trust me on this, or I can explain it to you.”

If, on the other, more common hand, you’re dealing with someone who prefers the view from 100,000 feet and is known for volatility besides, prepare yourself for a blow-up, and know exactly how you’ll handle it when it happens.

How you’ll handle it is first and foremost to be unsurprised. When the person you’re talking with loses his or her cool, if you’re caught off guard nothing good will come of it. If, instead, you’re expecting it you’ll know that now is the time to stay calm and to project calm. In a confrontation between volatile and calm, calm wins every time unless projectile weapons are involved, and if they are, calm is still your best choice.

How you’ll also handle it is to not interrupt. Instead, take notes ostentatiously, making the point with your non-verbals that you’re taking your counterpart’s shouting points at face value; also that you’re entirely unaffected by such an emotive display.

And, if and when your volcanic colleague runs out of steam, summarize. “Here’s what I understand your concerns to be,” you might begin before bulleting them out. “At some point, in order to resolve the situation, we are going to have to dive into the details. Would you like me to schedule another meeting so we can do this?”

This isn’t, I want to emphasize, the only way to deal with a hothead. While a bit riskier you might also choose to hold up your hand (a useful alternative to interrupting) and, when you have the floor, to suggest that when the other person is ready for a more businesslike conversation he/she should contact you and you’ll be happy to pick up where you left off.

The point here isn’t what the right preparation is. It’s to emphasize the importance of being prepared.

Which brings up one more aspect of preparing for a difficult interaction — to have an exit strategy. The more you expect the conversation to turn into a confrontation and the confrontation to become explosive, the more important it is to have a pre-planned way to cut the interaction short.

This doesn’t have to be anything more than having a “hard stop” because of another meeting you have to attend.

And you thought meetings have no business value.

Comments (6)

  • Excellent column. I might add that if the conversation has to do with sexism or racism, be sure it’s lead – or rather, co-lead by a leader from each side of the privilege gap.

    This shared power framework, if done well, tends to increase the sense of safety and empowerment for those on the short of the stick, while making it easier for many on the long side of the stick to know that their actions are more likely to be part of the solution rather than part of the problem and help facilitate the business culture changes needed to reduce sexism and racism in the work place.

  • “You can either trust me on this, or I can explain it to you” sounds a lot like a put-down along the lines of “I can explain it for you but I can’t understand it for you.” Maybe a bit of rephrasing would make it more palatable, something like, “Do you trust me on this, or can I explain it to you?”

  • I have worked for several people that, while not necessarily volitale, did have their ways.

    I would usually begin with something that would aggravate them. But was not related to me or the real issue I wanted to discuss.

    I think “deflection” is the correct term.

  • There is a third way to deal with a hothead, because some hotheads can become unnerved and even more agitated, when confronted with calm opposition. They’re used to evoking emotional responses and can’t read someone who’s not showing any. The (rational) words hardly matter in such cases. Showing some emotion however, provides them a form of feedback they understand and trust. Even if you are arguing something they didn’t expect or agree to at first. Escalation is a real threat however, so it’s risky to use this strategy. But then, dealing with hotheads is risky anyway…

  • Regarding the “hotheads”, if you know you are going to be dealing with a volatile person, you should take some time to figure out what their triggers are and what is likely to set them off about your topic.

    Often people get angry for one basic reason: some sort of perceived threat. For example, they might perceive that your solution to a problem removes some of their responsibility/power, which they see as a threat to their position. Alternatively, they might think your proposal is requiring them to do extra work and/or take on responsibility they don’t want, making their job more difficult. A third possibility might be that they’d end up connected to some landmine of a problem and they don’t want to be damaged by the fallout of a failure.

    If you can figure out what possible issues your proposal might bring up for your audience, you can figure out how to address that issue up front, before they get triggered by it. Or phrase your solution to avoid their problem area(s). Sometimes you might not be able to know in advance what is likely to set them off. In that case, try thinking (in advance) of some tactful ways to ask, to get at the heart of their concern. Or else, like Bob says, have your exit strategy prepared and use it. Then you can try following up in email: “We were discussing a resolution to issue X by doing Y and concerns about A? B? C? came up. Can you help me clarify?” – something like that.

  • Did you read “Never Split the Difference” by Chris Voss, a lead negotiator for the FBI? You’ve called out multiple techniques he uses including the obvious listen and empathize, but another key element is labeling (“here’s what I understand your concerns to be”) which gives them an opportunity to agree that you understand them, or correct you. Other ways to label include “It seems like…”, “It sounds like..”, “It looks like..” Chris says not to use “I’m hearing that..” because “the word I gets people’s guard up….If they disagree with the label, that’s OK. You can always step back and say “I didn’t say that was what it was. ‘I just said it seems like that'”.

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