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|In: Leadership|Last Updated:

Anticipating a difficult conversation? Want help? There’s plenty to be had, last week’s KJR being just one example among many. The short version: Know your goals, and plan for both the situation and how the other person is likely to respond, to the extent you’re able to anticipate it.

But how about the easy ones? The hard ones are … well, the word “harder” comes to mind … but just because they’re hard, that doesn’t make them more important.

And just because the other ones are easier, that just means they’re less hard. It doesn’t mean you should dismiss them as easy.

And even if they’re less important taken one at a time, in the aggregate they matter more.

Figure it this way: For every difficult conversation you have, you probably have 10 to 20 that aren’t hard in the usual sense. And if you’re like most of the busy managers I know, for every not-difficult conversation you have, there are probably another 10 to 20 you should have had, had you had enough time to have them.

Then figure it this way: A gram of prevention being worth easily a dekagram of cure (note to self: the metric system might be more logical than the English system, but it’s far less poetic) … where was I? That’s right, prevention, cure … handle the easier conversations and handle them well, and you won’t need as many difficult ones.

Some guidelines:

Know your goal: Are you trying to inform? Persuade? Learn? Collaboratively solve a problem? If you aren’t clear in your own mind about your goal, odds are your conversation will take too long and accomplish too little.

Know your meta-goals: When the conversation finishes, what state of mind do you want the other party to leave with? If, for example, you’re having the conversation to make you smarter about something, your meta-goal might be for the other party to feel energized because her manager values her expertise.

Schedule. Or don’t: The other person’s habits, preferences, and current time pressures, along with your goals and the complexity of the topic, all feed into your decision as to whether to IM, email, schedule a conversation, or just drop by (local) or call (remote) for a quick chat.

Choose wrong, like, for example, dropping by for a chat when the other person is crunching against a tight deadline, and what should have been an easy conversation can quickly turn difficult.

Plan: Sketch an outline for the conversation. For a group meeting this would be the agenda. Just because it’s a one-on-one that doesn’t mean you shouldn’t have a plan.

Be flexible: It’s just like any other plan — don’t insist on adhering to it if you find the conversation going in a productive direction you didn’t anticipate.

Location, location, location: The setting matters. You behind your desk in your office sets a very different tone from the two of you sitting at a table, which sets a very different tone from you in a chair facing the other person at his desk. Which in turn sets a different tone from meeting for coffee, which is different from meeting for lunch in the cafeteria or for beer after hours.

Phone calls have different dynamics entirely, and they’re different from web conferencing when there’s PowerPoint involved.

Have a meeting instead: Sometimes, when a lot of people need to hear the same message, you and they are better off all hearing it together. Also: If the message is a compliment, that’s no topic for a one-on-one conversation. Compliments should be delivered publicly.

Sequence matters: Sometimes you need to inform more than one person, or more than one group, about something of consequence. Talking to these individuals and groups in the wrong order can, in some situations, blow up in your face.

Especially groups, because once you’ve told the first group you should assume whatever you said will, within no more than a half hour, become public knowledge.

Do it: Yes, you’re busy. But ignore the easy conversations and you’ll miss opportunities, for example, to catch an employee’s deteriorating attitude when the issues are minor and easy to resolve. Instead, they’ll fester, until the situation is so bad that you now have to have a difficult conversation instead.

There are eight tasks of leadership — eight responsibilities leaders have to master. Of them, communication is the linchpin that holds the others together. It’s a multidimensional responsibility that encompasses listening, organizational listening, informing, persuading, and facilitation. There are lots of ways even the best leaders can get it wrong.

Don’t blow the easy ones.

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|In: Career Management|Last Updated:

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.

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