Prepare for a Difficult Conversation; Don’t Avoid a Difficult Conversation

Prepare for a Difficult Conversation

Your colleague sent you a passive-aggressive email and you want to sit down and address it face-to-face. Or perhaps you’ve got some tough feedback you need to give to a coworker. Or maybe you’ve decided to discuss some growing tension on your team with your boss. When you’ve resolved to talk through a difficulty with a colleague, it’s tempting to have the conversation immediately. No better time than the present, right? Well, not quite. In a conflict situation, emotions often run high and going into the conversation cold may set you up for an unproductive, contentious debate. Taking time to prepare mentally will help you remain calm, increase the chances that the conversation will go smoothly, and improve the ultimate solution.

You’ll also want to think about the logistics (where and when you meet) and your strategy (how will you frame the problem and what you’ll say first). But getting ready emotionally is perhaps the most important work you need to do before you get into the room. Here are a few things you can go do to get ready.

Check your mindset. If you’re getting ready for a discussion you’ve labeled “difficult,” you may be feeling nervous, stressed, angry, or upset about it ahead of time. To minimize those negative emotions, try to think about it as a regular conversation and frame it in a positive way. For example, [think that] instead of giving a negative performance review, you’re having a constructive conversation about development. Or you’re not saying “no” to your boss; you’re offering up an alternative solution.

This isn’t sugarcoating. Be honest with yourself about how hard the conversation might be, but also put as constructive a frame on it as possible. You might tell yourself: It will be a normal discussion, and we may have to talk about difficult things, but we’ll work through them together because Carol and I have always respected each other.

And focus on what you stand to gain from the conversation. Assume you have something to learn; assume there is a more creative solution than you’ve thought of. By entering the discussion with an open mind, regardless of your coworker’s stance, you’re more likely to find common ground.

See the situation from your counterpart’s perspective. Try to get a sense of what your colleague might be thinking. She had a rationale for the way she’s behaved so far, even if you don’t agree with it. What might that reason be? Imagine you’re in her shoes. Ask yourself questions like: What would I do if I were her, or if I were in R&D instead of marketing? What if I were someone reporting to me? What if I were my boss?

Also ask yourself: What is she trying to achieve? You’ll need a sense of what her goal is if you want to resolve it. Identify places where you see eye to eye on the issues. This common ground will give you a foundation to joint problem-solve.

If you’re at a loss, ask a colleague what he thinks is going on in your counterpart’s mind. You might ask the colleague you are consulting something like: “I’d love some advice and coaching. I haven’t worked much with XYZ before, but I know you have. Can you help me understand how she might be seeing this situation?” Don’t use the conversation to seek validation. Paint the situation for him as neutrally as you can. Cataloging every fault and misstep will probably get you sympathy but not constructive feedback, so focus on the problem.

And you won’t know everything ahead of time, so come up with a list of questions you want to ask when you sit down with your counterpart. This will help you, once you’re face-to-face, to show that you care enough about her perspective to think it through beforehand and to discover more about how she views the situation.

Before you get into the room, find a trusted colleague or a spouse or friend who can listen to you complain. Say everything you feel about the situation — the good, the bad, and the ugly. Don’t hold back. Be careful who you choose to vent to, though. You don’t want to go to the friend who just riles you up. Find someone who has a calming presence and will ask helpful questions.

Just suppressing your emotions [as different from managing them which you should] and deciding to bottle up something that has upset you, can lead to bad results. If you don’t express your emotions, they’re likely to show up elsewhere. Psychologists call this emotional leakage. When you bottle up your feelings, you’re likely to express your emotions in unintended ways instead, either sarcastically or in a completely different context. Suppressing your emotions is associated with poor memory, difficulties in relationships, and physiological costs (such as cardiovascular health problems). Prevent your emotions from seeping out — in the conversation or at home — by getting your feelings out ahead of time. That way, you’ll be more centered and calm when you’re having the discussion.

You may be wondering, Do I really need to do this for one 10-minute conversation? While it takes some time (though it will get easier the more you do it), there is a huge payoff. You’ll go into the conversation with the right mindset, feeling confident, knowing what you want to achieve.

Don’t Avoid a Difficult Conversation

As a leader, how can you confront the truth about a situation without fearing rejection, or disagree with someone clearly and cleanly without obsessing about causing offense?

In leadership roles the most important work often happens in the least comfortable spaces. Handled well, risky and confrontational conversations — especially those that surface awkward facts or get to the source of organizational tensions — can improve how we relate to each other, help organizations get a better grip on reality, and enable leaders to make better decisions.

Yet while we tell ourselves that these conversations are tough because we don’t want to upset the other person, usually the squirmy feeling we’re experiencing has less to do with our counterpart and more to do with our own unconscious anxiety about not being able to handle the conversation well. Overcoming these anxieties and having the tough conversations anyway is one of a top leader’s most difficult challenges — critically needed yet chronically hard to do.

Conversations on some of the trickiest topics in an organization can be: trust on teams, organizational restructuring, and addressing underperformance. By definition, these kinds of conversations require you to get out of your comfort zone. You may even feel like you’re betraying former loyalties to past products, old ways of working, personal affiliations, or previous professional identities.

That said, four elements make the difference:

First and foremost is a shift in mindset from seeing difficult conversations as a hurdle to seeing them as a resource. Difficult conversations can actually strengthen personal bonds if you handle them well. For example, one may be able to see a difficult conversation as a route to building trust in his team.

You have to be very wary of the indirect comments and conversations that are going around in a meeting. You might see or sense a couple of people who are threatened by the restructure or are a little unhappy about one element. One may say: “I sense that a couple of us here feel threatened by this, so let’s actually have this out as a team.” It may well build the levels of trust and openness among the team.

Second, leaders must have the skill of regulating their emotional responses in difficult conversations. Now, too many leaders understand this to mean that they have to take emotions out of it completely. That’s not realistic, and burying feelings can be as destructive as letting them all spill out. Instead, skilled leaders use their emotions in a constructive way.

Third, leaders need develop the ability to tell it as it is without waffle yet with compassion, balancing advocacy with inquiry.  

Fourth, the leader needs to be able to create psychological safety for the conversation. For example, a good but new leader could use appreciation and a clever dialogue to make it easier to have a sensitive conversation with her team in the new organization. She may arrange an off-site and ask them to help her understand the business. For such conversations, no tool works better than de Bono’s Six Thinking Hats to try to let their emotions out without compromising on the facts and rationale and legitimize them and also address their misgivings in a constructive manner.

Sources: Prepare for a Difficult Conversation by Amy Gallo, Harvard; Don’t Avoid a Difficult Conversation by Deborah Rowland, Harvard

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