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Why difficult conversations feel impossible

You know the conversation is overdue. You've been thinking about it for a fortnight, maybe longer. You rehearse it in the car, in the shower, in the moments before you fall asleep. And each day you find a reason not to have it.

Part of the reason we put these conversations off is that it feels as if we're being asked to choose between two things that matter equally to us: being honest with the person we need to talk to (the counterpart), and not being harsh on them. And that seems like a difficult equation to solve.

Research by Levine, Roberts and Cohen (2019) at the University of Chicago and Carnegie Mellon brings this out clearly: difficult conversations are ethical dilemmas. You hold two apparently conflicting moral motivations at once, honesty and benevolence.

However, while this perception is real, it is also, according to the research, almost always overstated.

Levine and Cohen (2018) ran a study in which participants committed to being fully honest in every conversation with every person in their life for three days. Before the experiment, people predicted it would damage their relationships and cause significant harm. In practice, they found the experience more pleasurable, meaningful and connecting than expected, and found it less harmful to their relationships than both they and neutral observers had predicted.

It therefore seems that there are two fundamental errors that explain why leaders dread these conversations more than they should.

We over-emphasis the short-term discomfort and under-play long-term benefit. You will see the person's face fall when you say it. But you probably will not witness their career trajectory in five years' time. The immediate cost is therefore far more salient that the long-term effects (Levine, Roberts and Cohen, 2019).

We overestimate how much harm we will cause. When the counterpart has reason to believe you are acting with good will, any feedback lands very differently from how you imagine it will. They are far more attentive to your intent and overall warmth than you anticipate (Kumar and Epley, 2018).

It is worth remembering that the conversation may come as a relief to your counterpart. There might be something that is bothering them that can be easily fixed. Perhaps they have good reason to feel under-appreciated or overworked. Perhaps there is something going on outside work that is a concern for them.

But in the moment, we often anticipate the worst possible outcome and feel like we are in a very difficult position. We can therefore be tempted to make one of a number of approaches that feel ethical but do not actually serve the person we are dealing with, or others who are impacted.

The four strategies that are tempting but not effective

Levine, Roberts and Cohen (2019) identify four common strategies leaders use to escape the honesty-benevolence dilemma. Each feels like a principled compromise. None of them optimally serves your counterpart.

Strategy

What it sounds like

Why it fails

Avoidance

Postponing the conversation, or leaving out the difficult part

Denies the person information they need; and unconvincing if we deliver only part of the message (Levine et al., 2018)

Brutal honesty

Delivering the truth without warmth or context

Invites the person to dismiss the feedback as unfair or personal

False hope

"You are doing fine, just keep going"

Denies accurate information; creates resentment if detected (Lupoli, Levine and Greenberg, 2018)

Equivocating

Saying something technically true but misleading ("your work on X is going well" when X is not the issue). The research calls this "paltering"

you are taking

The finding most worth emphasising is the one about omission. Leaving out the hard part feels like you are taking the ethical high ground because at least you did not lie. But if nothing changes you’ll be in trouble later on for not giving the necessary feedback earlier. You can’t expect a person to accept a poor performance rating at year end, if they could have been notified about concerns earlier.

So, the strategy most of us fall back on when we are unsure (saying less, softening, postponing) is often the one that damages trust most.

The approach that works

The research points to a different path if we want to get these conversations right. Rather than choosing between honesty and benevolence, or compromising on both, what we need to do is integrate them.

Make your benevolent intent unmistakable but, at the same time, still deliver the honest information.

Make your benevolent intent explicit

Yeager et al. (2014) tested what they called "wise feedback" in classrooms across the United States. Critical feedback was accompanied by a single framing sentence: "I am giving you these comments because I have very high expectations and I know you can reach them."

The framing sentence materially changed how students received the feedback. They trusted the feedback-giver more. They were more willing to act on the feedback. And in one version of the study, the intervention meaningfully narrowed the racial trust gap in how students responded to teacher feedback.

The reason this works is simple. Your counterpart is trying to work out why you are telling them this. If they have to guess, they may well guess wrong. If you tell them explicitly, they can focus on the content.

Most leaders assume their good intentions are visible. The research says it usually is not.

Provide something to work with

Honest information delivered without any sense of what to do next leaves the person to manage both the emotional impact and the path forward alone. Levine, Roberts and Cohen (2019) argue that genuinely benevolent difficult conversations do not end with the core message, but also give your counterpart resources for coping and acting: time, a follow-up, specific suggestions, practical support.

This is the difference between a conversation that is more likely to result in change and one which is more superficial.

How to prepare for, conduct and close your next difficult conversation

The research translates into a set of steps you can use whenever you have a difficult conversation coming up.

Before the conversation

  1. Hold both honesty and kindness as your goal, at the same time, in the same conversation.

  2. Clarify your purpose. Write down what you want to achieve from the conversation for yourself, for your counterpart, and for the working relationship (Patterson et al., 2012). If you cannot answer those three questions, you are not ready yet.

  3. Separate facts from story. List the observable facts (what was said, done, produced). Then, separately, list the story you have built on top of them. The conversation needs to focus on the facts.

  4. Draft your benevolent intent sentence. Write a single sentence that names why you are having this conversation. "I am raising this because I think you are capable of more and I want to help you get there" is one example. Rehearse it until it sounds like you.

  5. Check your state. If you are rushed, emotional or angry, the conversation will not go well (Gottman, 1999). Reschedule by an hour if you need to.

During the conversation

  1. Open with your benevolent intent, then deliver the content. The framing sentence comes first. It gives your counterpart a positive context in which to hear the rest.

  2. Use a clear behaviour-based structure. Situation, Behaviour, Impact (SBI) (Weitzel, 2000). Name the specific situation. Describe the observable behaviour. State the effect and impact you have observed. This keeps the conversation grounded in what happened rather than who the person is.

  3. Don't equivocate. Resist the urge to say technically true but misleading things to soften the blow. Your counterpart will experience it as a lie (Rogers et al., 2017).

  4. Listen properly. You are almost certainly listening less than you think. Kluger and Itzchakov (2022) found that high-quality listening by you will reduce defensiveness in your counterpart. Listen carefully to hear what they have to say, listen for what is unsaid, be genuinely curious. For more on listening well, see this post.

  5. Acknowledge before you disagree. Saying "I can see why that would feel unfair" does not concede the point. It signals you have heard them, and defensiveness drops as a result.

  6. Watch for overload. If either of you tips into heightened emotional arousal, pause. Gottman's research suggests at least 20 minutes is needed for emotions to settle down before productive conversation is possible again.

After the conversation

  1. Close with resources and support. Offer a follow-up. Name a specific next step. Suggest a resource. Do not leave your counterpart alone with what you have just said.

  2. Summarise in writing. Send a short summarising email within 24 hours. People remember conversations differently. Written agreements reduce the chance of misinterpretation.

  3. Plan the next conversation now. Difficult conversations rarely resolve in one sitting. Schedule a follow-up before you finish.

  4. Reflect on your own performance. What did you intend, what did you actually do, what was the effect on the other person? A short written reflection is a simple discipline with disproportionate value in improving your ability to deal with these situations over time (Argyris, 1991).

One important caveat

The research shows that this integrative approach applies where honest feedback genuinely helps the person in the long run. Not every truth does.

Feedback about things your counterpart cannot control or change can be damaging without producing any corresponding benefit. Levine (2015) calls this "unnecessary harm". A team member made redundant, for example, does not need to hear, on their last day, every way they might have performed better. Kindness should take priority in those cases.

The test is straightforward. Would this honest information, delivered well, actually help the person? If yes, integrate honesty and benevolence. If not, lean toward kindness.

The key takeaway

The conversation you have been putting off is probably not as harmful as you think. The strategies that feel kindest in the moment (avoiding, postponing, equivocating) are often the ones that serve your short-term comfort more than the other person's long-term benefit.

The research says what most of us know but rarely act on. People can handle honest information delivered with clear benevolent intent.

What they struggle with is honesty without warmth, or warmth without honesty.

You don't have to choose.

References

Argyris, C. (1991). Teaching smart people how to learn. Harvard Business Review, 69(3), 99-109.

Gottman, J. M., & Silver, N. (1999). The seven principles for making marriage work. Three Rivers Press.

Kluger, A. N., & Itzchakov, G. (2022). The power of listening in helping people change. International Journal of Listening, 36(2), 70-82.

Kumar, A., & Epley, N. (2018). Undervaluing gratitude: Expressers misunderstand the consequences of showing appreciation. Psychological Science, 29(9), 1423-1435.

Levine, E. E. (2015). Lie to others as you would have others lie unto you: Community standards of deception. Academy of Management Proceedings, 2015(1), 10533.

Levine, E. E., & Cohen, T. R. (2018). You can handle the truth: Mispredicting the consequences of honest communication. Journal of Experimental Psychology: General, 147(9), 1400-1429.

Levine, E. E., Hart, J., Moore, K., Rubin, E., Yadav, K., & Halpern, S. (2018). The surprising costs of silence: Asymmetric preferences for prosocial lies of commission and omission. Journal of Personality and Social Psychology, 114(1), 29-51.

Levine, E. E., Roberts, A. R., & Cohen, T. R. (2019). Difficult conversations: Navigating the tension between honesty and benevolence. Current Opinion in Psychology, 31, 38-43. https://doi.org/10.1016/j.copsyc.2019.07.034

Lupoli, M. J., Levine, E. E., & Greenberg, A. E. (2018). Paternalistic lies. Organizational Behavior and Human Decision Processes, 146, 31-50.

Patterson, K., Grenny, J., McMillan, R., & Switzler, A. (2012). Crucial conversations: Tools for talking when stakes are high (2nd ed.). McGraw-Hill.

Rogers, T., Zeckhauser, R., Gino, F., Norton, M. I., & Schweitzer, M. E. (2017). Artful paltering: The risks and rewards of using truthful statements to mislead others. Journal of Personality and Social Psychology, 112(3), 456-473.

Weitzel, S. R. (2000). Feedback that works: How to build and deliver your message. Center for Creative Leadership.

Yeager, D. S., Purdie-Vaughns, V., Garcia, J., Apfel, N., Brzustoski, P., Master, A., Hessert, W. T., Williams, M. E., & Cohen, G. L. (2014). Breaking the cycle of mistrust: Wise interventions to provide critical feedback across the racial divide. Journal of Experimental Psychology: General, 143(2), 804-824.

What Next?

All of my posts for new leaders are here.

How I can help you

Coaching - I have a few spots available for 1 to 1 coaching. I can help you prepare for the difficult conversations you need to have. There are more details here.

Have a great week

Martin

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