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The Hardest Part of a Hard Conversation

I was working with James (not his real name) last week who is the executive director and founder of a thriving nonprofit. The good news is they were finally able to hire a highly capable, experienced manager, Alice (also not her real name), to be the second in command and take some of the load off James. The bad news is that several months in, there’s still friction between James and Alice. While they immediately divvied up the most obvious roles and responsibilities – day-to-day management is Alice whereas building donor relationships is James – lack of clarity continues to swirl in other areas, leading to friction and conflict.


It’s time for Alice and James to have a heart-to-heart, face-to-face, hard conversation with one another.


But what’s the real issue here? Which concern lies truly at the heart of the conflict? Which problem, if solved, might help untangle all the other problems in the constellation surrounding the entire situation? Is it:


A. Lack of clarity around the chain of command and decision-making authority

B. Lack of trust in one another’s choices

C. Reluctance to change how things were done before (the way Alice did things in his prior organization versus the way James did things before Alice arrived)

D. Mismatch between the roles and responsibilities each person ended up with and their core values and strengths

E. Something else


The truth is, the first story shared by someone is rarely the real story at the heart of the issue. People have blind spots – both about themselves and about others – that get in the way of resolving problems and improving relationships.


Blind spots

The science shows that we have blind spots when it comes to our own behavior and even our own thoughts.


In a conversation, you are in full view of other people’s faces and body language from which over 40% of social cues are given. In any conversation, nonverbal cues are extremely important. Researchers like Sandy Pentland from the MIT Media Lab are able to predict the outcomes of speed-dating encounters, job interviews, even salary negotiations without taking any notice of the actual words that are said. Using data based purely on cues like gaze, posture, facial expression, gestures, spacing, turn-taking, the use of silence, and how something is said, yet they can predict whether two speed-daters will exchange phone numbers with 70-80% accuracy.


The catch is, we can’t see our own faces and body language unless we’re talking in front of a mirror or reviewing a video recording. We are blind to our own behavior much of the time. Honestly, our own behavior is better observed by others, which is why honest feedback delivered with compassion is so valuable.


Another blind spot comes from the fundamental attribution error. We judge ourselves based on the situation and give ourselves a break. We judge others based on their character and hold them 100% accountable. When James sees Alice ignoring his advice, it’s because she’s stuck in her ways and too stubborn to change. But when Alice advises him to just get some input from the team, make a decision, and move on, he ignores her. In his mind the situation demands a collaborative approach working towards consensus and that takes time.


What’s the biggest challenge here for you?

The solution is to approach the hard conversation with clarity on what Michael Bungay Stanier calls the focus question – “What’s the biggest challenge here for you?” – but to recognize that your conversational partner might come in with a different understanding of what’s the biggest challenge here for them. Only by putting those two things together, and really understanding where both parties are coming from, will they be able to identify the true heart of the conflict and solve it.


That is, James might see that the biggest challenge for him is B, lack of trust. Yet Alice might find the biggest challenge for her is D, mismatch between what she’s being asked to do and what she loves to do. Both views are correct. And both individuals have blind spots regarding their own behavior and judgements of one another. The goal of the conversation between them is to fully understand one another's biggest challenge so that they can find a resolution that works for everyone. If they can approach one another with an open heart and open mind and be willing to grow from what the other person sees, thinks, and feels, then the outcome will most likely be that the problem gets solved and the relationship improves.


Willingness to grow based on the feedback we receive is of utmost importance. It’s a defining characteristic of the most influential leaders and most trusted managers. You read that right, when leaders and managers are willing to ask for help and grow from feedback, their employees trust them more and follow their lead.


If I were to identify the one most difficult part of engaging in any hard conversation, it’s getting clear on “What’s the biggest challenge here for you?” both for you, and your partner. Too often, we jump into a hard conversation with a thousand different challenges, dumping problems A through Z on someone and swamping their working memory such that they are left feeling overwhelmed and confused. Alternatively, we fail to take the time to figure out the real problem and simply address the first problem that comes to mind, leading to a bandaid fix rather than a true cure. And sometimes when I’m really angry and pissed off, I jump in with, “You know, the real problem is YOU!” which, of course, solves absolutely nothing at all. My own most common failing is coming in with clarity on my own biggest challenge for me, but not being open and patient to listen and fully understand the other person’s biggest challenge for them.


The reason that last point is so important is because when you understand someone else’s biggest challenge from their point of view, then you possess the key to harnessing your partner’s internal motivation for making a change. This is what the truly exceptional communicators, diplomats, and negotiators do, and it’s how some people can go into the hardest of hard conversations and emerge with everyone hugging instead of hurling insults. According to the authors of Crucial Conversations who studied tens of thousands of conversations within hundreds of organizations, not only knowing your own biggest challenge, but truly understanding your partner’s biggest challenge, is how the most influential, successful individuals can do something like directly approach a senior VP that might be embezzling funds, tell a doctor that they’ve misdiagnosed a patient, or even confront their sixteen year old daughter who stayed out past 2 am.


Because we have our own blind spots, there are times when a trusted friend, confidant, or coach is essential to helping you figure out the biggest challenge here for you. Once you’ve done the hard work to identify it, then the rest of the hard conversation is comprised of skills anyone can learn (things like creating a safe container, being specific and clear, describing the impact, and working towards solutions).


Psst… last chance to join my workshop on transforming the feedback experience where I’ll be teaching these skills and the science behind them. (Sign up ASAP because we start this Friday January 13th on Zoom or next week Tuesday January 17th in person.)


So… when you think about that hard conversation you need to have (that nail biting conversation you've been avoiding) what’s the real challenge here for you?


Read More

Both of the books I mentioned here: Crucial Conversations and The Coaching Habit are exceptional. Highly recommended.


To learn more about the impact of nonverbal communication, check out Sandy Pentland’s lovely article “To Signal is Human” or this article by Vanessa Van Edwards on what makes some TED talks go viral.


Going Further

It’s your last chance to join Transform Feedback with a Shift Positive! You will walk away from this workshop with a script to use for THAT hard conversation you know you need to have but haven’t found the words AND six steps to improve the feedback system used in your organization. Bring a friend from your organization and get 20% off! Sign up today!


Right now, does your work feel heavy? Or perhaps overwhelming, frantic, and exhausting? What if the work of leadership could feel like play? Imagine just how different life as a leader could be if it were light, joyful, passionate, and almost effortless, surrounded by a group of inspired, seasoned professionals to wrap you in an authentic, supportive community. Each year, I hold space for one mastermind group of eight exceptional, passionate, visionary leaders. Reach out today to see if one of them might be YOU.


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