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Holly Weeks: An interview by Bob Morris

Holly Weeks

Holly Weeks publishes, teaches, and consults on communications issues. As principal of Holly Weeks Communication, she consults and coaches on negotiation and written and conversational communications issues, with a special emphasis on sensitive and difficult problems. She is also an adjunct lecturer in Management Leadership and Decision Sciences, teaching the Arts of Communication, at the Harvard Kennedy School and Visiting Pro-Seminar Instructor in Communication and the Vision Speech at the Harvard Graduate School of Education. She was previously an Associate in Communications in the Harvard Business School MBA Program. As a Distinguished Instructor, she taught Management Communication, and Negotiation and Conflict Resolution, at the Radcliffe Institute of Harvard University. And she taught Expository Writing at Harvard College. Weeks has a master’s diploma in literature from the University of Edinburgh and an AB cum laude in English language and literature from Harvard University. Her most recent published book is Failure to Communicate: How Conversations Go Wrong and What You Can Do to Right Them.

Morris: Your formal education suggests that you prepared to become a classroom English teacher and you seem to have expanded the “classroom” to include a variety of constituencies, including corporate executives. Is that a fair assessment?

Weeks: I did become a teacher of literature and writing, and I haven’t strayed very far from it. Communication and teaching are at the heart of all my work. Literature is the best of all ways to see the great motivations and the great conflicts play themselves over and over in the great stories of the human condition. The motivations, conflicts, and stories will revolve around people trying to communicate, and often failing in complicated and consequential ways.

Writing and the teaching of writing are great schools for finding ways to help people understand and improve what they are trying to do, when what they are trying to do is difficult and subtle, a matter of art and skill rather than fact and procedure.

I’ve kept the teaching, the literature, and the writing but I’ve added to the communications collection—negotiation, conflict resolution, presentation, and, of course, tough conversations.

Morris: Many of the worst conversationalists are also very poor listeners. Why?

Weeks: Holding aside that some people are so easily distracted, or have such short attention spans altogether, that they can’t stay focused on the back and forth of conversation with the people in front of them—and I wouldn’t underestimate how often that’s the case—there are two reasons why poor conversationalists and poor listeners come in the same package. First, some people see conversation as serial monologues, often competitive monologues, in the guise of dialogue. If they are competitive, they aren’t trying to listen, or to communicate at all, really; they are trying to “win” the conversation. As listeners, they dismiss all of what they hear that they can’t use to score. If they are not competitive, they are simply waiting out their counterpart’s turn to talk so they can begin the next of their monologues

Second, other poor listeners and worse conversationalists appear not to know what to do with what their counterparts say in conversation. They seem unsure how to respond to what they hear or don’t seem to have any context from which to respond. People say to me, “I don’t know what the next line is supposed to be.” They think of conversation more as a script than as an organic back-and-forth in the moment.

In both cases, the same people are often fine in actual monologue or in Q&A. And if two monologists or two scriptists are in conversation together, they’re fine. It’s mixing it up—monologist, scriptist, dialogist—that gives you a problem.

Morris: My own experience suggests that many communication problems are the result of not asking the right questions, or at least asking at the wrong time or with an inappropriate tone of voice. Your thoughts about that?

Weeks: I don’t believe that there is a single right time to ask a question in a difficult conversation and no other time will do. That would never work. It may be that asking the right question ahead of time would prevent a tough conversation, but that would require that, somehow, we divine a problem we don’t yet know about. That’s asking an awful lot of our intuition. I want people to have the skills to handle difficult conversations well specifically because preventing them entirely is so iffy.

The main reason I urge people to develop neutral as a way of speaking is to sidestep the problem of inappropriate tone of voice. If you’re not actively neutral, your counterpart may hear an inappropriate tone of voice better than what you actually say. Of course, your counterpart may accuse you of inappropriate tone no matter what you intend or do. Even then neutrality is your best friend when it comes to tone.

Two more thoughts on questions: It may simply be that the tough conversation you find yourself in doesn’t lend itself to a question and answer format—you and your counterpart might want to talk together, in regular conversation style, about the problem. Or it may be that the kinds of questions asked seem antagonistic, accusatory, or self-justifying, even if they are not intended to be. In that case, you might use the Mock Interview strategies or In Your Shoes tactics described in Failure to Communicate.

Morris: How important is body language?

Weeks: Tone is all the non-verbal part of the message we’re giving, and body language is the physical manifestation of tone. It matters as much as tone of voice does. In practice, that means that neutral body language is as valuable as a neutral tone of voice because body language and facial expression inflect your message just as your voice does. You don’t want your counterpart reading—or misreading—your body language instead of listening to what you say. Neutrality is not necessarily natural in a tough conversation; it’s an acquired skill and you use it so you will be heard without distortion.

Morris: In What Got You Here Won’t Get You There, Marshall Goldsmith identifies 20 of what he characterizes as “transactional flaws.” One of the most common is #5. Beginning a sentence with “No,” “But,” or “However.” That is, using negative qualifiers that send the message “I’m right, you’re wrong” or “You don’t fully understand.” How to respond when someone does this?

Weeks: I’m not entirely certain that negative qualifiers are a flaw in everyone’s mind. Competitive speakers who approach tough conversations as debates to be won want to be right and have you be wrong. Let me say that this is an odd way to handle a difficult conversation—it’s like trying to win a foxtrot against the person you’re dancing with—but it’s not an uncommon way for people with confirmed habits and a small range of skill. You may want to speak to the tactic behind the qualifier simply, clearly, and neutrally: “I don’t see this as a right/wrong situation.” “The problem isn’t that I don’t understand, although we may not agree.” You’ll find your own words.

On the other hand, there are people I call “innocent offenders”. They have no intention at all of being off-putting; they simply have unfortunate speech patterns and are unaware of the impression they give. But negative qualifiers are off-putting, so I would still speak to the tactic simply, clearly, and neutrally: “When you say ‘no’ or ‘but’, I can’t tell if you mean to push back on what I’m saying or not.” The advantage of using the same characteristics in reply to the two different scenarios is that you don’t have to guess which is which.

Morris: Now please shift your attention to Failure to Communicate. As you explain in your introductory chapter, “This book offers a system of strategies and tactics to help us navigate the treacherous minefields we may suddenly find ourselves in when we approach and try to get through – rather than avoid – prickly conversations.” How do you characterize a “prickly” conversation?

Weeks: Very simply, a prickly conversation is one that is difficult for you, for your counterpart, or for both of you. Three traits tend to set prickly conversations apart. First the combat mentality—the attitude that these conversations are battles with winners and loser—comes into play. Second, these conversations carry heavier emotional loads than ordinary conversations, particularly anger, embarrassment, or fear. And third, these conversations are very hard to read and when we try to read them, there are real breakdowns between what one side intends and how the other perceives it. We don’t often deconstruct these conversations this way. Usually we just suffer them and generalize about them, figuring that a particular kind of conversation is always disastrous, especially for those of us who are conflict-averse: a sudden confrontation, bad news, a power challenge, a counterpart on the offensive.

Morris: My own experience suggests that there is almost always a background story to most (if not all)  “prickly” conversations, at home or in a workplace. Sometimes I feel “ambushed” when becoming involved in one and have no idea why it is happening. Your own thoughts about that.

Weeks: In fact, two of the common types of tough conversations in Failure to Communicate are called “What’s going on here?” and “I’m being attacked!” and it’s true that tough conversations don’t always come at the same pace for both sides. One counterpart may be the initiator or be more prepared than the other. But to make your situation worse, Bob, there isn’t usually one background story to tough conversations, there are at least two and perhaps more. It’s like Balkan politics—one side points to a rotten event perpetrated by the other side that started all the trouble, and the other side points to an even earlier lousy event perpetrated by the first side as the real cause.

But behind your point is something else, I think: the hope that if only we had enough information, this wouldn’t be happening. And, in fact, if it were possible to know all the history and all the perceptions and all the intentions on both sides, then probably this wouldn’t be happening—the difficult conversation would be prevented. But I wrote a book on how to handle tough conversations well because I found that despite our fervent wish that we could prevent them all, we can’t. We don’t have all the information; by definition, these conversations are hard to read.

Morris: Given that response, what are some of the skills needed to make the best if the situation, the best of the situation? As you characterize them, “that will make you a better colleague, a better leader, and a better human being.”

Weeks: If I point to one skill that will help us make the best of a tough situation, it would be three-way respect: openly respecting ourselves, our counterpart, and the problem between us. Self-respect here has nothing to do with self-justification, self-righteousness, or self-aggrandizement. It means holding our own, and owning what we do. In practice, holding our own often means doing what we don’t necessarily want to do, which is avoid the conversation altogether or give in to an emotional reaction. Respect for our counterpart is a willingness on our side to look at their interests and concerns—not necessarily agreeing with them or deferring to them. Respecting our counterpart is a working attitude, a way to behave, not necessarily a deep-seated feeling. The third leg of three-way respect is respect for problems in the conversation itself. Difficult conversations have problems in them the way chess games have problems in them. It’s their nature. When we recognize that problems are in the conversation itself—on the chess board where the conversation is playing out, as it were—and respect them as genuine, complicating factors to be dealt with, the tough conversation begins to be less about us versus our counterpart and more about figuring out ways to get through those problems. It’s a relief to begin working that way.

Morris: In Chapter 5, you explain how to act “unilaterally.” What does that mean?

Weeks: I frequently hear that the only way to have a successful conversation on a tough issue is to start with a base of mutual respect, trust, and goodwill. If we have that base, we are in a “soft” difficult conversation because, realistically, in a more daunting conversation, those qualities are in short supply. As much as anyone, I would prefer to have any difficult conversation in an atmosphere of mutual respect, but I can’t require it up front because I can’t control the “mutual” part. Acting unilaterally means I bring the respect and self-respect myself. It also means that when a conversation takes a turn for the worse I change what I’m doing—my strategy or my tactics or both—single-handedly, because I’m looking for a way to put the conversation on a better track. If I wait for my counterpart to change before I am willing to change, I don’t think it will work. At best, my wait could be a long one. At worst, I’d be passive and reactive, and the conversation is likely to continue to degenerate.

Morris: In Chapter 11, you pick up on one of Carl Rogers’ most valuable insights when explaining why finding a middle ground, a neutral or “demilitarized area,” can be very helpful rather than losing control to an emotional extreme. Most people find that very difficult to do. Any advice?

Weeks: Actually, most people find middle ground between emotional extremes most of the time. It’s in difficult conversations that they don’t. The trouble here, as is so often the case, traces back to the three worst characteristics of difficult conversations: that they feel like warfare, they are hard to read, and they carry heavy emotional loads. If you’re thinking warfare, you’re thinking attack or defend, not neutral. If you can’t read your counterpart or what’s happening in the conversation itself, you tend to react, not think well. And that brings us to the heart of the problem—the emotional load these conversations carry. When you react, you react to your own emotions which, in the moment, probably aren’t helping. That’s what makes finding neutral hardest. The bad news is that there is a lot in difficult conversations that you can’t control. The good news is that you can control the most critical piece: you can break the pattern of reacting to your own emotions.

David Mamet tells actors who are flooded with emotion that, first, their emotions are not within their control and, second, they don’t have to feel like performing their action. “Your only task concerning emotions will be to learn to work through them.” It’s the same in difficult conversations. There’s no trick to handling a conversation well despite tough emotions, only skill. We know very well how to speak neutrally. The skill is in bringing it from our area of strength—ordinary conversation—to our area of weakness—difficult conversation. You commit to speaking from neutral even when you don’t feel like it. No emergency room nurses, no police officers, say to themselves, “Next time I’m not going to feel my emotional reaction to what I see and hear.” They know they will. But they have also mastered the skill of going to neutral and responding from there even in the face of a strong emotional reaction. We can learn it: know which of your reactions are your own worst enemies in difficult conversation; practice responding neutrally even when you don’t feel neutral; don’t hope that in the moment you will make the change spontaneously.

Morris: Which are the most dangerous “disaster-prone patterns” and how best to avoid or escape from them?

Weeks: The most disaster-prone patterns seem to fall into two categories: going into the conversation, and, mishandling what you find there. Going in, the three biggest problems are winging it (having no useful strategies or tactics), assuming that if your motive is good the conversation will go well (the delusion of good intentions), or assuming that you know all you need to know to make a pre-planned approach work (oversimplification). The best way to improve your situation going in is to have strategies for difficult conversations. That’s not the same as having a strategy for the problem you want to solve, or having a strategy meant to ensure the conversation won’t get tough. You will want the former, and you can try for the latter. But when people have strategies only for keeping a conversation on an even keel, they are empty-handed when it starts to take on water. You want a strategy that assumes there will be problems, a strategy that takes into account both your best guess as to how the situation looks to your counterpart and the willingness to ask if you’re right. Failure to Communicate will help you set up a strategy like that.

To work through the disaster-prone patterns in the ongoing conversation itself, our tactics need to be buffed up, or revised wholesale. Here, the biggest problem is an inability to handle what’s happening in the moment, usually because our pool of tactics is too small, and the problem splits into two parts. On one side, we can’t recover from our own mistakes because emotional history gets replayed, or we can’t disarm our own reactions, or we think we’ll look weak or “lose” in the conversation if we so much as acknowledge our mistakes. In fact, often, in order to come out on top, we actually escalate the conversation—go to war—to avoid dealing with our mistakes. On the other side, we can’t disarm the ploys our counterpart throws at us that undermine us. In both cases, our best choice is to know where we’re vulnerable, to know what always throws us off. The only way we can break the grip of their ploys is by mastering ourselves.

Morris: As a parent and grandparent, I think much of your advice can also help children become more effective communicators. Do you agree? Also, have you given any thought to writing a book with that objective in mind?

Weeks: You’ve read my mind. When I was a child, my brother had a toy, a pair of kangaroos with boxing gloves on, facing each other and stitched together at the toes. You’d squeeze the air bulb and the kangaroos would punch each other. You’d squeeze again and they’d punch each other again. That’s all the toy did, and most of the time that’s all we seem to do in difficult conversations — when we aren’t avoiding them completely. I want to see those conversations handled better and the best way I know to change two lousy choices of behavior is to start when people are young. My fantasy is to retire to an after-school program, pair kids up, and watch them improve the way they handle a tough conversation instead of duking it out. I guess then I’d be back where I started at the beginning of my career.

Morris: I often fantasize about hosting a dinner to which I could invite anyone I wish. Plato and William Shakespeare, for example. And probably Eleanor of Aquitaine. Let’s pretend that you are hosting a dinner to which you can invite those whom you believe to be the most interesting conversationalists. Who are few of them? Why did you select each?

Weeks: My own friends are excellent conversationalists and nothing makes me happier than their company. If I put together a fantasy dinner party that didn’t feature them, I’d invite Leonardo and Shakespeare, because how could I not; Richard III; Susan Sontag; Mary Magdalene; Franklin Roosevelt; and Bill Clinton. These are all people who could hold their own and they would be fascinated by each other’s information. My hidden agenda is to have everyone give Richard III a hard time.

Morris: Which question do you wish you had been asked – but weren’t — and what is your response to it?

Weeks: Bob, I think you’ve covered the ground beautifully.

*     *     *

Holly invites you to visit her Web site:

I also suggest you check out the wealth of resources at to which Weeks is a frequent and valuable contributor.

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