Category Archives: Crucial Conversations

Crucial Conversations QA

Feasting with Unruly Relatives

The following article was first published on November 17, 2010.

Dear Crucial Skills,

With the holidays quickly approaching, I have found myself caught in a sucker’s choice with my family. My wife and I have made it a tradition to travel to my parents’ home seven hours away for Thanksgiving. This year, my parents informed me that my sister will also stay there. My sister is a drug addict and has been in and out of jail for thirty years. Every time she gets out, she claims to clean up her life and my parents roll out the red carpet to help her. When she returns to her destructive patterns, they turn a blind eye.

For years, this has caused all kinds of problems between my parents and five siblings. I would love to keep my tradition of spending Thanksgiving with my parents, but I don’t feel comfortable staying in the same home with my sister. It’s a rural area so there are no hotels or other arrangements available.

I see only two options: either continue with the tradition and hate the experience (which could also be potentially dangerous), or forgo the tradition and hurt my relationship with my parents. I can’t find a win-win here. Please help.

Signed,
Stuck

Dear Stuck,

If you’ll give me some latitude, I’m going to wax philosophical and share my perspective on the purpose of life. My goal is not to persuade you that my view of life is right, but simply to share one perspective that gives context to my suggestions.

In my view, life is about achieving intimacy with those we’re inseparably connected to. Family is first and foremost in that category.

Now, how is that relevant to my dialogue with you? Because I walk in your shoes. I have dear ones who also struggle with addiction. Some of the most searing pain of my life has been watching them destroy months of progress—only to land once again in jail or on the street. Almost equally painful is watching those who care about them behave in ways that positively enable their self-destruction. It’s agonizing. And my natural reflexes toggle between an overwhelming urge to either take control of the situation or to distance myself from it.

And yet, neither impulse is consistent with my view of the purpose of my life, which is to develop the character to achieve intimacy with imperfect people. When I try to take control or distance myself from my struggling loved ones, I find that my life is the poorer and my character weakens.

When I find myself in your shoes, the question now becomes, how can I remain close in a way that exerts positive influence on those who are the most troubled?

Enough with the philosophy. So what about your situation?

First of all, you made a reference to danger. If by that you mean you might take children into a situation when your sister is using, I would decline and explain this concern to your parents. And when doing so, cleanse yourself of any intention of using this decision as a threat to get them to exclude your sister. Simply explain that you can appreciate their desire to include your sister—and hope it is a good experience for them and her—but that your children give you other considerations. You may even want to make a call on Thanksgiving Day and wish your parents and sister well so they don’t misinterpret the decision.

If you choose to participate in the Thanksgiving tradition, there are a couple of crucial conversations you’ll need to have:

1. Motives. You need to change your motives. This year may not be about peace and harmony in the home. It may be filled with uncertainty and awkwardness, but it might still be meaningful. In fact, it could be more meaningful than many others. Your goal will not be to fix your sister or to correct your parents. It will be to improve your relationships with all of them—to try to achieve greater intimacy. Doing so may increase your positive influence in the future in all their lives.

2. Boundaries. You can’t control your sister or your parents, but you can control yourself. Decide in advance what kinds of situations may play out. Then ask yourself, “If what I really want is to be a positive influence on my sister and my parents, how will I respond?” Don’t wait until the resentment of the moment hits to make this decision. Think it through in advance.

Then discuss these boundary conditions with your parents. Let them know you love them and want to be part of this holiday, and that you have your own view of how to deal with some of the potential challenges. You don’t ask that they agree with you, you just want to explain your intentions so they can understand your motives in case you behave in a way they find jarring.

For example, if your sister uses, you may choose to leave or you may call the police. Before you arrive, discuss these boundaries with your parents and see if you can come to terms on them. If you disagree in important ways, you may elect not to participate. If that is the case, do not announce that decision in a punishing way. Don’t use your decision as a way of provoking your parents to concede to you on these points. Honor their right to disagree. Affirm them. Express your love. Ask if it’s okay if you arrange another visit with them when things are simpler.

If after working through these two conversations you find yourself at the family gathering, be as good as your word. Take small steps to show love to your sister. Expose yourself to the discomfort of possible disappointment or rejection. You may well find, in some future situation, that your improved relationship with her puts you in a position of influence to help her take a steadier step toward sobriety. It may be one step forward and two steps back (it certainly has been with some of those I love).

While these situations are complex and difficult, I can tell you that this Thanksgiving, one of the blessings I will feel most intensely is the intimacy I now have with one who looked the most helpless for the longest time.

I hope I haven’t been too presumptuous. If I’ve misunderstood your situation or imposed my own views inappropriately, please forgive me and don’t let my imperfection drive distance between you and me.

Sincerely,
Joseph

Crucial Conversations QA

How to Broach a Difficult Topic

Dear Crucial Skills,

As the mother of two adult children who are each very intelligent and gainfully employed, I try and stay out of their personal decisions. However, one of them started smoking during his high school years. The smoking has continued for almost twenty years. His father and I worry about his health but have trouble understanding how to (or if we should) broach this topic productively with him.

Signed,
Uneasy Parents

Dear Uneasy Parents,

To broach or not to broach—that is the question. Or even better, how to broach without reproach? And it’s not simply a question of whether or not to bring up a particular topic, but also how to do it in way that’s positive and impactful. I find that when people are facing this, and similar challenges, they merge these two separate and distinct questions into one. And since they usually don’t have a good response to how to be positive and impactful, they easily dismiss the answer regarding whether to bring up the topic in the first place. In essence we think, “I’m not sure I’d be able to address (fill in your concern here), so it’s probably not worth bringing up.” We choose to “live” with the situation despite the negative consequences. So let’s tackle these questions one at a time.

First, to broach or not broach? The outcome from either choice seems to have a big downside—accept his smoking habit or ruin the relationship—especially in light of the current strains on an already weak relationship. In Crucial Conversations, we describe the pull toward these two alternatives as choosing between silence and violence. And in case you didn’t already notice, regardless of which you choose, you lose. So we end up choosing the more palatable option out of two bad alternatives—silence. Essentially, this means we’ve lost from the outset, before we’ve even taken any action. By choosing silence, we believe that we’re voting in favor of maintaining the relationship while really undermining the relationship we’re trying so hard to maintain. Let me give you an example:

Years ago, my wife’s sister and her husband had their first child—happy day for everyone! Well, maybe not everyone. In my wife’s family, it is assumed that her mother will be invited to the home to help take care of the new arrival. So my mother-in-law started to make travel arrangements even before the baby was born. However, these arrangements had to be undone because my sister-in-law had already invited someone else to come and help with the new baby without alerting her mother. You see, my brother-in-law had some mother-in-law issues. Instead of addressing the concerns in the open, my sister-in-law tried to brush them under the rug and created a whole new set of mother/daughter issues. This is a good example of the principle that what we don’t talk out, we act out. It never ends well.

To get out of this trap, try drafting a more complete consequence list for smoking. What do I mean by that? When faced with a difficult conversation, our head quickly volunteers to do the hard work of calculating the potential outcomes for speaking up and quickly saves itself from any additional hard work by quickly convincing you that a conversation won’t be worth it. We tend to focus on the short-term, negative consequences (like straining your relationship) and look past the long-term, positive consequences of actually sharing our concerns (like helping your son avoid a terminal illness). Relieve your brain of this responsibility by capturing all of the consequences on paper. When you’re able to consider a more complete and accurate list, you can make a more informed decision about how to proceed.

Once you decide the topic’s worth broaching, how do you go about it? Most often in these types of situations, my first thoughts are aligned with the STATE skills in Crucial Conversations. They provide the perfect framework to help people raise tough, controversial issues or concerns in a way that minimizes defensiveness and invites the other person into the conversation. And yet, how you describe your son in your question pulls me in a different direction—especially your description of his intelligence.

Many times, when talking with intelligent people about strongly entrenched habits like smoking, our approach invites defensiveness—even when using STATE skills. Why? Because we approach it as if the person needs more information about the negative impacts of his or her choices (the unsavory smell, coughing, emphysema, lung cancer, the list goes on). The other person has seen the ads, and likely know the statistics. More information is not the problem. Your son is already well-informed. Instead, try getting him to consider an insightful question.

Here’s what we’ve found: it’s very natural for people to resist when confronted head-on about issues that require significant effort to change. They hear your argument and treat it as an argument. That means taking a position, digging in to defend the position, and actively looking for ways to reinforce that position—which is not very conducive to an honest exploration. If you’re looking to create motivation, don’t start with sharing more information.

Bill Miller pioneered an approach that focused on influential questions. He found that exploration can be more powerful in creating the conditions conducive to change than explanation. For example, lead with a question like, “I was wondering how smoking interferes with (insert your son’s favorite activity or even an important role he plays, like at work, for example)?” This probing question produces far less defensiveness than, “let me tell you why I wish you wouldn’t smoke.” You’re not forcing him to take the opposite position from you, and it’s directing him towards something he regularly experiences. Get him to explore the implications of his choices so he is less ambivalent about making different choices.

These types of conversations are tricky and usually require a lot of love, concern, and patience. Hopefully these ideas will give you some options for approaching your son. I wish you the best in beginning this conversation and as you create the conditions to explore and reinforce the motivations for change that he probably already has.

All the best,
Steve

Crucial Conversations QA

Change Begins With Me: Reflections on the 2016 Election

This has been the most disturbing and divisive election cycle either of us can remember. We began writing this piece by assembling a list of sound bites that ought to be consigned to a political “Hall of Shame.” But as we did so, we began to realize we’ve made our own contributions to that hall as well.

Now, don’t get us wrong. We haven’t engaged in hate speech or called for the imprisonment of a candidate. But as we started throwing rocks at others’ behavior, we realized some of ours was not beyond reproach either. As we all reflect on the past year, there’s a hierarchy of culprits we can look to:

1. The candidates. Need we say more? And beyond Trump and Clinton, many of the primary and presidential contenders have lowered the bar on political discourse and election strategy.
2. The media. The media has brought in paid partisans who do little more than recite their campaign’s talking points. News outlets claim to give us “balance” when what we really want is objective analysis by unbiased reporters, producers, and news anchors. After all, the media is often touted as the fourth estate with the responsibility to hold the government to account, and from our perspective, the media has not acted any more responsibly than the before-mentioned politicians.
3. The alternative media. The Internet is festooned with fiction dressed up as fact. And most of its users have become witless distribution tools rather than cautious examiners of what it offers—causing us to “feel” informed rather than “be” informed.
4. Friends (or former friends) and colleagues. We published a study a few months ago that revealed how terrified many of us have felt to venture into political discussions – and rightly so. Over thirty-three percent of us have had a political discussion blow up in our face—causing us to lose a relationship—or worse. We can all point to others who have behaved badly as they’ve attempted to assert their views or influence the views of others.
5. Me. Our emotions turned from righteous indignation to humble reflection as we asked, “How have we contributed to the decline?” If our motive in reviewing the past is to assign blame, we could certainly start with number one on this list and move down in that order. But if we really want to influence change, we should probably reverse the order and start with ME.
With this sobering insight in mind, here are our top six political regrets from 2016 and resolutions for the future.

• Regret 1: We have allowed profound disagreement to turn into personal judgments.
• Regret 2: We have cowered from opportunities to share our honest views on issues of deep moral importance to us for fear of being punished by an angry virtual mob—or worse.
• Regret 3: We have spent enormous time commiserating with those who shared our views and precious little exercising genuine curiosity to learn from those who don’t share our views.
• Regret 4: We have been passively vulnerable to the tyranny of search engines—investing time in information that is manipulated by algorithms designed to reinforce our biases. Search engines today are a powerful force for reinforcing ideological divisions as they sense what you prefer to read and serve up more of the same.
• Regret 5: We have contributed to contention by chuckling and—gulp—“liking” postings that were insulting but clever, if they advanced our agenda.
• Regret 6: We complained about the final candidates but did precious little early enough in the process to produce a better slate of choices.
These are hard pills to swallow. But if we’re truly honest with ourselves, we let ourselves down. Thankfully, we woke up this morning knowing we can do better. We don’t have to experience this type of divisive and toxic election again, and we won’t—at the very least, we won’t be participants in one. In the future we promise:

1. To not turn vehement disagreement into personal attack.
2. To periodically seek out reasonable advocates of opposing views—and listen deeply to them.
3. To never outsource our political opinions to search engines.
4. To get involved in the political process earlier rather than complain later about weak candidate options.
5. To never again forward or “like” hatefully clever but intellectually vapid material even about candidates or positions we oppose.
6. To continue to engage in the political discussion—and do so in the way we hope others do with us—even if we are unhappy with the results of yesterday’s election.

How about you? Got any regrets? How have you behaved in ways that you are not proud of? What resolutions are you willing to make to help prevent the disgrace of this last election? Please share your thoughts in the comments section below.

We believe in the goodness of our readers and would like to rally around what can be possible, rather than what just happened. Let’s vow to make it different the next time around.

Best Wishes,
Joseph & David

Crucial Conversations QA

Health Challenges at Work—How to Create A New Normal

Dear Crucial Skills,

I was just diagnosed with a non-contagious medical condition. Now I know why I have been so fatigued these past months. Though my condition can be life-threatening, after having a pity party, I’ve decided to move forward and be as positive as I can. I told my supervisor and co-workers about my diagnosis but now feel they are avoiding me and showing me pity. Some people are not giving me the work they used to give me, and others have actually taken work away from me. It may be they are trying to “ease the burden,” but I just want to move forward, be busy, and continue to be a productive member of the team. I’m second-guessing my decision to come forward with my condition and the added stress actually aggravates my condition. It’s a vicious cycle! Any help would be appreciated.

Signed,
Moving Forward

Dear Moving Forward,

I am sorry to hear about the diagnosis. It sounds like you have gone through some overwhelming emotions as you’ve adjusted to this new reality. It also sounds like you have arrived at a remarkable place in determining to embrace life on these new terms. Congratulations on that. I admire your resilience and trust you’ll find strength in this decision.

I would not fault you for sharing the news with close colleagues. To me, life is about connection—and withholding such profound information from friends can only serve to make you less connected at a time when you need friends most. The challenge now is to negotiate the new relationship this information is provoking. That’s the conversation you need to have. I offer three thoughts that I hope are of use:

1. Let them process their feelings. Like you, your colleagues are going through a process of adapting to the new information about you. Clearly, you deserve much more consideration than they do under the circumstances. However, it’s helpful to know that they are being affected, and it will take time for them to integrate this reality and connect with you in a way that accommodates it. I don’t offer any of this to suggest that it is your job to service their emotional needs—you’ve got plenty to manage on your own. But perhaps being aware that their current behavior is not likely to be their final behavior can help you be patient as they go through their own fear, sadness, and anxiety.

2. Make it discussable. Many of your colleagues are dealing in the realm of mystery at this point. All they know is you have a medical condition. That’s all. They don’t know how it is affecting you physically, emotionally, or interpersonally. Should they lighten your load or treat you the same? Should they give you space or smother you with support? Should they pretend they don’t know about the diagnosis or inquire for details? In most situations like this, those around you are paralyzed with uncertainty. They feel awkward and incompetent and tend to respond to this anxiety with hand-wringing. They try to guess what you want or need—or shrink back to a safe distance to avoid their own discomfort. You have it in your power to end all of that. All you need to do is make the situation discussable. Find a medium that works for you: email, a private blog, perhaps even a team meeting. Take a few minutes to catch people up not just about the physiology of what’s going on with you, but the psychology. Tell them how you’re feeling. Tell them how that varies by day or week.

Then . . .

3. Teach them what works for you. Here’s the best part of my advice for you—you have enormous influence at this very moment. What your colleagues crave most is certainty. They simply want to know how to show up for you. They’ll likely respond to most any request you make. Tell them what questions you’d like or not like. Tell them how you’d like to be treated and not treated. Tell them how you would and wouldn’t like to communicate with them about future changes in your health. For example, will you tire of repeating the same update to everyone? If so, you might want to create a private blog and encourage people who are interested to get information from there so you don’t have to rehash the same story forty-three times at work. Or, you may ask a trusted friend to be the source of information for the group. Whatever works for you is likely to work for them. It’s up to you to teach them.

I wish you health and happiness in this coming phase. May your troubles be eclipsed by increased focus on what matters most and greater intimacy with friends and loved ones.

Warmly,
Joseph

Crucial Conversations QA

Are You Being Passive-Aggressive?

Dear Steve,

I recently took the Crucial Conversations course and learned about the silence-dialogue-violence spectrum. I believe my tendency is to go to silence at work, but violence at home. I’ve wondered why I react differently in these two situations. I speculated that perhaps the reason was that I felt safer at home. However, I recently realized that what may look like silence at work may truly be passive-aggressive behavior. This prompted the following question: Where does passive-aggressive behavior fall on the spectrum? Is it silence or veiled violence?

Sincerely,
Earnest Self-Reflection

Dear Earnest,

Some years ago, I happened upon an article in the Money section of USA Today. The section started with an article about former IRS repo men, and, quite frankly, I couldn’t imagine anything being more riveting. I was wrong. There on the next page, appeared a title as if illuminated in neon lights: “When You’re Smiling, Are You Seething Inside?” Hmmm . . . repo men? Or smiling while seething? I think you can guess that I quickly switched articles. What I thought would be an exposé on specific individuals’ behavior turned out to be an exploration of organizational behavior—or, more accurately, collective behavior within organizations. It not only outlined the impact of passive/aggressive culture, but also the industries that were most prone to foster this type of culture. Reading this article started me on a path of thinking about and observing (and on occasion participating in) both individual and collective passive/aggressive behavior patterns. And so, after years of study, I can definitively say that the answer to your question is yes. If that seems confusing, let me explain.

Over the years, I’ve noticed something interesting about the silence-violence continuum. It doesn’t always behave like a true continuum. There are many instances where it is more accurately represented as an arc—and not the altruistic kind like Noah’s or Joan’s. In the case of this arc, silence and violence remain the anchors, but instead of being represented as polar opposites, they bend back toward one another. In many situations they touch, facilitating the surprisingly quick jump from silence to violence or from violence to silence. And so to your question. Passive-aggressive behavior can easily assume the form of veiled violence or silence because it is.

This may seem a little counter-intuitive, but silence and violence are rooted in the same value—fear. And while it might seem easy to make the connection between silence strategies and fear, the fear-to-violence connection wasn’t as easy for me to figure out. Some examples of violence motivated by fear might be: “I’m afraid you won’t agree with me so I have to assert control,” or, “I’m afraid I’ll be seen as less, so I have to go on the attack.” So if we think about silence and violence strategies as different expressions of the same feeling, what used to be well established boundaries start to blur. And sometimes, they blur to the point of not being able to clearly categorize the behavior.

And now, on to a question you didn’t ask but that I feel warrants being part of the discussion. There are two types of passive/aggressive behavior that I see most often as I work with different organizations. They take different forms in different regions of the world. So as you review them, see if you can identify how and where they show up where you live and work.

Sarcasm. This first type is more of an aggressive/passive strategy. It’s one of the most common signs that someone doesn’t feel safe while, at the same time, causing feelings of insecurity in others. Because it’s readily available—and we are surrounded by so many examples—it’s widely used. To be clear, there is such a thing as playful, fun sarcasm. But a lot of what I see in organizations is sarcasm rooted in the origins of the word. Derived from the Greek sarkazein, sarcasm literally means “to strip off the flesh.” Ouch! And in a lame effort to ease the pain of the cut, it’s always followed-up with some version of the old classic, “I’m only kidding! Can’t you take a joke?”

Gossip. This second strategy is more of the tried and true passive/aggressive approach. The idea is that whenever you feel you’re in a weaker position, you launch an assault behind the other person’s back. Never share your concerns, reservations, or controversial perspectives in the moment while talking directly to the other person. Instead, wait until you find an uninvolved third party with absolutely no ability to resolve any of the issues you bring up. Extra bonus points if you can talk to someone who might eventually leak the details of your concerns, without naming who had them, to someone who can do something about it. This version may seem less vicious when compared to the previous example, and yet it’s just as real in its long-term impact on the health of both the relationship and the culture of the organization.

Just to be clear, I don’t dwell on these wedge-driving behaviors for fun. I believe that the sooner we recognize we aren’t in dialogue—especially when we find ourselves on more artful, subtle departures—the faster we can get back to dialogue and the fewer the casualties. I wish you many passive/aggressive-free conversations!

Best of Luck,
Steve

Crucial Conversations QA

How to Increase Your Conversational Skills

Dear David,

How do you make and keep friends when you are inept in conversation? I can be in a crowded room, sit in one corner and just people watch because I have nothing to say. Also, if I have an opportunity to go out to places where there will be more than two people, I find every excuse not to go. Sometimes I manage to push myself out the door, but rarely. Any ideas?

Sincerely,
A Couch Potato (in front of a computer)

Dear Couch Potato,

I can certainly say, “been there, done that!” I was painfully shy and socially inept well in to my thirties. Some would say I remain pretty socially inept. I guess my own situation explains in part why I chose to dive deeply into the study of psychology.

While in graduate school at Stanford, I volunteered at a Shyness Clinic that Phil Zimbardo was running as a part of his research. He eventually wrote an excellent book, Shyness: What It Is, What To Do About It. I recommend checking it out.

Before I began working with Phil, I had assumed most shyness was due to poor social skills. But it turned out I was wrong. The shy people we studied were actually quite skilled. The problem was they were also harsh self-critics and were extra-sensitive to social rejection. It turns out most of us fumble and stumble our way through social situations; and shy people notice their slip-ups more than the rest of us.

What helped these people the most was to practice conversations, warts and all, until they realized their fumbles weren’t any worse than anyone else’s. Of course, this practice also helped them improve their conversation skills. With that in mind, I’ll suggest a couple of ideas for practice.

Conversational Tennis. This game comes from my dear friend, Al Switzler. I’ve used it myself, and with many of my nieces and nephews. You play it with one or two other people, perhaps on a car trip or during a meal. Here is the setup: The goal is to keep the conversation going. One person begins by serving a topic across the net. The other person’s goal is to respond to the topic in a way that sends it back across the net, and keeps the conversation going. See how long you can keep the topic in the air. After a while, it will be the other person’s turn to serve up his or her own topic.

This game works well to practice keeping conversations alive. I find it’s really fun with teens who are used to responding in monosyllabic grunts and nods. They quickly see what it takes to participate in a conversation.

Topics to Discuss. You can find several websites that suggest conversation starters. And there is some excellent research on how the topics of conversations flow among strangers and friends. The basic finding is that we begin by talking about very broad and noncontroversial topics, such as the weather, traffic, or jobs. These are easy topics for others to hit back across the net. We use them to keep the conversation going while we listen for common interests and other, more personal, connections.

As we begin to feel safer with the person, we reveal more about ourselves. We test how safe and rewarding it is to disclose our interests, our hopes, and our fears. This phase of the conversation is a bit like a dance. Disclose too much too soon, or ask questions that are too personal too soon, and your partner will feel uncomfortable. Keep the conversation on surface topics for too long, and the person will think you don’t want a personal relationship.

The researcher, Arthur Aron, has studied this process in the lab, by giving strangers a series of questions to discuss with each other. The questions begin at a surface level but become increasingly personal over the forty-five minutes of the experiment. Because of the situation, people feel fairly safe with each other. As the questions become more personal, they often find themselves disclosing information they’ve never shared with anyone before. When they see the way their partner reacts to their revelations, they develop trust, liking, and even affection for them. In fact, these questions have developed the reputation as “The 36 Questions to Fall in Love.”

Rules of Improv. Where should you start? I suggest you begin with low-stakes conversations—perhaps with phone calls with family members. I don’t know about you, but I try to call my mom every day. Use conversations like these to test out topics that work for you. In addition, follow the First Rule of Improv: “Always AGREE, and SAY YES!” This rule doesn’t mean you should “agree” or “say yes” to everything your conversational partner says. Instead, it means you should respect what they’ve said, and hit the topic back to them in a way that is safe and easy for them to respond to. The rule is another take on conversational tennis.

I hope these ideas will be helpful. Now turn off your computer and call your mom.

Best Wishes,
David

Crucial Conversations QA

Manipulating Crucial Skills

Dear Joseph,

My boss is a big fan of yours, but I think he’s misusing his understanding of your material to bully people then patting himself on the back for being a great communicator.

I might approach him and say, “When I said [blank] in that meeting, you cut me off and responded in a tone that sounded sarcastic. I felt that you were not listening to my opinion.”

He’ll respond, “You need to ask yourself how you are perceiving the situation. You need to choose not to get upset. You should look at the situation as an opportunity to communicate. The more you practice, the better you will become.”

How can I approach this with him so that he will at least consider that he might need to change his own behavior?

Signed,
Not Just About Me

Dear Not Just About Me,

I can feel your frustration. You’ve got a boss who has the solution to his own problem in his hands, but appears to be using it on everyone but himself.

I felt a bit of embarrassment as I read your question because I realized I can be that guy sometimes, too. I think most of us are better at diagnosing others than fixing ourselves. So my advice to you is:

1. Look for the truth.
It seems that your focus is on how he is falling short of what he advocates. Don’t make the mistake of declining truth no matter the messenger. A friend used to say, “Even a hypocrite is useful if for nothing other than a bad example.” Your boss is challenging you to examine your own stories and emotions. If you want to gain the moral authority to ask him to listen to your feedback, first listen to his.

2. Challenge your view. Find a way to critique your own critique of the boss. Find others who might have a different view so you can confirm your criticisms of him aren’t exaggerated or self-serving. Be sure you aren’t taking things personally that others tend to brush-off. Confirm you are not making mountains out of what others think are molehills. Ask them for feedback about you as well so you can put your own house in order before attempting to address his.

3. Offer feedback. If you do a quality job on #1 and #2, you’re ready to talk. Begin by checking to see if he is ready. Acknowledge your concerns, but assure him your goal is dialogue not monologue. For example, “Boss, I’d like a few minutes to share some concerns and to invite your feedback as well. There are some things that are getting in my way. I realize some of them might be about me. Could we schedule some time when I could share my view and listen to yours, too?”

4. Give him a reason to listen. As you ask for this appointment, be sure to offer a Mutual Purpose. Asking, “Can I point out your flaws for fifteen solid minutes?” might not be very motivating to him. So help him frame this as a sincere opportunity to help him get something that is important to him—while also acknowledging its importance to you, too. For example: “After some of our staff meetings, I find myself feeling discouraged and disconnected. I don’t want to bring that to your team. I want to do my best work for you and for our customers. I want to feel 100% engaged in a way that you are thrilled about. That’s what this conversation is about. Can we talk?”

5. Share facts, not judgments. This is the tricky part. I worry from the tone of your question that you’ve got a lot of judgments about your boss. If so, you need to shed them as best you can. Otherwise, they will creep into your tone and word choice. You’ve got to see him as a reasonable, rational, decent person. You must come to see his weaknesses as human not villainous. I don’t mean to suggest you should put up with the weaknesses—just don’t turn him from a human into a villain because of them. As you offer your feedback, be sure to share facts and behaviors not judgments and emotions. For example, don’t say, “You misuse Crucial Conversations principles to bully people.” That’s a judgment. Rather, you might say, “When I try to share concerns about how you handled something in a meeting, you point out what I did wrong. This has happened four times.”

6. If he shows no interest, let it go and make a decision. No matter how scrupulous you are about examining yourself, creating safety, and offering facts, some people won’t listen. If, after making your best attempt, he appears impervious to feedback, you’ve got a choice to make. You must accept that this is who he is likely to be for the foreseeable future. Then you have to decide if you’re quality of life is enough at risk to make a change, or if this is trivial enough that you can cope. If you choose to cope, then acknowledge that you are making a decision to stay. Don’t play the victim by staying and blaming him. From this point forward, it is your choice to accept him as he is. If you can’t, then you have three options: 1. Stay, but find a way to distance yourself from his weaknesses; 2. Stay in the company but change bosses; or 3. Change companies. Some might complain at this advice, thinking, “That’s not fair! Why should his weaknesses mean that I have to change?” The answer is: “Because that’s how life works.” The only thing you can control is yourself. Everything else is about influence. If influence fails, controlling yourself is all you’ve got.

I hope influence works. It will be good for both you and him. And if not, I hope you can find a path to peace that works for you.

Sincerely,
Joseph