motivation barriers

This article is an excerpt from the Shortform summary of "Crucial Conversations" by Kerry Patterson. Shortform has the world's best summaries of books you should be reading.

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Do you want to know how to have difficult conversations at work? Are there issues you need to address, but you’re not sure how?

Having difficult conversations at work can feel daunting. But having those conversations is important. It will improve your management skills and the organization. Keep reading for examples of difficult conversations at work, and how to resolve them.

Why Should You Have Difficult Conversations at Work?

Having leaders and employees who skillfully handle crucial conversations can improve an organization’s performance, while poorly handled conversations and interactions can undercut it. So while it’s certainly hard to have difficult conversations at work, it’s a skill that benefits the whole group.

When employees have good conversation skills

On the positive side, the authors’ research shows that companies whose employees are skilled at crucial conversations:

  • Respond faster to financial downturns. 
  • Are less likely to be injured due to unsafe conditions.
  • Increase the productivity of virtual (remote) work teams.
  • Influence misbehaving or incompetent colleagues to do better.

Most leaders think that organizational productivity and performance are driven by policies, processes, or systems. When there are problems they adjust these things, but it often doesn’t work because the problem is behavior, not systems.

Solving behavior problems requires crucial conversation skills, and shows that employees benefit from learning how to have a tough conversation at work.

When employees have poor conversation skills

On the negative side, when organizations have performance problems such as snowballing costs, late delivery times, and poor morale, the biggest reason is employees’ unwillingness or inability to speak up (have crucial conversations) at key moments. These companies have not put the time into learning how to have a difficult conversation at work, and it shows.

For example, employees see others take shortcuts or make mistakes, and don’t say anything, which impacts safety, turnover, and productivity. Also projects can fail when employees stay silent about problems — for instance, when goals are unrealistic, team members perform badly, or leadership stumbles. 

How to Have Difficult Conversations at Work: Focus on These Two Things

First, the suggestion: One way people have succeeded in improving their handling of crucial conversations is by focusing on just two key principles: Pay attention to what’s happening, and ensure safety. These principles are universal in crucial conversations, and they can be applied when you’re figuring out how to have a difficult conversation at work.

1. Pay attention to what’s happening: Constantly ask yourself whether you’re in or out of dialogue. This makes a huge difference.

Even if you can’t remember the acronyms or steps you can help maintain dialogue by noticing whether you or others are falling into silence or violence. Even if you don’t know exactly how to fix the problem when you see it, it’s worth trying something to restore the dialogue.

You can use the statement, “I think we’ve moved away from dialogue,” to get back on track.

2. Ensure safety: When you notice that you and others have moved away from dialogue, do something to make it safer — for instance, asking a question and showing interest in others’ views.

Just do something to make others comfortable: smile, apologize if you’ve moved to silence or violence, or request a brief timeout. Although the book suggests specific skills (such as contrasting, mirroring, priming), there are many other things you can do to increase safety.

People often think their situations are unique and that dialogue skills outlined in this book don’t apply, or won’t work. According to the authors, the skills do in fact apply to virtually any issue, although some problems are more challenging than others.

Example of Difficult Conversations at Work

What’s next in learning how to have a tough conversation at work? Difficult conversations at work take many forms, but some are a little more complex than others. Below are examples of difficult conversations at work and how to resolve them.

Difficult Conversation Example #1: Harassment

You’re uncomfortable with the way you’re being treated, although you don’t view it as blatant harassment.


You find the behavior offensive, but it’s so subtle or sporadic that you’re hesitant to go to your boss or HR for fear of looking like you’re overreacting. Getting caught up in a villain story could drive you to respond in ways that end up hurting you.


Tell the full story. Admit it if you’ve put up with the behavior for a while without saying anything. Then discuss it with the other person. Try to treat the person as reasonable — even if the behavior isn’t. 

After establishing a mutual purpose for the conversation, STATE your path. If you can be respectful but firm, the individual usually will stop the objectionable behavior. If the behavior ever crosses the line, contact HR to ensure your rights are protected.

Difficult Conversation Example #2: Letting the Team Down

At work, you get together as a team and talk about how to improve, but some of your teammates don’t do what they agreed to do.


In an effective team, every team member is accountable. Team members speak up when they see violations. Lesser teams ignore problems or let the boss deal with them.


It’s your responsibility to speak up. When team members agree to a course of action, they must be willing to confront any team member who doesn’t live up to the agreement — or the whole thing can fall apart.

The team’s success depends not on flawless performance, but on teammates who hold crucial conversations with each other when necessary.

Difficult Conversation Example #3: Deference to Authority

People who work for you seldom take initiative on anything. They hold back their opinions and say what they think you want to hear.


When leaders experience deference or kissing up, which stems from fear, they make one of two mistakes:

  • They deny they are causing people to be afraid of them. That’s because they’re unaware of how they act under stress. The way they speak and carry themselves is creating fear/deference. 
  • They try to solve the problem by just telling employees to stop deferring. People agree to stop deferring, but they don’t. Extreme deference may stem from treatment by past bosses. You need to determine if you’re living with a ghost, or if you’re the cause of the fear.


Determine how you contribute to the problem. Ask a peer for honest feedback about your behavior. Develop and implement a plan, and seek ongoing feedback.

If the problem originated under previous leaders, bring it up at a team meeting and ask for advice. In your interactions with employees, reward risk takers, encourage opposing views, thank people when they’re honest, and play devil’s advocate.

Difficult Conversation Example #4: Failed Trust

Your colleague missed an important deadline, Now you wonder whether you should trust him again. It leads to needing to learn how to have a tough conversation at work.


Trust isn’t an either/or proposition where you either trust someone or you don’t. It can evolve and it’s specific to the situation. You may trust someone in some circumstances but not others. You may trust someone’s motivation in a situation but not her ability.


Focus on the issue, not the person. Take small steps to rebuild trust — first, just try to trust them in the moment. You don’t have to trust them in every circumstance. Discuss your concerns using STATE skills: Talk tentatively about what you see happening.

Difficult Conversation Example #5: Shows No Initiative

Your team members do what they’re asked, but no more. If they encounter problems they give up. This is a typical example of difficult conversations at work.


It’s a straightforward process to point out and address obviously bad behavior or performance, and to reward good performance. Dealing with people who lack initiative or persistence falls into a gray area and is more challenging to address.


Deal with the overall pattern, rather than a specific instance.

If you want someone to take greater initiative, tell them. Give examples of when they faced a problem and gave up. Brainstorm ways the person could have been more persistent in coming up with a solution. Tell them you’re raising the bar.

Also, be aware of the ways you’re enabling someone’s lack of initiative. Clarify your expectations and put the responsibility on them.

Difficult Conversation Example #6: Insubordination

How should you respond when people get angry, and then insubordinate?


Insubordination is rare, so when it happens it catches many leaders off guard. They buy time to figure out what to do. But this lets the person get away with egregious behavior, and it encourages future abuses.

(In dealing with rebellious kids, parents tend to respond in kind rather than buying time — they become angry and insulting.)


You cannot tolerate insubordination — speak up immediately. You need to stop disrespect before it gets worse. Change topics from the issue under discussion to how the person is currently acting. Let her know she is heading in a dangerous direction.

For instance, respond: “Let’s set aside this scheduling issue for a moment. The way you’re raising your voice and the words you’re using are disrespectful. I want to address your concerns, but I can’t do so if this continues.” If this doesn’t alleviate the problem, seek help from HR.

Difficult Conversation Example #7: No Warning

Sometimes when employees run into problems with an assignment or project, leaders don’t find out until it’s too late.


Leaders who are regularly being surprised are allowing it to happen. Typically, the first time an employee says, “Sorry but I ran into a problem,” leaders focus on the problem and fix it, thereby conveying that it’s OK to surprise them; they’ll take care of things.


Establish a clear “no surprises” rule. When you give someone an assignment, make clear that they need to either complete it as planned, or inform you immediately if they run into a problem.

The first time someone has a problem but didn’t inform you when the problem first came up, address it immediately: “We agreed you’d let me know immediately if you had a problem. You didn’t contact me — what happened?”

When you have difficult conversations at work, the task might seem like it’s too much to handle, and you may be tempted to avoid confrontation. But learning how to have a difficult conversation at work helps your communication skills, and improves your organization. So when you do have those difficult conversations at work, keep in mind that the result will be worth it.

2 Steps for Difficult Conversations at Work + 7 Examples

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Here's what you'll find in our full Crucial Conversations summary :

  • How to approach an argument without getting mad
  • The mistakes most people make when trying to listen to someone else
  • How to come up with win-win solutions that make everyone happy

Carrie Cabral

Carrie has been reading and writing for as long as she can remember, and has always been open to reading anything put in front of her. She wrote her first short story at the age of six, about a lost dog who meets animal friends on his journey home. Surprisingly, it was never picked up by any major publishers, but did spark her passion for books. Carrie worked in book publishing for several years before getting an MFA in Creative Writing. She especially loves literary fiction, historical fiction, and social, cultural, and historical nonfiction that gets into the weeds of daily life.

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