13 Warning Signs You Are Avoiding a Difficult Conversation

You already know the conversation you need to have. You have known for weeks, maybe months. You can picture the person's face. You can feel the knot in your stomach when you think about sitting down and saying what needs to be said. But you have not done it. And every day you do not, the problem gets a little worse.

You are not alone. Research from the Chartered Management Institute found that 57 percent of people would do almost anything to avoid a difficult conversation. A separate study from the University of Notre Dame's Deaconess Leadership Centre found that more than 80 percent of workers are holding back from at least one challenging conversation at work. And when Brene Brown's team surveyed leaders about the biggest barriers to courage in their organisations, one issue was ranked as the greatest concern above all others: avoiding tough conversations, including giving honest, productive feedback.

The cost of avoidance is not neutral. It is compounding. Every conversation you postpone becomes harder to have. The behaviour you tolerate becomes normalised. The team around you watches and draws conclusions about what is acceptable. And the person who needs the feedback? They are being denied the chance to grow.

I wrote my book Step Up or Step Out (10,000+ copies sold globally) because 50 percent of my coaching conversations with leaders focused on the same problem: a difficult person they did not know how to deal with. The pattern was always the same. The leader knew something needed to change, but they kept delaying, hoping the problem would resolve itself, rationalising why now was not the right time, and watching the situation deteriorate while they waited.

Here are 13 warning signs that you are avoiding a difficult conversation, what is really going on underneath each one, and what to do about it. If any of these sound like you, email me at jonno@consultclarity.org and let us talk about what is actually holding you back.

1. You Keep Rehearsing the Conversation in Your Head but Never Having It

You have thought about this conversation dozens of times. You have planned what you will say, anticipated how they will react, and played out multiple scenarios in your mind. But you have not actually had the conversation. The rehearsal has become a substitute for action.

This is one of the most common avoidance patterns because it feels productive. You are "preparing." But mental rehearsal without a scheduled conversation is just sophisticated procrastination. The longer you rehearse, the more catastrophic your imagined scenarios become, and the less likely you are to actually sit down and talk.

What to do about it: Stop preparing and start scheduling. Put a meeting in the diary for this week. You do not need a perfect script. You need a clear intention: what do you want the person to understand, and what outcome do you want from the conversation? If you want a practical framework for structuring these conversations, my book Step Up or Step Out walks you through a three-step system that works even if you hate conflict.

2. You Have Told Other People About the Problem but Not the Person

If you have vented to your spouse, your colleague, your manager, or your coach about someone's behaviour, but you have not spoken to the person themselves, you are avoiding the conversation. This is not "processing." It is triangulation, and it makes the problem worse.

Every conversation you have about the person rather than with the person adds a layer of complexity. Others now have opinions. The story grows. And when the conversation finally happens (if it happens), it carries the weight of weeks or months of accumulated frustration rather than the simple directness it could have had on day one.

What to do about it: Apply a simple rule. Before you talk to anyone else about the problem, talk to the person first. If you need to process before you have the conversation, limit it to one trusted advisor and set a deadline: "I am going to talk to them by Friday." Then do it. For more on how to approach these conversations constructively, read 29 Simple Strategies on How to Improve Team Dynamics.

3. You Are Waiting for the "Right Time"

There is never a right time for a difficult conversation. There will always be a project deadline, a busy season, a restructure, a personal situation, or some other legitimate-sounding reason to delay. The "right time" is a myth that the avoidant part of your brain uses to keep you comfortable.

Brene Brown's research is blunt on this point: clear is kind, unclear is unkind. Feeding people half-truths or withholding feedback to avoid discomfort is not kindness. It is a failure of leadership that costs the other person the chance to understand what is expected and change their behaviour.

What to do about it: Replace "the right time" with "the earliest reasonable time." If the person is in genuine crisis, waiting a few days is appropriate. If you are simply uncomfortable, that discomfort is not a valid reason to delay. Schedule the conversation within 48 hours of recognising it needs to happen. The longer you wait, the harder it gets. Email me at jonno@consultclarity.org if you want to talk through timing and approach for a specific situation.

4. You Have Started Managing Around the Person Instead of Managing Them

This is one of the most damaging forms of avoidance because it looks like leadership. You have reorganised responsibilities to compensate for the person's behaviour. You have assigned their tasks to someone else. You have restructured reporting lines. You have done everything except tell the person what the problem is.

The rest of the team notices. They see that the difficult person is being accommodated while they pick up the slack. This breeds resentment, erodes trust in your leadership, and signals to everyone that poor behaviour will be tolerated as long as it is inconvenient enough to address.

What to do about it: Before any structural change, ask yourself: "Have I told this person directly what needs to change?" If the answer is no, that is your first step. Structural changes may still be needed afterwards, but they should come after the conversation, not instead of it. My book Step Up or Step Out outlines how to set clear expectations so the person willingly decides to step up or step out within four weeks.

5. You Have Lowered Your Expectations Without Telling Anyone

This one is subtle and insidious. You have gradually accepted a lower standard of performance, behaviour, or contribution from someone because addressing the gap feels too hard. You have not formally lowered the bar. You have just stopped enforcing it.

This is avoidance disguised as tolerance. And it is devastating to team culture because it redefines what "good enough" looks like for everyone. Gallup's engagement research consistently shows that a lack of clear expectations is one of the biggest drivers of disengagement. Only 46 percent of employees clearly know what is expected of them at work, and that number is dropping. When leaders silently lower expectations for one person, clarity erodes for the entire team.

What to do about it: Write down what you actually expect from this person. Compare it to what you are currently accepting. The gap between those two things is the conversation you need to have. Start with this: "I want to get clear about what I expect from you in this role." Then lay it out specifically. If you need help getting clear on expectations before the conversation, email me at jonno@consultclarity.org.

6. You Dread Your One-on-Ones with This Person

If you feel a wave of anxiety or dread before a scheduled meeting with someone, your body is telling you something your mind is trying to avoid. The dread usually indicates an unresolved issue that surfaces every time you interact with the person but that you push back down as soon as the meeting ends.

Healthy working relationships do not produce dread. Respectful tension is normal, even healthy. But when you are physically avoiding someone or dreading their name on your calendar, there is a conversation underneath that feeling that you have not had.

What to do about it: Name the feeling and name the conversation. Ask yourself: "If I could be completely honest with this person about one thing, what would it be?" That is the conversation you are avoiding. Then refer to the three-step framework in Step Up or Step Out for how to structure it in a way that is direct, respectful, and focused on outcomes rather than blame.

7. You Keep Hoping the Problem Will Resolve Itself

Hope is not a management strategy. Yet a remarkable number of leaders operate on the implicit assumption that if they just give it time, the difficult person will change, the conflict will blow over, or the performance issue will self-correct. It almost never does.

Research consistently shows that unaddressed problems escalate. The Chartered Management Institute found that the longer an issue remains unresolved, the more resentment builds, resulting in a highly charged conversation that is much more difficult to navigate. The conversation you are avoiding today will be three times harder in three months.

What to do about it: Ask yourself a diagnostic question: "If nothing changes about this situation in the next six months, what will the impact be?" If the answer makes you uncomfortable, the conversation needs to happen now. Not next month. Not after the next performance review cycle. Now. Email me at jonno@consultclarity.org if you want help getting started.

8. The Person's Name Comes Up in Every Frustrating Conversation You Have

If the same person's name keeps appearing whenever you discuss team problems, project delays, or cultural issues, they are at the centre of a pattern you have not addressed. The repetition is not coincidence. It is a signal.

When a person's behaviour is causing enough friction that it affects multiple contexts, the cost of avoidance is multiplying. Every project they touch, every meeting they attend, every interaction they have is affected by the unaddressed issue. And every person who raises their name with you is indirectly asking: "When are you going to do something about this?"

What to do about it: When you notice the pattern, name it. Say to yourself: "This person's name has come up in three separate contexts this month. There is a conversation I need to have." Then schedule it. For the full framework on how to have these conversations without massive confrontation, read Step Up or Step Out.

9. You Have Given Feedback That Was So Soft It Was Meaningless

Many leaders believe they have addressed the issue because they have "given feedback." But the feedback was wrapped in so many qualifiers, compliments, and softening language that the person walked away thinking they were doing fine.

This is the "feedback sandwich" at its worst. You said something positive, slipped in a vague concern, then ended with more positivity. The person heard the bread. They missed the meat entirely. And you told yourself the conversation happened, when in reality, the message was never delivered.

What to do about it: Be specific and direct. Replace "I wanted to chat about how things are going" with "I want to talk about a specific concern I have about X behaviour and the impact it is having." You can be direct and kind simultaneously. In fact, directness is the kindest form of feedback because it gives the person something concrete to work with. Read 183 Tips to Build Your Team: The Five Dysfunctions of a Team Summary for the full framework on accountability.

10. You Have Started Documenting Instead of Talking

There is a version of this that is responsible management: documenting issues alongside direct conversation. But there is another version that is pure avoidance: building a paper trail so that when you finally act, you can point to months of evidence, even though the person was never told directly what the problem was.

If your documentation file is thicker than the number of honest conversations you have had, you are managing your own anxiety rather than managing the person. And if the day comes when you use that file in a formal process, the person will rightly ask: "Why did nobody tell me?"

What to do about it: For every documented incident, ask yourself: "Did I tell the person about this at the time?" If the answer is consistently no, pause the documentation and start the direct conversations. The documentation should reflect conversations you have had, not replace conversations you have avoided. Email me at jonno@consultclarity.org if you want to talk about how to balance documentation with direct feedback.

11. Other Team Members Are Starting to Leave

This is the most expensive consequence of conversation avoidance. When good people leave because you have not addressed a difficult person or situation, you are paying the cost of avoidance in recruitment fees, lost productivity, cultural damage, and institutional knowledge that walks out the door.

Exit interviews often reveal the pattern clearly. People do not usually leave because of the difficult person. They leave because leadership would not address the difficult person. The failure to act communicated a message louder than any difficult conversation could: this behaviour is acceptable here. And your best people decided it was not acceptable to them.

What to do about it: If you have lost team members and the same person or situation was a contributing factor, the conversation is now overdue. Have it today. The cost of another departure is significantly higher than the discomfort of a 30-minute difficult conversation. For a deeper understanding of how to build accountability into your team culture, read 100 Proven Tips for Working Genius in the Workplace.

12. You Have Convinced Yourself It Is Not That Bad

Minimisation is one of the most effective avoidance strategies because it works on you first. "It is not that bad." "Other people have worse situations." "They are not a terrible person, they just have a few issues." "Maybe I am overreacting."

You are not overreacting. If the issue has occupied this much of your mental space, it is significant. Minimisation is your brain's way of reducing the cognitive dissonance between knowing you need to act and not wanting to. The problem with minimisation is that it gradually adjusts your baseline. What was unacceptable six months ago becomes tolerable today, and normal six months from now.

What to do about it: Ask someone you trust: "Am I underreacting to this situation?" Get an outside perspective. Often, the people around you can see the impact of the issue more clearly than you can because they are not invested in avoiding the conversation.

13. You Are Reading This and a Specific Person's Face Is in Your Mind

If a specific person has been in your head throughout this entire article, you know what you need to do. The question is not whether the conversation needs to happen. It is whether you will have the courage to have it this week.

Most leaders delay difficult conversations not because they are weak, but because they care. They do not want to hurt the person. They do not want to damage the relationship. They do not want to create conflict. These are all understandable motivations. But they are also the exact reasons the conversation needs to happen. Because caring about someone means telling them the truth, even when it is uncomfortable.

What to do about it: Have the conversation this week. Not a perfect conversation. A real one. Start with honesty about your intent: "I care about you and I care about this team, and there is something I need to talk to you about." Then say the thing. If you want a proven framework for having this conversation without creating a massive confrontation, my book Step Up or Step Out was written for exactly this moment.

What to Do Next

If you recognised yourself in several of these warning signs, here is where I would start.

Step one: Identify the one conversation you have been avoiding the longest. Not the easiest one. The one that has been occupying the most mental space.

Step two: Schedule it within the next 48 hours. Put it in your calendar. Tell a trusted colleague that you are going to do it so you have accountability.

Step three: Prepare with a clear framework. Know what you want the person to understand, what outcome you want, and how you will open the conversation. My book Step Up or Step Out provides a three-step system that has helped over 10,000 leaders navigate exactly these moments.

I work with leadership teams, school leaders, and boards around the world to build cultures where difficult conversations happen early, directly, and constructively. Whether you need executive coaching, a team workshop on accountability, or a facilitated offsite to address the issues everyone can see but nobody will name, I can help.

I am the author of Step Up or Step Out, which has sold over 10,000 copies globally, and I host The Leadership Conversations Podcast with more than 230 episodes and listeners in over 150 countries. My Working Genius masterclass at the ASBA 2025 National Conference achieved a 93.75 percent satisfaction rating.

If you have a conversation you have been avoiding and you want help structuring it, email me at jonno@consultclarity.org. The conversation you are dreading is almost always the conversation your team is waiting for.

FAQ

Why do leaders avoid difficult conversations?

The most common reasons are fear of damaging the relationship, fear of emotional reaction, lack of confidence in their ability to navigate the conversation, and a cultural norm that values niceness over clarity. Brene Brown's research found that more than half of leaders attribute conversation avoidance to a culture of "nice and polite" that is leveraged as an excuse to avoid honesty. My book Step Up or Step Out provides a framework specifically designed for leaders who hate conflict but know they need to address difficult behaviour.

What happens when you avoid a difficult conversation for too long?

The problem escalates, the behaviour becomes normalised, other team members lose trust in your leadership, and good people start leaving. Research from the Chartered Management Institute shows that unresolved issues build resentment that makes the eventual conversation much harder. Avoidance also denies the other person the chance to understand expectations and change. The cost of delay almost always exceeds the cost of discomfort.

How do you start a difficult conversation without it turning into a fight?

Start with your intent, not your accusation. Open with something like: "I care about our working relationship, and there is something I want to get clear on." Then describe the specific behaviour and its impact without judging the person's character. Avoid "you always" or "you never" language. Focus on what you need to be different going forward rather than relitigating the past. My book Step Up or Step Out walks through this in detail. Email jonno@consultclarity.org to discuss your specific situation.

Can avoiding one conversation really affect team culture?

Absolutely. When a leader tolerates poor behaviour from one person, it sends a message to the entire team about what is acceptable. High performers who care about standards notice immediately and start questioning their commitment. Gallup data consistently shows that a lack of clear expectations and accountability are among the strongest predictors of disengagement. One avoided conversation can set a cultural tone that takes months to reverse.

What is the Step Up or Step Out framework?

Step Up or Step Out is a three-step system I developed for leaders who need to deal with difficult people without creating massive confrontation. The framework focuses on setting clear expectations, creating a structured accountability process, and giving the person the agency to decide whether they will step up to the standard or step out of the organisation. The entire process can work in as little as four weeks. The book has sold over 10,000 copies globally and is available at Amazon. Email jonno@consultclarity.org if you want to discuss how to apply it to your situation.

When should you involve HR instead of handling it yourself?

Involve HR when the behaviour crosses legal or policy lines, when there is a risk of harassment or discrimination claims, when the person has made threats, or when previous direct conversations have failed and formal process is needed. But do not use HR as a substitute for direct leadership conversation. The first step should almost always be a direct, honest conversation between you and the person. HR should support that process, not replace it.

NEXT READ: 10 Warning Signs Your Executive Team Is Dysfunctional (And What to Do About It)

About the Author

Jonno White is a Certified Working Genius Facilitator, bestselling author, and leadership consultant who works with schools, corporates, and nonprofits around the world. His book Step Up or Step Out has sold over 10,000 copies globally, and his podcast The Leadership Conversations has featured 230+ episodes reaching listeners in 150+ countries. Jonno founded The 7 Questions Movement with 6,000+ participating leaders and achieved a 93.75 percent satisfaction rating for his Working Genius masterclass at the ASBA 2025 National Conference. Based in Brisbane, Australia, Jonno works globally and regularly travels for speaking and facilitation engagements.

To book Jonno for your next leadership team workshop, executive coaching engagement, or keynote, email jonno@consultclarity.org.