Why is having difficult conversations so important?

The reality is that difficult conversations are a part of life, both in our personal and professional lives.  The problem is that handling them incorrectly or even ignoring them altogether can have a bigger impact than we imagine.  2024 SHRM research found that workers who rate their workplace as “Uncivil” are 3x more likely to be unsatisfied with their job and 2x as likely to leave their job in the next year.  In a time when turnover and filling roles continue to be a struggle for many companies, it only adds to the importance of having difficult conversations in the workplace. 

And it’s not just affecting turnover – lack of difficult conversations or good conflict management skills in the workplace have a financial impact on companies.  In 2022, EEOC found that there were 73,485 workplace discrimination charges in the US, which resulted in more than $39 million in damages for victims in federal court. This does not include hundreds of millions in damages granted by state and district courts. 

Luckily there’s good news, conflict management and difficult conversation training can have a huge impact.  A 2008 CPP study found that for employees and managers that receive this type of training, 95% of them report that the training helped them navigate workplace conflict positively and seek mutually beneficial outcomes. 

This article will help to identify why difficult conversations are so hard and best practices for difficult conversations for managers in the workplace with employees.

Why are hard conversations so hard?

The reasons why difficult conversations are so hard fall into two basic causes:

1.               You care about both the outcome and the relationship

There’s an inherent tension when you are aiming for a particular outcome, but you still want/need a positive relationship with the person you’re speaking with.  That’s what makes it so difficult.  If you didn’t care about the relationship, you could get away with being more aggressive in your approach.  If you didn’t care about the outcome, you could either avoid the conversation or give in to the other person’s requests/demands and ignore your own. 

2.               You have your own mindset about conflict

Just like the grooves of a vinyl record or the hiking path that’s been well travelled, your history and experiences have led you to think of conflict in a certain way and that pattern persists.  Whether you think of conflict as a bad thing and you need to run away from it, or you hate the idea of people being angry with you, or you think the best way to approach hard conversations is to yell at them – we all carry these thoughts/mindsets with us.  Mastering difficult conversations involves understanding these things about ourselves and learning how to control them.

How to prepare for them

They say that most battles are won long before they’re fought.  How you prepare can make all the difference between the outcome you want and the conversation going off track.  Good preparation involves 3 main aspects:

1.     Think through the purpose/your goal of the conversation

Being clear on your desired outcome isn’t just a thought exercise, it can help you clarify what needs to be said, the flow of the conversation, and help you stay on track in the event the other person tries to change the subject. 

2.     Prepare your feelings/mindset

Spend time preparing explicitly for how you’ll stay calm in hard conversations.  This means understanding what triggers your fight/flight/freeze response in these situations and having a plan of how you’ll stay calm and in control. 

3.     Prepare for the other person

Spend some time reflecting on the other person.  Figure out their communication style, what triggers them, and their personal/professional goals.  The more you can understand them, the more you can find ways to meet their needs and help them stay focused on the conversation.  If you’re giving critical feedback (either up, down, or across), it’ll be vital to bring documentation of behaviors or issues.  The more data you have, the easier it’ll be to stay on task.

How to structure hard conversations

Preparation is vital, but there’s also a way to structure a conversation to minimize the fight/flight response, both in yourself and in the other person. 

1.     Open strong and clearly

When opening a hard conversation, start with thanking the other person and then immediately bring up what you want to talk about.  Use plain language and don’t leave them guessing by being straightforward.  Starting this way helps to frame the conversation and provide a direction for the entire conversation.  By getting alignment on the goal from the beginning, you can bring the flow back if the other person tries to change the subject. 

2.     Set ground rules

Ground rules are often forgotten, but when done right, it can provide a level of security and safety for both you and the other person.  This helps reduce (but never eliminate) the fight, flight, or freeze response both in the other person and in yourself.  It gives you a foundation to stand on if either of you don’t feel safe to continue a conversation.

3.     Collaborative Problem Solving

While there is a framework called “collaborative problem solving” that is really useful for conflict resolution, it’s more important to transform your mindset.  Rather than looking at difficult conversations as “the other person is my opponent”, this approach reframes the conversation as both of you working together to solve the problem.  The key here is framing for everyone involved that you are more interested in solving a problem together, rather than you trying to fix the other person.  That allows the conversation to shift away from being seen as an attack, and more of a collaboration.

If giving critical feedback, focus on the facts, the impact, and give space for them to give their input into what they think led to the behavior/situation and collaboratively brainstorm what the future will look like.

4.     Ending strong and follow through

How you end can often make or break the entire conversation and what comes next.  If there needs to be follow up action, make sure it’s discussed clearly before ending the conversation.  The question I often get from managers and leaders in difficult conversations in the workplace is “how do I make sure someone is going to do what we agreed on?” 

There’s one magic question that I’ve found more useful than any other method, and it’s so simple:

“How will we address this if this doesn’t get done?”

Obviously, you can change the phrasing to match your situation, but the idea is the same – proactively and collaboratively planning for what will be your collective response.  And it doesn’t have to be phrased as being pessimistic about the other person following through.  This question can also recognize that sometimes life gets in the way of things and you want to work together to plan for unforeseen circumstances.

And in the workplace, if you take nothing away except for this, make sure you document the conversation and send copies to yourself and everyone in the conversation so there is no confusion about what was said or what the next steps are.  

Where do we go from here?

Difficult conversations are inevitable.  But the fear and anxiety don’t have to be.  The ability to communicate well, even in hard conversations, is something everyone can learn.  In fact, that’s the mission Lucie and I have embarked on.  We created a podcast focused on helping others communicate and live better, both in personal and professional situations.  Here are some resources and links to help you:

·       If you love podcasts, you can listen to our podcast here or anywhere you get your podcasts.

·       If you love watching videos, you can watch our podcast on YouTube here

·       If you prefer reading, I have a weekly newsletter where I walk through how to handle different professional difficult conversations.  You can sign up here

Even if these aren’t your cup of tea, I truly believe you can get better at difficult conversations and create true win-win conversations.  You got this!


Chris is a certified executive coach who brings a wealth of experience and expertise to the world of leadership and learning and development in the nonprofit space. As a licensed therapist, he is skilled in working through mindset and behavior changes. He has trained hundreds of leaders and led numerous successful organizational projects. Chris is also a skilled facilitator and public speaker in a variety of settings.

Certified as an executive coach, he has worked with leaders at all levels to strategically prioritize their work and navigate difficult conversations/relationships with confidence. Chris brings years of experience navigating non-profit, health insurance, and government systems.

Currently, Chris works with human service nonprofit executives to effectively execute their strategic plans. This includes helping leaders navigate difficult conversations, resolve conflicts, create high-performing cultures, enhance productivity, and cultivate an inclusive and equitable work environment. His expertise spans diverse areas, including leadership development, strategic planning, leading change, and diversity, equity, and inclusion.

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