How to Have Difficult Conversations

two ladies having a work conversation

How to Have Difficult Conversations

Navigating Difficult Conversations: Learning the Basics

group of people talking at work

Whether we’re talking about your personal or professional life, navigating difficult conversations is something you’ll want to understand.  A difficult conversation with a loved one, friend, coworker or boss can be challenging at best but detrimental to the relationship at worst.  Understanding the types of difficult conversations as well as some techniques on managing challenging conversations will better help you convey your concerns in an honest, non-confrontational way while resolving whatever issue is at hand.

How to have difficult conversations

As challenging as they may be, when handled maturely, empathetically and, in places of business, professional, difficult conversations can often build better relationships with people in your life.  Being prepared ahead of time is going to be key to ensuring you both leave feeling better having had the conversation.

Here are a few examples to help you approach difficult conversations:

  • Select a good time and place for the conversation.
  • Set clear goals as to what you would like to achieve from the conversation.
  • Listen actively rather than listening to respond.
  • Compromise as necessary.

The other person will want to be heard so it’s important to listen without the intent to respond, trying to understand their viewpoint, even if you don’t agree.  Empathy is key so don’t be afraid to compromise. It’s also important to follow-up afterwards to make sure each of you are on the same page.

conversation at work between man and woman

What are the 3 types of difficult conversations?


In order to learn how to navigate difficult conversations, it’s important to understand the different types.

  • Factual: The first type is based on things that are measurable such as facts, numbers or even specific events.  For some, this type of conversation might be easiest to tackle since they are data driven and have written proof as back-up. During this conversation, you’ll want to avoid assumptions on intent and keep people separate if you need to explore stories from multiple people.
  • Emotional: The second type are often related to interpersonal issues, many times on sensitive subjects that are hard to discuss. At the heart of the conversation are always feelings so be sure you understand your own first before jumping into this difficult conversation.
  • Identity-based: Perhaps the most difficult to navigate are those that may challenge a person’s beliefs, self-concept or values.  Understand that these are just as complex as the individuals within the conversation so look at all views in order to keep things productive and moving forward.

What Are the 4 D’s of Difficult Conversations?

Another important thing to understand about navigating difficult conversations are the 4 D’s or discover, define, discuss and decide.  Let’s dive into this a little further.

  • Discover: Understand the root cause of the issue (as best you can) before approaching the conversation.
  • Define: To ensure that you aren’t placing any unnecessary blame, address the problem clearly.
  • Discuss: A conversation involves more than one person so leave the dialogue open to hear and consider all perspectives.
  • Decide: In the end, you may not agree on the issue at hand, but it’s important that each of you agree on the resolution or at least the next steps to take.

How do you stay strong in a difficult conversation?


It’s easy for difficult conversations to take a turn in the wrong direction.  Emotions, misunderstandings and defensiveness can introduce a tone into a conversation, sending it southward quickly if you’re not prepared.  So before you begin, take time to think about what you want to say and how you want to say it.  It’s easy to come off as confrontational when addressing difficult things, so be respectful of the other person and their feelings.  Remain open-minded, listening actively and empathetically, willing to compromise if necessary.   Willingness to walk away is perhaps the most important thing to keep in mind.  It’s better to pick things back up on another day when everyone has had time to think about things then it would be to further damage a relationship.

If you’re still afraid that things might get off track, here are a few phrases that might help accomplish some of the things we just talked about:

  • Redirecting: Turn the subject to them.  Talk about something they are interested in; something positive.
  • Being heard: Ask questions like, “I’d love to hear what you think about what I just said.” “Here’s what I’m thinking.” “My perspective is…”
  • Open-ended questions: Leave room for them to respond, including questions like, “How does this affect you?” “What do need to understand?” “What would help us?”
  • Acknowledge a different perspective: “I hear what you’re saying but I have a different view on that and here’s why…”
  • Ending the conversation: Sometimes the conversation has taken an uncomfortable turn, in which case it might be time to offer to revisit another day.  Close with something like, “I know we are both very busy and need to get back to our days…”

Why do I struggle to have difficult conversations?


You may be asking, “Why do I struggle to have difficult conversations at work?”  Reasons can range from concern of damaging relationships to fear of conflict.  Just remember, the temporary discomfort of addressing an issue through a challenging conversation has far less consequences than avoiding it altogether.

The reason it’s so important to step outside of your comfort zone lies in the consequences of avoiding these challenging conversations.  Avoidance can cause:

  • Damage to an already strained
  • relationship
  • Increase in conflict, stress and anxiety
  • Missed opportunities
  • Decrease in productivity

Avoidance is the worst way to resolve issues in relationships, be it personal or professional.  It’s important to be upfront, open-minded and willing to listen to the other person’s perspective.  If it comes down to it, reach out for help from a mentor, colleague or professional to help prepare for these types of conversations.

How do you have an emotionally difficult conversation?

It’s safe to say that most of the difficult conversations we will have over our lifetime will involve feelings.  Whether it’s a behavior that needs to be addressed, a poor choice, mistake or bad news, the conversation itself is likely to evoke some emotions.  Always be sure you validate feelings involved – your own and the other person’s.  Be sure you’re in a private area where you both feel comfortable.  Although human emotions cannot be turned off, preparation and role-playing scenarios might help take the edge off before you begin.

One suggestion would be to use a difficult conversation preparation worksheet, which will help you to outline the main points you need to discuss, other viewpoints and the end goal.  Acknowledge the other person’s feelings, actively listen, don’t interrupt and take breaks if necessary. Give everyone involved a chance to express themselves without fear of judgment or interruption.

frustrated woman on the phone

How to have difficult conversations at work.


A number of different factors can affect the dynamics of the workplace, but none like workplace conflicts.  When they arise, it’s important to handle them professionally, quickly and as prepared as possible.  Make a list of discussion points for the conversation, including any facts and/or data that have to do with the issue at hand and an offer for resolution.  Leave plenty of time for discussion so that the other person feels heard.  Depending on the hierarchy in your business and nature of the relationship, it may be that things will seem confrontational, causing defensiveness.  To avoid this, don’t make general statements but rather be specific to note facts and observations.

If you’re wondering why you struggle to have difficult conversations at work, it may be as simple as a past  misunderstanding causing you to feel uneasy or maybe behaviors over time have led you to believe that things are better left unsaid.  Most often, the latter is not the case.  Poor performance, or lack thereof, can result in issues continuing to be pushed under the rug rather than addressed professionally amongst co-workers.  Read on to learn more about difficult conversations in the workplace.

How do you have difficult conversations professionally?

Because the reason behind the need for a difficult conversation may be emotionally driven, it is even more important to be sure that these conversations are handled with care.  It’s not always easy to leave the emotions out, but by preparing in advance for the conversation, committing to staying focused on the subject at hand, and having a positive end in mind, you will be able to handle a difficult conversation tactfully.  Being professional means being respectful, objective, emotionally intelligent and focused on a solution.

No one should feel personally attacked, unheard or disrespected.  Stick with what you know and those are the facts and how you propose to solve whatever issue is at hand.  Avoid accusations, allow time for response, and be empathetic in your approach so the person feels heard.  If you use statements that convey your feelings such as, “I feel this way…” rather than, “You don’t…” you’ll keep the dialogue non-confrontational and open to finding a solution together.


How to have a difficult conversation with your boss.


No one wants to have a difficult conversation with their boss.  However, addressing issues or concerns professionally may have a greater impact on your career than you might have considered.  Because difficult conversations have the opportunity to bridge the gap in relationships, putting your best foot forward and having this difficult conversation with confidence might move things in your favor.  You may be seen as a leader, someone who wants to see things get done and will also give your boss the chance to see the drive and passion you have for the company and your work.

Here are a few things to keep in mind on how to have difficult conversations with your boss at work:

  • Don’t feel intimidated but be sure to respect hierarchy.  Most of the time, those in positions of authority are there for a reason.  They put the work in to get to where they are and should be respected as such.
  • In cases where there is a lack of respect, treat your boss how you would like to be treated and leave your feelings at the door.  Humbling yourself in situations like this will help you in even more areas than you can imagine.
  • If the issue involves not being able to manage your workload, be sure you stay focused on the facts that you know rather than what you think should happen.  It’s okay to offer a solution and have ideas, but you want to leave room for professional growth so as to not appear to be overwhelmed for personal reasons but the overall workload itself.  Be sure you have solid examples and have kept track of what it’s like to work a day in your shoes..
  • If this involves creating efficiency in the workplace or common practices therein, great!  Most people in higher positions would love to hear about ways to make their team more productive and efficient with their time and resources.  Leave room for collaboration so you don’t feel emotions coming into play if they don’t jump on your ideas right away.
  • Do your homework.  This goes for any of the above.  Know what you’re talking about, have facts and data to back you up, then just be confident in handling this conversation with professionalism.

How to handle difficult conversations with employees.


In a leadership role, it’s inevitable that you will have to have a difficult conversation at some point with an employee.  It’s likely that you’ve learned to better approach these conversations every time they come up, whether they’re performance related, have to do with customer-service or interpersonal conflicts. But how much effort have you put into training your employees on having difficult conversations?

This vital part of educating your staff will not only enhance the interpersonal relationships within your team, but they will also help your employees to better handle conflict with customers and those you serve.  Investing in this training for your staff will increase performance as they feel more equipped to handle difficult situations, it will enhance relationships while employees are more confident addressing concerns and it will open the lines of communication between your team.

Summary of Having Difficult Conversations

In summary, difficult conversations, although challenging, can be a segway to enhancing personal and professional relationships, can help to build your confidence and even alleviate stress in many cases.  They are an excellent way to build trust and resolve conflict, as long as you don’t forget that empathy and preparation are key!  Success is possible if you implement some of these effective strategies we’ve talked about in this blog and always have the end in mind!