Tough conversations are essential to building a healthy and supportive workplace. They help identify and address problems early, promote transparency and communication, and foster a culture of accountability. By taking the time to have tough conversations, organizations can create a more productive and efficient work environment that is beneficial for everyone involved.

Difficult discussions are necessary to improve our relationships and foster understanding. They can be hard, but they are also essential for progress. There are many reasons why you should actively pursue tough conversations:

  • Identify and address issues early on.
  • Build stronger relationships.
  • Learn more about ourselves and others.
  • Find quicker solutions to difficult problems.

Do you have a conversation coming up that you’re dreading? Here are a few tips to get a more successful outcome.


Don’t be afraid to speak up: The benefits of sharing your thoughts and opinions.

In our fast-paced, constantly-connected world, we’re often taught to avoid difficult conversations and challenging issues. We’re warned that speaking our mind might lead to hurt feelings, damaged relationships or making the situation worse.

When we bottle up our thoughts and opinions, we’re not just doing ourselves a disservice, we’re also preventing others from benefitting from our insights. Difficult conversations are an opportunity to share what’s on our mind, and by doing so, we can often help resolve conflicts or misunderstandings.This can lead to more positive outcomes for all involved.

We need to remember that everyone has a different communication style, and not every challenging conversation is going to go well. There’s a chance that we might say something that hurts someone’s feelings or leads to an argument. But that’s okay.

It’s never easy to face up to the fact that we’ve hurt someone’s feelings, but it’s important to do so immediately. The longer we wait, the more awkward and tense the situation becomes. If we stay humble and take ownership of our mistake, we can learn from it and get a deeper understanding of the other person’s feelings. Hopefully we can avoid hurting that person again in the future.


Listen and learn: How to effectively listen to others and take something away from the conversation.

When you’re in a conversation, are you really listening to the other person, or are you just waiting for your turn to talk? If you’re not actively listening, you’re not getting the most out of the conversation – and the other person isn’t getting the most out of speaking with you.

Active listening involves staying open to new ideas, acting like a friendly investigator, and reflecting back what you’ve heard. When you do this, the other person feels heard and appreciated, and is more likely to listen to what you have to say.

Here are a few tips for active listening:

  • Make eye contact and pay attention to body language.
  • Be patient and wait for the other person to finish talking. Do not interrupt.
  • As you listen, seek to understand. Don’t worry about what you’ll say next. (It will come to you!)
  • Paraphrase what you’ve heard to make sure you understand correctly and do not assume that what you heard is what the messenger intended for you to hear.
  • Ask questions to clarify if something is confusing or vague.


Avoid triggers and distractions: How to stay engaged in conversations.

When you’re in the middle of a tough conversation and you’re addressing sensitive topics like behavioral issues or employee performance, it can be easy to off track.

You’re sure to have an awkward moment… or two! You may start planning what you’re going to say next, or you may become preoccupied with the other person’s reactions. Be conscientious of your “self-talk” when you’re in the middle of a conversation. If you start to tell yourself things aren’t going well or the situation his hopeless, you’re sunk! You should prepare, but don’t plan the outcome of the conversation in advance. You’ll rarely be right, and it’s often wasted energy.

Something else to consider ahead of time are your triggers. What might the other person do or say that could make you lose your emotional control?

I know I interpret the “eye roll, crossed arms, leaning back in the chair” reaction as a complete lack of respect. When I know I have to have a conversation with someone who does this from time to time, I prepare for it! Expecting the reaction helps it to have less of an effect on me.

What is it for you? Maybe they shout instead of talking calmly. Maybe they shut down and stop listening. Or maybe they start playing the “blame game” or try to make you feel guilty.

If you know what your triggers are, you will likely react less strongly to them. Should things get heated, take a break before things get out of control.

Remember to breathe and remind yourself that it’s getting upset over something small is generally not worth it! Remember that it’s okay to disagree with the other person – just make sure that you do so respectfully. Strive to find common ground.

You may consider setting some ground rules if you and the other person have had negative interactions in the past. Ground rules can lead to more successful conversations. (Here a list to get you started!)

In addtion to triggers, be sure to avoid everyday distractions too! Stay present and focus on the task at hand.

Put away your phone and turn and face the other person, not your computer! Avoid looking over the person’s shoulder at what might be going on in the background, and avoid looking at your watch. All of these actions make you appear unengaged and ready to end the conversation, even if you don’t really feel this way.

Redirect yourself when you find yourself mentally drifting off. (We all do it!) If you miss something, don’t be scared to ask the other person to repeat what they said.


Be open minded: Considering other people’s viewpoints can lead to more meaningful conversations.

Considering other people’s viewpoints can lead to more meaningful conversations. You may learn something new or see the situation from a different perspective.

Something I’m hearing a lot lately, and that I agree with, is the “stay curious” philosophy.

I remember the first time I heard someone say something that made me feel uncomfortable. I had just started my first job out of college and was sitting in a meeting with my new team. One of my teammates said something that came across to me as racist.

I was raised in a household where we were taught to accept everyone, so I was taken aback by her comment. I didn’t know how to respond, so I just sat there and silently judged her.

I later found out that I misconstrued her comment, but even so, it took me a long time to give her a second chance.

That experience taught me a valuable lesson: don’t judge others without trying to understand their perspective or getting the full story. We were all raised differently, and those experiences had a huge influence on how we “show up” as adults.

It’s easy to shut down if we hear something we disagree with, but we should seek to understand why people believe what they believe. Only then can we have meaningful conversations and build bridges between people with different viewpoints.

Curious communication is healthy communication. Assume less. Ask more questions. Find out the why. Staying curious is one of the best ways to create a more tolerant world.


In conclusion, finding the courage to have the conversation that matter is definitely a risk, but the benefits are well worth it.

What if we didn’t avoid these conversations? What if we learned to see them as opportunities for growth – both for ourselves and for the people around us?

By taking this risk and addressing challenges or conflict head-on, you can improve your relationships, resolve problems more quickly, and even learn new things about yourself. Don’t be afraid to approach tough conversations – just make sure you’re prepared for them. (More on that in a future post!)

By the way, I did a TEDx Talk on this very subject! You can view it here.

Does your team need to learn how to have more constructive conversations? Reach out and let’s schedule a discovery call!