December 13, 2022

How to Have Difficult Conversations: Taming the Elephant in the Room

Learn to embrace dialogue and turn disagreements into healthy boundaries with opportunities to grow. Understand these three stages of holding difficult conversations to start turning tension into trust today!

Picture of By Stuart Paap

By Stuart Paap

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How to Have Difficult Conversations: Taming the Elephant in the Room

As a leader, your job is to make sure the team is sailing smoothly with no ripples in the water right? 

Think again.

The best captains know – if you want to reach blue skies you need to sail through a few rough storms.

Successfully holding difficult conversations through dialogue can have huge benefits for you and your team. It can set healthy boundaries and expectations on behavior that can save miles of headaches down the road. 

In the end, difficult conversations are an opportunity to either build trust between you and your team, or to set someone on a better path (even when it means parting ways).

As a bonus – with the holidays coming up, all these tips apply to tricky conversations with family too!

Before we cast sail and get our sea legs, let’s start with acknowledging why we’re landlubbers.

STAGE 01 – Acknowledge the Challenge

Holding difficult conversations is hard, (that’s why they’re called difficult conversations) – many of us think about:

  • Vulnerability – sometimes we’re worried a difficult conversation will expose our own weaknesses. We’re afraid we’ll make mistakes or be seen as weak. Find out why this is the opposite of how you should be thinking about vulnerability.
  • Trauma – we’re likely talking the “little t” type here. You might have had some bad experiences – like rejection or growing up in a hypercritical or dismissive household – that cause you to shy away from conflict.
  •  How hard it is – yes. Difficult conversations are hard. But just like changing a habit – taking on a couple tough choices now could save a marathon of effort later.
  • Hurting others – you might genuinely be worried about hurting someone with your feedback. When it comes to delivering bad news around money or promotions, or even letting someone go, we tend to want to avoid doing it around the holidays, spoiling weekends, and more. The truth is, there is never a good time to deliver this type of news, but it does need to happen. Often getting difficult conversations out earlier is best, but there are situations where waiting might be better.

If the list above is stopping you from holding difficult conversations, the first conversation you need to have is with yourself (discover how to build your confidence in the workplace). 

You might be the one holding your team back, so it’s important to find the inner strength to face hard things.

The fact is setting boundaries around what is acceptable and setting expectations can lead to better performance, less friction between team members and in some cases can light a fire that helps someone let their best parts shine.

STAGE 02 – Prepare to Set Sail

1. Start with a plan

Dialogue isn’t walking into a room and letting the cat out of the bag – it involves talking back and forth. You’re going to lay down some difficult truth, so you need to have a general plan.


  • why are you letting them know this information?
  • what events have led up to this point? 
  • how has their behavior impacted others? 
  • how can you help them improve? 
  • what does “good” look like? 

It’s very important to have a rough plan but not a script – the person you’re talking with won’t follow a script, but if you don’t have a plan your message might not get delivered in the end. 

2. Relax and recharge

Our hectic work and lives can be exhausting, and dialogue can be draining. You want to come into this conversation relaxed, open-minded, and above all else you need to manage your emotions during the conversation. 

Collect yourself by:

  • taking a quick walk around the office or outside
  • practicing a mindfulness technique like deep breathing
  • having a quick coffee break 

3. Dive in

Don’t put it off. 

You’ve thought it through, you’ve put yourself in the right mindset. You’re likely as ready as you’ll ever be – it’s time to have a talk.

STAGE 03 – Head Into the Storm

You’ve set up the meeting and you’re finally in the room. It’s time to navigate through the storm with four guiding principles: 

1. Admit and acknowledge

You might not have all the answers, you might get some of this wrong.

Vulnerability can’t exist without courage. Starting by admitting you aren’t perfect, but you are there to do your best and work through something hard together can build trust.

Acknowledge their side too. They may feel hurt, ashamed, defensive, angry – these are all normal feelings. Putting yourself in their shoes will help you deliver the message and reach a constructive outcome together by finding overlaps in your viewpoints. They will likely have some critical feedback for you – be open minded, accept and reflect on that feedback.

2. Be direct

When it comes to setting boundaries and expectations it is critical to be as direct as possible.

For example, “you’re often late – you start at 9AM and I need you to be on time from now on” is much clearer than “we really need to put a full day in” (does that mean I get flex time now?). You want to build understanding and commitment, not ambiguity.

3. Listen and learn

Good leaders know that the most important part of any conversation is listening.

When you truly listen you can better understand the issues: 

  • what brought the person to this point? 
  • why do they behave how they do? 
  • what message are they hearing – is it the one you are delivering? 
  • what do they need to be successful?

When someone feels truly heard, they will be able to focus on the issue as the problem and not see you as the problem. 

No matter how many difficult conversations you have, there is always something new and unique that you didn’t expect to hear or see happen. Take the whole experience away afterwards and reflect on why the other person behaved how they did, why they felt how they did, what went well and what could have gone better. 

4. Follow up and follow through

When it comes to amplifying the impact of your difficult conversations you want to harness the power of commitment. We are looking for feedforward (turning conversations into lasting change) not just feedback. This means setting out a plan for both parties and committing to doing certain actions. Following through on this demonstrates you are committed to helping them make a change and grow. This is how we turn a difficult conversation into a golden opportunity and solidify trust. 

Following up and following through could mean committing to additional one-on-one coaching and feedback, it could mean providing a new connection for someone you’ve had to let go, or it can mean recognizing and praising positive change. There are endless ways we can commit to making lasting positive change for our teams.

Start Practicing

Difficult conversations are never easy, but they are necessary. With a bit of practice, you can become more comfortable and able to focus on the benefits of dialogue for both sides of the table. 

If you need a starting point, try picking a small issue or healthy boundary that you need to set with someone (this can be family or friends) and follow the steps above. You might be surprised at the positive change you can make today.

Interested in learning more about how to speak up and solve difficult problems?

Contact me here, or send me a DM on LinkedIn.

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