How to Have Difficult (Yet Compassionate) Conversations

How to Have Difficult (Yet Compassionate) Conversations
17 Jul 2023

A difficult conversation is one of the hardest experiences you will ever face. 

On both sides, people tend to be apprehensive - often fearing being disliked, rejected, or causing further harm to a struggling relationship.

Before forging ahead and hurting someone’s feelings, you need a plan that allows you to…

  • Manage Emotions
  • Mitigate Damage
  • Sustain Relationships
  • Encourage Forgiveness
  • Move Forward

It’s not enough to go into a meeting simply knowing what needs to be said… you also need to know how to say it. There are 8 billion people in the world with their own unique perspective and everyone will respond differently.

Your priority should be to focus on controlling the situation, trusting in your case and, most importantly, maintaining respect for all individuals involved. 

The 6 Ps to Handling Tough Conversations with Compassion

Whether you’re addressing an employee’s performance or denying a budget request, difficult conversations come in all forms. 

The way you handle each one will dictate the quality of the relationships you have with your stakeholders so you enter them with the right mindset. When you do so, you can foster learning and growth.

Acting too distant will build the (false) impression that you don’t care. Acting too regretfully will allow you to be taken advantage of. You need to find the balance, being compassionate without being influenceable.

Step 1. Prepare

The key to handling any difficult conversation with compassion is ensuring that you take the time to prepare properly.

During a brainstorming session, you’ll be able to identify the best way to communicate with the other party and deliver any bad news. Typically, you need to be prepared to encounter 4 typical stress responses which appear when people’s brains process a ‘threat’:

  • Fight: Facing any perceived threat aggressively.
  • Flight: Running away from danger.
  • Freeze: Unable to move or act against a threat.
  • Fawn: Immediately acting to try to please to avoid any conflict

To best prepare for these responses, you’ll need to choose…

  1. The channel you want to meet through.
  2. The tone of voice you want to use.
  3. An appropriate way to deliver your message.
  4. The people you want to be present.
  5. When the meeting should take place.

This preparation will ensure that you don’t let your emotions get the better of you and that you can remain sensitive and mindful throughout. This issue isn’t going to disappear, so you need to have this conversation and not shy away from the consequences. 

Step 2. Precondition

When a difficult conversation needs to be had, don’t wait until the last minute to notify the other person. This would be cruel and unfair - blindsiding them and damaging the relationship you’ve worked so hard to build. 

Give them as much notice as possible for the upcoming meeting and be really clear about your purpose. Where possible, ask for their permission to meet with you and let them set the time and date.

“Hi, Emily. We need to have a talk about your recent absences. Can you meet with me in the office sometime tomorrow afternoon? You’re not in any trouble, but there are some challenges we need to address. It would be best to do this in person.”

Step 3. Practice

Before entering any difficult conversation, be sure to practice, practice, practice!

Imagine different scenarios where the other person reacts to what you’ve said and plan your response accordingly. Are they angry, avoidant and blameful? Or rational, accepting, and open?

Where appropriate, ask someone you trust to sit with you and pretend to be the person on the other side of the discussion. Your roleplay might look a little something like this…

You: I’ve reviewed the budget for the remainder of this year and am not able to increase your salary by 15% as requested. However, I’m willing to revisit this in January.

Michael:  That won’t work for me. I need the pay increase by next month. My rent is going up and moving is not an affordable option for me right now.

You: I’m sorry to hear that. Are you aware that we cover relocation costs for our employees? We can aid you in moving closer to the office.

Michael: Really? That would be so helpful! Please may I have more information so I can talk to my partner about our options?

Step 4. Present

When receiving difficult news, people may exhibit a range of defence tactics, including: 

  • Avoidance.
  • Blaming another person.
  • Compartmentalising the news.
  • Denying challenges.
  • Making humour from the situation.
  • Rationalising the conversation.

Whichever response you anticipate, your preparation should allow you to present your case in a calm, clear, and concise manner. 

Don’t rush through the discussion and dedicate yourself to listening to what the other party has to say - explaining anything they are confused about and acknowledging their emotions throughout.

“I understand that this may come as a shock to you.”

Step 5. Provide

When an issue has to be communicated, always look for an alternative. What’s the next best option?

While you might not be able to offer a solution altogether (otherwise the difficult conversation wouldn’t have to take place), this doesn’t mean that you can’t mitigate the damage done. 

Identifying suitable replacements before delivering bad news will demonstrate a level of compassion that wouldn’t be there otherwise.

“Because of ongoing supply issues, we can’t meet our usual commitment of 5,000 units this month. However, we can produce 3,000 units using the materials we already have and will start speaking to another supplier about filling the gap.”

Step 6. Pursue

Regardless of how the difficult conversation goes, you can express empathy and demonstrate compassion simply by following up. 

Checking in with the affected party will go a long way to fix a potentially damaged relationship and allow you to rebuild trust and respect - both of which are crucially important to a business.

Throughout the process of having and conducting difficult conversations, you should always show empathy and respect for the other person, acknowledge their emotions, and agree on a way forward together. 

About Four Recruitment

At Four Recruitment, we don't just match CVs with job descriptions; we're here to build genuine, authentic connections between talented candidates and top employers.

We go the extra mile to uncover the best candidates, even if they seem elusive or hard to find. If we can't find them, they don't exist. That's how dedicated we are to sourcing the best talent for our clients.


Contact us to find out more.




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