How to Prepare for a Difficult Conversation: 5 Steps
No one wakes up thinking, "Yes! I get to have an awkward conversation today!" But the truth is that those stomach-churning discussions you're avoiding aren't going anywhere. And the longer you wait, the bigger that knot in your stomach gets.
In this guide, I'm breaking down how to prepare for a difficult conversation - whether you're calling out a colleague's toxic behavior or asking for the raise you deserve.
Difficult conversations are your ticket to growth. Time to stop dancing around the issue and tackle it head-on like the boss you are.
Why It's Important to Have Difficult Conversations at Work
Research shows that 70% of employees avoid difficult conversations at work and 53% of employees handle "toxic" situations by ignoring them.
Here's the hard truth: Your career is built on how well you handle uncomfortable moments.
Sure, you could keep swallowing your opinions and nodding along. But that path leads straight to resentment, missed opportunities, and a reputation as someone who can't stand their ground.
The most successful people aren't the ones who avoid conflict – they're the ones who know how to navigate it like pros.
It's easier to hide your head in the sand than problem-solve, which is why it's so important to shift your mindset and recognize that conflict resolution is a flex, not something to be avoided at all costs.
Types of Difficult Conversations at Work
Difficult conversations come in all shapes and sizes. Here are the heavy hitters:
Performance issues: Both giving and receiving feedback
Salary negotiations: Yes, talking about money is still taboo, and yes, that's ridiculous
Interpersonal conflicts: Because Karen from accounting isn't going to confront herself
Leadership disagreements: When your boss is wrong, and you need to say it
Personal boundaries: Because work-life balance isn't just a buzzword
It's possible to have a happy ending with all of these types of difficult conversations at work. It's overwhelming at first, but when you stay focused on the right intentions, you can resolve a conflict with pretty much any person.
Unless you're negotiating with a narcissist - those people are…special.
How to Have Difficult Conversations: 5 Steps to Prepare
These steps are your game plan. They won't make the conversation easy (nothing will), but they'll make it manageable.
1. Get Crystal Clear on Your Goal
Before you charge into that meeting room, answer this: What exactly do you want to achieve?
Not "I want to tell them they're wrong" or "I want to vent." What's your actual objective? Write it down. Make it specific. Make it actionable.
2. Gather Your Evidence
Your feelings are valid, but in a professional setting, you need more than emotions. Start difficult conversations armed with:
Concrete examples
Relevant emails
Documentation
Timeline of events
Impact on work/team/results
You might need more than this if you're dealing with a mean girl.
3. Practice the Conversation
Don't just rehearse in your head while shampooing your hair. Actually practice:
Record yourself on your phone: yes, you'll hate how you sound - do it anyway
Role-play with a friend: pick someone who'll give you honest feedback
Write out your key points: and back-pocket responses for pushback
Prepare for different reactions: including the worst-case scenario
The key is to practice out loud, not just in your head.
Your brain might be convincing you that you're ready, but your mouth might have different plans. Practice your tone, your pace, and your pauses. When used right, those moments of silence are your secret weapon.
You should also watch your body language (recording yourself on video can be useful to get a sense). Are you fidgeting? Crossing your arms? Not maintaining eye contact?
Non-verbal cues speak volumes about your confidence.
As a conflict strategist, I help my clients set themselves up for ongoing wins with 1:1 coaching and mediation.
4. Choose the Right Timing and Location
Timing is everything when it comes to difficult conversations and problem-solving. Follow these strategies:
Book a proper meeting, no "got a minute" ambushes
Pick a private space
Allow enough time because rushing through this helps no one
Consider the other person's schedule and mindset
Think about the energy levels too. On Monday mornings, people are usually drowning in emails. On Friday afternoons they're checked out. Mid-week and mid-morning tend to be your sweet spots.
If you're remote, make sure it's a video call with a good connection. Nothing kills momentum like "Can you hear me now?" technical difficulties or Zoom updates.
5. Craft Your Opening Statement
Your opening to the discussion is extremely important. It should:
State the purpose clearly
Show good intent
Invite dialogue
Set a collaborative tone
Here's your formula: "I wanted to discuss [issue] because [impact]. My goal is to [positive outcome]. I'd like to hear your perspective on this."
Write it down. Memorize it. This is your anchor when your mind goes blank, your heart starts racing, and you suddenly feel like you can't talk to save your life.
How to Mentally Prepare for a Difficult Conversation
Having a difficult conversation isn't comfortable. If your brain is screaming "Danger," that's normal. Here's how to deal with it.
You might be surprised to learn that most people actually want to be considerate and agreeable during a difficult conversation.
According to a recent study:
The vast majority of people (81%) admit there's more than one way to see a situation. Only a tiny fraction (6%) stubbornly stick to their guns.
Two out of three people actively work to make the other person feel at ease during difficult conversations.
A solid 78% prefer to get straight to the point.
65% of people are ready to admit they helped create the problem. Only 10% play the blame game and refuse to acknowledge their role.
Of course, some people do unpleasant things like trying to gaslight you. Ew.
But the majority of people want the difficult conversation to work out and are willing to be self-aware and empathetic.
Shifting your mindset and seeing a difficult conversation as an opportunity can help you feel better about it mentally.
Difficult Conversations at Work Examples
Here are some scripts to get you started in just a few minutes.
Addressing Poor Performance: "I wanted to discuss some concerns about recent projects. I've noticed [specific examples], and I want to understand what's happening and how we can work together to get back on track."
Requesting a Raise: "I'd like to discuss my compensation. Over the past [timeframe], I've [specific achievements], which have contributed [specific value] to the company. I believe it's time to adjust my salary to reflect these contributions."
Setting Boundaries: "I appreciate the trust you place in me with high-priority projects. However, the current workload is affecting my ability to maintain quality. Can we discuss how to prioritize these assignments more effectively?"
Stay calm, cool, and collected. Getting angry or showing you're upset doesn't help anyone.
FAQs
What Is Considered a Difficult Conversation?
Any conversation that makes you want to run and hide in the supply closet probably qualifies. More specifically: it's a discussion where stakes are high, opinions vary, and emotions run strong. If you're losing sleep over it, it's a difficult conversation. Think performance reviews, conflict resolution, or any conversation where you need to challenge the status quo or address behavior that's impacting your career.
How Do You Calm Your Nerves Before a Difficult Conversation?
Stop trying to calm down (it doesn't work). Instead, reframe that energy as excitement. Those butterflies in your stomach are your body preparing for peak performance. Channel that energy into focused preparation.
How Do You Psych Yourself Up for a Difficult Conversation?
Discomfort is the price of growth. Write down three times you handled a tough situation well. Remind yourself that you've done hard things before, and you can do them again. Better yet, keep a "wins" folder in your email with positive feedback and accomplishments - you can review it before tough conversations to boost your confidence.
What Is the Best Opening for a Difficult Conversation?
Start with intention and clarity. "I wanted to discuss [issue] because [reason]. My goal is to [objective]." No beating around the bush, no passive-aggressive hints. Just straight-up honesty with a side of respect. Remember to pause after your opening. Don't rush to fill the silence with nervous chatter.
What Not to Say in a Difficult Conversation?
Avoid absolutes like "you always" or "you never." Drop the accusations. Skip the "no offense, but..." (everything after "but" is offensive). Don't start with "we need to talk." Also, avoid minimizing language like "just" or "only" - if it matters enough to have the conversation, treat it with appropriate weight.
How Do You Control Your Emotions During a Difficult Conversation?
You don't. You acknowledge them. Big difference. Practice the HALT check before any tough conversation: Are you Hungry, Angry, Lonely, or Tired? If yes to any, reschedule. You need to be at your best. If emotions come up during the conversation, it's okay to say, "I need a moment to gather my thoughts" and take a brief pause.
How Do You Structure a Difficult Conversation?
All conversations are different, but typically you should 1) state the issue, 2) explore perspectives and solutions, and 3) agree on the next steps. Keep it focused on the future and solutions, not just rehashing past problems. End with clear action items and a timeline for follow-up. Don't leave things hanging in the air.
Get Support to Start Facing Difficult Conversations Head On
Difficult conversations never get easier - you just get better at having them. Each one you tackle makes you stronger, more respected, and more influential in your career.
If you're looking for support, learn more about 1:1 coaching with me (I do mediation, too!) and The Step Up Membership.
