Common Workplace Conversations You're Avoiding (And What to Say)

There's a conversation you need to have at work.

You know what it is. You've thought about having it a hundred times.

But you don't know what to say.

So you avoid it.

What if I gave you the exact words? Not scripts you have to memorise. Just frameworks for what to actually say when the conversation matters.

Let me walk you through the workplace conversations people avoid most—and exactly how to have them.

The Conversation Framework That Works for All of Them

Before we get into specific conversations, here's the framework that works for almost every difficult workplace conversation:

1. State your intention clearly ("I want to talk about X")

2. Be specific about the situation (not vague, not emotional)

3. Explain your perspective (why this matters to you)

4. Ask for their perspective (what are they thinking?)

5. Move toward a solution (what do we do about this?)

Keep it simple. Keep it professional. Keep it human.

Now let's get into the specific conversations.

Conversation 1: Asking for a Raise

Why you're avoiding it: You're scared they'll say no. You think you don't deserve it. You worry they'll think you're ungrateful.

What to actually say:

Step 1: Request the conversation

"I'd like to talk about my compensation. Do you have time for a conversation this week?"

Don't do it impulsively. Give them a heads up so they're ready.

Step 2: Make your case (without being aggressive)

"I've been in this role for [timeframe]. During that time, I've [specific achievements]. I've taken on [additional responsibilities]. Based on market rates for this role and my performance, I'd like to discuss adjusting my salary to [number or range]."

Be specific. Use data. Use market rates. Don't ask for more money because you need it—ask because you've earned it.

Step 3: Listen

"What are your thoughts on that?"

Let them respond. They might say yes. They might say no. They might say they need to check with finance.

Step 4: Move toward a solution (if they say no)

"I understand. What would need to happen for us to revisit this in [3-6 months]?"

Get clarity on what would make them say yes. Then actually do that thing.

Real example of what to say:

"I appreciate the opportunity to work here. I've really enjoyed the past two years and learned a lot. I think my contributions have been strong—I delivered the X project ahead of schedule, built the Y process that's now saving us time, and took on mentoring responsibilities. Based on market rates for someone with my experience and achievements, I'd like to discuss increasing my salary to £[X]. What are your thoughts?"

That's it. Clear. Professional. Based on performance, not need.

Conversation 2: Telling Your Manager You're Thinking About Leaving

Why you're avoiding it: You're scared they'll fire you immediately. You think they'll make your life hell. You worry they'll tell everyone.

What to actually say:

Step 1: Request a private conversation

"Can we grab a coffee/call? There's something I want to discuss."

Don't ambush them. Don't do it in public. Give them a heads up.

Step 2: Be direct

"I've been thinking about my career trajectory, and I've decided I'm going to start exploring other opportunities. I wanted to tell you directly rather than you hear it from someone else."

You're not quitting today. You're telling them you're exploring. That's honest and professional.

Step 3: Reassure them

"I'm not leaving tomorrow. I want to give appropriate notice and make sure we transition things smoothly."

They need to know you're not about to disappear.

Step 4: Ask what they need

"What would be most helpful for you in terms of timeline and transition?"

This shows you're thinking about their needs too, not just yours.

Real example of what to say:

"I really appreciate what I've learned here. I've realised my priorities have shifted and I'm looking to explore a new direction. I wanted to tell you first so you hear it from me. I'm planning to stay for [timeline] to make sure we transition things properly. Is that workable for you?"

That's it. Respectful. Honest. Professional.

Conversation 3: Asking for Flexible Working or Specific Accommodations

Why you're avoiding it: You think they'll say no. You worry they'll judge you. You're scared it will hurt your career.

What to actually say:

Step 1: Frame it around business benefit (if possible)

"I've been thinking about how I work best and how I can be most productive. I'd like to discuss the possibility of [working from home two days a week / flexible hours / compressed week]."

Start with the benefit to them, not the benefit to you.

Step 2: Explain why it would work

"I find I'm most focused when I have deep work time. I'd still be available for meetings and collaboration, just in a different format."

Be specific about how you'll stay connected and productive.

Step 3: Offer a trial period

"Could we try this for a month and review how it's working?"

This makes it feel lower risk to them.

Real example of what to say:

"I've been thinking about my working style and I believe I could be even more productive with [specific accommodation]. I'd be available for all meetings, just in a different format. Could we try this for a month and see how it works?"

Conversation 4: Giving Your Manager Feedback (When They're the Problem)

Why you're avoiding it: They're your boss. They have power over you. You're scared of retaliation.

What to actually say:

Step 1: Request feedback conversation (be careful with framing)

"I'd like to get your input on something. Do you have time?"

Don't accuse. Ask for their perspective.

Step 2: Describe the situation specifically (not emotionally)

"I've noticed that in recent meetings, decisions are made without consulting the team. From my perspective, that makes it harder for me to feel invested in the outcome."

You're describing impact, not attacking character.

Step 3: Ask their perspective

"I'm curious what your thinking is on that?"

They might have a good reason you hadn't considered.

Step 4: Suggest a solution

"Would it be possible to get input from the team before finalising decisions on X?"

Make it about process, not personality.

Real example of what to say:

"I wanted to share some feedback because I think we could work better together. I've noticed decisions are sometimes made without input from the team. I work best when I have a chance to contribute. Could we explore ways to make that happen?"

Conversation 5: Asking Someone to Mentor You

Why you're avoiding it: They're senior. They're busy. You think you're bothering them.

What to actually say:

Step 1: Be direct about what you're asking

"I really admire your work and your perspective. I'd like to ask if you'd be open to an informal mentoring relationship."

Be specific about what you're asking for. Don't be vague.

Step 2: Make it easy for them

"I understand you're busy. I'm flexible on timing. I was thinking maybe once a month for a casual conversation."

Show that you've thought about their constraints.

Step 3: Be clear about what you want from them

"I'm navigating a career transition and would value your perspective and guidance."

Tell them what you're working on so they know if they can help.

Real example of what to say:

"I've followed your career with interest and I think your perspective would be really valuable for me. I'm working on a transition into [field] and would love your input if you're open to it. I'm flexible on timing—maybe once a month for coffee?"

Most people are flattered to be asked. Most will say yes.

Conversation 6: Having a Boundary Conversation (With Your Manager or Colleague)

Why you're avoiding it: You don't want to seem difficult. You worry it will affect how they see you.

What to actually say:

Step 1: Be specific about the situation

"I've noticed that [specific behaviour]. I want to address it because it's affecting my work."

Don't generalise. Don't accumulate complaints. Address the specific thing.

Step 2: Explain the impact (not the blame)

"When [behaviour happens], it makes it harder for me to [do my job / focus / feel valued]."

You're describing impact, not attacking intention.

Step 3: State what you need going forward

"Going forward, I'd like us to [specific ask]. Is that possible?"

Be clear about what needs to change.

Real example of what to say:

"I wanted to talk about something. When meetings are scheduled at the last minute without checking my calendar, it makes it hard for me to prepare properly. Could we agree that meetings get scheduled with at least a day's notice? That would help me do my best work."

Conversation 7: Asking for Honest Feedback on How You Come Across

Why you're avoiding it: You're scared of what you'll hear. You think you know you're doing something wrong.

What to actually say:

Step 1: Make it clear you genuinely want feedback

"I'm working on developing as a professional and I'd really value your honest feedback."

Tell them you want real feedback, not nice feedback.

Step 2: Ask specific questions

"In meetings, do you think I come across as confident? Is there anything I do that undermines my message?"

Ask specific things rather than vague "what do you think of me?"

Step 3: Promise you won't get defensive

"I want to hear your honest perspective and I promise I won't get defensive."

Then actually don't get defensive. Listen. Say thank you.

Real example of what to say:

"I'm working on my presence in meetings. I'd love your honest feedback. Do you think I'm adding value in those spaces? Is there anything I could do differently?"

Conversation 8: Telling Someone You Admire That You Admire Their Work

Why you're avoiding it: It feels vulnerable. You're scared they'll think it's weird.

What to actually say:

Step 1: Be genuine and specific

"I've been following your work and I think [specific thing] is really smart. The way you [specific example] impressed me."

Don't just say "I like your work." Say specifically what you admire.

Step 2: Keep it simple

"I wanted to tell you that because I think people don't always know the impact they're having."

That's it. You don't need to ask for anything. You're just acknowledging them.

Real example of what to say:

"I've been impressed by how you've built that team and the culture there. The way you handle difficult conversations with such directness but kindness is something I aspire to. I wanted to tell you because I think that kind of leadership often goes unrecognised."

Most people will be genuinely moved by this.

The Conversations That Change Careers

Here's what I've noticed: the conversations that change careers are usually the ones people avoid most.

Not the big dramatic conversations. The small, honest ones.

Asking for a raise. Admitting you're struggling. Requesting help. Setting a boundary.

These conversations feel risky. So people avoid them.

But avoiding them is riskier.

Because not having the conversation means:

• You stay underpaid

• You burn out quietly

• You never get the support you need

• You never build real relationships

• You never move forward

The conversation is the thing that moves you forward.

What Happens After the Conversation

One thing to know: the conversation itself isn't usually the hard part.

The hard part is the anticipation. The imagining. The catastrophising.

Once you actually have the conversation, it's usually fine. Sometimes better than fine.

And even if it doesn't go perfectly, you've done the brave thing.

You've moved from passive to active. From stuck to moving.

That's what matters.

Common Mistakes to Avoid

Mistake 1: Having the conversation when you're emotional

Wait 24 hours if you're angry or upset. Have it when you're calm and clear.

Mistake 2: Ambushing people

Give them a heads up so they can be present and thoughtful.

Mistake 3: Being vague

Be specific about what you want to discuss and what you need.

Mistake 4: Making it personal

Keep it about behaviour and impact, not personality and character.

Mistake 5: Not listening

Ask for their perspective and actually listen. Don't just wait for your turn to talk.

Mistake 6: Being too apologetic

You're allowed to ask for things. You're allowed to have needs. You don't need to apologise for that.

How to Prepare for Any Difficult Workplace Conversation

Step 1: Get clear on what you want

Before you have the conversation, know what you want from it. A yes? Information? Changed behaviour?

Step 2: Anticipate their perspective

What might they say? How might they react? What are they worried about?

Step 3: Think about what matters to them

Frame your ask in a way that acknowledges their perspective or benefits.

Step 4: Write down key points (but don't read from paper)

Know what you want to say but say it conversationally.

Step 5: Practice out loud

Say it to yourself or a trusted friend. Hear how it sounds.

Step 6: Calm your nervous system before you go in

Take some deep breaths. Remember: you're just having a conversation with another human.

The Conversation Framework for Any Situation

If none of these specific conversations match yours, here's the universal framework:

1. "I want to talk about [topic] because [reason it matters to you]"

2. "Here's the situation as I see it: [specific, not emotional]"

3. "Here's how it affects me: [impact, not blame]"

4. "Here's what I need: [specific ask]"

5. "What are your thoughts?" [Then listen]

6. "How do we move forward?" [Then collaborate]

Simple. Professional. Human.

Frequently Asked Questions About Workplace Conversations

What if they react badly?

Some people will react badly. That's on them, not you.

You can say: "I understand this might be surprising. Let's take some time and circle back to this."

Then you know where you stand. And you can decide what to do next.

Should I have these conversations over email?

No. Email is for confirming things you've already discussed.

Difficult conversations need to happen in person (or on the phone if in-person isn't possible).

Email removes nuance. It removes the ability to clarify. It often makes things worse.

What if I get emotional during the conversation?

It's okay to get emotional. You're human.

If you feel tears coming, you can say: "I'm sorry, give me a moment." Take a breath. Continue.

Showing emotion isn't weakness. It shows you care.

Should I bring someone with me?

No. Not in most cases.

You're an adult. You can have a conversation with another adult.

Bringing someone makes it adversarial. You want it to be collaborative.

What if the conversation doesn't go how I hoped?

Then you've learned something.

You know where they stand. You can decide if you need to escalate, accept their answer, or move on.

But at least you're not wondering anymore.

The Courage It Takes

Having these conversations takes courage.

It takes courage to ask for what you want. To set boundaries. To be honest. To be vulnerable.

But here's the thing: you have that courage.

You just haven't used it yet.

And the only way to build courage is to do the thing that scares you.

So pick one conversation from this list. The one that scares you most.

And have it this week.

You'll survive. You'll probably be proud of yourself.

And your career will shift, in some small way, because you were brave.

Your Next Steps

This week:

Pick one conversation from this list. The one you've been avoiding.

Write down what you want to say using the framework.

Say it out loud to yourself.

This week (before Friday):

Have the conversation.

It will be scarier in your head than in real life.

Final Thought

The conversation you're avoiding is the one that's going to change something.

Not the easy conversation. The hard one.

Have it.