How To Have Hard Conversations At Work

Most people think the hardest part of leadership is making big strategic decisions. In reality, it's the conversations you'd rather avoid.

For me, it showed up in subtle ways at first.

Instead of pushing back on unrealistic deadlines, I thought proving I could do everything made me look stronger.

Instead of giving tough feedback, I just did the work for my team - which meant they lost the chance to grow.

And every time I told myself, "It's easier this way."

Spoiler: it wasn't easier. It just meant I was exhausted, my team wasn't growing, and people saw me as someone who could get things done - not as someone ready to lead.

The first time I truly leaned into a hard conversation was when I had to let someone go. I couldn't delegate it. I couldn't water it down. I had to sit across from a human being and deliver a hard truth with clarity and compassion.

And one of the hardest - but most pivotal - conversations of my career was negotiating my VP title. I'd made it all the way through the interview process, got the offer, and then… the title wasn't VP. The board didn't feel comfortable because I hadn't been a VP before.

Most people would have accepted it. I didn't. I pushed back. I said, "I understand you can't give me the title right now, but let's put together a plan so that if I hit all my KPIs within six months, we'll revisit this." They agreed. I delivered. And that's how I earned the VP title.

Had I not had that conversation, it never would have happened.

That's when I realized something: leaders don't avoid hard conversations. They professionalize them. And that ability has changed the trajectory of my career.

Why Hard Conversations Matter

Hard conversations aren't conflict. They're opportunities.

Opportunities to create clarity where there's confusion.

Opportunities to build trust where there's tension.

Opportunities to show authority where others hesitate.

Executives don't get promoted because they're good at avoiding tension. They get promoted because they can hold it and work through it.

Here's the mindset I wish someone had given me sooner: discomfort is data. If it feels hard, it probably matters.

So while you might feel like running away to avoid those feelings, what you need to do is get comfortable with being uncomfortable.

Instead of avoiding hard conversations, learn to show up and navigate them like a pro.

Here’s how.

Step One: Choose Your Battles Like an Executive

One of the biggest mistakes I made as a new manager was trying to tackle every issue. Every missed deadline, every disagreement, every awkward comment in a meeting - I thought it was my job to call it out.

But if everything is urgent, nothing is.

Executives don't jump into every battle. They weigh the cost of speaking up against the cost of staying quiet. They ask themselves:

• Impact: Will this materially affect the business, or is it just about my personal preference?

• Pattern vs. One-Off: Is this a recurring issue that signals risk, or a one-time slip I can let go?

• Timing: Is now the right moment, or will waiting give me more clarity and leverage?

• Risk/Reward: What's the upside of speaking up versus the downside if I don't?

This doesn't mean ignoring problems. It means conserving influence so when you do raise your voice, people pay attention.

Step Two: The Executive Playbook for Hard Conversations

Once you decide the conversation is worth having, the question becomes: how do you handle it without damaging relationships or credibility?

Here's the playbook for having hard conversations:

1. Prepare with Purpose

Get clear on what you want to achieve - clarity, alignment, or action. Separate facts from feelings. Anticipate how the other person might see it, so you're ready to meet resistance with perspective.

Pro tip: Write it down. You may lose focus or get distracted when the conversation heats up, so use a bullet point list to stay the course.

2. Deliver with Authority + Empathy

Go straight to the point. Executives often use BLUF (Bottom Line Up Front): state the issue clearly, then add context. Don't sugarcoat, don't steamroll. Use language like: "Here's what I see, here's what we need, here's how we move forward."

Pro tip: Ask yourself in advance, “How will this make them feel?” or “What would they object to?” and take that into account when you speak.

When I had constructive feedback for a team member, I knew it would be painful for them to hear. I knew they might also be upset or angry. Instead of ignoring their feelings, I validated what they were going through, but I didn’t stop or baby them with “it’s alright”. I gave them some space to process and then continued.

3. The 24-Hour Rule

Don't rush in while emotions are high. Wait just long enough to settle, but not so long it turns into resentment. A 24-hour pause gives you space to think strategically, not impulsively.

Pro tip: This is how you avoid angry emails you will end up regretting.

4. Name the Discomfort Up Front

I stole this one from Brené Brown: vulnerability diffuses tension. The people sitting across from you may be bracing for impact, so be open about what is about to happen.

Acknowledging it: "This is a tough conversation, and it might feel uncomfortable. My goal is to be direct and respectful so we can solve it together."

It may sound obvious but it helps set expectations.

5. The "Third Point" Approach

This one if from Harvard’s Difficult Conversations Project.

Shift the focus from you vs. them to you and them vs. the problem. Instead of, "You're missing deadlines," use: "Let's look at the project timeline together - here's where we're off track, and here's the impact."

Pro tip: This strategy will also work for when you get feedback or criticism.

Instead of thinking: “I’m failing. I’m not VP material. They don’t value me.” → defensive spiral.

You redirect the conversation to something you can both look at together:

“When you say strategic, can we look at an example together? Maybe we can map out a recent project and identify where I stayed too tactical versus where I could have elevated the strategy.”

Now it’s not you vs. your manager → it’s you and your manager vs. a shared framework.

6. Build Your Courage Muscle with Small Reps

Everyone I know struggles with hard conversations. You don’t become an expert overnight, but you can practice on low-stakes moments. Pushing back on a meeting invite or saying no to extra projects so that by the time the high-stakes conversations come, you're already stronger.

Hard conversations get easier the more you do them. It’s like going to the gym - you develop a stronger muscle.

7. Follow Through

Hard conversations don't end when the meeting ends. Summarize agreements. Check in afterward - not to reopen the debate, but to show accountability.

Trust and credibility depend on your ability to follow through.

What’s the point of having a hard conversation if nothing changes?

Build consistency so people know: this isn't about one tough talk, it's about trustworthy leadership.

Step Three: Scripts in Action

Here are a few real-world scenarios where executives lean into the conversation instead of avoiding it:

• Pushing back on a project

"Given our current resources, here's what we'd have to de-prioritize if we take this on. Which path would you prefer?"

• Giving tough feedback

"I value the impact you've had on this project. To keep you on track for success, here's one area we need to strengthen."

• Letting someone go

"This is a difficult conversation. The decision is final, and it doesn't take away from your contributions here. What I want to focus on is giving you clarity and support for what's next."

• Setting boundaries with your manager

"I can deliver X by the deadline. If Y is a priority too, let's align on what should move off the list."

• Asking for help

"Here's where I'm stuck. Here's what I've already tried. Here's the support I need to get us back on track."

What Happens When You Stop Avoiding

When you start treating hard conversations as part of your job and not something to avoid, everything shifts.

People stop seeing you as “nice, but not ready.” They start trusting you as someone who can handle complexity without flinching. And that trust? That’s what gets you sponsorship and promotions.

Here’s the truth: the people who keep dodging tension usually stay stuck in middle management. The ones who lean in, who can face the uncomfortable moments with clarity and calm, those are the people who get seen as executives.

Your Next Steps

What's one conversation you've been avoiding that, if you had it this week, could unlock momentum in your career?

Don't wait until the stakes are higher. Practice now.

And if you're not sure how to show up in these moments with the confidence and presence of an executive - that's exactly what I help my clients master. Book a call, and let's turn your next hard conversation into a promotion opportunity.

I believe in you, and I’m rooting for you

Maya❤️