Hospitality Leadership and Navigating Difficult Conversations

Dec 13, 2024
Alison Arth, Kimberly Belle, and Kate Cayanni at Prospect in San Francisco

Kimberly, Kate, and Alison at Prospect restaurant in San Francisco.

We are thrilled to welcome Kate Cayanni, owner of Good Smart Funny, as a Guest Coach in The Walk-In: a 6 month group coaching program to become the leader you’ve always needed in this industry. 

Kate is an HR pro, a seasoned industry vet, and an extraordinary coach who empowers leaders to develop meaningful, people-centered systems for growth. Her insightful approach helps leaders build intentional team dynamics while navigating the complexities of human resources. Blending humor with expertise, Kate is passionate about guiding leaders to succeed with confidence, clarity, and joy. 

Members of The Walk-In, which kicks off in February of 2025, will benefit from a full week of coaching support from Kate during the program, giving you a place to ask your burning questions related to the hardest part of owning a food business: people. 

In this blog on navigating difficult conversations, Kate shares directive, clear, and compassionate guidance to kick avoidance to the curb and embrace the courage to say the hard thing. I don’t know of a more powerful leadership skill than this one. 

We hope you learn as much from this article as we did. 

Alison & Kimberly

Navigating Difficult Conversations: A Guide for Hospitality Leaders

by Kate Cayanni, Good Smart Funny

If you’re leading a food business, chances are there’s a difficult conversation you’ve been putting off. 

Maybe it’s…

  •  the team member who consistently arrives late
  •  the manager who’s underperforming, or
  •  the chef whose creative vision doesn’t align with the business goals. 

Often, these loom over us, complicating an already hectic and stressful work day.  

We avoid navigating these difficult conversations in favor of comfort…that glimmer of hope that the problem will resolve itself with a little time. Unfortunately, they rarely do. Avoiding them won’t make the problem go away. On the contrary, the longer you wait, the harder it gets.

In this article, I’ll cover:

  •  How to prepare for difficult conversations 
  •  Sample scripts for exactly what to say (and what NOT to say)
  •  How to deliver hard conversations with clarity and kindness
  •  Tips for effective follow-up that improves team accountability

The hospitality industry is a fast-paced, people-driven environment where emotions run high. This can make navigating difficult conversations particularly challenging. Let's dig in together so you feel ready to tackle hard conversations across your leadership life head-on. 

How to Navigate Difficult Conversations in the Hospitality Industry 

I struggled personally for years in my own hospitality leadership journey to address the team member, or to act on the knowledge that it was time for an employee to go. I learned to say the hard things when I realized that not saying them was hurting me and my own well-being, more than anyone else.  

Since then, I’ve coached many leaders to navigate these difficult conversations successfully by approaching them intentionally and with clarity on what they want the outcome to be. Here are some practical tips for facing difficult discussions head-on.

Know What’s at Stake

Before you engage in a difficult conversation, take a step back and assess what’s really at stake. 

  •  Is the issue affecting the quality of service?
  •  Is it impacting team morale? 
  •  Perhaps it's an unresolved interpersonal conflict that’s simmering under the surface. 

When leaders avoid addressing these issues, the problem doesn’t just stay contained…it spreads. 

 

In a hospitality environment where every team member’s contribution directly affects the guest experience, unresolved problems can have a domino effect. 

 

That cook who isn’t meeting expectations? It could be slowing down service. 

The front-of-house team that’s frustrated with inconsistent scheduling? It might lead to high turnover, which increases hiring and training costs.

Prepare with Purpose

Preparation is key to approaching hard conversations effectively. 

#1 Start by clarifying the core issue you need to address. Write down your main points so you stay focused during the conversation. Be specific. Vague feedback like “You need to do better” won’t give the other person much to act on.

#2 Consider the outcome you’re hoping for. Are you looking for immediate changes in behavior? Do you want to open a dialogue for the employee to share their perspective? Having a clear goal will help steer the conversation in a productive direction.

#3 Take time to reflect on your own emotions. It’s easy to let frustration build, but starting a conversation from a place of anger can make the other person defensive. Instead, center yourself in the outcome you want, and approach the discussion with an open mindset.

Choose the Right Time and Setting

Timing matters. 

The worst time to have a tough conversation is in the middle of a busy shift or when emotions are already running high. Find a quiet, neutral space where you and the employee can talk privately. This signals that the conversation is important and that you respect their time and input.

In the fast-paced restaurant world, finding the right moment can feel impossible. But it’s essential to carve out time. Schedule the conversation for the start or end of a shift when the pressure is lower, and ensure there are no major distractions. You want both parties to be fully present and able to engage without feeling rushed.

Lead with Empathy

One of my guiding principles is that empathy isn’t just nice to have, it’s a critical leadership skill. 

You deal with a wide range of emotions on a daily basis, from stressed-out cooks to front-of-house staff managing difficult customers. When you bring empathy into a difficult conversation, you create space for real connection and understanding.

Start by acknowledging the person’s contributions and strengths. If this is a team member who is struggling with performance, for example, you might say: “I know you’ve been working hard, and I appreciate your effort. There’s something we need to address to make sure we’re all on the same page moving forward.”

This sets the tone for a constructive dialogue, rather than a confrontation.

 

Empathy doesn’t mean avoiding accountability.  Empathy means recognizing the human side of the conversation while taking responsibility for addressing the issue head-on. 

 

Hospitality leaders often shy away from hard conversations because they don’t want to hurt someone’s feelings or cause conflict. But in an effort to soften the message, they can end up being too vague or unclear.

This leads to confusion and frustration for both parties.

To avoid this, practice using clear, direct language. Be specific about the behavior or issue that needs to change, and avoid getting into character judgments.

For example, instead of saying “You’re being lazy,” you could say, “I’ve noticed that you’ve arrived late three times this week, and it’s starting to affect the kitchen’s ability to prep on time.”

Framing feedback around behavior (rather than personality) helps to keep the conversation focused and productive. It gives the other person a clear understanding of what needs to change without making them feel attacked.

Listen Actively

A hard conversation isn’t just about delivering feedback…it’s also about listening. 

Give the other person an opportunity to share their perspective. There may be underlying reasons for their behavior that you weren’t aware of, like personal challenges or a lack of training. By listening actively and putting to use your hospitality communication skills, you show that you’re invested in finding a solution together.

Use open-ended questions to encourage dialogue, like, “Can you help me understand what’s been going on?” or “How do you feel about the current situation?” Then, practice reflective listening by summarizing what the person has said. This shows them that you’re engaged and genuinely care about their input.

Collaborate on Solutions

Once you’ve aired the issue and listened to the other person’s perspective, it’s time to collaborate on a solution. Instead of prescribing what needs to happen next, invite the employee to co-create the path forward. This fosters a sense of ownership and accountability.

You might say something like, “What do you think we can do to improve this situation moving forward?” or “How can I support you in making this change?” By framing the conversation as a partnership, you empower the other person to take responsibility for their actions while also offering your support as a leader.

Follow Up and Stay Accountable

The conversation doesn’t end once you’ve discussed the issue and agreed on next steps. Follow up with the employee to see how things are progressing. This shows that you’re committed to their growth and that the conversation wasn’t just a one-off event.

Schedule a check-in a week or two after the conversation to discuss any improvements or ongoing challenges. This keeps the lines of hospitality communication open and demonstrates that you’re holding both yourself and the employee accountable to the agreement you made.

Stay Open to Feedback Yourself

Hospitality leadership isn’t just about giving feedback, it’s also about receiving it. 

After a hard conversation, be open to hearing how you can improve as a leader. This might be uncomfortable, but it’s an essential part of building a healthy, transparent work environment.

Invite feedback with questions like, “Is there anything I can do differently to support you?” or “How can I communicate more effectively with the team?” By modeling this openness, you create a culture where hard conversations are normalized and everyone is empowered to speak up when issues arise.

Navigating Difficult Conversations More Easily

Navigating difficult conversations is never easy, but it’s a critical skill for hospitality leaders who want to lead with intention. By preparing thoughtfully, leading with empathy, and focusing on solutions, you can turn even the toughest discussions into opportunities for growth, both for your team and for yourself as a leader.

At Good Smart Funny, I help businesses like yours navigate the human side of leadership with confidence. I’m excited to be partnering with Salt & Roe as a guest expert for their upcoming group coaching program, The Walk-In. Together, we’ll equip you with the tools you need to lead your food business with clarity, empathy, and purpose.

Behind you, 

Kate

We've been called wise big sisters and restaurant whisperers. 
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