Coaching Up: 5 Ways to Strengthen Leadership at the Highest Levels

Hospitality businesses often invest heavily in developing frontline associates, supervisors, and mid-level managers. Countless hours and resources go into teaching them guest service skills, compliance standards, administrative know-how, and operational excellence. 

When it comes to the very top of the organizational chart, however, professional growth often stops…or at least really slows down. The assumption tends to be that once C-suite executives have "made it," they no longer need the same structured support they once relied on to climb the ladder. They have spent years generating positive results (and were rewarded with promotions, bigger salaries, and hefty bonuses), so they must know what they’re doing, right? 

The thing is, though – sometimes they really don’t, because past success doesn’t always guarantee future readiness. They may have blind spots in how they manage people, how they communicate, or how they adapt to change – gaps that might have stayed hidden until they were promoted onto a larger stage. 

If you're in Training, HR, or Operations, you may be among the first to recognize when executives could benefit from guidance. Supporting development at the senior ranks may feel intimidating, but it’s one of the most important ways to protect and strengthen your culture. Coaching, feedback, and skill-building aren't just tools for new managers – they’re essential across the entire organization, including those at the top. 

The quiet drift at the highest levels 

Leadership gaps don’t happen overnight. They're usually the result of years of shifting circumstances, missed opportunities, and well-intentioned decisions that made sense at the time. 

For one, generational differences can play a huge role. Many senior personnel in hospitality today built their careers in a very different era – one where command-and-control management and "tough love" were the norms. In those environments, leadership often meant protecting authority, showcasing control, and maintaining clear hierarchies – priorities that made sense at the time but feel out of sync with today’s more collaborative expectations. 

Communication norms have also changed dramatically. Some upper-level managers may still use words, jokes, or gestures that were once considered acceptable but now seem outdated, insensitive, or even offensive. It’s not usually malicious, but rather a gap in cultural awareness that, if unaddressed, can quickly erode trust with employees and guests alike. 

Fast expansion can also deepen the problem. Small, close-knit hotel and restaurant chains sometimes grow into sprawling operations and move into new areas – resorts, entertainment, global tourism – that their founders might barely recognize. As businesses scale up, senior teams can unintentionally grow distant from daily operations, which makes it harder to spot emerging problems or stay connected to the people they lead. 

Expansion also forces many companies to bring in outside talent when internal leadership pipelines aren't ready. These external hires often come from environments where hard metrics, efficiency, and cost control mattered more than guest experience or emotional connection. When they step into hospitality roles, however, the cultural differences can quietly undercut morale and performance. 

And finally, these gaps will most likely continue to grow as we move forward as an industry. The strategic playbooks that helped hospitality decision-makers overcome challenges in the 1990s and early 2000s weren’t built for the pressures of 2025 and beyond. Today’s leaders face an entirely new set of challenges: international tariffs, AI disruption, frequent mergers and acquisitions, and rapidly shifting guest expectations. Without active coaching and support, even the most experienced professionals can feel unprepared to navigate these higher stakes. 

Small moves can make big impacts 

Thankfully, the development work you do at the frontline doesn’t have to stop there. With the right approach, you can extend those same skills upward and help strengthen the executive team, too. The goal isn’t to "fix" them overnight or point out everything they’re doing wrong. It’s to create small, consistent opportunities for growth, and to do it in ways that are practical, respectful, and low-risk. 

If you start noticing gaps, here are five leadership capabilities that may need strengthening, plus two practical ways you can help nudge them forward. 

1. Help them reconnect with people, not just processes: It's easy for executives to get buried in numbers, compliance reports, and operational checklists, especially in a high-pressure environment. But hospitality isn’t driven by spreadsheets; it’s fueled by human connection. When senior leaders lose sight of the emotional pulse of their people and guests, everything else can start to crack.
   
   • Re-center on staff members: Create low-pressure opportunities for executives to interact directly with frontline staff without a formal agenda. They could simply walk through operations for a few minutes and have quick conversations with those working, or they could drop into a frontline team's quick huddle before their shift begins. The idea is for the executives to meet with real people and connect with the real heart of their operations.
   • Share wins: Regularly send short employee stories up the ladder that highlight real moments of service or teamwork. It doesn’t need to be a long report, but rather just a bite-sized update on what’s been happening in the field. And if possible, include photos of the people included to help your leaders recognize them the next time they are in their hotel or restaurant.
2. Boost their cultural and generational awareness: Today's workforce is the most diverse in history in age, culture, values, and expectations, but leaders who grew up in different business eras might unintentionally miss important shifts. The key to bridging this divide is creating learning moments that develop awareness gradually and respectfully, rather than through criticism or formal sensitivity training. Remember, these are the decision-makers who steer your company and approve your department's budget (and most likely sign your paychecks), so the goal isn't to highlight what they're doing wrong, but to subtly help them evolve their understanding while maintaining their authority and confidence.
• Refresh key documents: Volunteer to update one policy, orientation slide, or handbook section to reflect more modern, inclusive language, and show your C-suite team how these revisions can improve clarity and morale.
• Drop in ‘culture moments’ naturally: In leadership meetings or communications, briefly highlight cultural observances, holidays, or trends, especially those that connect naturally to guest or employee experiences. You might mention how Lunar New Year impacts travel patterns, for example, or how Pride Month events can increase group bookings in major cities. The goal here is to build casual cultural fluency and make awareness feel like a normal part of any business conversation.
3. Show executives how early input builds better outcomes: Many senior leaders are still used to an old-school "decide first, announce later" approach where changes are made behind closed doors and only revealed once everything is finalized, but today’s employees expect transparency, inclusion, and a voice in the process. If executives don’t engage employees early enough, rollout gaps widen, valuable feedback gets lost, and employees can feel dismissed or hurt, which quietly erodes trust in ways that are hard to rebuild later.
• Pre-change ‘gut checks’: While visiting operations, encourage leaders to do a few casual one-on-one chats with a mix of frontline employees before rolling out a change. Without a formal agenda, they should just ask, “If we changed X, what would you want us to think about?”
• Micro-feedback polls: Before finalizing a new process, draft a 1-2 question anonymous poll for frontline teams (something they can answer in 30 seconds) and invite executives to review the responses. An example might be, “We're updating the guest welcome script. Which matters more to you: A) keeping it short or B) making it more personalized?”
4. Support small actions that prove people matter: It’s easy to say “employees come first” in a speech or presentation, and those words might make people feel good for a moment, but it’s the regular, visible gestures from leadership that feel more genuine to employees and have a bigger long-term impact. Helping executives find quick, simple ways to show care – without adding hours to their workload – is where you come in.
• Hand-deliver good news: When an employee is recognized, ask executives to deliver the good news themselves. Recognition from the C-suite feels 10x bigger when it’s personal rather than passed through layers of management. If that might not be possible due to the size of your company or remoteness of your locations, provide your senior leaders with pre-printed thank-you cards (or even simple email templates) and challenge them to write two quick notes of appreciation every week.
• One-ask routines: Advocate for leaders to regularly end employee conversations with, “Is there anything I can help clear up or make easier for you right now?” It signals humility and shows that leadership is accessible without needing to schedule extra meetings.
5. Help them guide, not command: The higher up someone goes, the more pressure they feel to have answers ready and make quick decisions. That’s why many executives slip into a “just do it” mindset and give directives instead of developing people. But today's best leaders don't just hand out instructions; they help their teams think critically, solve problems, and grow. Your role is to model and encourage small shifts in how those in the C-suite hold conversations and make guidance – not control – the norm.
• Switch directives into questions: If an executive starts to give an order ("Move the check-in desk over here"), gently reframe by asking, "What’s the outcome you’re hoping for?" or "What problem are we trying to solve?" This tiny shift models curiosity without confrontation and encourages leaders to pause and think about goals, not just tasks.
• Turn observations into openers: Instead of immediately fixing things during a location visit ("You need to clean this up"), suggest that your leaders start with a simple question like, "What do you notice here?" or "How do you think this looks from a guest’s perspective?" It opens a dialogue instead of dropping a command, and it will build ownership on the spot.

When they’re ready for more 

Sometimes a few nudges, new habits, and conversations are enough to spark real change. But occasionally, a company leader will recognize – or at least be open to hearing – that they could benefit from deeper, more personalized support. If that moment comes, you can be ready to offer a next step: suggesting a professional leadership coach. A skilled coach can help executives spot blind spots, strengthen emotional intelligence, and build more adaptable skills through honest feedback and customized development plans. 

And if getting a coach is approved, you don't have to start from scratch to find someone. If you're a member of the Council of Hotel and Restaurant Trainers (CHART), you already have a powerful resource: you can ask fellow trainers about leadership coaches their companies have hired, or you might consider reaching out to one of the many members who are certified coaches themselves. The CHART community is built exactly for these kinds of real-world hospitality development needs. 

To help get you started, here are a few of my colleagues from the association who might be a good fit for your organization: 

• Curt Archambault, People and Performance Strategies
• Donna Herbel, Blue Phoenix Learning
• Jason Lyon, Wicked Smart Performance Strategies
• Nadine Willems-Antersijn, Momax Trainings & More 

Coaching up is an act of leadership 

Helping executives grow isn’t about overstepping or criticizing – it’s about strengthening the entire business from the inside out. Great leadership at the top doesn’t just happen; it’s built the same way service excellence is built at the front lines: with steady coaching, honest feedback, and consistent reinforcement over time. 

Every small effort, every thoughtful exchange, and every resource you share will make a difference. Even if the changes are slow, and even if they’re hard to see at first, the impact will ripple through your culture in powerful ways. It won’t always be easy, but it’s real leadership, and it’s work worth doing.

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This article was inspired by the breakout session, “Culture Within Culture: Honoring Heritage to Build a Values-Driven Hospitality Business,” presented by Stephanie Barnes, CHT, Senior Training Manager for Operational Training at the Choctaw Nation of Oklahoma, during the CHART Conference in Louisville this past spring. Her session explored the real-world struggles of guiding a fast-growing organization through cultural shifts, leadership gaps, and the challenges of staying true to core values while still evolving to meet new demands.