What’s Past Is Prologue: The Sales Challenges Hospitality Still Hasn’t Solved

Customization is like air to me. Every organization’s challenges feel unique — until you realize how often the same patterns repeat. I tailor my coaching and training programs for each client because it’s the only way to ensure they receive the focused attention they deserve in the areas they want to strengthen.

Recently, I interviewed a seasoned hospitality executive at a prominent regional resort. He reached out for a training initiative, and as part of my due diligence, we discussed the areas where he felt his sales and service teams needed the most support.

Here is what he shared. See if any of these challenges sound familiar.

Prospecting & Pipeline Weaknesses

• Need to uncover new business sources (running only 50% occupancy)

• Limited awareness of broader market opportunities

• Reliance on “the same old clients”

• Lack of structured prospecting campaigns

• Difficulty setting appointments in advance

Skill Gaps (Listening, Questioning, Follow-Up)

• Weak probing questions

• Underdeveloped listening and questioning skills

• Inconsistent or delayed follow-up

• Insufficient attention to clients after booking

Partnership & Internal Alignment Issues

• Underutilization of resort resources

• Limited collaboration with conference services

Mindset, Drive & Motivation

• Need for renewed spirit and energy

• Bad habits, lack of drive, and sloppiness affecting performance

These concerns are common across the industry. But here’s the part that should make every leader pause.

This list is not from 2024 or 2025.

It’s from 1999.

Twenty-seven years ago.

And yet, if I read this list to most hospitality leaders today, they would assume it was written last week. As much as our industry has evolved, many challenges have simply resurfaced with new labels and new packaging. What’s old is new again — both good and bad.

Shakespeare was right: what’s past is prologue.

Many Things in Sales Can’t Be Fixed With AI

AI can write an email template. It cannot make someone curious, accountable, or hungry. Most of the issues above are people-centered: habits, drive, discipline, curiosity, and follow-through. These are not solved by a quick prompt.

In hospitality — where turnover is high and experience walks out the door every year — the past becomes even more important. It holds the lessons, the codes, and the approaches learned through decades of trial and error. But the next wave often doesn’t know what they don’t know, and they don’t know how to find out.

Leaders must step in.

Don’t assume people will learn by osmosis. Don’t assume they will “figure it out.” Invest in them. Coach them. Equip them.

Upskilling Is Not Optional

Think not only about helping your teams close more sales, but also about helping them avoid losing sales. Sales and service must work together seamlessly, or the customer suffers. Salespeople need an intrepid spirit, not a reactive one. They need a toolkit — and the wisdom to know when to use it.

You can’t buy that in an online course. You can’t outsource it to AI.

If you’re a hospitality leader, part of your job is to recognize opportunities, strengths, weaknesses, and areas of needed improvement. Another part of your job is to act on them.

Give your people a fighting chance to improve their skills through coaching. Help them handle customer curveballs, stay resilient when “shift happens,” and elevate their performance to a level that leaves competitors behind.

The past is a playbook, not a museum.

Let them learn like it’s 1999 again. 

Because what’s past isn’t just prologue — it’s a roadmap, if we’re wise enough to use it.