Organizations typically have teams dedicated to this. From those teams, we pluck the best of the best, move them up the chain of command, and replace them with new sellers. The best become our leaders. This continues until, eventually, the best run the show. Sounds good, right?

Who doesn’t want the best sellers from days of yore leading and guiding those new sellers? Surely, they can bring the new folks up to their level.

Remember that old adage: “Those who can, do; those who can’t, teach.” Turns out, that phrase is a complete and utter fallacy. Some of the best doers in history were also teachers: Albert Einstein, Richard Feynman, Stephen Hawking, Clara Barton, J.R.R. Tolkien, C.S. Lewis, and Maya Angelou, just to name a few. All these individuals were arguably at the top of their game; recognized experts in their field(s) of study.

And what’s the one thing they all have in common? They never stopped doing while they were teaching. Which brings us to the point: We pluck the best of the best and thrust them into leadership positions. We assume what made them great sellers will make them great leaders. We also bet that once removed from the thing they were great at, they’ll maintain the edge that once made them great.

Unfortunately, and all too frequently, the great seller remains rooted in what made them a great seller. They’re tied to the processes they used and the technology that was available at the time. They’re frozen in the days of yore and that’s what they impart to the folks they’re charged with hiring, training, and mentoring.

A Changing Environment

Take a stroll back in your brain to the mid-1990s or even the early ’00s. The world was a different place. How many of you had a computer on your desk? How many ways were you able to reach a client? Was it easy to walk into their office and have a conversation?

For most of today’s senior leaders the answers to those questions are as follows:

• Their office had perhaps one computer on an admin’s desk.
• They communicated by phone, fax, snail mail, and in person (either at a hotel or in the client’s office.
• They were able to walk in and see clients without a gatekeeper and if not, they could get an appointment easily.

Back in those days, you had to write everything down then hand it off to someone else to process or file. If you called someone, there was a high probability they would answer their phone. If they didn’t, they would return the call. You got to know your clients personally because you could visit with them over lunch or in their office without an issue.

What does the client relationship landscape look like today? Everyone has a computer on their desk. They have access to a variety of different pieces of technology to facilitate their processes. They have an office phone, a mobile phone, email, text, video chat, and other technology platforms to help with communication. The sheer number of ways they reach a customer is overwhelming, and yet, they rarely can reach that person.

Today’s leaders can’t relate. It was relatively easy for them to stay in contact with limited means. Now the means are seemingly endless but it’s harder to develop relationships. Sellers are looking to their leaders for guidance, but leaders can only tell them what they did a decade (or more) ago.

The Ripple Effect

And this is where the problem comes in. Their former success, the very accomplishments that likely put them in their current chair, are holding their teams back. Those leaders are using a printed road map from 1994 to try to navigate the path to success in 2024 – and you can’t get there from here.

Here’s the dirty secret. Our property level sellers know it. They know their leaders can’t guide them through the quagmire that is today’s disjointed sales process. They realize they often have more knowledge about how to manage the process than their leaders do. And, because of this, they often feel disjointed from leadership’s plan.

This leadership gap negatively impacts daily operations, the ability to attract new talent, and employee retention. Compounding this gap in the last few years have been rapid changes in the way we work, workforce pressures, and attitudes about work-life balance.

Rapid changes in technology transformed our industry, creating new jobs and skill requirements. Societal shifts have also significantly altered the workplace landscape. Some leaders may not possess the hard and soft skills to operate effectively in these new environments. Doing things the way we always have won’t work in today’s environment.

How Do We Fix It?

We expect property level people to be flexible and roll with the punches. They must adapt to the ever-changing industry landscape. But when is the last time your leadership strategy changed?

Ask yourself these questions:

Are you still running the three demand generators in siloes?

• Sales, marketing, and revenue management should be your organization’s most powerful triumvirate. But all too often, they’re still independent departments with limited interaction at the leadership level. This isn’t the case at the property level. By necessity, on property, these departments work in conjunction with one another. But above property, the synergy doesn’t exist. Does your organization have leaders in place with an eye toward being a cohesive unit? Or do they still view each department as its own fiefdom, with individual initiatives, goals, and metrics? If the answer to any of these questions is “yes,” you have a leadership issue.

Who owns your technology stack?

• This isn’t about the technical requirements or even the security of your tech stack (that part should be owned by a CTO or IT team). This is about who’s monitoring the technology to make sure you’re using it effectively and efficiently and that every staff member (including your leaders) is fully versed on all its functions. Additionally, who’s responsible for prescribing the best way to use technology? Are those plans revisited regularly? You can’t assume that everyone in your organization (at all levels) walks in the door knowing how to use your tech stack. You need a process geared toward teaching them your best practices. Most importantly, you need a process to review and update best practices to reflect today’s landscape.

When is the last time your leadership innovated?

• If you’re still churning out the same old marketing plans your company used in the ‘90s, you have your answer. Today’s world is entirely too fluid. Something you create in July probably isn’t even applicable by January. Your leaders should have figured out a better way to manage processes that allow hotels to pivot quickly, fail fast, and recover faster.

Are you retaining talent?

• The hospitality industry is transient by nature. Is your retention related to this native transience? Or is it a factor of leadership? If you aren’t supporting, mentoring, or effectively training property level talent, they’ll simply move on to someplace that will provide it.

Can your leaders walk the walk?

• That isn’t the same question as did they walk the walk – this is about what they can still do. Can your leaders record a video message that will attract customers? Do they know how to respond to a request for proposal (RFP) both quickly and effectively? When’s the last time your sales leaders were effectively in the field? Perhaps it’s time for a field trip so they can understand.

Whether we want to admit it or not, a leadership gap exists in our industry – perhaps not in every organization, but in more than anyone cares to admit. It continues to contribute to our staffing issues and is likely hindering long-term recovery at many hotels – a true recovery not just the rising tide that’s lifting all boats.