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Asset Managers: This Is Why Your Hotel Sales Teams Don’t Close More Deals Despite Your Extensive Investments | By Doug Kennedy

21 January 2026
Asset Managers: This Is Why Your Hotel Sales Teams Don’t Close More Deals Despite Your Extensive Investments
Asset Managers: This Is Why Your Hotel Sales Teams Don’t Close More Deals Despite Your Extensive Investments

You have approved every request for new sales automation systems, because salespeople report being overwhelmed with inbound leads. Now RFPs are responded to promptly, just like all those hotel technology salespeople said was the number one way to close more bookings. You’ve added AI-powered drip campaigns so that all buyers receive so-called “personalized” follow-ups.

You’ve authorized expenditures for AI-powered revenue management systems powered by the best data in history.

You’ve okayed extra funding for purchasing display ads on event planning software platforms.

Your hotels have paid for third-party email marketing campaigns.

Investment has been made in sleek-looking website inquiry systems that capture demand from those searching for venues.

Perhaps you have even invested in platforms that enable the instant, online booking of groups, meetings, and events.

Yet still, your hotel sales teams are failing to gain market share from their comp sets. Here’s why.

Perhaps the above factors are really just symptoms of the underlying cause of lost group and event business, which is that hotel sales leaders simply have forgotten how to sell, or that they never really learned how to do so.

Many long-term veterans hanging on until retirement have gotten away from the sales habits that made them successful in their early years. Their once-sharp sales skills became dulled during the 2010s by years of revenue growth that exceeded projections. The tidal wave of pent-up business post-Covid provided additional cover for their lack of proactivity. Through no fault of their own, many younger sales superstars have never had strong mentors to show them the subtle nuances of sales success. The work-remote model of hotel sales has exacerbated this lack of mentoring.

If any of the aforementioned issues and trends have caused you to question your hotel sales teams’ processes and systems, you may now be wondering how to start shifting the trajectory. The first step may be to get your hotel sales leaders to recognize and admit that there is a problem. Now, given that having a big ego and strong self-confidence may be the most common personality trait for successful salespeople, it is uncomfortable to ask the hard questions needed.

Over my many years of presenting hotel sales training workshops, I have developed a simple method of catching everyone’s attention regarding their sales process efficiency, or lack thereof.

You could hire sales trainers like me, but this is also super easy for those you already employ to do themselves. At the micro level, it can be done by a GM, and with proper training, this can be undertaken at the macro level by regional sales, revenue, and/or operational staff you already employ.

First, I sit with each salesperson and ask them to walk me through each step they use in the “flow” of their sales process when a new lead arrives. Of course, nearly everyone says they do all the right things! Next, I ask them to display the lists of leads that came in from 45-90 days back. I then ask them to share documentation of their follow-up action steps. Ideally, if they have been using their CRM correctly, they can easily share records of notes from conversations, online meetings, and the “traces” of each next-step action. Otherwise, we look at whatever “trail” they have, which might be found in their sent message folders and even handwritten notes.

The objective is to look for factors that ultimately impact conversion such as: response methods (calls, emails, virtual meetings), response times, timeliness of sending written follow-up (emails, in-platform messages such as in CVENT, Wedding Wire), and also how they have personalized and contextualized the messaging in their correspondence and proposals (vs. sending generic copy/paste messaging.) I also ask them to show me records of any virtual meetings, in-person site visits, and phone calls for the last month or so.

In conducting these types of audits for a huge diversity of salespeople, I consistently find that about 20% of hotel salespeople are running a fully optimized, human-centric, and tech-optimized sales process. Unfortunately, the remaining 80% are basically content to live off of inbound demand they secure through polite order-taking.

By conducting a sales process assessment like I do, the real reasons why your hotel sales teams don’t close more deals will become obvious and easily fixable with some sales training focusing on the skills needed in today’s sales habitat.

Originally published in CoStar News Now.

Contact

Doug Kennedy
Phone: +1 (678) 466-9173
Email: Doug@KennedyTrainingNetwork.com

Organization

Kennedy Training Network (KTN)
www.kennedytrainingnetwork.com
5370 Highway 92, Suite 210
USA - Fairburn, GA 30213
Phone: (678) 466.9173
Email: info@kennedytrainingnetwork.com
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