Homelessness in the U.S. and Managing Its Impact on Your Hospitality Operation

View from Above Recap from CHART 110 Boston Hospitality Training Conference

Ryan Dowd
Atty., MPA, Homeless Training

Watch previous webinar on-demand of this topic, or read Ryan’s previous in-depth article on this topic.

Ryan Dowd had a heads-up for CHART Boston attendees: The hospitality industry may need to prepare for a significant change in how homelessness affects its employees and businesses.

But first, he wanted to clear up a common misconception. Homelessness is not one monolithic experience.

Dowd explained that there are different populations of people experiencing homelessness, and most do not fit the stereotypes people often imagine. He described three broad groups. The first includes people who experience homelessness for a relatively short time, often because of an economic crisis. The second includes people who may experience homelessness for several months while dealing with one significant barrier, such as a medical, legal, substance use or mental health issue. According to Dowd, people in both groups often come into restaurants, hotels and other businesses without employees ever knowing they are homeless. They look, act, and interact like any other guest.

The third group is where Dowd said the hospitality industry is most likely to encounter significant challenges: people experiencing chronic homelessness, generally defined in his presentation as homelessness lasting a year or longer.

This population is more likely to experience serious challenges, including PTSD, substance use disorders, traumatic brain injuries, and other cognitive or mental health conditions that can affect how they interact with others. Dowd’s point was not that everyone experiencing homelessness is difficult or dangerous. In fact, he spent considerable time emphasizing the opposite: Most people experiencing homelessness are not going to behave differently from other customers. The challenge for businesses is understanding and preparing employees for the smaller population whose circumstances may lead to difficult or unpredictable interactions.

And, according to the data he shared, that population has been growing. Dowd compared 2020 and 2025 homelessness figures and noted increases in the total number of people experiencing homelessness, families experiencing homelessness and, especially, chronic homelessness. He said the number of people experiencing chronic homelessness had increased by 41% during that period. That increase, he suggested, may help explain why many organizations feel as though their interactions with people experiencing homelessness have changed in recent years.

But his bigger insight was what could happen next.

Dowd outlined three federal policy shifts that he believes could affect where resources are directed and which populations receive support. He explained that one major shift would move the focus away from long-term support for people experiencing chronic homelessness and toward helping people with shorter-term barriers get back on their feet more quickly. He acknowledged that there is a benefit to helping those individuals recover faster. His concern was that people with the most significant and long-lasting challenges could be left with fewer options for support.

He also described changes that, in his view, could shift resources geographically and reduce the amount of funding available in areas with the highest rates of homelessness. With shelters already at or near capacity in many communities, Dowd’s shared that more people experiencing chronic homelessness could end up spending more time on the streets. He expects the effects to be felt most strongly in urban areas, particularly as changes to funding and vouchers take effect over the course of 2027.

So, what does all of this have to do with hospitality training? For Dowd, it all comes back to kindness.

He made the case that treating people with respect isn’t just good hospitality. In difficult interactions, it can also be an important part of de-escalation and employee safety.

One of the simplest strategies he shared came from his training on interacting with people experiencing homelessness: introduce yourself and ask for the other person’s name within the first five seconds of the interaction.

“Hi, I’m Kelly. What’s your name?”

Simple. Human. Respectful.

And, Dowd pointed out, it works with everyone – not just people experiencing homelessness. Starting an interaction by showing basic respect can help de-escalate tension before it has a chance to build.

Employees don’t need to diagnose someone, determine whether they are experiencing homelessness, or try to figure out what is happening in their life. Instead, they need the skills to respond calmly, respectfully, and appropriately to anyone who enters their business.

Dowd’s message was ultimately a call to prepare. If his projections are correct, particularly for businesses in urban areas, hospitality employees may encounter more complex situations in the coming years. Training teams have an opportunity to get ahead of that by helping employees understand de-escalation, body language, respect and how to respond when an interaction becomes challenging.

Because kindness, as Dowd’s presentation made clear, isn’t just about being nice. Sometimes, it’s a safety strategy.