...to help my local organization?Call or check their website to see if they need volunteers or specific donations. Donations may include work or business clothes, socks, underwear, toiletries, backpacks, sleeping bags, gas cards, water bottles, canned food, and more.
...when I encounter a homeless person?Look them in the eye and smile; introduce yourself and ask their name. Consider carrying gift cards to local fast food restaurants, bus passes, hand warmers, or cards with phone numbers of local resources or 211 (www.211.org) to share. Or, offer to buy them a cup of coffee or meal. For conversation, ask about where they were born or bring up the local sports team or current political issues.
...if I am not sure someone is homeless?Try, “Do you know anyone that can use [this gift card to McDonald’s, $5.oo, this extra bus pass, etc]?” That seems to work while maintaining the dignity of everyone involved.
...if I own or manage a local business?Consider which positions would be appropriate for on-the-job training and contact your local service organization to see if they can recommend a candidate from within the homeless community. In addition, encourage your city council, or other local government, to reach out to neighborhood businesses and support that same willingness.