Learning the Ropes

Charles “Chuck” Day has always been a helper. Now 60, he comes from a diverse background as a longtime elementary school teacher in Boston who has also done a lot of construction in his time. He and his wife also owned a 175-year-old bed-and-breakfast until last year. Day’s knowledge of old homes and passion for learning and sharing knowledge make him a great fit for what’s next—home inspection.  

A graduate of Inspection Certification Associates (ICA), Day spent much of spring and summer 2025 working with 2023 ASHI Past President and 2025 ASHI National President Elect Lisa Alajajian Giroux to get his associate license in Massachusetts. “I’m an old intern,” he laughed as he shared his experience in the mentorship program. “I’ve been going out on inspections with her. She’s so good. She’s thorough and fantastic with the customers.” 

Several steps are required to become a licensed home inspector in Massachusetts—from taking a class and passing the national test to completing 25 ridealongs with licensed inspectors. When we spoke in June he was in the midst of his ridealongs with Alajajian Giroux. 

After the 25 ridealongs, inspectors must complete 100 of their own inspections before then applying for their associate’s home inspector license, as required by the state, Day said. “You have to write the report and someone watches you—how you do it and to make sure the reports are OK. After that, you can apply to become a fully licensed home inspector.”

Day is also a member of the National ASHI and New England ASHI groups, which he said is helpful. “Everybody has a different background, and that’s great, too,” he said. 

Day lives on Cape Cod and is excited about a future that involves helping people when they’re making one of the biggest decisions of their lives. “I really like working with younger buyers—first-time home buyers—to inform them and walk them through the different systems. ‘Here’s the water shutoff, here’s the electrical shutoff.’ You need to know those things in an emergency.” He looks forward to answering any and all questions, from landscaping to roofing to water issues. “All those little things that new homeowners probably won’t know,” he said. 

Day found working with Alajajian Giroux through a mutual connection. He said the mentorship has been invaluable, and that it’s important for inspectors starting out to find someone they work well with. “That’s important—to find the right person or people who are on your level, because there’s a ton of different ways to be an inspector,” he said. 

It’s been a good working relationship for Alajajian Giroux, too. “Watching Chuck’s progress has been nothing short of inspiring,” she said. “Thank you for letting me be part of your journey.”

Day said it’s important for inspectors to develop their own way of working. “Lisa seems to be on the same wavelength as I am, where we want to do a really thorough job, take our time, and make sure everybody understands everything.” 

Alajajian Giroux and Day do a lot of follow-up after the actual inspection, too, he said, to review any issues. This includes web-based conferences with all her clients. “I think that’s a huge part of the whole inspection—being able to communicate different issues that come up and how everything looks,” Day said. “In every house there’s going to be something you find, but it’s conveying the message that it’ll be ok; you’re just pointing it out.” 

Part of Day’s appreciation of mentorship may come from his many years in the classroom. “When I was teaching I always had student teachers in my classroom. I had one or two every year for years,” he said.

He said some seasoned inspectors are a bit hesitant to take on a mentee, especially in Massachusetts, as there are so many requirements, but he’s been fortunate to work with the best of the best in the industry. “Unfortunately sometimes people think about it as training your competition. I don’t think it’s like that. I think you bring other people in to raise up the whole industry,” Day said.