An Interview with Diana Giles
Diana Giles is the president and owner of Skyline IT Management, an MSP based in Oklahoma. 
And, she’s also the founder of sensible cyber parenting.com. It’s a free resource website to help parents protect their children online.
Diana got into IT by accident after her degree – she was always the go-to person in the office to fix computing problems. And she enjoyed it so much that she decided to make it her career.
The Challenges of Being a One-Man Band MSP
Diana says the most challenging thing is when she needs to be in several places at once. She adds that she strives to provide good service, so sometimes she rushes to get work done that isn’t that urgent for the client.
“I have to see if it’s really necessary or if it can wait. And having an outsourced helpdesk makes a difference. I can respond quickly to people even if I’m tied up with other work.”
How Diana Spots Potential Clients Who Aren’t a Good Fit
Many MSPs will write someone off immediately if they mention price straight away. However, Diana says if that’s their only focus it’s a red flag. “And another one is if they have really outdated technology.
“They’re not interested in upgrading. They just want to manage with what they’ve got. Limping along with unsupported operating systems is bad for them and for you. It’s better if they know they need help to upgrade.”
The Most Challenging Part of Running an MSP
Like many MSP owners, Diana admits that sales are hard. She got plenty of referrals but she wasn’t as busy as she wanted to be. And she didn’t do any marketing, but things ticked over.
Most SMBS are loyal to their IT support person until something goes wrong and they need someone else. But getting people to switch provider is hard. The other challenge is security. “Especially now, because we’re all thinking about it all the time.”
Being a Female MSP Owner in a Male-Dominated Space
Diana is often the only woman in the room when she goes to events. However, she says that has never been a problem. When she started in the industry in the 90s, she was hired by a woman. And half of her colleagues were women too.
“There don’t seem to be many women business owners around. But I’m not sure what the solution is. Because I don’t think they’re being left out intentionally. So maybe they aren’t interested in the industry.
“It would be good to have more women around. I think I have more patience in some situations. But asserting authority is easier for men. We all have different strengths that we bring to the table.”
Being a Mother and Running a Successful MSP
Diana has always managed to make being a mother and a business owner. But she admits there were times she had to take the kids with her. Or drop them at her husband’s office.
She did most of her work when the children were at school, but her plan was to build a lifestyle business. So she was as busy as she wanted to be. “But there were still times when I was pulled in different directions. And the kids did their homework in customers’ offices sometimes!”
The Sensible Cyber Parenting Website
On a few occasions, Diana has helped clients and friends whose child had been exposed to undesirable content. Or even become addicted to pornography or similar and had a problem.
Diana stepped in and securing the device to prevent the young person accessing harmful material. She had to work hard to keep her own kids safe, so she realised that there were less techy parents who would really struggle to do the same.
“I could set the security up for them, but sometimes another problem would occur with the computer. And the parents have no idea what to do. So, I wanted to empower them to do it themselves. The website is designed to provide them with the right resources.”
How to Connect With Diana Giles
- Skyline IT Management
- Follow Diana on Facebook
- Connect with Diana on LinkedIn
How to Connect With Me
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Mentioned in This Episode
- To Do
- Book: Richard Tubb: The IT Business Owner’s Survival Guide: How to save time, avoid stress and build a successful IT business
- CompTIA
- The Tech Tribe
- Pax8
- Sensible Cyber Parenting
You Might Also be Interested in
Richard Tubb is one of the best-known experts within the global IT Managed Service Provider (MSP) community. He launched and sold his own MSP business before creating a leading MSP media and consultancy practice. Richard helps IT business owner’s take back control by freeing up their time and building a business that can run without them. He’s the author of the book “The IT Business Owner’s Survival Guide” and writer of the award-winning blog www.tubblog.co.uk
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