Ryan Lee

Ryan Lee is the Director of IT at E.W. Wylie. Ryan knew at a young age that IT was the right path for him, and today there are about 400 team members under his sphere of influence in the transportation industry.

Ryan Lee Explains How He Fills IT Roles

Ryan shares his background and what led him to be in the role he occupies now. He also gets into his approach to problem solving and how he navigates difficulties in his own work as well as with his team. He later shares his insight on how he stays up-to-date with the latest in technology and his trick for dealing with silos.

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187. Ryan Lee Explains How He Fills IT Roles
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Episode Show Notes

[0:30] How did you get into IT?

I knew IT was going to be in my future since 9th grade. I looked at my career opportunities and settled on a path in technology. I went to college in my hometown, and once I graduated, I worked full-time for a company I interned with.

[4:32] I’m sure there’s been one or two companies who have wanted their exfiltration rules versus the majority who are concerned about what’s inbound.

The variety of companies, the company size, their appetite for risk, and the ability to take direction and guidance is all over the board. I tell them right away: “I’m not commissioned. I’m here to put in a stack that will keep your company successful.”

[11:39] So tell me more about the current environment you’re working in.

We have a very strange structure after all the mergers and acquisitions that have been done. There’s a corporate environment with operating companies underneath operating companies.

[13:09] How many different TMS or mobile communication systems are you dealing with?

We have three different TMS we deal with, the main one being the Cloud. It’s a good platform, there’s just a lot of single points of failure that restrict implementing anything yourself. It’s not the most nimble and adaptable, but it does what it needs to do.

[16:25] I noticed one of the things inside of your experience was data centers. How many of those are a data center versus a closet? Have you developed any methodology around this?

I like to set groundwork right away. What’s the tech stack? What’s currently going on? I’ll do my homework to get a default list of items for network gear, routers, and firewalls, and what our standards are. An acquisition is one of the easiest times to scrap things that don’t need to exist anymore.

[21:57] What are your thoughts on hiring very skilled individuals versus training up from within an organization?

I don’t think of anything in black and white; everything is a shade of grey to me. I will hire outside talent when the need dictates. I will also pull in talent from places I’ve worked in the past and have relationships with already.

[26:36] Where do you get your security news?

Quite a few different sources. I get up at 4:30 in the morning and listen to podcasts. It’s not uncommon for me to listen to podcasts while I walk slowly on the treadmill and fire off some emails.

[30:56] What are some tips or tricks you’ve learned over time to deal with silos?

Ask 100 IT people in the room how they feel about their work-life balance. Having most people be happy with their balance is unusual. My goal is to find the common cause and help them work more regular hours through documentation.

[40:47] What’s the part of your work you struggle with the most?

This comes more from my personality than anything else. I’m kind of fatalistic in that I believe what’s going to happen is what’s going to happen. Laying the groundwork and framework for change, whether it impacts them or not, is difficult for me.

[46:26] What’s your most memorable helpdesk moment?

Sadly, I was never proactive enough to save any great tickets or emails that have happened, but I do have one. I was in manufacturing—the largest manufacturing plant in North America at the time. So, someone’s mouse wasn’t working, and I recommended they plug it back in. This person was frustrated and wanted me to come out and look at it. The mouse clearly had a cable that was not plugged into the machine.

[51:43] Do you have any personal things going on that you want to share?

I’ve always been huge into helping upcoming talent and removing obstacles in the industry for the next group of people who come through. If you want to reach out for guidance or mentorship, feel free to message me on LinkedIn.

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