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Feb 9, 2023 12:00:00 AM7 min read

Shocking Stories from the Technology Trenches

In almost ten years of technology sales, I’ve encountered several unique situations, and stories have begun to pile up. I love listening to stories, and I also enjoy telling stories. I feel like I learn more when I visualize a situation, and stories help me do just that.  

I’d like to share four stories that may help demonstrate why it’s better for a small to mid-size company to outsource some of its IT, instead of relying solely on in-house IT.  

A Phone Call  

He called me in a panic. "I need you to come out and meet with us as soon as possible. Our IT Manager just put in his two-week notice!" The call was from the CEO of a midsize, but very profitable company that services the healthcare industry. Several months prior to that phone call, I had met with the CFO of the company, but I had not yet met the CEO.  

In any initial meeting, I typically ask, "Why did you take this meeting?" I had done that at that meeting as well, and the CFO had informed me that their in-house IT Manager might be retiring "sometime in the future", so the company was contemplating the strategic direction of outsourcing their IT. After that meeting, he suggested that I stay in contact with him, and asked that I follow up with him the following year.    

Neither the CFO nor the CEO of the company was prepared for the curveball that the IT Manager sent them when he put in his notice two years ahead of schedule.  

A Health Scare  

One time, a friend of mine recommended that I call the CFO of a multi-location home healthcare company, to introduce myself and see if I could do anything for her. In my initial call, I said, “We don’t know each other, but I’m a friend of (we’ll call him “Sam”). He said it may be good for me to introduce myself to you. I work for a company that specializes in an outsourced IT model where we essentially become your IT department. If that’s something you’re interested in discussing, I’d love to talk.”  

The CFO said, “This call is nothing short of divine intervention.” I remember those words, “divine intervention.” Most people don’t throw that phrase around lightly, so I asked about what was going on with the company that would make her feel like my phone call came at the perfect time.  

Apparently, their Director of IT had been hospitalized that day. Unfortunately, he was incapacitated and unable to speak. Although the practice had grown rapidly, they were completely dependent on that one person for all their technology needs. He literally had “the keys to the kingdom.” They could not even pay payroll without him. Needless to say, they were in a bind.  

An Odd Request  

On a cold Thursday morning, in the Fall of one year, I woke up early, checked my calendar, and saw that I had a networking event planned. Someone from HCA was going to speak on the campus of Lipscomb University at 7:00 am, and the topic was on “Big Data.”  

My body moved in slow motion as I got into my car and thought, “Well, at least they’ll have coffee at the event.” I was running late, and I thought, “I’ll listen to the topic, but I don’t have much gas in the tank for conversations.” If I can just chat with one person, that will be completely fine with me.  

During the event, I noticed that there was a man at my table drawing charts, graphs, circles, diagrams, and pictures while listening to the speaker. I quickly moved my attention away from the speaker in front of me and over to my right, casually glancing at what this man was doing without trying to draw a lot of attention to my innocent but curious spying. He was taking notes on the topic, but in a way I’ve never seen before.  

When the meeting ended, I said, “You have to tell me what you were just doing. I’ve never seen that before.” “It’s called ‘Mind Mapping,’” he said. “I learned it in college and have been doing it ever since.” We talked for fifteen to twenty minutes or so, mostly about mind mapping, before I even introduced myself and before we exchanged names.  

After my crash course on mind mapping, I introduced myself and asked what brought him to the meeting. He said, “I’m the CIO of” and named a very well-known company, with locations all over the country, but based out of my hometown, Nashville. I chuckled and said, “Well, you definitely would never want to meet with me. I work for a company that replaces the need for in-house IT at companies your size. Our strategic play would be to take over the need for your role.” 

I was simply being honest with a person I had just met, but when his head tilted sideways, and he expressed interest, I was taken aback. He said that he wanted to meet with me because IT had been assigned to him several years ago when leadership realized that he could “fix a computer,” but his real passion was the business side of the company. He said, “I would love to outsource my function! Can we meet?”  

A Cyber Attack  

I recently received a request to meet with the COO of a fast-growing, West Coast firm that had just encountered a cyber-attack. The company had 100-200 users when we met, and they have quickly grown to about a thousand employees in about three years. 

When you experience that type of growth, there is an enormous need for technical expertise, guidance, and wisdom. Because of the firm’s rapid growth, everything related to technology had been dumped onto this one person’s lap. She was in charge of IT, administration, operations, and about five other important strategic parts of the business.  

And, then one of the leaders in the company was phished, and a ransom was demanded. A police report and insurance claim had to be filed, and lots of boxes had to be checked, just to put this incident behind this fast-growing company. But, it was also time for leadership to have a “gut check” and think through its overall technology strategy.  


In each of these four stories, the leaders decided to work with me and outsource some, or all, of their IT needs.   

There is a risk in keeping all of your IT in-house.  

One of the risks is that your people may leave you. IT people, affectionately known as "Geeks", get bored easily. They are smart. They are intelligent. They thrive on challenges. They want new obstacles to overcome. They like to be able to "create their world" and then move on. In addition to that, they may get sick. They may retire. They may leave you. And, they may leave you earlier than you expect. Even if you think you are prepared for this, you may not be.  

Instead of relying solely on one IT Director, you can work with Provisions Group to outsource, insource, or even “rightsource” your technology needs.  

Our program gives you pre-planned, budget-controlled, just-in-time access to exactly the skills you need fractionally. Whether you spend $2,500 per month, $5000 per month, or $10,000 per month, you have access to all of our teams of domestic Sr. level engineering and architecture experts as you need them. gives you an easy way to spread your money, monitor the spending, control or flex the amount, and expand your Engineering and Architecture capabilities without hiring an army of new hires (who will require more money than your existing team). This is a smart approach vs. overhiring, wrong hiring, overpaying, and then having to lay people off. When you actually need to hire FTEs, ConciergeIT also provides discounted recruiting fees to our seasoned team of in-house tech recruiters. 

Trust your IT to Provisions Group, you get a team of over 200 IT professionals who love what they do and won’t leave you vulnerable to turnover issues or cyber-attacks.  

About the Author 

Stuart Cooper is a Client Development Director for Provisions Group, a privately-owned technology company and one of the top 5 largest tech companies in Nashville. Stuart has over 23 years of sales experience, including almost a decade in technology sales. He has an Executive MBA from the Haslam College of Business at the University of Tennessee and a Bachelor’s Degree in Speech Communications from the University of Tennessee. Stuart lives and works in the greater Nashville, TN area. He has been married to his college sweetheart, Jenny, throughout his entire career, and they have 4 wonderful children.