How I Work. An Interview with our CEO, Greg Henson

Henson Group, in addition to funding migrations to Azure, is Microsoft’s #1 CSP and Azure Expert MSP.  Today, we talked to our Chief Awesome Officer and CEO, about his career, his daily schedule, why he wakes up at 4:30, and how he gets his work done.

Greg Henson Interview
Picture: Greg Henson, CEO of Henson Group in his office on the 85th Fl, 1 World Trade Center, NYC


Current Gig: CEO at Henson Group

Current Computers: 15” Surface Laptop 3, Surface Studio 2, and Surface Go

Current Mobile Device: iPhone 11 Pro

One word that best describes how you work: Kaizen

First of all, tell us a little about your background and how you got to where you are today.

Growing up with just my Mom, I had to begin early to find ways to “earn my keep.” Mowing lawns, shoveling driveways, raking leaves, and newspaper routes progressed to painting houses, all small sort of one-man type of shop businesses.

All that ended in 1996 when I graduated Baylor University and went right to work for Perot Systems after which I moved to Microsoft, working for Microsoft Consulting Services in New York. It made sense to me to start in Corporate America so I could gain experience in how large corporations work in terms of processes, procedures and all that stuff you can’t learn if you’re not in a big organization.

Then 9/11 happened and the attack on the World Trade Center took almost 3,000 lives but impacted so many others. Tens or hundreds of thousands lost their friends and family members, their jobs, along with their sense of security.

Many of the companies that went out of business in the aftermath of the attack included Microsoft Partners, some of them very large firms that supported many of the large banks, financial services firms, and other major corporations whose operations were halted when the towers fell.

My reaction to the disaster was somewhat counter-intuitive. Certainly I saw it as the forest fire it was, burning out of control, resulting in business failure after failure. But after the hard work of building alternate data center facilities and getting all the displaced tenants back into operation, it occurred to me that this forest fire had cleared much out, giving smaller firms, “little trees” if you will, a chance to grow and get some traction. Following the strategy of the investor who buys right after a crash confident that the market will recover, I chose this moment in time, in 2002, to start my own IT services organization, The Henson Group.

For the first nine months The Henson Group was a group of one, with me providing all the consulting services himself until I could produce sufficient revenue to hire a full-time employee, then another and another.

We just turned 18 years old, The Henson Group today employs a team of over 200 employees and associates located worldwide.

Take us through a recent workday.

One goal of someone who leads a business like mine is to always be a living reflection of the company. Running a global company requires something approaching “non-stop” energy. I’m big on “early to bed and early to rise,” My day starts around 4:30am eastern US time with a cup of green tea, no coffee, no breakfast, and a beeline to my laptop to see what’s happening in our European, African, and Middle East operations including India.

After 45 minutes I still have about two hours before the rest of the US starts working and emailing. I use this time to plan out the important tasks which must be accomplished that day with a tacit target number of no more than ten major tasks in any given day. I’ve come to recognize if I get 10 things done per day that are on that urgent list, that’s a good day.

Trying to be realistic, I try hard to delegate at least 20{1f0cc4060f4fe9fc982bbd4bbe2778698630254e28c6e7cd32c637f8f4aaee17} of these tasks to my “generals” recognizing that the time I spend showing them how to do certain things will pay back every time that task comes up again.

I’ve learned that for me, it’s important to put something I don’t like followed by something I do like.  So, for example, if I have to work in a marketing campaign, that’s something I do like, so I’ll put that as number one and then I’ll put maybe, you know, a pipeline review or some analytical something after that. It motivates me to get to the thing I don’t like knowing that there’s something I do like coming up.

A Day in That Life continued

As the New York “working day” begins, I’ll walk from midtown down toward the Henson Group office at the new One World Trade, sometimes stopping at 14th Street to take the subway for the rest of the trip.

I’m not listening to any music. I’m just thinking about the day to come. Any sort of urgent issues or situations that need my attention. The sights and sounds of the city and my fellow New Yorkers helps to clear my head, so it’s an enjoyable journey.

It’s not just a time to think about work, but also reflect on my family, my kids, my wife, where I’m going, you know, in my balance, all the sort of questions that are good to ask every now and then. The time from arrival at the office until the end of the business day is simply consumed by back-to-back calls or meetings.


On Work/Life Balance

I try to get out of the office by 5:30pm. Back to my apartment, my wife and I most often cook a nice dinner together. We find that relaxing, and also bond building. We have a nice dinner, maybe watch a little TV.

The workday isn’t over, though, as Australia, New Zealand and other countries are coming online on the other side of the world around 8pm. Its time to work with those managers and teams until about 10pm when it’s time to end the day and get ready to begin again.

Henson on The Henson Group

The core leadership team of people that run the different areas of the company already from legal to accounting to marketing to sales, human resources, those are the people I really rely on. They’re very competent in what they they’re doing. They’re very experienced, they have a lot of knowledge and so I sleep well at night knowing that I don’t need to worry.  I always look at it like I work for my employees. They don’t work for me.

That includes supplementing areas in which my team may have less experience. Some of them don’t have a lot of P&L experience or budgeting experience, so there’s different ways to groom them. So, it’s all about giving them that experience, which will help them here as well as in their next job.

While the management team is my primary interface, I always make it a point to call people from every level of the group to get their input on how things are going. Their perspective is often closer to the customer and the reality of what they face each day, providing a balanced view of the company from top to bottom.


Taking a Break

How does a “type A” high-energy leader like my take a break? It’s important to take time for myself. To do things that I enjoy some of the things that I do, obviously reading, I really enjoy reading. Business books. Maybe the best advice I’ve ever received from reading is best expressed in the phrase “let go or be dragged.”

All of us experience pain in our life. Whether it’s business, family, people that have really hurt me in unimaginable ways. People can hold on to that pain and really grovel over it and it really makes them bitter and sour. That’s the holding on and being dragged, right? And some people just say, I forgive you. Not because not for you, but for me. Let go of that pain. Heal that wound. It helps improve your view on the world.

What is Kaizen

I’m hyper-focused on the Japanese term I started this article with, called Kaizen.  It means continual improvement. I’m actually half Asian, really turned on to that word, and really believe in that.

After 18 years in business, our biggest growth really started in the past three to four years. The company is now considered a high growth company achieving three times revenue growth year over year, over and over again. With that, comes a ton of chaos and unmanageability. The problem I’m always trying to solve is, based on where we are in what cash we have, how do we reduce the chaos and reduce the unmanageability through automation, whether it’s through contracts or through migration.

For core operations and departments, I’m constantly working to figure out how to improve efficiencies, which ultimately boils down to finding a better way to do, well, everything.

“Also, underlying that is the human emotion element of a company and understanding that having your finger on the pulse of what people are thinking, what you are saying, how they’re reacting. You really can’t rely on systems and surveys and policies to think that people are happy and things are going great. You really need to talk to the people. They don’t teach you that in business school. They teach you to look at the KPIs, the HR surveys and that’s all good. They don’t tell you to talk to the folks and do one-on-ones with people that are four levels down below you. Emotions are inaccurate science.

What makes it exciting is that there’s “never a goal line.” Everything is always evolving, moving, changing. A system implemented today may be outdated and outgrown in just a few short months. You have to constantly be improving everything.


Listen to Henson Group’s CEO Greg Henson speak at MS Ready with Microsoft Corporate Vice President, Gavriella Schuster and iSolved IT Director, Chad Young.