What It's Like to Be a First-Time CIO

Day One: Locked Doors, Missed Connections
I showed up for my first day of work at my new office in downtown Manhattan at 7:30 in the morning carrying a box filled with family photos, framed college degrees, certificates, awards and code samples. I reported for duty wearing jeans and a Pink Floyd T-shirt. Not exactly how I envisioned my first day as a CIO, but I had arrived in New York late the night before with my wife, two kids, dog, cat and luggage, and I simply didn't have time to unpack my power suit.

The Innovation Ads office was previously used as the set for the fictional Mode magazine office featured on the sitcom Ugly Betty. I stepped off the elevator on the 21st floor, but the door to the hip, brightly colored office was locked. I was the first one there, and since I didn't have a key, I couldn't get in. A few minutes later, a stylishly dressed employee showed up. I introduced myself to him as the new CIO and asked him if we could get into the office. He pulled a credit card from his wallet, slid it between the door jam and the bolt, and opened the door. Note to self, I thought, Improve security on office doors.

I located my sleek corner office, put my stuff down and went to find my boss, Iain Grae, the president and cofounder of Innovation Ads. He wasn't in his office so I tried calling him. No answer. I later learned that he was in Europe.

Iain and I first met and became good friends when we were students at Florida Atlantic University in the late 1990s. In 2005, he offered me the CIO job at Innovation Ads, but my career at Corporate Express was going very well, and a move to New York simply wasn't feasible for me at the time. (I was living and working in Florida.) Iain and I stayed in touch, and two years later he asked me again to join Innovation Ads. The timing was much better for me and my family. I had just finished a big project at Corporate Express and was ready for a change. And Innovation Ads was in a much stronger position when Iain approached me in 2007.

I wandered back to my office and just sat there, not quite sure of what to do. I knew I was expected to be a contributing member of the team on day one. Yet I had no specific direction. Was there something I should be doing on that first day? Were we in the middle of a project? It was definitely a little disconcerting and very different from my previous experience at Corporate Express. Each time I moved into a new position there, I spent the first week moving into my new office, getting my stuff together and meeting new staff. I could ease into it. But here there was no ramp-up time. The first day I walked in, it was as the CIO.

By 9 o'clock the five members of the IT staff started showing up. They stared at me through the windows surrounding my office as if I were a fish in an aquarium, and I peered back at them with uncertainty. After 15 minutes I said to myself, This is ridiculous, and I went out and introduced myself to them. I told them about my background and about my extensive programming experience. They looked at me like I was full of it. In essence, they told me: "Everyone who comes in here tells us they know systems and development." I asked them about their jobs and about the company. I was just trying to get the lay of the land.

It was an interesting first day, for sure. I felt like a boxer who had survived round one against a world heavyweight champion: I didn't win. I didn't knock down the champ, but I didn't lose or get knocked out either. I was relieved I got through day one without any major issues.

Next: Facing Down Loneliness, Fear, Frustration and Self-Doubt
Facing Down Loneliness, Fear, Frustration and Self-Doubt
My first week on the job was frustrating. I didn't know any of the staff. I didn't know any of the vendors. I didn't know the interactive marketing industry or its terminology.
At Corporate Express, when someone talked about delivery problems or FIFO and LIFO costing, I could speak that language. At Innovation Ads, everyone was talking about campaigns, enrollment management and lead generation. I didn't know what they were talking about. People were giving me projects, saying, "We need this client to be able to do a co-reg, but they're also driving an affiliate network." I was scribbling down notes but I had no idea what they were asking me to do. That was scary.

There were times when I wondered, Oh my god, what if I make things worse? What if I can't do this job? I imagined the core system crashing for five days and the company losing $10 million. What would I do? I didn't know who my go-to people were. I didn't know if my staff was going to accomplish what I needed them to accomplish.

In my previous role, I had a lot of people I could ask for advice. I had known them for a decade, and they were always happy to talk things out with me. Here, I had no one to ask. I had to rely on myself and do what I thought was right.