Staring Myself Down


I was on the elevator heading up to my office on the first day of a new job. “What does the month look like for you?” a fellow passenger asked another, unaware of me. “Hoping the new system is fixed in time for everyone to get paid,” the other retorted with a nervous laugh. Then dead silence. As the new district head of data and technology, I let that sink in. As they got off the floor before mine, I felt an aching in my gut. Sure, every district in which I had led technology previously also had its hidden challenges. But payday? This was going to be a bear of a first day.

This district had launched an ambitious multi-million dollar enterprise business solution, to bring its business systems into the 21st century. And not just any system, but one of the top products in the industry. One that you would expect to find in the corporate offices of a successful company. The strategic goal was to align administrative operations in one system that could identify efficiencies and cost savings. I had no background with this digital solution.

I got to my office characteristically early; no one else was in yet. I sat down with my thoughts racing through my head and that dull aching in my gut. Where do I start? What do I need to know? What do my senior staff colleagues already know? How about the superintendent? Thankfully, I was interrupted by my executive assistant introducing herself, which led to a whirlwind tour of the building with endless introductions. And just when I thought I was catching my breath, word came down that a meeting had been convened for business department heads to meet with me in thirty minutes.

Yup. I walked into a room of a couple of dozen people, all ready to fill me in on the enterprise system implementation challenge. The air was thick with worry and anticipation. I was the guy that was going to clean up the mess. And as intent as the group was to fill me in with measured words, they were also obviously holding back. So as quickly as they tried to describe the situation, I was asking questions in return; taking notes, drawing diagrams, trying to make sense in the moment. It was obvious there were three key staff who had answers I needed. As the meeting concluded, I asked them to meet me in a small conference room, where they offered further detail they didn’t feel comfortable sharing in front of everyone. It’s all about asking the right questions, and it helped. I left them feeling I had a better grasp of the situation. The goal, according to a fellow senior staffer, was to keep this from hitting the front page of the local big city paper. In short, make sure payday happened in a few weeks.

This was the greatest test of my leadership I had ever faced. Could I do this? Was I in over my head? Was it even logistically possible given the time line? I felt duped. Did I have to accept this? I’m sure the district I just left would take me back. I hadn’t even sold my house back there yet It was frightening and exhilarating at the same time. In one interminable moment I stared myself down, and underneath the uncertainty, questions and doubt I found the answer. I didn’t take this job because I thought it was going to be easy. I took it because it was a logical next step professional growth. Yes this was more than I had bargained for, but I was staying and I was doing this.

I got a hold of the vendor who was working with us on the implementation project and I worked hard to learn every word and every requirement of that contract. I sat down with the superintendent and informed him of the situation. He looked gravely concerned and disappointed hearing the news, but it confirmed what he had been afraid of for some time, and he gave me the wherewithal to do whatever I had to do to save the failing project and make sure payday happened. Pulling together facts and figures coupled with whatever expertise, instincts and systems thinking I could summon, I delved into the work.

It was lonely. My immediate colleagues were all bracing and posturing themselves for the worst. And as I drilled down it became apparent that the failure wasn’t the technology but the outdated business practices staff held onto in spite of the consequences. I found the technical expertise I needed, but it was actually my soft skills that would resolve the impending crisis. Functional analyst work, the listening and processing of business needs that must be reconciled with the enterprise system, was the key to getting the job done. And I’m here to tell you, as any tech leader will, that that fight over longstanding business practices was more dug in and difficult than any technical roadblock. Hard coding and troubleshooting is logical and impersonal, unlike getting longtime department heads to talk to each other and come to eventual agreement. But even they didn’t dare stare down the specter of an impending payday not happening…and that was my leverage.

It didn’t get any easier. Every day I ran non-stop, full throttle, and every night I went home feeling I had made small, hard-won gains towards my payday goal. No big breakthroughs; just slow, steady, methodical progress. And while everyone meant well, no one made it easier, in spite of themselves. People threw tantrums. People quit. People played games and made threats. And as I dug deeper and deeper down inside, my resolve strengthened and I knew I could do what was being asked of me. In fact, the longer I stayed the more my sense of ownership grew. No one was going to stop me from acting in the best interests of the organization, no matter what the outcome.

In the end, payday happened without incident. Everyone exhaled and there was a quiet, exhausted sense of relief around central office. There were no congratulatory moments. No high-fives. No celebrations. The only indicator of a successful save is life goes on without interruption or incident. In the months to come my team not only tied up the loose ends and successfully closed out the implementation contract with the vendor, we went on to develop a plan to use the enterprise business solution as a wrap-around for all our instructional systems, creating a single master source for all district data with the ability to reconcile our business practices with instructional ones. Ultimately, we worked to provide accountability for every district dollar spent and its correlation to teaching and learning.

Leadership is not easy. It is fraught with the unknown. And no matter how attractive the next opportunity appears to be, it will present you with surprises for which you may not feel prepared. But that’s when leadership growth happens; when you have to muster up experiences and lessons you’ve learned along the way and apply it in new, unfamiliar contexts. It’s where you stare yourself down, rally your resources and test the mettle of your inner-leader. Not sure you want to sign up for these kind of gut-wrenching, heart-pounding moments? Then maybe leadership is not for you. Because it’s in those moments that your colleagues will see you as a leader they can believe in…that they can trust…that they are willing to follow…even when their paycheck is on the line.

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