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  • Writer's pictureNick Caldwell

The toughest challenge for leaders of rapidly growing teams

I get asked a lot, “what’s the biggest challenge for leaders that need to rapidly grow a team?” You may think it’s hiring, strategy, org structure, or new processes. Yes those are tough, but here’s quick story from my past that may give another perspective.

There was a time, early in my career, when I was managing a small eight-person team at Microsoft. I knew every person on the team incredibly well and we worked together on machine learning/NLP projects that we were all intensely passionate about. It was absolutely the most connected I’ve ever felt as a manager.

But I’d been at that job for years and had gotten too comfortable. I knew that to grow I had to do something different however I wasn’t sure which direction to go. I needed advice.

It just so happened, that the Senior Vice President of Microsoft’s Business Division had recently moved into our building. His name was Kurt and he had a huge office on the top floor, where he oversaw an organization with thousands of people and several billion-dollar products like Word and PowerPoint. I decided that I was going to meet Kurt.

Of course, as an SVP he was six levels higher in the org chart than me and his time was well-protected by his executive staff. According to his assistant, Kurt wouldn’t have free time on his calendar for weeks. However, I knew his office number and fortune favors the bold. One afternoon I parked myself just down the hall from Kurt’s door and waited for an opportunity.

Eventually, I saw that Kurt was free and the door was left wide open. I’d brought a manila folder stuffed with enough paper print-outs to look like serious business. Gripping that folder and walking with the all the urgency I could muster, I zipped right past Kurt’s executive assistant and into the office.

“Hi Kurt, can I take 15 minutes of your time for some advice?” Surprisingly, he popped up from his desk and immediately welcomed me in. We ended up talking for an hour and thirty minutes about Microsoft, leadership, a new opportunity, and more.

Although I don’t remember all the details of our chat, one moment has always stuck in my mind. At the end of the conversation I was feeling very bold. I asked candidly, “So, what exactly do executives do all day?

Kurt nodded at the question, got up, and motioned me over to his computer monitor. He wiggled the mouse and an Excel spreadsheet filled the entire screen. He said, deadpan, “I change the numbers in this spreadsheet.

I laughed out loud, thinking he was kidding, but Kurt didn’t crack a smile. He zoomed into the spreadsheet to show me more detail. It was a list of all the product teams in his organization, with numbers next to them, and notes. The notes briefly described each team’s mission for the quarter. And the numbers were things like total budget, potential revenue, team size, and other resources. If he changed one number, like budget, then the other numbers got recalculated instantly.

“I think about the strategy of our business all day. I collect advice from my leaders. I look at our metrics. And then I change this spreadsheet.”

Then he added, “You may not believe me, but the hardest part of my job really isn’t figuring out why we should change these numbers. The hardest part of my job is remembering that changing any of the numbers impacts real people.”

The conversation ended shortly after that. I shook Kurt’s hand, thanked him for the time, and went back to my office on a different floor. My manager and his manager were stunned that I’d gotten the chance to meet the head of the business division. But I remember not being really satisfied.

As an engineering manager who spent hours of each day agonizing over project details and timelines side-by-side with his team, I didn’t believe Kurt’s story that an organization could be managed with a spreadsheet. It felt so impersonal.

Years passed. I got my first director-level job, learned a ton, and kept climbing the corporate ladder. My team got big and I admit that at some point Dunbar’s number struck and I couldn’t recognize most of my employees by name.

One late night I found myself planning how to restructure my organization to take on a new business challenge. I wanted to move 30 people into a new developer platform team. I was looking at this exact spreadsheet:

I realized at that moment Kurt was right.

“What is your biggest leadership challenge?” No matter what level of organization you are at, the answer is going to be the same: people. But there’s a unique challenge that only leaders of large teams will face.

As your team grows your connection to individuals will lessen. It will become easy to think of people as numbers or “resources.” You must resist this mentality.

Always remember that people are the most valuable part of your organization and the best part of being a leader. This holds true at any team size.

One more thing. When you’re running the show and some bright-eyed new engineer on the team works up the courage to knock on your corner-office door and ask for advice, say “yes,” welcome them in, and stay connected.

rock on -nick



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