Loving People Out

© Pete Longworth

© Pete Longworth

Today is hard. Today, Maria—an extremely valuable member of my executive team—leaves my company. I'm writing about it because we don't talk about the hard days in leadership as often as we should. And we should. So, here's what's going through my head today. I hope it helps.

Big hugs to any of you who are out there having a hard day as well.

I used to get this gut-wrenching feeling every time I found someone's resignation notice in my inbox.

I'd beat myself up. "I must be a terrible leader," I'd think. "My company will never be able to compete." It didn't feel fair. Here I was with this dinky cleaning company. I couldn't offer competitive wages, I couldn't offer glamorous job titles, and I couldn't even afford to have snacks in our office. Every time someone quit on me it was just another reminder of my fear: that everyone in my company would eventually leave me, and I'd be left to run it all alone.

Now, it’s not always a tragedy when someone wants to leave an organization. We’ve all known people who should leave: people who don't embody the values, who abuse trust, who do unethical things, who hurt others—those people need to go. And fast. The people I was afraid of losing were the wonderful people. The ones who had incredible strengths and made valuable contributions. I wanted to keep those people forever.

But here's what I know now, after running this company of mine for more than a decade: People move on. Even when you treat them like gold. Even when you truly care about them and they truly care about you. Even when your organization has a clearly defined purpose that inspires people. Even when you can finally afford the salaries, the bonuses, and the glamorous titles. Not everyone will, but some will. And there's nothing you can do to stop them.

Nor should you.

Adding to their compensation packages and promising them more in their roles just to convince them to stay is wrong and selfish. I'm not going to lie: I've done that. But now, when someone decides they are ready to move on, I let them. We have to let them. And we must send them off with love, not resentment. Leaders don't clip wings. They help people get their wings and then stand back when they're ready to use them.

But here's the good news: You can make this whole moving-on thing easier.

Once, during an executive team retreat, I gave everyone a blank piece of paper and asked them to pick a date at least three years down the road. Then, I asked them to describe what they thought their lives would look like then. What job did they have? What kind of impact were they having on the world? Where did they live? How much money were they making? Were they married? Did they have kids?

Then I told them it was perfectly okay if Student Maid wasn’t anywhere on that paper. A few people looked up in surprise because they had never heard me say that before. They were used to the Kristen who would go to the ends of the earth to keep someone she loved at our company.

Some wrote in detail and others wrote only a few sentences, but when everyone was finished, we went around the room and shared. At first it was a little uncomfortable. These were plans that would affect the entire team, and no one wanted to come across as selfish. But after some hesitation, each person spoke up. One shared that she wanted to move to Portland to be closer to her family, but she didn’t want to leave Student Maid; she hoped to be able to keep her position and work remotely after she moved. A few said confidently that they wanted to be at Student Maid for the long haul. But then, one said she planned to move in a year to start a life somewhere else with her boyfriend.

Someone telling me they wanted to move on from the company—especially someone in a leadership position—used to terrify me. But now, it was inspiring to see what everyone wanted for their lives. I loved being able to talk about our individual futures as a team, and it made us promise to hold each other accountable to the dreams that were important to us.  From a business standpoint, now that I knew there were people who wanted to explore other options or work remotely one day, I had time to prepare for that.

That conversation (and the ones we've had since then) created an environment where people feel comfortable openly expressing their wants and desires for their lives. Which brings us to Maria.

A year ago, Maria came forward and said that she wanted to move to a different city and explore other job opportunities. She said she loves us and she loves our company, but she was ready to learn and grow somewhere else, especially because Student Maid was the only place she'd ever worked. We decided on her final day and had an entire year to prepare for her departure, ensuring the smoothest transition possible.

I realize that giving a 365-day-notice isn't the norm. But if we can get better at asking our people about their futures and help them feel comfortable sharing their personal goals with us, we can make goodbyes easier to plan for.

So, if you're like me and goodbyes are hard, here's what I want you to remember the next time you have to send someone off: A leader's success isn’t just determined by the people who are still sticking around. It’s also determined by the people who felt free to leave even better for having worked with you.

Big Hugs,