When the team’s request for flexibility conflicts with the needs of the business
What do you do when one of your most dedicated employees asks for flexibility during a time when you really need them?
This happened just a few weeks ago.
Let me set the stage:
Monique, our Chief of Growth who I’ve been working with for 12 years, recently asked for some flexibility around attending a team meeting.
The meeting conflicted with an event Monique really wanted to attend that happens only a few times a year. She had missed it in the past because of work, but she was really hoping to attend this year.
Ninety-nine percent of the time, it would be totally okay with me if she skipped a team meeting. We’re a very flexible organization with a four-day workweek and unlimited paid time off, and we give people freedom to focus on their lives outside of work when personal priorities pop up.
But on this particular day, I needed everyone in attendance. It was the meeting right before our Human Leadership Program, a virtual, public event that we host four times a year that brings an audience of anywhere from 200 to 400 people. Our team hops on Zoom before we kick off the program to check for tech issues, go over last-minute changes, and set our intentions so that we can be sure we’re ready to lead the best possible program.
The meeting doesn’t take long, and we often end up with extra time and take a long break before regrouping again, so I totally understand why Monique asked for flexibility. The challenge for me was that for this particular Human Leadership Program, we had hired a videographer to film me behind-the-scenes. Monique is the design guru on our team and had been very involved in making sure that my office would look great on camera, so it was important to me that she was on the call because I wanted her to sign off on the final look. I also wanted her to be available to help answer any questions from the videographer before the program started.
When she made her request, Monique proposed two options: She could either join the meeting from her phone while she attended the event, which meant that she would be multitasking, or, if I didn’t think we’d need her, she could miss the meeting but be back in time to kick off the Human Leadership Program.
I sat with Monique’s request, and for a moment, I struggled with how to handle it. I knew how excited she was about this event and that it was important to her, and I really wanted her to be able to go. At the same time, we had invested a lot of money to hire a videographer, and I wanted Monique’s guidance as we set up for filming.
Monique shared her request via WhatsApp (a way that we often communicate on our team), and after thinking about it for a moment, I wrote her back. I asked that she join the meeting from her phone. Or, if she wanted, she could join late if she thought she could get home from the event before it ended. No matter what, I needed her to be there for the majority of the meeting because of the videographer.
When I made that point, Monique told me that she had completely forgotten about the videographer and she understood why I needed her there. She told me she would be happy to join from her phone, and I was happy that we had found a way to meet both of our needs. She got to do something that was important to her, and I got to make sure that we had our bases covered for the business. When the day came, thank goodness Monique was there: Turns out that we did need her help! But she was still able to do what she wanted to do, and our team had a successful start to the Human Leadership Program.
I share this because I think that balancing the needs of the team with the needs of the organization is one of the toughest challenges for leaders. It’s hard to know how to do it compassionately while successfully navigating the moments when those needs conflict.
For a long time, I struggled with when to allow for flexibility. One of my biggest concerns was fairness: Not everyone’s roles allow for the same amount or type of flexibility. For example, when we had the cleaning business, working from home was not an option for our cleaning team like it was for those who worked in our office. I also worried about setting a precedent. If I said yes to one person, I felt like I had to say yes to everyone so they wouldn’t think I was playing favorites. There were a lot of times when I granted flexibility and it came at a huge cost to the business. I often felt like I was giving everyone else what they needed, but as a result, all of their responsibilities fell to me, which left me feeling resentful.
I don’t think there’s a leadership playbook for how to handle situations like these, but I’ve learned a lot about what not to do over the years. I thought I’d break down my thought process that went into handling this decision with Monique in hopes that it might help you the next time you are faced with a similar dilemma. And by the way, even if you aren’t the leader of a team, I hope that what I share will help you have the best chance for success when you are seeking flexibility. Maybe one day, you’ll need to have a conversation with your leader similar to the one that Monique had with me.
When Monique first made her request, here’s what went on in my brain:
I thought about Monique’s track record: Monique is consistent with her results, and I know I can rely on her. Any time I’ve needed flexibility or support, she’s been there for me, so I wanted to be there for her. I also knew that she wouldn’t make this request unless it was important to her.
I thought about the impact that granting flexibility would have on her: I knew that being able to attend her event would help Monique show up to the Human Leadership Program at her best.
I thought about what the rest of our team and what our business needed: We had done the Human Leadership Program more than 12 times by that point, so I wasn’t worried about Monique having less prep time than usual. But the videographer was an X factor. I knew that I would need Monique’s help and input to make sure the investment was worth it.
I thought about the solutions Monique proposed: Monique proactively thought about how her absence might affect the meeting, and she offered a compromise. In the past, there have been times when people have asked me for flexibility, but it didn’t feel like that person had put any thought into how their actions might affect me, the business, or the rest of our team. I appreciated that Monique did consider those things and that she didn’t give me an ultimatum. She expressed what she wanted to do, asked for my feedback, and was open to a discussion about how we could make this a win for us both.
I thought about the solution that would address both of our needs: Monique going to her event while also calling in for the meeting was a win-win. Both of us would have to compromise a little, but it met both our needs.
I thought about what would happen if it didn’t work out: I knew that Monique and I would have an open conversation if the solution ended up not working out so that we could learn from it.
As leaders, I think it’s really important to offer people flexibility, especially those who have built trust with their results. At the same time, it’s important to make sure that when you offer that flexibility, you aren’t putting the organization—or yourself—in a bad spot. Doing so can lead you to a place of resentment and cause you to feel like everything is falling on you.
Of course, there are times when the business’s needs need to be sacrificed because the person’s needs are greater and become the only priority—and vice versa. When it isn’t a moment like that, though, I believe the best way to approach these decisions is to find a compromise that supports both your people and your organization.
I’m curious . . . have you ever been faced with a dilemma like this one? If so, how did you handle it? Whether you had to choose whether to grant flexibility like I did or ask for it like Monique, I’d love to know. Hit “reply” and tell me more! My team and I would love to know how you’ve navigated these moments.
Big hugs,
