Upstream Academy logo

Episode 127:

The Perils of Waiting to Communicate, and Other Unexpected Lessons

Jeremy Clopton

Description

On the same Saturday his grandmother passed, Jeremy Clopton’s oldest daughter played her first varsity softball game. On this solo episode 127 of The Upstream Leader, Jeremy turns that collision of grief and celebration into a working case study on leadership communication. Jeremy and his wife chose to delay sharing the news until after the game, a decision made with good intentions that still slipped out of their control once family members posted online. That gap between plan and outcome becomes the entry point for a broader lesson: leaders can build the most careful timeline for sharing difficult information and still watch it unravel, which means adaptability matters more than the plan itself. From there, the conversation moves into holding conflicting emotions at once, drawing on all his daughters’ unfiltered reactions to grief and joy, to make an unexpected case for why teams navigating change need room to feel contradiction rather than resolve it immediately.

About the Guest

Upstream Academy logo

Highlights / Transcript

Hello everyone and welcome to The Upstream Leader. My name’s Jeremy Clopton, so glad to be with you here today. We are coming back from the Labor Day holiday here in the U.S. And I don’t have a long episode for you here today, we’re between some of our guest episodes, so you’ve got me for a solo episode. I’ve been going back and forth on what are the topics that I really want to dive into and. It’s one of those situations where sometimes life just kind of happens and you realize there was a really important lesson there, wasn’t there? So I thought today I’ll take a little bit more of a personal note on the show here and it’ll be a fairly short episode. But we recently in the family experienced a loss of a grandparent; my grandma passed away just a couple weeks ago. It was one of those days where you realize despite your best efforts as a leader, in this case, as a parent, you can learn a lot through maybe some things that didn’t go exactly as you planned.

And it was an interesting day in the fact that it started off with the news that my grandma had passed. She’d been sick for quite some time, so it was not completely unexpected, though always challenging as you would expect. It was also the day of my oldest daughter’s first softball game. She’s a freshman playing at the varsity level, had her first game, home opener, all the things, lots of excitement, that got the win, she was pitching, you know, got to go out to dinner with family and friends. And it’s one of those days where you just kind of feel like you are going through a bit of a rollercoaster of emotions.

And in that day there were two lessons that as I was thinking about what I wanted to talk about on the podcast, I realized these are the two lessons that I really need to share: One is all about strategic communication. As I mentioned, the news that I received about my grandma was pretty early in the morning, I want to say it was around four thirty or so, so pretty early in the morning, one of those where you’re kind of up for the day at that point. I had made the decision, you know what, this is incredibly important, and at the same time, simultaneously, the start of the softball season was also important to my daughter specifically. And I’m not looking for parenting advice here. I’m not looking for anybody to come in and judge how I did this. But my wife and I, we made the decision, okay, let’s wait until after the game. We’re going to wait until a little bit later in the afternoon. It was a morning game. My oldest had been quite aware of what was going on, but we said we want her to be able to focus, she’s been working hard toward this, so we waited to communicate.

What I learned about communication is this: No matter how strategic you are, no matter how well-intentioned you may be, at some point, if you continue to wait to communicate, you always run the risk that the communication is taken out of your hands. So what ultimately had happened is we waited to communicate, we’re waiting till after the game, we ended up going to dinner with some family and friends, early dinner after the game, and ultimately family members had posted it online and somebody had mentioned it to my oldest daughter. Like I said, she already kind of knew what was going on, we’d had conversations around it, so she wasn’t necessarily surprised, but it’s one of those moments where you realize, “Man, that didn’t go the way that I wanted.”

It’s not uncommon in leadership for this same thing to happen. We have information that we know is important. We have information that we maybe really want to share. But we also know that timing is critical. We share something too early, it may go awry, if we wait too long, it may not go perfectly. And the leadership lesson is that even if you have the perfect plan, we still have to remain adaptable, we still have to remain flexible, and at times if the information is communicated in a different way, we’ve got to own it. And that’s essentially what happened, is having to say, “Hey, I understand you found out, that is not at all the way we wanted you to hear, but here’s what happened, here’s why we waited.” And it actually led to a very grown-up conversation to be having with a freshman in high school, but it was a very productive conversation. What I learned in that is that as a leader, like I said, best laid plans don’t always go according to plan, and that sometimes we’ve got to own it. We’ve got to step up and say, “You know what? That’s not how I wanted it to happen. I realized my intentions were great, the execution may not have been, and how do we move forward?” You simply own the communication snafu, if you will.

The second thing that jumped out at me as I’ve reflected the last couple weeks was a comment that my youngest daughter made that evening when we were talking about it, and she said at one point she said, “I’ve been so happy, now I’m so sad. Why is this happening?” I’ve got to say, my youngest daughter, my nine-year-old, is very articulate when she is processing emotion, I don’t know if she’s necessarily, maybe articulate is—very verbose, how about that? She likes to talk through things. But when she said that, I remember thinking, “Wow, there is so much wisdom in that comment that she probably doesn’t even realize.” And the leadership lesson there that I realized in that moment is, “You know what? You’re a hundred percent right. You have two very strong emotions that are very contradictory at this moment, and you can actually feel both.” But what she did that was so valuable is then she felt all of the emotion of the sadness she had, felt all of the emotion of the happiness earlier, and then she was able to essentially work through those in a way because she allowed herself to feel both.

And when we think about working with our team members, our colleagues, our peers, there is a lot of change going on in the profession. There are so many times when we’re asking people to change, that they may hold simultaneous emotions that are very contradictory. They may be really excited, but also at the same time, very scared. They may be really angry about something, but at the same time, excited by an opportunity. It is okay for those that we lead, for us as leaders, to feel both of those emotions simultaneously. Where it becomes challenging or perhaps detrimental to us as leaders, is when we try to ignore either, or try to simply just skip past them. Being able to simply slow down and acknowledge in the moment, “Yeah, I’m really excited about this opportunity. There’s this going on in the firm, or whatever it may be, and I’m really excited about that,” and then taking a beat and also saying, “But you know what? I’m also scared about this, this, this, this, and that. I’m not really sure what to expect and I don’t really know how to get that information.” As leaders, we can help our team members by working through both of those so that then after the fact, they can figure out how to move forward.

Like I said, sometimes it’s amazing to me how life serves up these lessons and leadership lessons from nine- and fourteen-year-olds that aren’t trying to teach leadership lessons. I know I sure as heck wasn’t looking for a leadership lesson on that Saturday. I was, like I said, experiencing lots of highs and lows. And I guess the third lesson, now that I think about it as I’ve shared this, is it’s also okay to just want a hug, right? Maybe not in the professional setting, HR might have something to say with that. But sometimes it’s okay just to sit with the emotion and just feel it all, and not have to say anything, not have to talk it out, not have to make a decision, but just take some time to experience it. And that’s the lesson that my twelve-year-old almost always provides. It’s okay just to experience it, to be present with it, not to judge it, not to evaluate it, not to analyze it. Sometimes we just need to sit there and we just need to feel it, whatever that emotion or that experience is teaching us, and just reflect on it.

Like I said, definitely wasn’t looking for leadership lessons on a day like that, but the more time that has passed, the more that I’ve thought about it, the more that time goes on and memories just kind of do what they do and work through your mind, I realized, though it may have been an emotional rollercoaster of a day, there was a lot of value that was provided from the kids in the experience. All three of our daughters taught lessons in their own way. They weren’t looking to teach, but just going through that and seeing the experience definitely provided some interesting insights. So, as I said, this isn’t a normal episode on the show. If this is the first time you’re listening, I would encourage you, obviously, listen to some other episodes as well. We have some great guest episodes in the past, we have some great guest episodes coming up as well. Some solo, and as you know, I’ll occasionally be on with Justin, our producer, bantering back and forth on things. But I thought this is too important of a lesson not to share it. So I hope you’ve enjoyed this episode of The Upstream Leader. I thank you for joining me, and I look forward to talking to you very soon.

Host

Managing Director

Subscription Options