Strategic Leadership in Baseball (and in the Delivery Room)
On the day Big Time was born, Erin asked me why we weren’t taking the most direct route to the hospital. I told her it was because I wanted to stop by my favorite coffee shop on the way. She thought that was a ridiculous idea.
To avoid a huge fight about it, I gave in and skipped the coffee shop.
But before you judge my plan too harshly, consider that there was no active labor, we totally made it by the appointed 7 am arrival time, and my coffee shop had online ordering, which meant the stop would have only taken a minute.
Besides, if you’re showing up anywhere at 7 am and want to be as alert as possible, coffee must be part of the plan. Essentially, the coffee stop was a selfless investment in being a good partner for the birth process. 😁
Ever since then, whenever I find a story of another father’s comparatively worse behavior, I send it to Erin to bolster my argument that the coffee stop wasn’t that bad. This week, ESPN helped me by running an article titled “MLB trade deadline 2025: GMs tell their best trade stories,” which included a story about how former Tampa Bay Rays executive Andrew Friedman conducted an entire trade in the delivery room.
His colleague at the time said, “We went back and looked at the time stamp of when he had sent texts and when the baby was born…. It was minutes apart. So we asked him what was going on in there? He said she was kind of propped up, and behind her head, he was texting stuff about the trade.”
Judge my commuting strategy all you want, but at least I was 100% focused during the delivery itself! :)
I was also struck by how another anecdote from the article—this one about White Sox general manager Chris Getz—reflects many of the strategic leadership practices I’ve written about these past weeks.
“[W]hen his uncle died during the offseason, Getz made sure to attend the funeral and even was asked to be a pallbearer. But on the day of the proceedings, the White Sox top decision-maker’s phone was buzzing. ‘There’s a GM out there who if there is interest, he doesn't stop calling,’ Getz recalled. ‘So I told him my uncle had passed away and I have his funeral, but don’t worry, we’re going to do the deal.”
During the funeral, the other general manager kept calling. Getz said, “It wasn’t actually ringing when I was carrying the casket, but it was close enough.”
The Getz story is an example of how potentially critical and urgent business decisions can come at inconvenient times. But when you’ve protected time for strategic reflection (practice #1 and practice #2), you’re much more likely to have a framework to help you know how to approach it, rather than flying by the seat of your pants.
If you’ve implemented continuous learning routines (practice #3), you’re likely to know already what your customers and stakeholders would think of your potential decision. That enables you to make decisions quickly and with confidence.
If you’ve aligned the team on the strategy and given them tools to make great strategic decisions (practice #4), you’re able to empower them to take action, even if you’re temporarily absent—whether at a funeral, in the hospital, or simply out of cell phone range.
If you’ve invested in building strong relationships and understand power in your organization (practice #5), you’re less likely to end up like former Baltimore Orioles general manager Jim Duquette whose team spent “16-hour days” working on a big trade and crafting an “elaborate presentation” to convince the team’s owner, only to have the owner reject the idea at the last minute without explanation.
And if you’re proactively managing your energy (practice #6), you’re more likely to tell whether the opportunity or problem in front of you is even worth working overtime for, and more likely to have the energy reserves to do so when necessary.
In the book, the practices are listed separately, but they’re all related.