The Performance of Vulnerability
My heels leave the plush, patterned carpet of the ‘Grand Oaks Ballroom’ and for a split second, I am weightless, a human sacrifice to the gods of Corporate Alignment. The air in the room smells of expensive eucalyptus and the desperation of 12 middle managers trying to remember if they actually like each other. Jeff from Sales is supposed to catch me. Jeff, who hasn’t met a quarterly target since 2022, is currently my sole tether to a world where I don’t end up with a concussion. This is the ‘Strategy Summit,’ a 2-day marathon of performative vulnerability and expensive catering that has, thus far, successfully avoided mentioning that our flagship product is currently hemorrhaging users at a rate of 32 percent per month.
We are here because the CEO read a book about ‘radical candor’ on a flight to Zurich and decided that the only thing standing between us and market dominance was a lack of scenic vistas and artisan sourdough. So, here we are, $50,002 deep into a retreat that feels less like a strategic pivot and more like a high-stakes field trip for adults who forgot how to talk to each other without using the word ‘bandwidth.’
[The expensive ritual of the offsite is an avoidance tactic disguised as progress.]
Owen L.-A., our digital archaeologist, is leaning against a mahogany pillar in the corner, his eyes tracing the trajectory of my fall with the clinical boredom of someone who has seen civilizations crumble under the weight of their own euphemisms. Owen doesn’t participate in the trust falls. He spends his time digging through the ruins of our Jira tickets and internal Slack logs, piecing together the story of how we got here. He’s the one who pointed out that we spent 42 hours last month debating the hex code of a button while the checkout flow was fundamentally broken for 72 percent of our mobile users. To Owen, this offsite isn’t a strategy session; it’s a burial rite.
The Pull vs. Push Metaphor
I think back to earlier this morning when I walked toward the heavy glass doors of the resort’s breakfast wing. I pushed with all my might, my shoulder colliding with the frame, only to realize the handle clearly said ‘Pull.’ It was a small, stupid moment, but it felt like a metaphor for our entire organizational culture. We are pushing with everything we have against a door that only opens if we stop, look, and change our fundamental approach. We are trying to force growth through sheer, uncoordinated exertion, ignoring the signs right in front of our faces because we’re too busy performing the act of ‘moving forward.’
Strategy, in its realest form, is about making difficult choices. It’s about saying ‘no’ to 92 ideas so you can say ‘yes’ to the 2 that actually matter. But offsites aren’t built for ‘no.’ They are built for the ‘yes-and’ of corporate improv. We add more layers, more initiatives, more complexity, until the strategy is a 112-slide deck that no one will ever read again after we check out of this resort.
The Strategy Choice: Push vs. Pull
Slides Created
Ideas That Matter
The Digital Archaeologist’s View
Owen L.-A. once told me that most corporate data is just a ghost story we tell ourselves to feel less alone in the dark. He’s spent 12 years looking at the digital footprints of failure. He knows that when a company stops talking about its product and starts talking about its ‘vibe,’ the end is usually 2 years away. He watched me fail to catch Jeff’s eye during the ‘Vulnerability Circle’ and later whispered to me that we are effectively rearranging the deck chairs on a cruise ship that has already hit the iceberg, but at least the chairs are ergonomically designed and the gin is top-shelf.
“Most corporate data is just a ghost story we tell ourselves to feel less alone in the dark.
[Real strategy requires the political risk of being the loudest voice of dissent in a room full of consensus.]
Why do we do it? Why do we spend $52,222 on a weekend that leaves us with nothing but a hangover and a framed piece of cardstock with a meaningless slogan? Because it’s easier than the alternative. The alternative is sitting in a cramped conference room back at the office and admitting that the project we spent 22 months on is a failure. It’s admitting that the leadership team is out of touch with the customers. It’s having the conversation where someone might actually get their feelings hurt, or worse, lose their status.
We crave the performative because it feels like progress without the pain of actual change. We want the transformation without the trauma of the ‘death’ part of the cycle. But you can’t have a rebirth without something dying first. In our case, what needs to die is the idea that we can solve structural problems with a change of scenery. We don’t need a resort; we need a mirror. We need to look at the fact that our 2 main competitors are out-innovating us while we’re busy learning how to make artisanal pizza in a team-building exercise.
The Prosperity Paradox
I remember a specific moment in 2022 when our team was smaller. We were 12 people in a basement, and we didn’t have a mission statement. We had a problem, and we had 2 weeks to fix it or we’d run out of money. There were no trust falls. It was the most productive 12 days of my career. We weren’t worried about ‘alignment’ because we were all looking at the same cliff’s edge. Now, with our $522,000 marketing budget and our ‘Culture Vanguards,’ we’ve lost the ability to see the cliff because we’re too busy admiring the view from the balcony.
Owen L.-A. calls this ‘The Prosperity Paradox.’ The more resources a company has, the more it can afford to insulate itself from reality. Small companies can’t afford $50,002 offsites, so they have to settle for the truth. Large companies can buy their way into a comfortable delusion for at least 2 or 32 fiscal quarters before the math finally catches up with them. Owen is currently cataloging the artifacts of our current delusion: the 222 colorful sticky notes that represent ‘our shared future,’ which will likely be thrown in the trash by the cleaning crew at 2 AM.
[Comfort is the enemy of clarity.]
The Final Shuttle Ride
I catch Owen’s eye as we head toward the shuttle. He gives a small, almost imperceptible shake of his head. He’s already thinking about the next dig, the next set of ruins he’ll have to sift through when this particular civilization finally runs out of eucalyptus-scented air. I walk toward the bus, reach for the handle, and this time, I remember to PULL.
