🤔 Dear Lewis, my retreat taught me to be vulnerable. How do I make my team share too?
A VP wants to recreate his transformative retreat experience with his engineering team. Here's why that's a dangerous idea.
Here we are again, my friends, back for another installment where I share the real (but anonymized) stories from my coaching practice. Today’s tale is about good intentions, power dynamics, and why transformative personal experiences don’t always translate to engineering leadership.
“I’ve never felt so connected to other leaders,” Mark told me, eyes bright from his recent executive retreat. As the newly promoted VP of Engineering at a high-growth startup, he was eager to bring back the magic. “We shared our deepest fears, our failures… I want my engineering team to experience this too. We could do it during our next architectural review sprint!”
I couldn’t help but smile. Not because it was funny – but because I’ve seen this movie before, and I knew exactly how it would end if we didn’t rewrite the script. It was time to guide Mark through what I call the SAFE framework, but first, let me share a story that might sound familiar.
A few years ago, I had a client – let’s call him Tom – who tried something similar. He ran a “trust-building” workshop where everyone shared their biggest professional insecurities. During the session, one of his best senior engineers admitted to severe imposter syndrome despite having architected their most successful product. Two months later, during layoffs, guess who got cut first? The same engineer who had opened up about their struggles.
“But I would never use that information against my team!” Mark protested when I shared this story.
“I know you wouldn’t intend to,” I replied. “But let’s work through this together.”
S - Switch Seats
“Quick thought experiment,” I said. “Imagine your CEO asks everyone to share their deepest insecurities in next week’s architecture review…”
Mark shifted uncomfortably in his chair. “That would be… inappropriate.”
“Why?”
“Well, they control our careers and… oh.”
The color drained from his face as the realization hit. “But I’m different from the CEO, right?”
“Are you? Let’s dig deeper.”
A - Analyze Context
We broke down what made the retreat feel safe:
Everyone was a VP from different companies
No one could impact each other’s careers
Anyone could opt out or leave anytime
Relationships were temporary
Professional facilitators created safety
“Now,” I asked, “imagine one of your senior engineers sharing their deepest struggles during your vulnerability exercise. Three months later, you’re picking technical leads for a critical project with a hard deadline…”
“I see where you’re going,” Mark interrupted. “But I can separate personal sharing from professional decisions!”
F - Future Impact
“Let’s play this forward,” I continued. “Sarah, your strongest backend engineer, shares that she struggles with anxiety during high-pressure deployments. Next month, there’s a critical production issue at 2 AM. Who are you going to call first?”
Mark stared into his coffee. “Not Sarah.”
“Even though she might be the most qualified?”
“I’d be trying to protect her…”
“And she knows this. Everyone knows this. Each vulnerability shared becomes a data point that could impact their career. It’s not about your intentions, Mark. It’s about the power dynamic.”
E - Explore Alternatives
“So how do I build the trust and connection I felt at the retreat?”
Now we were asking the right question. Here’s what we developed for Mark’s team:
Create Safety Through Consistency
Regular 1:1s focused on career growth
Clear, documented decision-making processes
Predictable response to mistakes and failures
Enable Optional Vulnerability
Share your own relevant technical struggles after they’re resolved
Create space for post-project retrospectives
Allow team members to opt-in to mentorship roles
Build Trust Through Actions
Protect your team during high-pressure situations
Give credit publicly, give feedback privately
Stand behind technical decisions made by your team
Here’s the truth: The most vulnerable conversation in engineering isn’t about personal traumas – it’s about saying “I don’t know” or “I made a mistake.” Create an environment where those admissions are safe, and you’ll build more trust than any forced sharing exercise ever could.
Two months after implementing these changes, Mark got an unexpected result. During a tense architecture review, his newest engineer felt safe enough to challenge his technical approach – something that had never happened before. “That’s when I realized,” Mark told me, “real trust isn’t about knowing each other’s deepest secrets. It’s about knowing you can be honest without consequences.”
Want to build genuine trust with your engineering team? Start by respecting their boundaries. Create safety through consistency. Let vulnerability emerge naturally. And remember – sometimes the most powerful thing a leader can do is give people space to not share.
Keep striving for greatness,
Lewis C. Lin
Simple, right? Well, not always
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