Remember when we all thought 2020 would be “our year”? Cue hysterical laughter

In the span of what feels like both forever and yesterday, I’ve led teams through a global pandemic (still have the Zoom fatigue to prove it), navigated an acquisition where we all developed eye twitches from stress, and guided two clients through organizational overhauls that resembled those videos where they implode entire buildings. Spoiler alert: leadership during these times looked nothing like the stock photos of people confidently pointing at whiteboards.

Here’s the unfiltered version of what I learned while trying not to visibly panic in front of my team.

1. The Brutal Truth About Transparent Communication

Business books talk about transparency like it’s just sharing information. What they don’t tell you is that real transparency is awkward, messy, and occasionally makes you look like you have no idea what you’re doing (spoiler: sometimes you don’t).

During our acquisition, I started daily 15-minute check-ins, initially thinking I’d have updates to share. What actually happened:

Me, Day 1: “I have some preliminary information about timeline.”
Me, Day 7: “Still waiting on confirmation from legal.”
Me, Day 12: “No updates, but I’m having lunch with the integration lead tomorrow.”
Me, Day 18: shows up with bed head after an all-night emergency meeting “So… things have changed.”

Here’s the plot twist: those “I don’t know yet, but here’s what I’m doing to find out” days actually built MORE trust than days with clear updates. People don’t expect you to be omniscient; they just want to see you’re in the trenches with them.

My most successful transparency hack? The “anxiety acknowledgment” – literally saying, “I know this is causing anxiety, and I feel it too. Here’s how I’m managing mine…” Watching stress visibly melt from people’s faces was worth the momentary vulnerability hangover.

2. The 60% Rule That Saved Our Sanity

When the pandemic hit, we had exactly 11 days to transform our in-person service model to 100% virtual delivery. ELEVEN. DAYS.

I developed what I now call the “60% Rule”: If you have 60% of the information you’d want in an ideal world, and the decision is reversible, MAKE THE DECISION NOW.

This is where I learned that perfectionism is just fear wearing a fancy outfit. Some examples of the 60% rule in action:

• Purchased new tech platforms based on limited trials because waiting meant zero capacity
• Reorganized entire team structures via a napkin sketch that I later found crumpled in my desk drawer
• Approved budget reallocations in text messages at 11pm because morning would be too late

Was every decision perfect? Absolutely not. But the momentum created by decisive action carried us through. When helping a healthcare client restructure, we literally wrote on whiteboards: “Is this decision reversible? If yes, decide TODAY. If no, decide by FRIDAY.” (It was Wednesday. We weren’t monsters.)

3. The Empathy Paradox No One Talks About

Here’s where it gets interesting. During one client’s organizational overhaul, we eliminated several departments that had existed for decades. I watched people who had built careers around specific functions struggle with what felt like professional identity death.

The leadership paradox I wasn’t prepared for: you have to simultaneously honor people’s grief while building enthusiasm for a future they can’t yet envision. And you have to do this while managing your own emotions about the changes.

What saved us wasn’t structured change management (though we did that too). It was the unplanned moments:

• The 30-minute meeting that turned into a 2-hour story-sharing session about the company’s history
• The virtual happy hour where people could vent without judgment
• The “no agenda” coffee chats where the real concerns finally surfaced

I learned to build in what I call “emotional processing time” – deliberately unstructured spaces where people could metabolize change at their own pace. This feels counterintuitive when timelines are tight, but skipping this step is like trying to drive with the parking brake on.

The Leadership Lesson That Changed Everything

The most profound thing I learned through all these pivots wasn’t a strategy or framework. It was this: leadership in chaos isn’t about having a perfect plan—it’s about creating enough psychological safety that people can function amid uncertainty.

In my most honest moments, I realize that what teams needed wasn’t my strategic brilliance (good thing, since that was often in short supply). They needed to know that someone was paying attention, that their concerns mattered, and that we’d figure it out together.

The best compliment I received came from a team member who said: “You didn’t always know what to do, but you never pretended you did when you didn’t. That made all the difference.”

Sometimes I think that’s the whole game right there.

What about you? What’s the most unexpected leadership lesson you’ve learned during times of major change? I’d love to hear your stories in the comments below.

P.S. Yes, I still have my pandemic sourdough starter. No, it’s not the original one. I’ve killed at least three. Leadership lessons don’t always transfer to breadmaking, apparently.