Hey everyone - it’s off-the-grid hiking time for me again, and this is my last post until the second week of September or so. Keep the comments and ideas coming, and I’ll be back to weekly-ish posting in about 3-4 weeks.
Now, it’s story time.
Dana ran a team of eleven people. On a Tuesday in March, three of her best people were shuffled away into a reorg that moved them under a different VP, with no replacements or backfill. At the same time, her team had planned a big update for June that had been promised for months.
In her weekly 1:1 with Sam, one of the engineers who stayed on her team, she opened with a standard line. “We’re doing well and I’m excited about June.” Sam had heard some version of that from her every week since the reorg.
“You know you don’t have to only tell us the good part, or minimize anything,” he said. “We can tell you’re stretched thin. You don’t have to pretend you’re not, just to keep us excited about the launch.”
Dana started to say she wasn’t pretending, then stopped, because that wasn’t quite true either. She’d been giving the team the exciting version in every standup and saving the exhausted version for the drive home, as if the two didn’t belong together. She told Sam that, actually, the last six weeks had been some of the hardest of her career, and she was also more excited about June than almost anything she’d ever worked on. Both things were true.
Sam nodded like that was the answer he’d been waiting for. “That’s the version I believe,” he said.
This story is what I’d like to try and write about today. The two conversations Dana had been having, and how both could be true at the same time.
Two Different Conversations
Most leaders don’t lie to their teams. They often split the truth into two conversations. The hard stuff goes in one conversation, usually the one with a partner or a peer at another company who won’t repeat it. The good stuff goes into another conversation, the one everyone can see, like standups, all hands, and Slack channels. It feels like they’re protecting people from the parts they can’t fix anyway.
I’ve tried this myself, and I’ve found that this is exhausting to maintain, and it doesn’t hold up nearly as well as it seems like it should. People read tone constantly, even when they’re not trying to. Dana’s team didn’t need her to list every detail of the reorg fallout. They just needed her to stop performing something that wasn’t the whole picture. Sam noticed the gap before Dana did, which is usually how this works out. Most of the time it’s easier to see something and name it when you’re not caught up in the middle of it.
The Stockdale Paradox
Jim Collins wrote about this in Good to Great, though he borrowed it from Admiral James Stockdale, who spent seven years as a POW in Vietnam. Collins asked Stockdale how he made it through. Stockdale’s answer became one of the most quoted ideas in leadership writing.
“You must never confuse faith that you will prevail in the end, which you can never afford to lose, with the discipline to confront the most brutal facts of your current reality, whatever they might be.”
Stockdale also noticed something interesting about the prisoners who didn’t make it. The optimists who kept saying they’d be home by Christmas, then Easter, then Christmas again, and eventually died of a broken heart. Blind optimism just doesn’t survive contact with reality, and neither does grim realism without anything to hope for.
Sure, we need to rally the team around big releases and victories, and we also need to be honest about the hard stuff and share it with our teams.
Why Leaders Split It Instead
I wrote about a version of this recently in Being Wrong at the Right Level. That post was about the cost of defending a bad call instead of naming it. This is the same instinct wearing a different costume. Naming brutal facts feels like a risk, like it might spook the team or make you look like you don’t have your shit together. So you edit yourself down to the optimistic half, and you carry the other half by yourself. It’s basically the same ego move, just aimed at your own state instead of your last decision.
Swap But for And
The fix is probably as simple as a sentence that tells the entire truth at once. Dana could have said something like, “This stretch is genuinely hard right now, and I’m also really excited about what’s on the other side of it.”
Consider swapping “but” for “and.” “But” makes the second half of a sentence sound like a correction or a cancelation. “And” lets both things remain true at the same time. “I’m carrying a lot, and I’m excited about the future.” sounds a lot better than “I’m carrying a lot, but I’m excited anyway.”
Your team already knows when you’re editing yourself. Giving them both halves of the unedited version is what actually will sound the most real.
If you want to think through what that looks like for your team specifically, I’d love to talk: https://tidycal.com/19xqg4y/introductory-call-free
What I especially like here is the idea that leaders often do not lie — they split the truth. That feels much more accurate.
People usually sense when they are only being given the polished half of reality. And I agree that “and” can change the entire tone: difficulty and confidence do not cancel each other out. A leader can acknowledge that something is genuinely hard and still believe deeply in where the team is going.
To me, that is more credible than optimism without context.