Save Yourself From Overshare Regret

The Problem

Vulnerability can feel like a volume dial that’s tough to set just right. Turn it down too low, and you come across as guarded or withholding. Crank it up too high, and the room goes quiet. You wonder: Was that too much?

As a leader, your every word gets dissected. So when you share:

Too much rawness creates anxiety.
Too much frequency becomes exhausting.
Too much openness in public leaves you (and others) exposed.
Too much polish keeps people at arm’s length.

I’ve stepped in it myself, sharing too much too soon, hoping it would build trust. It didn’t. And the other extreme isn’t pretty either. Hold back completely, and I come across as cold, judgy, like I think I’m above it all.

Vulnerability can accelerate trust. But how do you strike the right note so it builds your team up instead of weighing them down?

The Discovery

In the Stanford classes I facilitate, I’ve seen vulnerability go many directions. Sometimes someone shares something big, early on, and the room freezes. You can almost hear people thinking: Holy hell, what did I just walk into? Is this the price of admission? Do I have to share like this too to belong?

Other times, one honest moment knits people together in new ways. Someone says what others have been feeling but haven’t dared to admit. The tension breaks. People exhale. The room softens. Suddenly that person is seen as more human, more multidimensional.

The paradox is that vulnerability can draw people closer, and it can push them away. Once you’ve felt the rush of connection it creates, it’s tempting to think it’s always the answer. It isn’t. It’s powerful, but it’s not a cure-all. 

The Experiment

If you’re wondering how vulnerable is too vulnerable? Try looking at your share through these five lenses.

1. How Early

Vulnerability builds trust, and it also relies on trust to land well. Share too soon, before any foundation is there, and it can feel abrupt or performative.

Ask yourself:

• Is it the right moment in the relationship to share this?

• Has trust been earned, or am I forcing closeness?

• Have we had enough smaller moments of trust to support something bigger?

⚖️ If it feels early, pause. You may be offering something the relationship isn’t ready to hold.

2. How Raw

Vulnerability lands best when you’ve worked through it enough to share with perspective. If you’re still caught up in the feelings, others may feel like they have to manage you instead of learning from you.

Ask yourself:

• Do I still get swept up when I talk about this?

• Can I distill a learning, or is it still just the experience?

• Will sharing this steady the team or unsettle them?

⚖️ Raw stories spill over. Processed stories land.

3. How Often

People are human. Even with the best intentions, empathy has limits. If you return to the same theme again and again, it creates fatigue even if it’s still true for you.

Ask yourself:

• Have I shared this before, or something close to it?

• Does sharing this again deepen the message, or dilute it?

• Am I sharing to connect or just to process out loud?

⚖️ Even true stories lose their power if people have to hear them too many times.

4. How Public

Context matters. What feels right in a 1:1 can be out of place in a town hall. And once it’s shared publicly, you can’t pull it back.

Ask yourself:

• Does this setting allow for nuance and care?

• Would I be okay if this were repeated outside the room?

• Am I considering how power dynamics shift when I share this publicly versus privately?

⚖️ What builds intimacy in private may feel exposed under the spotlight.

5. How Relatable

Vulnerability isn’t just about you, it’s about us. It builds trust when others can see themselves in your story.

Ask yourself:

• Will people see themselves in this, or does it only make sense from my seat?

• Am I naming a shared emotional thread here?

• Is this building a bridge, or just asking to be witnessed?

⚖️ The strongest vulnerability doesn’t spotlight you. It connects us.

The Takeaway

Save yourself the cringe loop of an overshare gone sideways. Pick a vulnerable moment, recent or upcoming, and run it through these lenses. Notice where the vulnerability dial feels turned up too high or too low. Ask what a 5% adjustment would look like to fine tune.

The goal isn’t to share more. It’s to share wisely.

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