^{Forwarded this email? Subscribe for more.}

Hey, I’m Tim! ☕

I’ve had jobs where I didn’t feel psychologically safe, and others where I felt invincible.

As a cofounder, you’re the foundation of psychological safety, not just for your cofounder, but for your entire team.

The problem is it’s like glass: meticulous to build, easy to shatter. It’s your job to build it intentionally and protect it from breaking.

Fragile Foundations

Psychological safety is not a personality trait.

It’s the product of an environment, carefully constructed in such a way that there’s an absence of interpersonal fear.

You do not feel psychologically safe by default. Stranger danger. It takes time to create that space.

You first need to recognize when someone feels unsafe.

Here are 7 common signs:

1. Self-Censorship
   You have a bold idea but you stay quiet because your cofounder has a history of shutting them down with dismissive comments like “that’s unrealistic.”

2. Defaulting to Silence
   Your cofounder suggests a strategy that you think has flaws but you nod along. Later, when the strategy backfires, you regret not speaking up.

3. Second-Guessing Decisions
   After presenting a proposal, your cofounder’s curt response leaves you replaying the interaction in your head for hours.

4. Walking on Eggshells
   Your cofounder has a short temper, so before every meeting, you rehearse your points to make sure they won’t be interpreted as criticism.

5. Withholding Vulnerability
   You’re overwhelmed but your cofounder has previously dismissed emotional concerns as unproductive. You say nothing and push through alone.

6. Avoidant Behaviors
   Your cofounder suggests grabbing dinner, but you decline even though you’re free. You want to limit your interactions to essential business matters.

7. Over-reliance on Formalities
   Where you used to exchange friendly banter, conversations with your cofounder now feel like you’re writing emails out loud. Humor and spontaneity are gone.

If you’ve felt any of those before, you know it feels like walking through a minefield. Every word, every action feels precarious, as if one misstep could lead to disaster.

But it’s not just the absence of safety that’s a problem. It’s what replaces it.

Two destructive dynamics creep in:

Paternalism: respect is granted but without sufficient autonomy. Respect will be given in terms of your ability to follow orders rather than self-initiation.

Exploitation: permission is given but without any respect. It’s an attempt to extract value from you without respecting your value.

What Can You Do About It?

Back when I was teaching, I noticed that some students stayed quiet by default, but when called upon, gave the most beautifully insightful answers.

All it took was “I’d love to hear your thoughts, even if they’re different from mine.”

Why does this work?

1. It grants permission to contribute. No more invisible barriers.

2. It conveys respect for their perspective, no matter how unconventional.

3. It normalizes curiosity. It shows you’re actively inviting fresh angles and ideas.

[Btw, I prefer “different” over “disagree” because it keeps the conversation open and avoids any confrontational tone that might make people hesitate].

Most people think of psychological safety as a destination. But it’s not a finish line.

It’s a garden.

It needs continuous care to thrive and even small moments of neglect can cause it to wilt.

The good news is that psychological safety is contagious. When one person feels safe, they start creating safety for others.

To sum it up:

1. Notice if there are any of the 7 signs of feeling unsafe.

2. Use open language to celebrate dissent.

3. Reciprocate with your own curiosity.

If you want personalized advice on how to do that, book a call below.

Brought to you by:

Enjoyed this? Copy your custom referral link and share Cherrytree with a friend.
^{Top referrers every month win a cash prize.}

Thanks y’all,

Tim He