Stand out and think like a leader with these 3 bold moves

Carlina, my chief of staff, made a decision last week without asking me.

She was talking to a potential partner who wanted to give away a few signed copies of my book at a leadership trade show.

Without running it by me, she told them:

“Jenny would also be happy to offer a 30-minute group coaching session for the winners.”

She sent me a voice memo right after:

“Hey! I hope this is okay…I added a coaching session to sweeten the deal. I figured since you’re doing a few sessions already, this wouldn’t be a big lift.”

Her voice was shaking.

I could hear the hesitation. The fear. The internal monologue:

“I hope this doesn’t upset her.”
“I hope I didn’t overstep.”

She was bracing for a “Wait, you did what?” response.

Let me pause here and give you some context:

Since Wild Courage hit the New York Times bestseller list, my schedule’s been completely slammed. Lots of speaking requests, meetings, book events, and emails I haven’t even opened yet.

Adding a gratuitous small-group session to my plate? Could have been a risky move.

But I listened to Carlina’s message…and instantly smiled.

She was right.

In the end, it wasn’t a big lift.

It was a brilliant value add for prospective clients. 

Carlina didn’t just “guess right.”

She made a strategic call:

– She knew the offer was aligned with something I was already doing
– She understood the value it would add for the partner
– She knew I’d probably say yes…so she saved us both the time

Carlina thought her decision would upset me.

But what I actually thought was:

Wow, she’s thinking like a leader.
What else could I hand off to her?
What bigger calls is she ready to make?

The Problem

Most managers aren’t looking for someone to follow instructions.

They’re looking for someone who:

– Thinks ahead​
​– Solves problems​
​– Adds value (without being asked)

The Big Small Thing

That voice in your head? The one saying:

“This might be too bold…”​
​“What if I’m overstepping?” ​
​“I should probably check with someone first…”

That voice feels responsible. Safe. Smart.

But here’s what I’ve learned—both from managing teams and being on them:

What you think is risky is often the exact thing your manager wishes you would do.

What You Think vs. What Your Manager Thinks

Example #1:

❌ You: “I might be overstepping.”

✅ Your Manager: “They’re not waiting for me to spell it out. They’re thinking like a leader.”

Maybe it’s making the call in the moment instead of waiting for a “Let me check.” Or saying, “I went ahead and sent it” before you were technically told to. You’re not overstepping. You’re stepping up.

Example #2:

❌ You: “What if my boss thinks I’m trying to take over his/her job?”

✅ Your Manager: “I’m busy. If I could do it myself, I wouldn’t have hired you.”

A bold call made quickly beats a perfect one made too late. When you keep momentum moving, your boss sees someone they can delegate to again.

Example #3:

❌ You: “What if my colleagues think I’m pushing it by doing something outside of my roles and responsibilities?”

✅ Your Manager: “Are your colleagues signing off on your promotion? No? Then stop asking them for permission.”

Knowing the bigger picture and making a smart judgment call isn’t foolish. It shows you’re thinking like an owner.

If your hands are a little shaky before you speak up…
If your heart’s racing before you hit “send”…

…that’s not a red flag.

That’s the feeling of becoming the person your boss trusts (and can’t wait to promote).

Want more? Subscribe to my newsletter!

How This Helps You Get What You Want

You want to be trusted with bigger things.

You want your manager to see your potential and bet on you.

That doesn’t happen when you wait for permission.

It happens when you get out of your head, trust your gut, and make the dang call.

And suddenly, you’re not just helpful anymore.

You’re indispensable.