Transforming People Pleasing into Assertiveness

I’m learning that simply swapping my countless exclamation points for periods in work emails and Zoom chats doesn’t magically boost assertiveness or confidence. At 34, you’d think I’d know by now — nothing is an easy fix.

Building genuine confidence as a mega-people-pleaser takes much… much more effort. While reducing exclamation points did help me sound a bit more authoritative, it was barely a drop in the bucket. A brain shift was needed — and maybe some healing, too.

My phone background is now a cheat sheet — a “Confidence Card” of reminders I glance at before meetings. It includes grounding truths like:

“I’m allowed to take up space.”
“My perspective has value, even if it’s still forming.”

And it gives me ways to jump into conversations — a skill that seems like it came built-in for everyone else but me:

“Building on that…”
“Can I share a quick reaction?”
“Wondering if this might be worth exploring?”

Knowing what questions to ask — or even remembering to ask them at all — is hard when your instinct is to people-please and wrap things up quickly. These prompts have helped:

“What’s the most important outcome here?”
“Where does this fit into our overall priorities?”
“Is anything dependent on this that we should flag early?”

I’m learning to level up my people-pleasing. It’s possible to be helpful and supportive without shrinking. For example:

“Would it help if I mapped a few paths forward?”
“Here’s where I think I can add value on this.”
“I’d like to own part of this if there’s room.”

There’s a way to offer high-level support that serves the team — and honors your voice.

Follow-up phrases are also key for people like me (and my whole team) who process things over time. I’ve been experimenting with:

“I want to sit with this for a moment — can I follow up afterward?”
“Let me look at this through [your lens — strategy, data, design, etc.] and share some thoughts.”
“I’ll put something together and we can build from there. It’ll help me think it through too.”

Even with this cheat sheet, building the habit will take time. And healing what created my people-pleasing tendencies in the first place will take even longer. I know self-doubt will still creep in. That’s okay.

Just like I want to offer up my rough-draft thinking, I’m offering up a rough-draft me.

Developing assertiveness is an ongoing journey. It’s full of practice, discomfort, and self-reflection. It’s about gradually discovering, embracing, and amplifying your once-tiny voice — even when it feels unnatural. Every step forward is a victory. Writing this is a victory.

This journey feels even more worthwhile as I raise a young girl. Learning to speak up — kindly, clearly, fully — will be one of the most valuable tools in my toolbox as I teach her to set boundaries and navigate this world as a woman.

I’m curious: how do you find your voice in meetings? If you come across this and can relate, I’d love to share experiences and support each other on the path.

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