🤔 Dear Lewis, I’m overly deferential. How do I become more assertive?
In today's edition, a deferential VP discovers the surprising power of standing her ground.
Another week, another story from the trenches of leadership. This one’s about a VP—let’s call her Claire—who came to me with a familiar problem.
“I think I’m too nice,” she confessed as we sat down for our first coaching session.
Now, when someone says they’re “too nice,” it’s rarely about niceness. It’s usually about boundaries—or the lack of them. And sure enough, as Claire began to unpack her situation, the real issue came into focus.
“I defer too much,” she admitted. “I let people talk over me in meetings. I downplay my ideas. I’m terrified of coming across as pushy or difficult. And honestly? I think it’s holding me back.”
She wasn’t wrong.
Claire was smart, driven, and had a track record that would make most leaders envious. She’d built high-performing teams, closed deals that made jaws drop, and turned struggling regions into revenue powerhouses. But when it came to asserting herself, she was about as firm as a wet noodle.
And here’s the kicker: Claire wasn’t new to leadership. She’d been a VP for two years. But her boss had recently told her she wasn’t being considered for a bigger role because she didn’t “own the room.”
If you’ve been following along with my newsletters, you know where this is going. Claire didn’t need to change who she was. She needed to change how she showed up.
So we got to work.
The Diagnosis
Here’s what I noticed about Claire right away:
She apologized for everything.
Even when she wasn’t at fault. Someone interrupted her in a meeting? “Sorry, go ahead.” Someone disagreed with her? “Sorry, maybe I wasn’t clear.” Someone bumped into her in the hallway? “Sorry, my bad.” Every unnecessary “sorry” was a tiny act of self-erasure.She avoided conflict like it was contagious.
When her team proposed ideas she didn’t agree with, she’d nod along, secretly hoping they’d realize their mistake on their own. Spoiler alert: they didn’t. Instead, they’d run with their flawed plans, and Claire would end up cleaning up the mess.She used language that undermined her authority.
Her sentences were peppered with qualifiers: “I think,” “maybe,” “kind of,” “possibly.” She’d pitch ideas like she was asking for permission rather than presenting a solution. Her boss had once joked, “Claire, you could sell water in the desert, but you’d probably ask the buyer if they were sure they wanted it first.”She froze under pressure.
When her boss challenged her in meetings, Claire’s brain would go into full blue-screen-of-death mode. She’d either backtrack or stay silent, which only reinforced the perception that she lacked confidence.
Sound familiar?
The Plan
Claire didn’t need a personality transplant. She just needed a new playbook.
Here’s what we did:
1. The “No More Sorrys” Rule
We started with the apologies.
I told Claire she wasn’t allowed to say “sorry” unless she’d genuinely done something wrong. At first, she looked at me like I’d just asked her to stop breathing.
“What if I come across as rude?” she asked.
“You won’t,” I said. “You’ll come across as someone who values her own voice.”
We came up with alternatives:
Instead of: “Sorry, can I add something?”
Say: “I’d like to add something.”
Instead of: “Sorry, I don’t agree.”
Say: “I see it differently.”
Instead of: “Sorry, I might be wrong.”
Say: “Here’s my perspective.”
At first, she felt awkward. But after a few weeks, it started to stick. And something fascinating happened: people started listening to her more. Turns out, when you stop apologizing for existing, people take you more seriously.
2. The “Conflict is a Gift” Mindset
Next, we tackled her fear of conflict.
I told Claire to think of disagreements as opportunities to sharpen her ideas, not threats to her authority.
We practiced reframing conflict as curiosity:
“That’s an interesting perspective. Can you help me understand why you see it that way?”
“I see it differently. Let me explain my reasoning.”
“What would it look like if we combined elements of both approaches?”
Conflict didn’t have to be a battle. It could be a dance. And Claire was starting to learn the steps.
3. The “Power Words” Upgrade
Claire’s language needed a makeover.
We replaced her qualifiers with statements that projected confidence:
“I think this might work” → “This will work because…”
“Maybe we should consider” → “We should consider…”
“Kind of like” → “Exactly like…”
We also practiced cutting the fluff. Senior executives don’t have time for long-winded explanations. Claire learned to get to the point in 30 seconds or less.
4. The “Boss Challenge” Playbook
Finally, we prepared her for the moments that made her freeze: when her boss pushed back.
We created a script for when she was caught off guard:
Step 1: Pause. Take a breath.
Step 2: Validate the challenge.
“That’s a great question.”
Step 3: Buy time if needed.
“Let me think about that for a moment.”
Step 4: Respond with confidence.
“Here’s how I see it…”
The Twist
Here’s where the story takes an unexpected turn.
About three months into our coaching, Claire had her first big test.
Her boss was in a particularly fiery mood during a leadership meeting. When Claire presented her team’s Q3 strategy, he interrupted her halfway through.
“This isn’t ambitious enough,” he snapped. “We need to double these targets.”
The old Claire would’ve folded. She would’ve nodded, apologized, and left the meeting feeling defeated.
But not this time.
Claire paused. Took a breath. And then she said:
“I understand the need for ambitious targets, and I agree we should aim high. At the same time, I believe doubling these numbers without additional resources would put our team at risk of burnout. Here’s what I propose instead…”
The room went silent.
Her boss stared at her for a moment, then nodded. “Alright,” he said. “Let’s go with your plan.”
After the meeting, one of her peers pulled her aside. “I don’t know what you’ve been doing,” he said, “but that was badass.”
The Lesson
Here’s what Claire learned—and what I hope you’ll take away from her story:
Assertiveness isn’t about being loud or aggressive. It’s about being clear, confident, and unafraid to stand your ground.
It’s about knowing that your voice matters, even when it shakes.
And sometimes, it’s about surprising yourself with just how much power you already have.
Keep striving for greatness,
Lewis C. Lin
Simple, right? Well, not always
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