http://www.sherylkline.com/blog

If you’ve ever walked out of a meeting thinking, “That was a lost opportunity… I could’ve been more prepared,” please know you are not alone. It happens to even the most capable, high-performing leaders. And yet, those small windows of time (whether it’s a 15-minute 1:1 or a brief hallway conversation with a senior leader) are often the moments that matter most.

They’re the moments that shape your influence, your visibility, and the confidence others have in your leadership.

I’ve been there myself. It’s frustrating, and it can sting. But I want to make sure it doesn’t continue happening to you.

There is a proven way to walk into these interactions feeling grounded, clear, and ready. Both you and the person you’re meeting with can walk away feeling energized, aligned, and confident.

And it starts before you ever say a word.

Start by Putting on Their Goggles

When we prepare for an important meeting (especially one with an executive) we often feel pressure to talk fast, showcase our wins, and prove our value. That’s normal. But it’s not the most effective way to lead the conversation.

Before you jump into your updates, accomplishments, or ideas, you need to create what I call the runway.

That runway begins with the other person’s world, not yours.

Ask yourself:

What pressure are they under right now?
Who is putting expectations on them?
What’s keeping them up at night?
What might they be worried about as we head into this next quarter?

This is not about being perfect or reading their mind. The beautiful thing is, it’s okay if your assumption isn’t exactly right. What matters is that you are showing genuine awareness and care.

This immediately lowers defensiveness, increases trust, and sets the tone for a productive interaction.

How to Start the Conversation Strong

After the basic pleasantries, you might say something like:

“It seems like there’s a lot of pressure right now to accelerate growth in Q1, and I can imagine that’s creating a lot of urgency.”

That simple sentence does three powerful things:

It acknowledges their reality.
It validates the pressure they’re carrying.
It signals that you’re thinking beyond your own priorities.

From there, one of two things will happen:

1. You’re spot-on.

They’ll say, “Yes, exactly,” and then give you more context.

2. You’re slightly off.

They’ll say, “That’s important, but what’s really stressing me right now is…”

Either way you win, because you gain insight you didn’t have before. And insight is influence.

More importantly, you’ve already built trust in the very first moments of the conversation. And trust is the foundation of impact, visibility, and upward momentum in any organization.

This Is Just Step One

If you struggle to feel fully prepared for short but important meetings, this is your starting point: Lead with empathy. Lead with awareness. Lead with their world first.

Next time, we’ll talk about how to structure your message in a concise, clear, and influence-building way, so you get the biggest return on even the shortest interactions.

If I can support you or your team in any way, I’m here for you.

And if you’re interested in being featured on the Fearless Female Leadership podcast, or you’re a leader looking to gain clarity on ‘what’s next’, how to build more cohesive and high-performing teams, and lead with greater confidence and influence, let’s have a confidential conversation.

Cheering you on always!
– Sheryl.

http://www.sherylkline.com/blog

If you’ve ever walked out of a meeting thinking, “That was a lost opportunity… I could’ve been more prepared,” please know you are not alone. It happens to even the most capable, high-performing leaders. And yet, those small windows of time (whether it’s a 15-minute 1:1 or a brief hallway conversation with a senior leader) are often the moments that matter most.

They’re the moments that shape your influence, your visibility, and the confidence others have in your leadership.

I’ve been there myself. It’s frustrating, and it can sting. But I want to make sure it doesn’t continue happening to you.

There is a proven way to walk into these interactions feeling grounded, clear, and ready. Both you and the person you’re meeting with can walk away feeling energized, aligned, and confident.

And it starts before you ever say a word.

Start by Putting on Their Goggles

When we prepare for an important meeting (especially one with an executive) we often feel pressure to talk fast, showcase our wins, and prove our value. That’s normal. But it’s not the most effective way to lead the conversation.

Before you jump into your updates, accomplishments, or ideas, you need to create what I call the runway.

That runway begins with the other person’s world, not yours.

Ask yourself:

• What pressure are they under right now?
• Who is putting expectations on them?
• What’s keeping them up at night?
• What might they be worried about as we head into this next quarter?

This is not about being perfect or reading their mind. The beautiful thing is, it’s okay if your assumption isn’t exactly right. What matters is that you are showing genuine awareness and care.

This immediately lowers defensiveness, increases trust, and sets the tone for a productive interaction.

How to Start the Conversation Strong

After the basic pleasantries, you might say something like:

“It seems like there’s a lot of pressure right now to accelerate growth in Q1, and I can imagine that’s creating a lot of urgency.”

That simple sentence does three powerful things:

• It acknowledges their reality.
• It validates the pressure they’re carrying.
• It signals that you’re thinking beyond your own priorities.

From there, one of two things will happen:

1. You’re spot-on.

They’ll say, “Yes, exactly,” and then give you more context.

2. You’re slightly off.

They’ll say, “That’s important, but what’s really stressing me right now is…”

Either way you win, because you gain insight you didn’t have before. And insight is influence.

More importantly, you’ve already built trust in the very first moments of the conversation. And trust is the foundation of impact, visibility, and upward momentum in any organization.

This Is Just Step One

If you struggle to feel fully prepared for short but important meetings, this is your starting point: Lead with empathy. Lead with awareness. Lead with their world first.

Next time, we’ll talk about how to structure your message in a concise, clear, and influence-building way, so you get the biggest return on even the shortest interactions.

If I can support you or your team in any way, I’m here for you.

And if you’re interested in being featured on the Fearless Female Leadership podcast, or you’re a leader looking to gain clarity on ‘what’s next’, how to build more cohesive and high-performing teams, and lead with greater confidence and influence, let’s have a confidential conversation.

Cheering you on always!
– Sheryl

http://www.sherylkline.com/blog

I am deeply and genuinely grateful for you. Without you, there would be no Fearless Female Leader community, no cohorts showing up with courage, no 1:1 clients pushing boundaries in boardrooms and beyond, and no powerful voices rising on stages and in conversations that matter. You’ve made an impact this year (in big and small ways) and I want you to know how much I see you, appreciate you, and cheer you on.

This year hasn’t been easy. There have been challenges, change, and moments that asked for more courage than comfort. And still, you showed up. You spoke up. You shook up old patterns and stepped into rooms and roles that stretched you. If you felt imposter syndrome along the way, remember this: feeling this is a sign of bravery and courage! It means you raised your hand for something meaningful… something that required growth. That takes grit, heart, and leadership of the highest kind.

I hope you’ll pause to feel grateful not just for family, friends, food, and warmth… but also for yourself. We can be so hard on ourselves, especially as women. Please take a moment to honor all that you’ve accomplished so far and how you’ve showed up for others.

And from my family to yours, I wish you a happy and healthy Thanksgiving.

Cheering you on always.
- Sheryl