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A client I worked with recently had just landed a VP-level offer at a growing fintech company.

He’d navigated multiple interviews, built strong alignment with the CEO, and was excited about the role. The offer came in at $225K base - strong compensation for the geography, exciting company, and clear upward momentum.

But before signing, he had two things he wanted to address:

1. A base salary increase to $250K
2. Four weeks of pre-booked vacation in the back half of the year

After his final conversation with the CEO, the CEO asked him to send a short email outlining any remaining questions or requests. That’s when he reached out to me for help. He’d written a draft but was looking for feedback before pressing "send".

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That's when I dove in.

The ask was right. But the email was signalling all the wrong things.

It was polite. Thoughtful. Reasonable.

It also read like someone who didn’t fully believe he belonged at the level he was stepping into.

Instead of a confident, strategic note, it read like an apology for wanting more.

Here’s the original draft (recreated with permission and some anonymizing):

SUBJECT: Excited to Join the Team!

Hi [CEO’s Name] & [CFO’s Name],

I want to start by saying how excited I am about this opportunity. I believe this team is building something really special, and I’d be thrilled to contribute.

Before moving forward, I wanted to share two things I’ve been thinking about as I get closer to making a decision:

1. Compensation While I’m incredibly appreciative of the $225K base offer, I want to ask to increase the base salary to $250K. My current company will likely match your offer and increasing the base salary to $250K will help make this move worthwhile. In addition, the role has more travel demands than my current position and the increase will help my family make the necessary adjustments.

2. Vacation I wanted to mention that I have two trips already booked for later this year - one in August and another in November. These are longstanding plans with my family that are important to me due to how hard I've worked, and I hope they can be honored. I understand your vacation policy may not accommodate four full weeks, so I’m happy to talk through how to make that work.

Let me know if you’d like to book a call to talk through these items. I remain very excited about the offer and truly appreciate the time and energy you’ve invested in this process.

Warmly,

[J’s Name]

So - what’s the problem?

It’s not what he’s asking for.

• It's an 11% raise (very resonable)
• It's 4 weeks of vacation (most VP roles have at least this)

It’s how he’s asking.

The email was full of justifications and personal context. J told me he was feeling guilty about the ask and that guilt came through in his email. He didn't believe that his ask was, in fact, reasonable. Unfortunately if you believe that, it makes it VERY hard to negotiate and make your request with confidence.

And let’s be clear: that’s completely normal when you’re negotiating at a new level.

This was the most money J had ever earned in one year. He’d never negotiated a salary like this before AND he was used to working his tail off while minimizing his vacations.

This was a new ball game.

The problem is that when his nervousness leaked into his writing, it diluted his power. If he'd pressed "send" before editing, it would have left the leadership questioning whether J actually saw himself at their level.

What happened?

We stripped the emotion out of it. We removed the backstory. We focused on the ask.

And what we ended up with was an email that signaled clarity, leadership, and confidence.

Here’s the version he sent:

SUBJECT: Excited to Join - Final Questions

I want to start by saying how excited I am to take on this role. I’m deeply aligned with the vision for X and energized by the opportunity to help bring the A and B teams together. I believe we can build something impactful and I’m ready to make it happen.

To move forward, there are a few details I’d appreciate discussing further:

1. Compensation

I’d like to propose a base salary of $250,000. This adjustment will help me make a clear decision, especially as I expect [my current company] will match your original offer. I’m ready to commit and this will help me do so with full focus.

2. Vacation

I realize we haven’t discussed the vacation policy yet. I’d like to understand the policy, and share about two pre-planned breaks that I booked.

• Vacation A
• Vacation B

Look forward to seeing the benefits package and how we can make that work in the back half of 2025.

I’ve had a great conversation with XZY and appreciated the demo. It reinforced my excitement about the opportunity and the team.

I’ll send my references over in a separate email shortly.

Let me know what the next steps are here.

Warmly,
[J's Name]

That’s the entire rewrite.

No justifications. No over-explaining. No nervous hedging.

Just a confident, level-headed email that made it easy for the company to say: “Yes.”

How HR responded

The next day, HR sent over a reply:

✅ $250K approved

✅ Vacation approved

✅ Updated offer letter included

No phone call. No back and forth. No friction.

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So what’s the takeaway?

Negotiation isn’t just about what you ask for. It’s about how you ask.

Most companies don’t reject your ask because it’s unreasonable. They hesitate because you’re not communicating like the level you’re stepping into.

So if you’re negotiating a job offer and find yourself writing paragraphs about your family budget, the cost of travel, or why you’ve “earned” a vacation - pause.

Ask yourself:

• What am I trying to explain instead of simply state?
• What am I asking them to feel instead of just decide?
• Does this sound like someone who’s already doing the job - or someone asking for permission?

Here’s a quick test for your negotiation email:

✅ Is it under 300 words?

✅ Does it avoid emotional appeals?

✅ Does it ask for exactly what you want - no more, no less?

✅ Does the tone reflect the level of the role you’re stepping into?

If not, you’ve still got editing to do.

This is the kind of work I do with clients every week. We don’t just talk about confidence - we operationalize it. Line by line. Word by word.

If you’ve got an offer on the table (or are hoping for one soon), click [HERE] to book a free Career Strategy Call.

You don’t need to justify your worth. You just need to sound like the level you’re ready for.

Let’s do that together.

Until next week,

Beckie

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