Ep 105 Career: How to negotiate salary and job offers

Show notes

Welcome to the 105th episode of The Crazy One Podcast. I’m your host, Stephen Gates, and this is the show where we talk about creativity, leadership, design—and today, your career.

You can find the show notes and all past episodes at thecrazyone.com—that’s the crazy and the number one. While you’re at it, make sure to subscribe on your favorite podcast platform so you’ll always get the latest episodes as they drop.

The Crazy One is now on YouTube! I’m sharing career coaching, tutorials, masterclasses, and past keynotes there. Head to thecrazyone.com/youtube to check it out and hit subscribe.

If you’ve got questions or just want to keep up with my not-so-adventurous pandemic life, follow me on Twitter or Instagram. You can also follow the show on LinkedIn or Facebook.

Why We’re Talking About Negotiation

Right now, a lot of people are changing jobs—or losing them. In those conversations, I keep asking:

Have you ever negotiated your salary or job terms?

The answer from most people, even senior leaders, is no.

That needs to change.

Negotiating your salary, your role, and even your exit terms is a normal and essential part of the career process. I’d argue that your success is often driven by your ability to understand the business, advocate for yourself, and set yourself up to succeed—both in your work and financially.

The Lesson I Learned (the Hard Way)

I didn’t start out being good at this. I learned by accident—or maybe arrogance.

Before I joined Starwood, they approached me several times while I was working at McCann in Texas. I wasn’t impressed. The structure was wrong, the team setup didn’t work, and the whole thing felt misaligned.

But then their head of digital asked me to come to New York for dinner to just talk. I wasn’t that interested, so I went with nothing to lose. I put together a 10–12 page doc detailing everything that was broken: the team, the setup, even that they weren’t using Macs. I laid it all out—my vision, my “crazy” demands.

And to my surprise, he said: “This is exactly what we’ve been looking for.”

They agreed to everything. And that taught me the most important lesson:

You will never have more power in your career than the moment between when a company wants to hire you and when you say yes.

Why People Don’t Negotiate

• Confidence: Too many of us feel lucky just to get the offer.

• Perceived inequality: We assume the company has all the power.

• Business acumen: Many creatives don’t understand how to negotiate.

• Emotional decisions: We guess. We lead with emotion. We hope they see our value later.

But the truth is:

If you wait to prove your value after you’ve accepted, you’ve already lost your leverage.

What to Expect in the Negotiation Process

1. Ask opening questions: What’s negotiable? What’s off-limits?

2. Build your case: Prove your value with data and examples—not emotion.

3. Expect resistance: This is a conversation. Be prepared to go back and forth.

4. Stay professional: Be firm, but not inflexible. Stay grounded and unemotional.

5. Understand their thinking: Ask how they arrived at the numbers.

6. Know the full picture: Salary, bonus, stock, benefits, paid leave, education support—everything.

7. Look ahead: Ask about promotions, raises, and metrics for success.

8. Get it in writing: Verbal offers are not enough.

Never Take the First Offer

Unless it’s labeled “best and final,” never accept the first offer.

Companies almost never start at their final number. They expect to negotiate. If the budget is $100k, they’ll probably offer $85k or $90k to see where you’ll bite.

If you say yes right away, you just left money on the table.

Do Your Research

Use sites like:

• Glassdoor

• Payscale

• Salary.com

Understand your city, your role, and your level. Establish a range—not a single number—based on market data and your experience. Know where you want to land and why.

Understand Leverage and Risk

If you’re unemployed, you may not want to push too hard.

If you’re employed or in demand, you’ve got more leverage.

Gauge how much risk you’re willing to take and how much leverage you actually have.

Master the Craft

This stuff isn’t easy for creatives. It’s not taught in art school. But you have to learn.

If you want to go deeper, I highly recommend Chris Voss’s Art of Negotiation on MasterClass. He’s a former FBI hostage negotiator who now trains business leaders. His lessons on mirroring, labeling, and trust-based influence are game changers.

Final Thoughts

Negotiating is not arrogance. It’s how you take control of your career.

Too many of us feel like we should be grateful and quiet. That we don’t deserve power or control. That’s just not true. You’re an equal in this process—and you have a right to advocate for your value.

The only real luxury we have is time. And I’m honored you chose to spend some of yours with me.

Now go out there. Negotiate. Kick ass. Know your worth.

And as always—stay crazy.

Tagged as:
career control career growth fina financial future job offer negotiation maximizing income negotiating salary negotiation tips professional development salary negotiation salary strategy Stephen Gates The Crazy One podcast understanding value