Earn More as a Leader (Festive Special 4 of 5)

Last week’s issue: Upgrade your Mindset

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Dear Team,

Merry Christmas!

Let's talk about something most leadership newsletters avoid: money.

Not in an abstract "create value and rewards will follow" way. I mean the actual mechanics of earning more as a leader, how to negotiate better, how to position yourself strategically, and how to choose opportunities that compound your growth instead of just paying the bills.

Because here's what nobody tells you: being good at your job is not the same as being good at getting paid for your job. They're related, but they're different skill sets. And most talented leaders I know are significantly better at the former than the latter.

This isn't about being mercenary. It's about recognising that your earning potential is one of the most important levers you have for building the career and life you actually want. And like any other leadership skill, it can be learned.

The scene: You get a job offer. You're excited. They say $140K. You were hoping for $160K but don't want to seem greedy or difficult. You counter at $150K. They meet you at $145K. You accept, grateful they came up at all.

What just happened: You left $15K on the table. Compounded over a career, that's hundreds of thousands of dollars. Maybe more.

Here's the thing about negotiation that took me years to understand: the goal isn't to get them to say yes to your number. The goal is to have a conversation about value where multiple variables are in play.

Stop thinking about salary as a single number you're fighting over. Think about it as a package with multiple components you can optimise:

Base salary — This is your floor, and it matters because bonuses and raises are often percentages of base

Signing bonus — Often easier to negotiate than base because it's one-time, not recurring

Equity/Stock options — Can be worth more than salary if you choose the right company; ask about vesting schedule and strike price

Performance bonus structure — Is it discretionary or guaranteed? What are the actual payout rates?

Title — Affects your next negotiation; sometimes worth trading money now for positioning later

Professional development budget — Executive coaching, conferences, courses; negotiate this explicitly

Flexibility — Remote work, schedule autonomy, sabbatical options; these have real economic value

Start date — Delaying 2-4 weeks can give you leverage and rest between roles

Instead of: "I was hoping for $160K"

Try: "I'm excited about this role. Based on my research and the scope of what you're asking me to take on, I was expecting the package to be in the $160-170K range for base. I'm flexible on how we get there, whether that's base, signing bonus, or accelerated equity vesting. What's possible?"

Notice what you just did? You anchored higher, showed you've done research, demonstrated flexibility, and invited them into problem-solving with you. You're not demanding. You're exploring what's possible together.

The move most people miss: After they respond, pause. Let the silence sit for three full seconds. You'd be amazed at what people offer into silence.

Negotiating well matters. But choosing the right moves matters more. Here are the strategic positioning plays I've seen multiply people's earning potential:

The prestigious company with the fancy logo often pays well. But it's also stable, which means there's a ceiling on how fast you can grow.

Early-to-mid career, consider taking the less famous company that's growing fast and needs senior leadership. You'll get:

A friend took a VP role at a Series B startup for 30% less than she was making at a Fortune 500. Eighteen months later, she was promoted to Chief of Staff to the CEO with equity that's now worth more than she made in her entire previous job. The growth trajectory matters more than the starting point.

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Learn more.

Being a "well-rounded leader" is fine. Being the person who can definitively solve an expensive problem is worth 2-3x more.

Right now, these skills command premium compensation:

Pick one. Get exceptional at it. Make sure everyone knows you're exceptional at it. Then watch the opportunities (and offers) compound.

This is counterintuitive, but your direct manager has more impact on your growth and earnings than the company does.

A great manager at a mediocre company will:

A mediocre manager at a great company will keep you stuck regardless of how strong the brand is.

How to evaluate this in interviews: Ask the hiring manager directly: "Tell me about the last person you managed who got promoted. What did you do to help make that happen?" Their answer tells you everything.

"Should I join this team?" is the wrong question.

The right question is: "Will this team help me build the capabilities I need for where I want to be in three years?"

Most people optimize for comfort (teams where they'll fit in easily) or prestige (teams with impressive people). Both are traps if they don't build the specific capabilities you need next.

Sit down and honestly answer:

Then evaluate every opportunity against that map. The highest-paying role right now might be the wrong move if it doesn't build what you need. The lower-paying role that puts you on the critical path to where you want to be in three years? That's often the right bet.

A colleague turned down a $200K director role at a stable company to take a $160K director role at a scaling startup specifically because she needed to learn how to build a function from scratch—something the stable company would never let her do. Eighteen months later, she leveraged that experience into a VP role at $280K. The "lower-paying" job was actually the higher-value move.

Here's what I've learned watching hundreds of leaders navigate their careers: the people who earn significantly more aren't necessarily better leaders. They're better at strategically positioning themselves, negotiating confidently, and making calculated moves that compound over time.

That might feel uncomfortable. We like to believe that good work speaks for itself. Sometimes it does. Often it doesn't.

Your job is to be excellent at what you do AND excellent at making sure that excellence translates into the compensation, opportunities, and impact you deserve.

Both matter. And only you can do the second part.

This Week's Action:

Pick one thing:

You don't have to do all of it. Just one thing. This week.

Because the difference between leaders who earn what they're worth and leaders who don't often comes down to whether they treat their career as something that happens to them or something they actively architect.

Be well,

P.S. - The most common response I get when I send newsletters like this is "I wish I'd known this ten years ago." Don't let that be you ten years from now. Start now.