The executive formula to asking for more

Start asking now - like interest, it compounds.

👋 Hi, it's Greg. AI has just been upgraded - from summer intern to MBA analyst. So I’m lecturing on AI as an Advanced Thought Partner for Personal Math subscribers on April 17. Sign up for free.

Tom Burt made me rich (okay, not billionaire rich, but rich enough) and changed my life. I lost touch with Tom years ago and still can’t find him. But not a year goes by that my wife Cindy and I don’t toast Tom. He gave me what I was not willing to ask for: more.

In the 90s, I was co-founder of an ecommerce startup, 2Market, that got acquired by AOL. 2Market had a lot of “founders,” so my equity stake wasn’t enough to make me rich. And because I wasn’t sure if I wanted to stay at AOL, I didn’t fight for more – I didn’t want to be selfish.

Tom fought for me. He got me a bigger equity stake, and I ended up staying at AOL for five more years, when it was the best-performing stock on the NASDAQ. I didn’t have the courage to ask for more – but he did, for me.

It’s still hard for me to ask for more. Maybe it’s my Canadian (humble) and British (defer to authority) upbringing. But here’s what I’ve learned.

No one will give you a prize for taking a lower budget, salary, team size, or scope. You’ll only hurt yourself, especially if you don’t ask for more early in your career.

Here’s how to ask for more without coming off as entitled or greedy. Start now – like interest, it compounds.

Greg

Why we don't ask for more

We're taught the wrong lessons early in our careers:

• Stay in your lane

• Come in under budget

• Don't rock the boat

• Be grateful for what you have

• Don’t stick your neck out

These values are deeply ingrained in us. Add to that, most of us don’t think we deserve more – because we’re not qualified enough, senior enough, etc.

And right now, the job market sucks and the chaos monkeys in Washington are about to start a recession, so most people are thinking in terms of self-protection. When we want to protect ourselves, we tend to contract rather than expand.

We think, “I’ll make myself (salary, budget asks, team size) as reasonable as possible to show I can do more with less, and they won’t pick on me.” But that’s wrong.

You don't get rewarded for maintaining the status quo. What gets rewarded is growth, momentum, and progress – especially when the market is down.

Sure, some people get fired for asking for 2x headcount and then delivering half. But the best way to get rewarded and promoted is to ask for more, then use it to deliver more.

The method behind an ambitious ask

Don't ask for more just for the sake of getting more – most bosses see through that immediately.

The magic formula to asking for more is simple: "Here's what I could do for you if I had more."

There are four parts to it:

Know your baseline. What's the typical ask in this situation? If you're asking for headcount, look at the size of similar teams in your org. If it's budget, ask around for the average budget by department and see how yours compares. If it’s salary, do your due diligence on what your role typically makes.

Push past your comfort zone. Once you know what's justified, add 20% more. This is where growth happens. Ask yourself: "What's the additional scope I could crush, but would make me a little uncomfortable?"

Justify the incremental. This is where most people fall short – they ask for more, but they don’t give a clear reason for the extra spend. You need to clearly connect the dots between the increase and the value it will create. "Give us an extra $15K a month and I'll get you one full-time engineer who will cut our release time by 25%."

Acknowledge the stretch. Be upfront about the ambition of your ask. "I understand this is a stretch, but here's why I think it's worth it..." This shows self-awareness and confidence at the same time.

I want you to reframe your ask – it's about maximizing your potential, not being selfish.

My advice

If you are in the top 25% of your team, then it’s time you start asking for more.

No one wants to lose high performers – especially those with a decent amount of institutional knowledge. So you are in a good position to ask for more budget, headcount, salary, etc. … if you can show what you’ll do with it.

Think about what you’d do with 20% more, then ask for it. The people who advance fastest are those who ask for more than what feels comfortable – but less than what would be delusional. And then work their ass off to deliver.

Start now, especially if you’re early in your career. It pays dividends.

Have a great week,

Greg

P.S. I’m lecturing on AI as an Advanced Thought Partner for Personal Math subscribers with my brilliant friend and colleague, Lucas Miller, on April 17. Sign up for free.

P.P.S If you need help asking for more, reach out to rfernandez@sectionai.com so we can find time to chat. I want to pay it forward. It could change your life.