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5 Ways To Get Better At Talking About Money

Money is the language of business. Here's how to have a not-awkward conversation about it!

Kathryn O'Day
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March 11, 2025

Talking about money is SO IMPORTANT.

Possibly the easiest and most impactful way to improve your startup or make more money.

I spell it out with these 5 examples.

But how do you actually do it if you’re not used to money talk?

“Talking” really means “asking questions” which leads to helpful conversations!

What are the unwritten rules about these questions and conversations?

Here are my best how-to tips to get a money conversation started!

Get the information that will help you negotiate better deals, understand term sheets, pay (or ask for) market rate salaries, and 100 other benefits of talking about money!


*HOW* To Talk About Money

If you’re new to asking about finances, contracts, margin, revenue, or other money and business topics, here’s 5 suggestions to get started!

1. Do it 1:1

Keep it to an intimate conversation or small group to start. Often people can’t share info in public settings but they can (or will) privately.

Important: don’t believe the news!

Often what’s reported publicly is not the full story. Get the nuanced info from an insider.


2. Keep it casual and matter-of-fact

Of course you are asking about money. And of course they are going to answer you. You don’t need to be apologetic or act like it’s confidential.

Asking questions in a neutral, matter-of-fact way is a key business skill!

It may take a few tries to nail the right tone. That’s okay!

Just get started (ideally with a founder friend or mentor) so you can get the awkward ones out of the way.


3. Start with a general question

If you’re not sure how someone will react, an indirect money question is a good warm up:

  • What’s a typical salary for a role like that?

  • What kinds of offers did you see when you raised money?

  • What’s the price range per square foot for property like this?

You’re not asking personal financial specifics. It’s a general, informational question.

You can even ask about non-money numbers to start:

  • How many sales people do you have? How quickly are you hiring?

  • Approx how many deals per quarter are you closing?

  • How many locations do you have? Do they vary in size or pretty standard?

Here’s the funny part.

Most (business) people will immediately jump in and say:

Oh, I’ll just tell you. Here’s what we paid. Here are the terms we negotiated. Here’s our margin. And this is what we’re going to do this quarter and next quarter.

Seriously.

Business people love to talk about money!


4. Explain why you’re asking

Occasionally, someone will give me a vague or general answer. UGH. Annoying.

Then I explain:

I love hearing about the specifics so I can learn and share with other founders so they know what is normal.

Floodgates unlocked!

If you explain that you want to learn, you love business, you’re building a startup and want to negotiate well for all involved, I guarantee people will share!


5. Remember: *business* people

I do NOT recommend talking about money at the next church potluck or school party.

(Or at least feel them out carefully — see #3!)

A lot of people fall into the “money is private” category. Or, sadly, the “I don’t understand money” category.

I DO think the world would be a better place if we could talk more honestly and openly about money.

(Note: posting expensive things on social media is NOT the same as talking about money!)

I encourage everyone, especially people historically excluded from financial systems (ahem, women and people of color), to normalize talking about money and sharing financial information!

High tide raises all boats. Expensive boats. Like yachts.

How much did that yacht cost, btw? 😉


You Know You’ve Made It

When you go out to lunch with business friends and only talk about revenue, COGS, and growth projections…

When you get a great holiday gift and start asking questions about the cost and time to make 30 homemade cookie cakes…

When you go to a store, meet the owner, and ask what their highest volume and margin items are…

CONGRATULATIONS!

You’re a money conversationalist and certified business nerd.


What strategies do you use to broach sensitive business topics? Do you find that people share information if you ask? What’s the most random money conversation you’ve had??

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