Talking about Money with clients can be painful — So try these tips

tweet share share pin email

For much of his early career, comedian and former Tonight Show host Jay Leno employed a famously tough-as-nails manager — many called her vicious — named Helen Kushnick.

Kushnick negotiated ferociously on behalf of Leno and all of her other clients, and her strong-arm tactics were credited in many cases with earning her clients career-making, highly lucrative deals. But in the process she earned a reputation around Hollywood as a monster.

And eventually, when that monstrous reputation threatened to spread to Leno himself, he was forced to fire Kushnick from her role as Tonight Show executive producer.

Bad luck with clients? Trade your worst clients for some of the best companies in the world with our premium gig list, SolidGigs. Join this month and get your first gig list FREE.

Of course, Jay Leno survived that episode with his easy-going, nice-guy reputation intact. Indeed, he has enjoyed a long career — still going strong today, in fact — as one of the entertainment industry’s most likable stars.

As you can probably imagine, Leno found it invaluable to have a feared and fearless business manager negotiating on his behalf — while sparing him the ugly moments of those negotiations. Because like you, Jay Leno is a creative at heart. And creatives are notorious for hating the business side of things.

You want to create, not deal. You want to focus on your art, not such crass matters as money and running a business.

But if you’re a creative freelancer, the truth is that you are running a business, first and foremost, not merely a creative shop. And that means — like it, hate it, or really, really hate it — you will need to have difficult conversations with clients and prospects about rates, terms, late payments and other money matters.

You can’t simply avoid these conversations and hope everything works itself out. That is not a successful business strategy.

Psst... Looking for more passive income as a freelancer? Learn from 4 solopreneurs who built their own passive income streams from scratch. Enter your email below and we'll send you a link to our free guide. Or preview it here.

And because you’re not Jay Leno, and you probably can’t afford to have a Helen Kushnick to scream at your clients for you (which would be a lousy strategy anyway), you’ll need to develop a system for dealing with these difficult subjects when they come up — and they will come up.

So here are a few ideas to help make handling the business side of your creative enterprise a little less awful.

Referring to a ‘process’ for payment requests

In conversations with clients about business or money issues, always refer to a process, third party or some external source — so your requests don’t feel or sound personal.

When you are starting a relationship with a new client, and that client asks you to sign an NDA before she can send you the background material to start your first project, what do you think of that request? Do you shout, “What? An NDA? You don’t trust me? This is no way to begin a professional relationship! I’m offended!”

Of course not.

What you think is, Yeah, an NDA makes sense. The company needs to protect itself. And my contact asking me to sign one is just protecting herself and following the rules.

This, by the way, is the same reason you don’t get offended at a rental-car counter when the rep asks to see your driver’s license. It’s just the company’s process.

Well, guess what? You’re a company, too. And you have a process of your own.

So when you need to ask a client for part of your project fee upfront before you can get started, or when you ask the client to sign a contract that details your rates and payment terms — more on this below — you can make that conversation a lot easier on yourself by referring to your process.

“I’ll just need to you to sign this agreement — for my files.”


“Before I can start the project, my process is to receive a 30% payment of the project fee upfront. Then I’ll get rolling immediately.”

You can even refer to another party to the transaction:

“I need to request that your accounts payable folks send that past-due payment right away — or my accountant won’t leave me alone.”

(Also, note: In that statement above, I’ve even placed the hypothetical blame on the client’s “accounts payable folks,” whoever they might be. Even if you’re pretty sure your client’s company doesn’t have an accounts payable department, suggesting that the blame on their end lies not with your contact but with someone else can make it easier for them as well — a powerful way to preserve both their dignity and your relationship.)

Develop a ‘go-to’ phrase when talking money with a client

When you have to bring up an uncomfortable money issue with a client, always have a go-to phrase — even a casual, humorous one, if that puts you at ease.

A friend of mine who worked as a real estate appraiser once told me her strategy for collecting payment. For her this was particularly uncomfortable, because she would need to be paid in person when she was finished with her onsite inspection of the borrower’s home.

So she developed a great go-to phrase. When my friend had completed her inspection of the property and was ready to leave, she would say to the homeowner with a smile, “Well, we’re all done here — except for the hard part.”

In almost every instance, the homeowner knew exactly what my friend was referring to — that it was time for payment. And in almost every instance the person would say, “Okay, how much do I owe you?”

You can develop a similar go-to phrase for all of the standard money conversations you’ll need to have with your clients — whether asking for payment of an overdue invoice, telling a client you are raising your rates, etc.

Clarify your agreement terms

Draft a detailed term sheet that includes all information a client will need regarding your rates, what each project includes (and excludes), your payment terms, and any penalties for violating those terms — and go over this document with every new client.

Of course, you can minimize some of these difficult business conversations — like having to call a client because he’s weeks or even months late paying your last invoice, or fielding an unpleasant call from an unhappy client who expected assets included in your draft that you don’t offer as part of your service.

But to do this, you will need to make your terms extremely clear at the beginning of your relationship with every new client.

To that end, it’s mission-critical to your business that you draft a rate sheet/term sheet/agreement document that offers all relevant details about how you expect to work with your clients.

This document should include details about how you charge for your work (hourly, on a flat rate for each project, on a weekly or monthly retainer, etc.), and what your rates include and don’t include.

For example, if one of your copywriting services is to write case studies, and you charge a flat rate, you need to include in your rate sheet exactly what the client will receive for her fee. Will it include one draft? Two drafts? Will you interview the client or internal subject-matter experts at the client’s company?

Will you suggest layout and graphical assets, or copywriting only?

The document should also clearly state your payment terms. Will you require a percentage of the fee upfront? Will you expect invoices paid within 15 or 30 days, or at some other interval? What if any discounts will you offer for early payment? What if any penalties or fees will you charge if a payment is late?

Put all of these details in a standard document that you will share with every new client. And, just as important, create a two-party signature portion at the bottom of the document — which both you and your new client must sign. Ideally, you should also plan a short phone conversation to run through these items with your client before they sign.

This way, your relationship hasn’t officially begun, so there shouldn’t be much if any emotion involved. You will just be “running through the particulars” — a good go-to phrase you might want to use to kick off this call.

Outsource money matters to a virtual assistant

If you simply can’t handle any money conversations with your clients, you can outsource these calls to a virtual assistant.

This is really a last-resort type of suggestion. It would be far better for the long-term health of your creative freelance business — not to mention for your own personal growth — if you can apply the strategies above and develop cues and strategies to make these money conversations with clients easier for you have.

But if you just can’t do it, if the mere thought of calling a client to discuss a late payment is so distasteful that you might just let that client slide on payment indefinitely, you can always outsource.

You can’t hire Jay Leno’s Helen Kushnick, of course. She would be far too expensive. (Besides, she died 20 years ago.)

But thanks to the Internet, you can hire a virtual assistant to handle difficult business tasks such as making calls to a client until that client signs your working agreement, or contacting a client to ask when an overdue invoice will be paid.

Virtual assistant services like GetFriday and AskSunday are both reputable and affordable examples of such services.

Do you have any other tips for making uncomfortable client conversations less awful? Please share them here.

tweet share share pin email

Say Goodbye to Roller Coaster Income

Your income doesn't have to be a guessing game every month. Let 4 thriving solopreneurs show you how in our free guide.

About Robbie Hyman

Robbie Hyman has been a freelance copywriter for more than a decade, writing for startups and multibillion-dollar businesses. He is also co-founder of MoneySavvyTeen, an online course that teaches smart money habits to young people. Get to know him at

Leave a Comment



  1. Grace Keogh says:

    Some great tips here. Money issues really do my head in and stress me out – I prefer to do the creative stuff and tend to shy away from following up clients pay issues. Thanks for sharing some good tips


Need more clients?

Download our free guide:
25 Top Freelance Job Sites for Real Clients with Big Budgets