For Your Bag of Tricks

What if you knew exactly what to say when your client comes to you with the most ridiculous, impossible, outrageous requests?

What if you knew the magic words to make your client reconsider their horrible idea and give into your expertise?

What if you could stop having to delicately explain that your client’s 14 year-old’s idea for the new website is, well, terrible?

Friends, I know those words.

Those words are “Yes, if….”

By Rubin 110 via

A close relative of the ever helpful “yes, and…,” “yes, if…” is a way to get the other side to keep listening to you even when they won’t like what you’re going to say.

“Yes, and…” is helpful in disagreements. When you are arguing over something “yes, and…” allows you to recognize the other person’s contribution to the conversation without having to agree with what they’ve just said.

“Yes, if…” is what to use when a request is so off the wall, so strange, and yet so earnest, that you don’t want to say “no” but you also know you can’t give an unqualified “yes.”

Let’s try it out:

“Can we move the timeline up by three weeks?”

Yes, if you’re willing to hire another freelancer to help with the workload and pay my rush fee.”


By davidandbecky via

“I really like orange; can we make the background more orange-y? Not like fruit orange, more like orangutan orange.”

Yes, we could do that if you’re willing to change the powder blue you chose for the font color; that color combination won’t work for the type of web presence you want.”


“I was thinking it might be fun if we all went on a team vacation together, you know as a team bonding exercise. We could have 24/7 togetherness and really build our synergy. What do you think?”

Yes, if you’re willing to pay for my travel expenses and my hourly rate of $125/hour.”


The thing that makes “yes, if…” great is that it makes the client (or collaborator, or whomever) responsible for rejecting or accepting their own idea.

Instead of putting you in the awkward position of having to say “That will never work because of these six things you aren’t thinking about,” “yes, if…” allows you to present the same exact information you would when saying “no,” while relieving you of the responsibility to flat out reject the idea.

“Yes, if…” is also helpful for establishing boundaries. Some people like to test boundaries and they’ll keep poking until they find a weak spot. “Yes, if…” allows you to keep and clearly articulate your professional or emotional boundary without encouraging more poking. It’s a way of saying, “Sure, I’ll entertain your harebrained idea, you just have to do the following things that are important to me.”

Finally, “yes, if…” helps you take advantage of opportunities. I know a number of artists who talk about their “f*ck you price,” the price they quote when they don’t want to take the job but don’t want to say “no.” “Yes, if…” works in the exact same way.

Instead of just saying “no” to a request, you can think about what it would take for you to say yes, and you can make your pie in the sky request. If they agree to your terms and conditions, you get work and money you wouldn’t have gotten otherwise; if they say no, you haven’t lost a thing. Just make sure your “if” is really what you need in order to follow up on the “yes.”

By Wendi Gratz via

So put “yes, if…” in your bag of tricks and use it the next time someone comes to you with a ridiculous request or idea.

A special shout out and thanks to the members of Ed Cheetham’s Portfolio and Professional Skills class at Ringling College of Art and Design! I spoke to the class about negotiation and contracting in the great big world of freelance design. The class asked great questions and I had a blast talking with them. Thanks y’all!

Got a class you’d like me to come speak to? Drop me a line.

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