Industry News

HOW Design Today: HOW to Negotiate Like a Natural

For so many of us, negotiating is a particularly unique form of professional torture. In the space of a single interaction, we’re expected to confidently place a dollar value on ourselves and our services, then justify that price—and fight (or not) for it.

So: What’s a creative to do … especially those who are introverts or hate discussing anything financial at large?

Turn to the pros. At HOW Design Live 2023, Terri Trespicio interviewed Ilise Benun about the subject of negotiating, which they tackled head on in their session “Wiggle Room.” 

As Trespicio broke it down, “If you don’t ask, you don’t get. And yet far too many people—women, specifically, even seasoned executives—will avoid an awkward conversation at all costs. And when I mean all costs, I mean it’s going to cost you a lot. If we prefer not to negotiate and we try to skip it, we’re going to lose out—not just on money and other perks, but on opportunities to get better at doing it.”

As we work on the program for HOW Design Live 2024, set to kick off in the fall, we’ve been focused on putting the “how” in HOW like never before—leaving you with as many powerful, tangible takeaways as possible. In that spirit, we’ve been revisiting HOW-To highlights from last year’s show and sharing them with you—and here, we offer a bevy of negotiating insights derived from the best in the business.

Slow Down

Our natural inclination is to rush through a negotiation simply to get it over with—a veritable Band-Aid rip of an uncomfortable situation. But you’ve got to slow down. By doing so, Benun said you create the space to ask all the questions necessary to make an informed, strategic decision about what the rate for the project should be, what the job salary should be, and so on. By asking smart, thoughtful questions, Benun added that what you’re actually doing is showcasing to a client or employer why they would want—heck, need—you on their team. 

Moreover, “Absence Bias” is a fancy term for the sheer fact that people can’t see what’s not in front of them. In other words: “If you don’t show it, they won’t know it,” Benun said. So if you’re in a negotiation and wondering why someone won’t pay you what you’re asking, you perhaps haven’t yet fully articulated all your strengths—which carry true monetary value. And speaking of value …

Know the Difference Between Worth and Value

Benun noted that there is really no such thing as worth. And it certainly isn’t the same as value—which, crucially, can vary based on who you’re talking to. “Value is how the world sees you,” she said. “It’s how much value they put on what you do, what you bring to the table, what your experience is, and it’s in the context of them and their needs. So your value to one person is going to be totally different than your value to another person. That goes back to the [idea] of not rushing the conversation—because what you’re trying to understand is what they value, so that you can see not only [if] you have that to give, but are they going to value you in that way.”

Negotiate for More Than Money

A critical point to always bear in mind: We tend to think of negotiations exclusively in terms of financial compensation. But you’re often negotiating for so much more. Such as, say, experience, connections, introductions, exposure … and on and on. Benun urges creatives to bring their creative side to the negotiating table, and really take a critical look at what a company or industry could offer. Where are you trying to get to, in a bigger sense—and how could this opportunity get you there? You’ll probably discover a lot on that table beyond a dollar amount.

Remember: Negotiations Don’t End

OK! You might think as you pour a celebratory shot. I have negotiated, I got through it, and now it’s over!

But if you really want to do right by your career, you have to embrace the notion that negotiations should always be ongoing. The smart creative renegotiates after a certain amount of time and perpetually keeps the door open for more—especially as projects change in scope, you prove your immense value, and all factors beyond (not least of which is inflation).

Always Ask for More (and What to Do If They Say They Don’t Have It)

One of Benun’s best lessons to the HOW audience: Always ask for more money, more billable hours, more

Sure, a company might say they don’t have it in the budget. If so, just tell them what you can accomplish within their budget. 

“You’re going to give them an option that they can afford. And then you’re going to offer them something better based on what you know your value to be,” Benun said. “[E.g.,] here’s what you can get for your $40. But if you really want the kitchen sink or the premium or the hot fudge sundae, then it’s going to cost you a little bit more.’ And if they want that, and if they want you, they will find the money.”

Afraid of looking greedy?

“You cannot care about what they think if what you are doing and saying is the right thing—if you know, This is what I need to do for myself.”


In the end, the most important thing about negotiating is simply that you do it.

“When you don’t negotiate, you lose respect,” Benun said. “That’s disrespectful to yourself, because it says, ‘I’ll take whatever you give me. You can walk all over me.’ And it’s a slippery slope.”