The Ace Freelancer’s Guide to Asking Questions: Testing the Water Questions

Hey Ace Freelancers! This next installment of The Ace Freelancer’s Guide to Asking Questions introduces you to a type of question you can use to figure out what your client really wants before you send them a proposal.

One of the difficult parts of negotiating is trying to figure out what the other side is really willing to accept. You can work hard to put together an offer or proposal that you think is fair only to get a sound rejection.

The Ace Freelancer's Guide to Asking Questions

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Wouldn’t it be nice to know how they’ll react before you make an offer?

With a bit of effort and the right questions, you can.

Testing the Water Questions
Testing the Water Questions are questions that, you guessed it, allow you to present possible offers and gauge the other side’s reactions. Rather than forcing anyone to commit to a particular term or condition, these questions allow both sides to stay in a collaborative, creative frame of mind and generate lots of different potential solutions.

Testing the Water Questions are essentially hypotheticals: what would happen if? would you be interested in? could you?

The fact that they’re hypothetical questions eases the pressure to get everything right and the fear that someone will hold you to whatever you say in the moment. It makes the negotiation much more about brain storming and exploring possible options than about Winning or Losing. And we all know negotiations are better when we focus on possibilities instead of positions.

Another nice thing about Testing the Water Questions is that you can discover what the other person really can and can’t do in the deal. Hypotheticals get people thinking about all the different steps they have to take to make something work. That sometimes uncovers an easily missed or overlooked issue that has the potential of impacting the deal going through. If you can find those things early, it will save you from many a headache later on.

Ace Freelancer's Guide to Asking Questions

By Ryan Kemmers via

How to Use Testing the Water Questions
As with many things, when using Testing the Water Questions you can either be blunt:

“If I offered X, what would you be able to do?”

or more subtle:

“In the past I’ve done X when working with some of my clients. Would you be interested in something like that?”

How you use Testing the Water Questions will largely have to do with your style and what feels most comfortable to you. But don’t let that be the only deciding factor in how you use these questions.

Pick questions that the other person is more likely to answer. How do you know? Pay attention to how they’ve shared information with you up until this point.

Do they offer up information easily? Do they encourage brainstorming and creative solutions? These types of folks are primed to share information and a direct question is less likely to make them run for the hills.

If the person you’re negotiating with has been more cagey when it comes to details (pushing you to make the first offer or only answering the exact question that’s answered), then a softer, more subtle style of question might be more helpful.

Ace Freelancer's Guide to Asking Questions

By Maia Engeli via

A subtle Testing the Water Question sets aside the immediate negotiation, and that can help them relax and put their guard down a bit. For these folks, proposing possibilities as things you’ve tried with other clients can be particularly helpful; instead of worrying about what you might be trying to talk them into, they can focus on your former client (even if it’s an imaginary or composite client you invented just for this purpose…) and evaluate whether what that client did works for them.

When to Use Testing the Water Questions
Testing the Water Questions can be particularly helpful at the beginning of a negotiation when you’re gathering information. They’re also valuable if you’re encountering some pushback you weren’t expecting.

At the beginning of a negotiation when you’re gathering information about what the other person wants, Testing the Water Questions can allow you to fly through a list of possibilities in a relatively short period of time. This is due in part because, at the beginning of an engagement, people are used to exchanging information and expect that they’ll need to provide you with details about the gig.

Use this opportunity to get an understanding of how they view the things that are most important to you in the negotiation. So, for instance, if money is important to you, you might float a few Testing the Water Questions.

“I can bill monthly or based on milestones; do you have a preference?”

“I’m curious about your deadline; if I were able to finish the project early, would that be helpful to you? Would you be willing to offer an incentive fee in that situation?”

Ace Freelancer's Guide to Asking Questions

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Important point! Don’t forget the lessons from your Babysitting Questions in these situations! Don’t float something you absolutely don’t want to do. There is no point in seeing if they’re interested in something you aren’t.

If you’ve encountered resistance in the midst of a project or negotiation and you weren’t expecting it, Testing the Water Questions can help you figure out where things went wrong.

“Nasim, it seems that when we started discussing IP ownership things got more complicated. If we were able to structure the deal so that you can control and license the property, and I get a fair royalty for my work, would that help address your concerns?”

Important point II! Don’t stop once you’ve asked your question. Use the information you get to dig deeper and uncover even more valuable information.

So, if Nasim says “Yes, that could work,” your next set of questions should be about what “a fair royalty” means in this context. Whatever she says isn’t what you have to agree to, but the way she answers your questions and the information she provides will help you craft an offer and explain why it is the right solution for this deal.

Testing the Water Questions can help take the confrontation out of a negotiation. Instead of having to be on guard against the other person’s squirrelly tactics, both sides can focus their energy on brainstorming potential solutions.

Ace Freelancer's Guide to Asking Questions

By Rodney Campbell via

In the next installment of The Ace Freelancer’s Guide to Asking Questions, we’ll dig into questions that can help make your argument for you.

Categories: How To, The Ace Freelancer's Guide To Asking Questions

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