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Advice / Job Search / Job Offer

Negotiation Q&A: What Questions Should I Ask Before Negotiating?

Hi Victoria,

In your article about giving your salary requirements, you talk about asking diagnostic questions to get a better sense of what your potential employer or current boss is looking for and leverage that.

Can you provide me with some examples of diagnostic questions and potential answers so I gain a stronger understanding of this negotiation tactic?

Hi there,

This is a great question! First, a little background: Diagnostic questions are the cornerstone of interest-based negotiation strategies and tactics. The questions themselves are simple—who, what, where, when, why and how—but powerful, as they call for thoughtful answers with the potential for revealing hidden interests that could greatly increase your chances of getting what you want.

Basically, you ask these questions to diagnose the needs, fears, desires, preferences, priorities, fears, and hidden constraints that underlie your bargaining partners’ negotiation positionsi.e., the money or product or business advantage they say they want. Rarely are our superior’s genuine interests transparently put on the negotiation table, but if you can uncover them, you stand a better chance of fulfilling your negotiating partner’s desires and yours at the same time.

Understanding these interests is particularly useful to women, who too often experience gender “blow back” when asking for something for themselves. But when they know what their bargaining partners really want to accomplish, they can lead with benefit, making the negotiation seem more collaborative.

Now, our bosses generally want pretty much the same things we do—to be effective in their jobs, to avoid conflicts, to stay within their budgetary restrictions, to please their bosses, to chart a path to promotion, and, during times of economic uncertainty, to keep their jobs. How they plan to accomplish those goals, however, is as idiosyncratic as the ways in which we wish to fulfill our own needs.

Here, then, are some diagnostic questions you can ask your superiors in an attempt to assess their interests before entering into negotiation.

How’s business?

This is an amazingly productive question. Think about it: We’re in a jobless recovery. Even though most major businesses are sitting on piles of cash, they haven’t re-hired the workers laid off in ’08 and ’09. Everyone is working beyond their job descriptions with fewer resources for less money. Few workers have had raises or promotions during the Great Economic Unpleasantness, and our bosses have been asked to produce better and better results with fewer and fewer resources.

So if the response to this question is “great,” dig deeper.

“I’m happy to hear that. I haven’t heard anyone say business is great in a long time. What do you attribute our success to?"

This approach is not only flattering, but it also requires a well thought-out, narrative response. Listen, and keep on asking diagnostic questions until you get the full picture of the business success your boss is experiencing. Persistence will pay off either in information you can use to justify a raise (“So, business is great—but I haven’t had a raise in five years,”) or in an admission that business, frankly, blows. And in that case, move on to:

How can I help?

I’ve been in the business world for nearly 40 years now, and I can safety tell you that I have never heard anyone turn away help.

I have, however, heard, “There’s nothing you can do to help, but thanks for asking.” And this is typically offered to avoid either a painful topic or an extended conversation.

If the former, do what all negotiators are taught to do at the commencement of any deal-making opportunity—create an atmosphere of hope and safety.

“I know it may seem as if I can’t personally help, but I’ve got an entire division of potential help at my fingertips,” you might say if you’re a manager. That offer suggests that there is hope for a solution. The modesty of your proposal signals a genuine desire to be of assistance, which is an early building block of trust and safety.

What resources would you need to crack that nut?

Here’s where you really get into the good stuff. You’re not only going deeper into the quandary, you’re beginning to help your employer problem-solve by breaking the dilemma down into manageable pieces. Whether it’s a human or material resource problem, you can offer to call in favors or simply to brainstorm possible solutions.

You can also try: Who do you believe might be able to help us accomplish that goal? What interim steps are necessary to fulfill those requirements? When does management need the plan, and who can green light it? Why has management decided we need to meet these goals in so short a time? Where might we look for help in getting this job done? And so on.

Listen very, very carefully to the themes and problems your negotiating partner brings up over and over. Is it budget constraints? A problem department or employee?

Only after you’ve exhaustively diagnosed your superior’s interests—including obstacles to their fulfillment—do you offer up your own proposal, which satisfies your needs as well as his. For example, “I’ve got an excellent relationship with your superior’s brother. In fact, we’ve been friends since the late ’90s. I rarely tap my friendships for business advantage, but I can see us acting as a team to get us both what we’re looking to accomplish here—me, to move into a leadership role and you to incentivize your boss to pull that obstacle out of your way. What do you think? Would teaming up make sense?”

If you don’t have people resources, by all means think hard about developing them. You can also use your underused skills to help solve a superior’s or department’s pressing problems. "I know my current job doesn’t require me to use my IT management skills, but they saved my last company about 20% annually when they tapped me for company training. You can offer that up to support your current initiative if that would help you. In exchange, I’d need your help in accessing clients more often and assignments that are more likely to advance me to the next level.”

By simply engaging in a problem solving conversation, you have put yourself on your boss’ side of the table. You and me has become we. You’re a partner in the solution, and a willing and able resource in the problem solving process. In a best case scenario, you’ve made yourself an indispensable partner in fulfilling your boss’ needs, his superiors’ requirements, and your goals at the same time.

These questions can be adopted as an opening negotiation strategy in just about every circumstance—seeking a raise or promotion, negotiating flex time, getting the training or experience you need to advance in the organization, or moving past obstacles in the way of your own career goals.

To learn more, check out our free list of diagnostic questions for salary, price setting, and deal and issue negotiations at our home site,

Photo of man negotiating courtesy of Shutterstock.