How to Negotiate the Impossible

Most negotiation advice focuses on what to do when everyone's working together to find the best solution.

We know that most negotiations don't work like that.

Often, the best solution isn’t clear cut, and we’re not all holding hands skipping through a field.

How do you handle the impossible situations, where you feel backed into a corner, forced to choose from a bad set of options? Where you repeatedly cover the same ground with no resolution?

What if there were a simple shift you could make to negotiate the most impossible situations powerfully—without being aggressive or getting steamrolled?

A client did exactly that when she found herself in an ongoing, high-stakes negotiation with her new boss.

Here’s how she stayed true to herself, got to the right solution, and exponentially improved her value in the process.

How to Get What You Want and Have Others Thank You for It

My client (let’s call her Ashley) recently encountered an unwinnable situation.

Not long after starting a new job, Ashley’s boss handed down a set of objectives that was completely at odds with her role.

Ashley listened, waited a few days, and responded with a solution that met her boss’s immediate needs and allowed Ashley to keep her original responsibilities.  

Her boss agreed. Ashley could breathe again. All was well in Negotiation Land.

Until her boss returned a few days later with an ultimatum:

1) Take the new role with reduced pay, or

2) Leave

Ashley was shocked and disappointed. Yet, she listened, waited, and returned with a third option. Their negotiation continued, and they agreed on a solution.

Following the meeting, Ashley’s boss sent an effusive email, complimenting her leadership and poise, and reaffirming how important Ashley was to the future of the organization.  

Ashley not only negotiated a better solution, she exponentially improved her standing with her boss, who just days before had challenged her to accept the terms or walk.

Let’s understand how Ashley did it.


The Hidden Agenda that Determines Negotiation Success

You already know that “win-wins” are the cornerstone of successful negotiations. But this approach assumes all parties are rational and their needs overlap.

Deborah M. Kolb and Judith Williams, two of the foremost authorities on negotiation and gender, argue that negotiation is not just about the issue at hand. There’s a parallel negotiation with an unspoken, often-hidden agenda that determines bargaining success. They call this the Shadow Negotiation. 

In the shadow negotiation, you negotiate how you’re going to negotiate—whose interests and needs come first, whose opinions matter, and how cooperative you’re going to be in reaching an agreement. 

Think about arguing with your significant other about how you load the dishwasher. Is it actually about the Swiss-like precision you demand for your utensils, or are there much more important dynamics at play?

Ashley and her new boss were ostensibly negotiating the role. But they were also negotiating the dynamics that would govern their working relationship.

Ashley succeeded because she went beyond finding a “win-win” solution. By expertly managing the shadow negotiation, Ashley and her boss walked away feeling good about themselves and each other.


Beyond the Win-win: Why Women Lose Negotiations

Kolb and Williams contend that women face a significant disadvantage when it comes to the shadow negotiation, where power, biases, and gender dynamics come into play.

[Pause for chorus of dissenting voices].

Women problem-solve with great skill. But they often fail to recognize the shadow negotiation, thus losing the argument before they even get to the bargaining table.

As we’ve learned, negotiation is about the problem itself and the relationship between the negotiators.

The key to managing the relationship? Advocacy and Connection.

We advocate by signaling that we came to play, actively engaging in decisions, and making it clear that our opinions carry equal weight. As my friend and fellow coach advised me during a challenging contract negotiation, “Show them you are not a person to be trifled with!” 

Advocacy isn’t aggression or rudeness. If you treat the negotiation as adversarial, it will be. Enter connection.

The hidden agenda is the real agenda. Our job is to draw it out, acknowledge and validate the other person’s needs.

Through the simple act of listening and waiting to respond, Ashley showed she took her boss’s concerns seriously. She understood the motivations, emotions, and needs behind her boss’s requests, and designed her responses accordingly.

Her boss felt heard, so she listened, so the conversation continued.


4 Tricks to Negotiate Like the Boss You Are

1. It’s not what you say, but how you say it

Set the tone. How do you want the conversation to feel? Ashley wanted a heart-to-heart-we’re-in-this-together vibe. Notice how that frame establishes advocacy and connection: they’re both on the hook to resolve this.

2. Begin with the end in mind

Get perspective by clarifying your long-term objectives. What’s the most important message you want to communicate?

Ashley wasn’t interested in a role that would impede her career progression or earnings. Nor did she want to abruptly depart. 

She was honest and transparent about why the first two options wouldn’t work for her: it was about integrity and completing the work she came to do. Her candor facilitated an open exchange where they could find common ground.

3. “No” is the beginning, not the end 

There’s always another solution. Kolb urges us to view “no” as a starting point for continued negotiation. 

Notice the tenor of the initial offer from Ashley’s boss, “Here’s a bad set of options. Choose one.” Ashley values her autonomy above all else, so proposing a different option—any option—was as important as the content of the option itself.  

4. Don’t demote yourself

Ashley was a senior leader in the company. Yet when her boss gave her the ultimatum, she felt powerless.

Then Ashley remembered that her boss hired her for a reason. She decided to approach the problem as she would any other…as a calm, solution-focused leader who makes bold decisions.

It worked.

Ashley won her boss’s admiration because she handled the situation like a boss. The solution was secondary. Shadow negotiation at work.


Claim Your Seat at the Table

We lead when we bring our full potential to a situation—not easy when the walls are crumbling around you. 

As Ashley’s experience illustrates, we can overcome even the most impossible situations. If Ashley can do it, so can you.

The key is to be that person—the one you were hired to be, the one you want to be, the one you are now. You define your power, not your circumstances.

Getting what you want is easier than you think. It simply requires clarity, intention, and deft handling of the shadow negotiation.

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Author Bio: 

Before becoming a coach, Caroline spent 20 years in management consulting and financial services. She's made it her mission to help people grow, contribute, and get wherever they want to go.

Caroline wants women to recognize how much power they truly have to define their careers. The life and career you want really is possible once you have the roadmap. Take the first step by downloading her free guide.

She’s also a tennis fanatic, aspiring Minimalist, FIRE (Financial Independence and Retire Early) enthusiast, and Aloha Spirit seeker 🤙. She loves to share stories from her unconventional life and career focused on freedom, creativity, fun, health, family, and community. If she can do it, you can, too.

If you want to hear more about my twisty-turny career journey, here's my story.