The Easy Yes
“What does he really care about?”
At first, I was stumped and then I offered my dad, “Ummm…influence, making money, and his legacy. “
“O.K. then, do you see a way you might propose what you want that also caters to what he cares about?” he chimed back.
“Uhh yeah, I think I do.”
Over a decade ago, I learned the antidote to The Easy Yes, and since then, I've helped countless people navigate tricky conversations with confidence and success. It's not as simple as snapping your fingers, but the principles below can pave the way to achieving your goals.
Perhaps it’s time to fly the coupe and make your employer your first client. Maybe you're sitting across from your boss, heart pounding, asking for a raise. Or you could want to persuade your partner to try that new restaurant finally.
Whatever the case, flexing curiosity, care, and clarity can help do the trick.
Curiosity
Interesting people are interested — so the saying goes. This is not feigning interest, it's about demonstrating authentic curiosity. When you approach conversations with a genuine desire to learn and understand, you disarm others and create an environment ripe for partnership.
Next time you're gearing up for a heavy conversation, take a moment to consider the environment, mood, and mindset of your listener. Are they receptive to your ideas, or could they use more context? If you’re asking powerful and generous questions it’s likely your pitch will go down a lot smoother. Even a frosty person can start to warm up to your ideas.
For example, if you’re seeking a raise you might try swapping a demand for a dialogue. Removing the binary choice of a ‘yes’ or ‘no’ from your boss and replacing it with a candid conversation can change everything.
Seeing your career as a continuum and remaining open about where you think you are on this trajectory and where you’d like to be— enrolls your listener to play a part in your growth.
Your job is to observe, listen, and gain insights into what motivates your audience.
Care
We make decisions based on what we care about. So caring about what others care about is the key to making it easy for them to say yes. Whether you're trying to convince a colleague or sway your manager, understanding their motivations is key.
You might be thinking this is just an elaborate way of describing empathy. You wouldn’t be wrong. You demonstrate empathy when you understand the needs, interests, and perspectives of your audience without necessarily agreeing with them.
Consider adopting what master negotiator Chris Voss calls "weapons-grade empathy." By focusing on interests rather than their stated positions, you can uncover creative solutions that benefit everyone involved. Remember, empathy isn't about agreeing with others; it's about understanding and acknowledging their perspective and from here finding common ground.
Your position might be that you only want to come to the office on Mondays and Tuesdays. Meanwhile, your interest is that you want to be around the house more often as a companion to your great aunt who is living with you. Assuming your superior appreciates your interest and you focus on theirs — which is for you to be present for a strategy meeting on Wednesday mornings—you could discover a creative option that benefits all. Your employer offers to sponsor your aunt for a music program at the neighboring community center that morning. Voila! You can attend the meeting and your aunt gets to make new friends to boot.
Clarity
Originally I was going to call this third principle; conversion. But I dislike that term as it conjures up a Glengarry Glen Rossy feeling of seeing people as mere wallets.
The laws of human nature apply to all of us. We are fallible, irrational, and imperfect. What this means for you is that when you appeal to someone’s humanity and discover coherence together — it should feel good, not icky.
When you show that you can see others’ situations in fresh and revealing ways you might discover problems they didn’t even know they possessed. Attuning to another’s perspective helps you enmesh with future actions and outlooks and arrive at a mutually appealing outcome.
The Easy Yes is not about being pushy, it’s about being honest. With access to the same information these days, it’s increasingly hard to hide your cards. Express your wants and needs clearly while also considering those of your counterpart.
Perhaps you’re wondering about the difference between being persuasive and being a master manipulator. Take stock: Are you being disingenuous? If you’re telling yourself a convenient story that you’re being empathetic when something else is going on, it’s time to re-evaluate. If you’re questioning your method, then it’s time to rethink your strategy.
Exercising control insidiously to gain an advantage is just bad news. We should always treat people like people — not pawns to be pushed over. But no need to ruminate long — because the guiding principle whichever you slice it is that honesty is the best policy and clarity is kind.
The next time you find yourself gearing up for a tough conversation, remember the principles of The Easy Yes. With a little empathy, a lot of curiosity, and a healthy dose of clarity, you'll be well on your way to getting what you want—and making it look easy in the process.
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(In) Practice
The Setup: Sam’s been a creative at a fashion brand for nearly 5 years. In millennial land this is ages. It’s time to make a move and her hope is that her superiors would be supportive; offering mentorship, industry connections, and future contractual work.
His director cares about quality while the VP is concerned with reliability and money. In the realm of their professional lives, this is what matters to them. Indeed it’s likely they also care about their family, whether the sun will shine tomorrow, and who will win the Presidency.
It’s been a year of laying the groundwork to leave — and it’s time.
The Outcome: First thing first, it was important that Sam get her emotions in check. She was bitter that she wasn’t given the pay raise she was promised and needed to clear this resentment before any conversation took place.
Next was to share her intentions with her Director. This wasn’t a ‘Hey it’s been fun! I’m outtie.’ No, this was a series of carefully planned conversations at a time and in an environment conducive to psychological safety. She enrolled her Director and together they brought in and influenced the VP.
This is where Sam practiced clarity—expressing what she wanted which also took into account what her superiors were interested in: quality, reliability, and money (making and saving it). She had already demonstrated these capacities over the last 5 years and with quiet confidence she continued to reinforce them. Then she dropped the ball: ‘It’s time for me to stretch and challenge myself — and I’d be grateful for your support.’ Clarity is kind.
With her last formal paycheck she not only navigated this chapter with grace she also closed it out with a celebration. Inviting both current and former employees of the brand to a shindig — Sam was overwhelmed with the recognition and love she was showered with. Everyone showed her they valued her sense of humor and the energy she brings to work and beyond.
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Go Deeper
Books: To Sell is Human and Getting to Yes
Substack: The Zen and Art of Listening
Ted Talk: Never Spit the Difference