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  • Writer's pictureJared Yellin

Ask For What You Want, But First Define The WIN-WIN

“Having the courage to ASK for your optimal outcome but always knowing the WIN-WIN is how you get someone who most can’t even access to say YES to you.” - Jared Yellin

Malcolm Gladwell states that it takes someone 10,000 hours to become an expert in nearly any field as long as there is complete commitment and immersion in the subject matter.

Although I agree with Malcolm's thesis, the 10,000 hours can’t be spent in a classroom or by reading books and instead can only be gained when the skill is being applied for this extended period of time, which is approximately 10 years.

When it comes to sales, I have been working on this skill for nearly 20 years, 8 hours each day of the week, which is approximately 32,000 collective hours, so I would never consider myself an expert in teaching this skill, but most certainly in the top .0000001% when it comes to executing on the skill.

And what I have learned, which is, unfortunately, something most are missing in their selling dynamics, is that there is a completely frictionless way to close a deal, which is called…

Know Your WIN-WIN Before Stepping Into The Frame Of Your Pitch!

One of the reasons I have been able to perform at such a high level in high-stakes selling environments is by stacking the cards for a WIN-WIN in various ways:

  • Talking to “insiders” who want a WIN-WIN as much (or even more) than myself.

  • Collect data from past experiences where not having my offer led to a suboptimal outcome.

  • Have a third party endorse me prior to the call even happening to the person I want to create a WIN-WIN with.

  • Get someone to hype up the call so the anticipation is underway before the meeting.

  • Send a text message the day before the call expressing my enthusiasm and my desire for this call to be the beginning of the beginning.

  • Post consistently on social media (and ensure we are already connected) so the person gets an idea of who I am, my values, what I stand to do, etc.

Just so this is clear…

All of the above is done integriously, but when I am sure of a WIN-WIN outcome based on what I have learned prior to the call/meeting, the only thing that matters during the encounter is the WIN-WIN outcome, which means I will do anything, and everything to ensure this happens — EVEN stacking the cards in my favor which happens to be in their favor too!

WIN-WIN outcomes remind me of falling in love because usually, one person in the intimate prospective relationship is more aware than the other of the potential union, and they will go out of their way to help the other person see what they see. 

They will romanticize them…

They will have friends reach out on their behalf…

They will surprise and delight them…

They will persist with them…

They will “coincidentally” show up where they are going…

And by no means does anyone interpret this as “going too far,” but some would interpret stacking your cards in the favor of a WIN-WIN in sales as influencing the outcome – which happens to be your moral responsibility when you know the other party is better off with you than without you.

So the lesson of this story is…

WHEN you know there is a WIN-WIN – treat this opportunity like an initial date with your future soulmate and do WHATEVER it takes to ensure they see what you see!

6 Strategies To Guarantee A WIN-WIN

So You Can Win In Every Selling Dynamic, Which is Also A Win For The Person Who Says “YES”

Outside of stacking the cards for a WIN-WIN, there are 6 specific strategies that will guarantee the outcome you are committed to. As I mentioned earlier – it’s your MORAL RESPONSIBILITY to ensure the other party can see what you see and commits to the outcome – which is a WIN-WIN!

1.Past - Present - Future

You must collect data even if you feel you already know the path to a win-win from prior research. Your goal in any selling dynamic is to control the flow of the dialogue, which means you need to have a swift first step when joining the call or meeting and then ask a version of the following questions:

  1. PAST: What have you done? What are you most proud of? Tell me about your past.

  2. PRESENT: What are you doing? What are you most excited about? Tell me about your present.

  3. FUTURE: What do you plan to do? What is your vision? Tell me about your future.

You need to better understand their past, present, and future – and even if they attempt to have you speak first, circumnavigate their questions to ensure you are collecting all data. This is directly in service to them because the more data you collect, the more you can speak into their listening. 

2. Back Pocket WINNING Questions

Now, this is important! If during your collection of PAST - PRESENT- FUTURE you did not collect enough data to identify and ensure the WIN-WIN conclusively, you need to tap into your back pocket WINNING questions, which is a series of questions that will help you collect more data to ensure you can help:

  • What’s working?

  • What’s not working?

  • What do you wish you could do that you can’t currently do?

  • Who handles _____________________ for you?

  • Where does this person need the most support?

  • What is the one thing that would help you the most right now to achieve your goal?

The purpose of these questions is to ensure you HAVE what you need from a data collection perspective so that you can speak directly into their listening, which makes them feel like your encounter is serendipity in the making because each word you utter is being delivered to their soul because you know so much about where they are, where they want to go, and where they REALLY want to go!

3. Declare The WIN-WIN

Once you KNOW - with every fiber in your being - the WIN-WIN outcome - you MUST declare it.

It has become abundantly clear that we can WIN together in the following ways:

  • Launch a business

  • Fall in love

  • Refer 7-figures of sales

  • Make connections

  • Hit our goals

  • Earn a ton of money

  • See the world

  • Meet cool people

  • __________________(fill in the blank)

You want to become the voice of WINNING by DECLARING the outcome. Let the receiver begin to envision what is possible once they say YES to whatever your offer is because they are better off with you than without you.

The more they can see it – feel it – and envision themselves living within it – the more likely they are to commit to it!

4. ASK For What You Want

The ONLY sustainable human dynamic is where both parties get what they want. I know countless people who deliver on the WIN for one person – but they are NOT getting what they want and need, which eventually leads to resentment and a complete subluxation of what’s possible. 

Therefore - don’t be most people - and ASK for what you want.

RIGHT after you declare the WIN-WIN, say some version of this…

“I am going to be completely transparent with you regarding where and how I want to WIN because if we both have a WIN-WIN outcome, it leads to a very sustainable working dynamic, so my WIN is the following, and any support you can offer to help me get to where I want to get to faster frees me up even more to ensure you get to your desired outcome as well.”

5. Take 100% Responsibility For A Successful Outcome

Once the WIN-WIN is declared and you have communicated your ASK, it’s 1000000000% your responsibility to drive the dynamic forward. Just pretend like the other party will NOT take the first step unless you do, and they won’t have the courage to take the 100th step either, which means you will become a complete waste of potential if you get them to a resounding YES, but in the end, there is no actual commitment. 

DO NOT wait on the other party. They won’t act, they won’t show up, they won’t take the lead, so instead – YOU DO IT!

Take 100000000% responsibility for your most successful outcome and have ZERO excuses that give you the permission to fall short.

  1. Focus On 51/49

Win the game of giving more than you receive by 1% — don’t allow for inequitable relationships in the early stage because that dynamic will BECOME the reason the entire union FLOPS. 

Someone has to give more – just commit to being that someone.

  • Help them make more money.

  • Help them connect with the unconnectable.

  • Help them find talent.

  • Help them get better rates.

  • Help them plan for something big.

Just go out of your way to win the arm wrestle on WHO GIVES MORE because when it’s YOU,  the other party - if they are aligned - will do everything in their capacity to find a way to at least break even on your support. 

Now What?

If there is no WIN-WIN — don’t CLOSE!

There is a karmic element to sales, and “closing at all costs” is guaranteed to come back and haunt you more than the “WIN” of the sale because of the reputational damage, unnecessary litigation, chargebacks, disputes, stress, wrong customer, etc.

It’s WIN-WIN or NO-WIN — that’s the game I play.

But it’s imperative to KNOW how you WIN too, because if all you do is help other people WIN and you don’t – it’s unsustainable. So, really focus on WIN-WIN and follow this article to a T because I am over 32,000 hours deep into the most important skill you can ever master, and it’s not called sales — rather — it’s called WIN-WIN at all costs!

Live with Intention,


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