The Rule of 5 NOs

Our greatest weakness lies in giving up.
The most certain way to succeed is always
to try just one more time.

Thomas Edison

When someone says NO to our request, our promotion, our idea—it hurts our feelings. A proverbial door slammed in our face. And we can put our fluffy tails between our legs and sulk away to tend to our fragile egos.

You have a proposal that is so obviously meritorious. Any rational person who cares and is paying attention would instantly approve and even applaud when they receive it.

But this is where the challenges begin. With our fear of failure. Our fragile feelings. And our amnesia about how decision-making works.

How many NOs, does it take to get to a favorable decision? In other words, how many times can you be declined before you give up?

I devised the Rule of 5 NOs after thousands of attempts at pitching ideas, raising money, and asking for approvals. I witnessed the human behavior in the selling process when I managed sales operations, fundraising groups, when I held the purse strings for foundation grants, and venture capital.

You often must sustain a minimum of 5 NOs to get to the promised land.

To be clear, once you get a YES you move on. 😊 But you don’t bail when you get turned down the first 4 times!

If we think about it, we remember how complex human communication is. It is a small miracle when what someone hears lines up with what was said. Verbal transactions are fraught with interpretation. And misinterpretation is a normal outcome. You throw in body language, mood, bias, what happened immediately before the transaction, and the fidelity of the communication barely has a chance.

The single biggest problem in communication is the illusion that it has taken place. George Bernard Shaw.

That’s why so many people say, they don’t want to be in “sales” or why so many people dislike fundraising. The fear of rejection. Yet all of us are in sales. We have to sell ideas, we have to promote ourselves, we have to seek approvals for increased budgets, staffing—We are all in sales.  

If you just blurt out an idea at an unsuspecting decision maker, you trigger a reflexive response, and it is usually NO. No one likes surprises. The recipient of every communication, even those we think are of the same mind, see the world so differently from you. The recipient possesses a deep library of reasons, rationales and experiences that power the launch codes for the NO missiles. They are ready to blow up any “bad” ideas in an instant. NO is pre-loaded. A YES is locked and protected behind a set of doors and a maze of doubts.

The biggest mistake is being one and done. You take your one shot and get rejected. You take it personally and you, villainize the rejecter, and build a house of negativity that impacts everyone around you.

Rejection is a detour. Declination reveals preferences. All selling, pitching, asking, fundraising is iterative. You get feedback and you version the approach.


  • The first three (up to 5) NOs are on me. Meaning, I did not communicate well, I made mistakes, I bumbled and mumbled it. In other words, “MY FAULT.” I take full responsibility for the failure to communicate.
  • Each NO puts me back in the garage to re-tool my pitch. To do my homework. To test new approaches. To incorporate and address the objections that have been cited. I research, rehearse, review, revise, rinse and repeat!
  • Don’t take things personally. From the Book the Four Agreements: As you make a habit of not taking anything personally, you won’t need to place your trust in what others do or say. You will only need to trust yourself to make responsible choices. You are never responsible for the actions of others; you are only responsible for you. When you truly understand this, and refuse to take things personally, you can hardly be hurt by the careless comments or actions of others.
  • The fourth NO is the moment of truth. While this pitch was my best yet, if I sense resistance. I ask for one last chance.
  • The 5th NO is my out. And I gracefully thank the prospect, the decision maker, for their patience and their interest. And keep them in the future prospect file—because they were interested!

Just did this recently. The team hearing my pitch for the fourth time, said, “Admire your persistence John.” I know that can be interpreted both ways, but I did see it as a compliment. 😊 I apologized for my poor presentations before and appreciated their time and indulgence. I told them about my rule and that this was the last time they would see me if the fourth attempt did not get us to a negotiating point. They were surprised that it had been three times hence and about my rule. As I write this, my proposal is still alive!

If we care about our work, the mission, the product, the idea we are hocking, pitching—then it is difficult to not take it personally. It is disappointing. Especially if we are trying to advance our career, our salary, our ambitions. That’s how you feel. How others feel is not in your control, that is the difference.

My experience is persistence pays off. That an educated pitch and conversation overcoming a series of NOs can forge better outcomes for all.

One of the funniest sales stories that I ever heard was from my roommate in college. His parents were immigrants who picked crops in the central valley of California. His childhood poverty gave him an appreciation for hard work. He was always hustling small jobs to make ends meet. One summer he took a job selling dictionaries door to door in Pennsylvania. I know that sounds crazy. Long ago, door to door sales was a real thing, most encyclopedias were sold that way. He developed this technique that would have endangered his life today. He was a six foot five Mexican American. He would knock on the door and say with a huge smile.—He had a beautiful smile. He would introduce himself and make a compliment about the front yard. “I’m here to sell you these fantastic dictionaries. Would you like to see them?”, he’d say, with great enthusiasm and charm. And more often than not, people would scowl and quickly say, “No thank you.” And many would slam the door in his face. If he felt there was any chance, he would go around the house and knock on the back door.  The same woman would appear perplexed and say, “What do you want now?!!” And he would say with that same beautiful smile and positive energy, “I was hoping that you’re in a better mood than the woman who lives in the front of the house.” He told me 50% of the time the woman would laugh, listen to his pitch and even offer him a glass of lemonade!  He did this to overcome the initial NO. At the end of the summer he was one of the top dictionary salespeople in the company! He did not take rejection or declination personally. It did not dampen his enthusiasm for life of why he was there. He felt grateful to have the chance to talk to people about a dictionary. As silly as this sounds that old story continues to guide me. Because I’m always wondering if the person at the back door is in a better mood 😊

Never accept the initial NO or even the first four NOs! A great pitch evolves. Don’t take it personally. Don’t give up. Enjoy what you do! Smile! And keep going!

Released last week, I was honored to be interviewed by Caren. We had a lively conversation about navigating life's changes, challenges and chances. Check out Vitalcy and their growing library of resources for people confronting transitions and especially those planning their retirements.

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