If You Don’t Ask, the Answer Will Always Be No

Many businesses and professionals fail due to their inability or unwillingness to ask for the sale

“Hope is the quintessential human delusion”

The Matrix Reloaded

If you want something — a sale, a raise, some private time for your mental health — you need to ask. In business, everyone is competing to succeed; no one is giving anything away.

Of all the great scenes in the movie “Fight Club,” there is one that is probably the most overlooked. Edward Norton’s character (Narrator) calls Brad Pitt’s character (Tyler Durden) on the phone after a meeting and they share a drink together. Towards the end of the conversation, it becomes apparent that the Narrator isn’t getting what he wants:

    • Narrator: Oh, it’s late. Hey, thanks for the beer.
    • Tyler Durden: Yeah, man.
    • Narrator: I should find a hotel.
    • Tyler Durden: [in disbelief] What?
    • Narrator: What?
    • Tyler Durden: A hotel?
    • Narrator: Yeah.
    • Tyler Durden: Just ask, man.
    • Narrator: What are you talking about?
    • Tyler Durden: [laughs] Three pitchers of beer, and you still can’t ask.
    • Narrator: What?
    • Tyler Durden: You called me because you need a place to stay.
    • Narrator: Oh, hey, no, no, no, I didn’t mean…
    • Tyler Durden: Yes, you did. So just ask. Cut the foreplay and just ask.
    • Narrator: Would – would that be a problem?
    • Tyler Durden: Is it a problem for you to ask?
    • Narrator: Can I stay at your place?
    • Tyler Durden: Yeah.

A single line from that conversation got stuck in my brain: Is it a problem for you to ask?Many businesses and professionals fail due to their inability or unwillingness to ask. Fear of rejection is a powerful thing.

What it takes to be a sales professional

I ran across an article in Harvard Business Review about what it takes to make it in sales. The article is 15 years old, but it whittles down the problem to two things 1.) Empathy: You need to be able to understand the wants and needs of your prospects, and 2.) Ego Drive: Something propels you to conquer. Empathy is a great quality that all humans should possess. It is the need to conquer that makes a business successful. Businesses need revenue, and they need customers to provide that revenue.


Entrepreneur is a French word: entre = between, preneur [from prendre] = to take; one who takes.

A looser definition could be “one who engages in.. Google Translate turns “entrepreneur” in French to “contractor” in English. A simpler definition could be “middleman.” In the business world, it has come to be defined as one who organizes and runs a business firm; one who comes up with a great idea and turns it into a market solution —either a product or service.

Another definition of entrepreneur? One who continues to move forward despite being told “no” on a regular basis. Prospects, investors, potential partners and employees, the collective “market” – all say no. Yet, the most successful entrepreneurs continue on. They continue to ask.

Thomas Edison famously said “I have not failed. I’ve just found 10,000 ways that won’t work.” This is the essence of entrepreneurship. It’s not for everybody.

Success has many definitions

A college professor of mine used to say, “Success has many definitions.” He was referring to the audition process or the pitch for investors. He liked to use a baseball analogy:

  • If you strike out 9 times out of 10 – you are average.
  • If you strike out 8 times out of 10 – you are a pretty good player.
  • If you strike out 7 times out of 10 – you are one of the best in the history of the game.
  • If you strike out 6 times out of 10 – you are the best baseball player that ever lived.

I always loved the story, so naturally, I did a little digging. The best career batting average in history is Ty Cobb at .366. The best baseball player that ever lived had a success rate of 37%!

Given the number of transactions your business makes on a regular basis, do you consider a 60% failure rate as success? You may want to reconsider.

“Ask for the order”

When I took a position in sales over 13 years ago, my manager asked me a crucial question, “Can you ask for the order?” It’s a simple question, and some people have no problems answering it. Others may see it as begging; still, others find it humiliating. It still needs to be done. The business needs revenue and the sales team is responsible for acquiring it. It’s their job to ask.

The worst they can say is no

While hearing the word “no” can be extremely painful, it also gives you closure. Now you can move on to someone else and you don’t have to wonder anymore. Hearing “no” can provide amazing emotional wellbeing and relief. It’s liberating and sets you free. It provides clarity and certainty. You can invest your time more wisely on something or someone else.

Is it a problem for you to ask?

Cut yourself some slack. Sales is not for everybody. Some people are made for it. Some are made for supporting roles in other parts of the business. Forgive yourself if you are not bred for this type of activity. Employees who bring value will be rewarded for their contributions and businesses that provide value for their customers will be rewarded with consistent business. The challenge with this is it will be on their terms, not yours.

If you want something, and you feel you deserve it, ask. Your success, and the survival of your business, could very well depend on your ability to ask for it.

Be brave. You got this. Here’s a closing thought from Mr. Edison:

“Many of life’s failures are people who did not realize how close they were to success when they gave up.”

Dana Curtis

Dana Curtis


Dana Curtis is the founder and CEO of Biztools, a strategic consulting firm that helps small businesses multiply revenue through improved customer experience and pivot to new markets.

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