Mark Suster explains why you should never be afraid to ask for what you want.
The one word the best entrepreneurs never accept.
I said it.
Now let me walk you through a broader story because avoidance of the word in and of itself will seem cliche. Stay with me.
When I was little I had a role model for entrepreneurship - my mom. She was a natural leader. She was president of the UJA in Sacramento. From this I saw civic involvement and leadership first hand.
She was a nurse but was never graduated from a four-year college. Still -- she can do the NY Times crossword puzzle better and faster than I. Even today.
She was a hustler. And a ball buster. And a natural sales person. She was never afraid of the word "no" even to the point of embarrassing me.
My youth was filled with her arguing with vendors if they tried to pull a fast one. As my wife will tell you -- arguing is cultural -- you grow up with it or you don't. I did. It's very Jewish. For better or worse. She's learned to embrace it in me. If a maitre d' tries to seat me at a table in huge traffic flow or a corner she knows not to bother sitting down.
My mom bought our family's first computer and encouraged me to learn it at 13.
She opened two businesses -- a bakery and then a restaurant. I worked in both before leaving to work in a software company at 17. I never knew a world in which you weren't supposed to work and make money. Even though my dad was a doctor and in retrospect I probably didn't need to earn my own money. My mom always taught me it was my responsibility to do so.
When I was younger my mom taught me something I never forgot:
"You don't ask, you don't get."
It's simple. I know. But it amazes me how many people don't really get it.
Here are two stories:
When I lived and worked in London my wonderful assistant was Deborah Halliday, who was raised a very "proper" British young lady. Her brother played rugby for the English rugby team and went to Oxford. That’s kind of like having a brother in the NFL in the US.
If there was any society in which being a hustler was out of step with the norm is was England. Yet I was a foreigner so I got away with being different.
I used to ask Deborah to book my travel plans in France and Germany were I went one to two times a month. There were online tools to book this stuff but the Internet booking sites were early.
I would tell Deborah, "I found this hotel near the Champs Elysees for 170 Euros. But I don't want to pay that much. Tell them I'll stay if they'll give it to me for 120 Euros."
"What? You want … what? Mark, you can't do that! You can’t just name your own price."
Me: "Of course, I can. Tell them you found a hotel down the street for 100 Euros but I prefer to stay at their hotel. Haggle. See what you can do."
Deborah was mortified. Bless her cotton socks. I put her outside of her comfort zone.
Me: "Deborah, you don't ask, you don't get! What’s the worst they can tell you? "No?" If so, we'll call back an hour later and pay 170 Euros. It's not like they're going to tell you 'no' in an hour. You might as well try!"
Classic Mexican Road strategy.
Here's the thing. They NEVER said 'no.' Such were the times. They weren't fully occupied.
She began to love it. It was liberating. I taught her to make it a game. I would challenge her to see how cheap she could get rooms. I can still hear her giggle at how ridiculous it was in her mind's eye. And yet how eye-opening it was that you could have almost anything you wanted. If you just asked.
Fast forward. My son Jacob. He's now 10. When he was seven or eight, my wife used to sit down with him to do homework and train him in the importance of getting it done early and well. Luckily I have such a terrific and organized wife. Or Jacob would be screwed.
They sometimes did homework at Le Pain Quotidien. And if Jacob was good, he could get a treat.
Tania once took him up to the counter to pick out a treat. He pointed at a chocolate cake and told Tania he wanted a piece.
"No, honey. That's a whole cake. You can't have a piece. It's not cut. Why don't you find something else?"
Jacob: "Of course I can have a piece. Just ask them!"
Jacob has IJ. He knows to ask for what he wants. He is respectful. But he has an inner compass that instead of saying "O.k." to adversity he says "Why not?"
She had him ask the lady behind the counter directly. She said, "No problem."
My wife smiled and couldn’t wait to tell me the story.
My wife thinks Jacob's an over negotiator but she secretly loves it. I always take it as a compliment.
Both stories have something in common. Not being ashamed to ASK. As I tell people almost weekly, "What's the worst that could happen? That they would say 'no'?"
And I mean it. I promise you that 95 percent of the people I meet are afraid of people telling them no. They are personally embarrassed by it. Or insulted. Or view it as failure.
I'm told "no" all the time because I often ask for more than others do and therefore you need to be willing to hear "no."
I was on a flight last year from DC to LAX. I had a business class seat due to status of flying a lot and my family was in economy. I felt bad and was planning on rotating.
But when I sat down I asked if my family could upgrade since there were three open seats. I assumed the answer would be "no" but I figured I had nothing to lose.
The flight attendant said "O.k., but you’ll have to pay a small upgrade fee and I can't move them until after take-off." But move them she did. And she decided it wasn't really important to make me pay since the seats were unoccupied.
We had also just been upgraded from London to Baltimore.
Two times in a row--unreal. My wife was a bit incredulous (but grateful). I simply pointed out that our kids learned a more important lesson than the downside consequence of their expecting to always sit in business class (which isn’t going to happen!).
They learned to ask, "Why not?"
You don't ask. You don't get.
And here's the thing about "no."
I know first hand just how chicken people are about hearing it. I've sat through so many meetings where sales reps didn't ask for the order. I've been pitched by hundreds of entrepreneurs who never actually asked me whether I would invest. Very few people do.
Here's an experiment for you.
Hold interviews with tech people, marking people, ops people, finance people -- whatever. They always finish the interview with a "thank you" and barely ask next steps.
Any great sales person will ask you at the end of the meeting, "So, how'd I do? Who else have you spoken with? How do I stack up? What do I need to convince you of to get an offer? What is the next step in the process?"
Great sales people are trained to "ask for the order." If you interview a sales person and they don't ask for the order, be worried.
I like to flip things on their heads. I like to ask in reverse in interviews, "If we did get aligned to offer you this role, do you plan on accepting? What other offers do you have? What do we need to do to win? What steps do you still need before you decide to go with us?"
I want to know. And I have nothing to fear in the answer.
My favorite (not!) is dealing with lawyers (or VCs) who say, "As a firm, we never do a, b, c." Let me tell you now that often this line is BS. But my standard response is, "I don't care what you normally do. I think it's right for our situation. So unless you explain to me logically why it doesn't make sense at our company, my assumption is that it's a good idea."
In summary, I recommend some honesty with yourself. "Asking" is a skill that can be practiced and learned but you need to be self aware.
How comfortable do you feel with asking for the order? How confortable do you feel with asking awkward questions or asking for things that are out of the norm, "Could we have your room for 120 Euros so we don't have to stay down the road?"
If you don't find it within your confort zone - practice in small ways for asking for slightly unreasonable things just to get used to it. It's a skill you're going to need as an entrepreneur.
After all--you don't ask, you don't get.
This post originally appeared on Both Sides of the Table.
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