The Art of the Ask

In business you learn quickly that there are only two types of people: buyers and sellers. It’s very easy to know who the sellers are. They make themselves obvious. They are actively trying to part buyers with their money. The hard part of doing business is knowing who the buyers are. They are not always obvious. They often don’t think of themselves as buyers and they sure as heck have no intention of parting with their money. Asking people to buy, or to even consider becoming a buyer if they are not actively in the market, is an art form that few sellers master.

The Art of the Ask is not just limited to selling a product or service. It applies to asking people to donate to a worthy cause. It applies to asking people for advice or introductions. It applies to asking people to join a club, volunteer their time, or support a Kickstarter campaign. We are all not sellers as much as we are all askers. To be successful at anything, we must learn to be good askers.

By way of background, I don’t hold myself out as a Master Asker. I am still an apprentice by most standards, but I have been in the presence of true Masters. What I have learned by observing them is that everything you do in life, every person you meet, is an opportunity to practice and refine the art of asking.

I learned the basic techniques as Rush Chairman for my college fraternity. When people show up at a rush event, they often don’t know anything about the Greek system or the fraternity they are visiting. They come to party and leave with a bid to pledge – making a lifetime commitment in the process.

After college, I went on to run a national non-profit foundation where I had to ask people for sizable gifts, including leaving a chunk of their life estate to the foundation. I ended up as an entrepreneur, where I needed to ask people for tens of millions of dollars in funding — using required investment documents that say: “If you invest in this company you will probably lose all of your money.”

All of these “asks” were tall orders, but they were all achieved by applying good asking techniques. There are true Masters far better than I to explain them to you. In any case, they can’t be explained as much as they need to be observed and practiced. With that disclaimer, allow me to share a few basic tips.

Asking is not selling. Every sale is an ask, but not every ask is a sale. Asking is way more effective than selling. You need to distinguish between the two. Being a good asker will lead you to becoming a good seller.

No one wants to be sold, but everyone wants to buy. People know when someone is trying to sell them something. No one wants to be sold. We all have a defensive, visceral reaction to being sold, as in, “They are trying to sell me a bill of goods.” We don’t want anything pushed on us, we want to make the choice to buy. A good asker will make us believe the decision to buy is ours. And more importantly, that what they are asking for is authentic.

No good ask results in a no. Most people don’t become good askers because they fear rejection. The best way to overcome this fear is to always ask in a way that the answer can never be no. Examples:

When I was extending someone a bid to pledge the fraternity, I never asked, “Will you accept our bid to join?” I always asked, “If I were to extend you a bid, what are the things that might prevent you from accepting it?”

When I was asking someone to donate to the foundation, I never asked, “Would you consider a tax deductible gift to the foundation?” I always asked, “In addition to taking care of your family, in what ways do you envision leaving your legacy?”

When I was raising money from accredited investors for one of my startups, I never asked, “Are you interested in investing in our Series A?” I always asked, “Given all the deals you see and have the opportunity to invest, what interests you most about the companies you decide to invest in?”

The answers to these questions lead to more good asks, which eventually lead to the prospective buyer asking for the terms under which they “might” buy. At that point, they become obvious and active buyers. They are choosing to buy, or are at least considering it. They never feel like they are being sold.

An ask is a give in disguise. Master Askers never think they are asking for anything. They believe in their heart-of-hearts that they are giving something valuable. The person being asked also believes that the thing they are being asked for will result in them getting equal or greater value by saying yes.

Ask twice, either or. A good ask is made more than once in the same conversation. The second ask is more subtle and is phrased differently than the first time it was asked. A good ask is never a “take it or leave it” proposition. A good ask always presents an option: If not this, than how about this?

Yes is confident, easy, painless or risk free. Even if the ultimate ask is expensive and involves a high degree of risk on the buyer’s part, a series of small, interim yeses can alleviate the objections and turn a likely no into a yes. This is why “free trials” work so well. Over the course of my career, I have often said, “Hey, if it doesn’t work out, I’ll buy it back from you for what you paid plus 10% for your trouble.”

Every ask carries gratitude and reciprocity. Lots of asks are favors. Master Askers never forget a favor and look for any opportunity to repay them — without being asked to do so. Always say, “Thank you very much, and please let me know if there is something I can do for you.”

If you master the Art of the Ask, you will truly be the master of your own destiny.