Why we’re afraid to ask

Last week, I wrapped up a two and a half million dollar fundraise!

That is, by far, the most money I have ever tried to raise. One of the issues I had to face was my fear of the close, of asking the question, “Would you like to invest?”

It is one thing to tell a good story, complete with compelling data. It is more difficult to ask someone to purchase what you are selling.

I can’t share the specifics of why, together with a few close friends, we were trying to raise the two and a half million dollars, but we were ultimately successful, even though the deal fell through.

As I went through the process, I wrote down reasons why I was afraid to make the final close and some strategies to address each of those fears.

Concern: Taking advantage of people

One of the most common concerns I hear about selling is the fear of taking advantage of your prospective customer.

Most people find coercive salesmen offensive. But there is a big difference between relying on pressure to close your deal, and never asking people to buy in the first place.

If I’d let my fear of taking advantage of someone stop me, I’d never have started Robin’s CafeResponsive Conference or Zander Media. More importantly, I wouldn’t have developed the courage that I’ve learned along the way.

Answer: They get to decide

Define what you mean by “taking advantage of people.”

Inherent in that phrase is the belief that you can force people to do things against their better judgment. And while I could, theoretically, use physical force or the threat of violence, the kind of gentle persuasion that I encourage is the furthest thing from that force.

Here’s my shortcut: If you are the kind of person worried about forcing or coercing someone, you don’t need to worry about taking advantage of your prospective customer.

The person you are talking to gets to decide what’s best for them. There is no such thing as “taking advantage of someone” when you don’t use force, believe that they are their own best expert and trust that they will decide for themselves.

Concern: Using force and pressure

Inexperienced sales people don’t close a deal or make their ask because they are afraid to pressure their prospects. And the experience of being pressured by a salesperson is unpleasant.

I have built up a robust immune response to that kind of pressure. If someone pressures me, I leave, even if the pitch was something I’d otherwise have agreed to.

But as unpleasant as being pressured is, being a pushy salesperson yourself is more so. The fear of pressuring someone else can be so intense that that we don’t even try to sell.

Answer: Know your emotional state

To ensure that you aren’t using force or pressure, learn to assess your own emotional state. If you’re not sure how you are feeling, check in.

Pressure usually comes from the significance we’re placing on a specific sale. I don’t sell unless the thing I’m selling really matters to me. And if it matters that much, I can get attached to the outcome.

Any single sale isn’t worth the feeling of having pressured someone else.

Use that knowledge to let go of your own pressure. Know yourself and what you are feeling. Ensure that you aren’t feeling pressure. Then show up with your customer with the desire to help.

Concern: Rejection

I learned to juggle in high school, and eventually became quite good. Inherent in juggling is dropping balls, which we could call failing to juggle.

Inherent in asking people for things is being rejected, being told “no.” That’s a part of selling.

Getting turned down when something matters can be unpleasant, absolutely, but it can also be just another data point. As with dropped balls while juggling, get rejected is part of the process.

Answer: Rejection is less scary than you think

Oftentimes, our fear of rejection is the thing we’re actually scared of, even more than the declination itself.

In selling, a rejection means nothing about you. It is actually great because it provides you data about how to improve and the simple clarity to move on to your next prospect.

Since clear answers in life are pretty uncommon, a rejection is cause to thank your prospect for their clarity. They were able to give you a clear answer, which is a compliment to everyone involved.

Concern: Danger to your reputation

Another common fear is that asking people to buy your thing will endanger your reputation.

Sorry to break it to you, but people will judge you based on what you ask for, what you promise and what you deliver.

Answer: Sell things you are very confident in

The answer is to have the utmost confidence in what you are selling and then to be very honest about the the risks and benefits involved.


Next time you are on a sales call or ask a friend to lunch, notice what concerns come up for you. (I keep a pen and paper nearby to take notes.)

Take a few notes about how you are feeling. Afterward, come back to the specifics of the sale and evaluate your feelings.

Assess how you felt and why you felt that way. What were you believing about yourself and the other person?

The more practiced you become at identifying your concerns, and the more you explore them, the better you’ll be at addressing and avoiding those fears in the future.

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