You Have to Be Willing to Make the Direct, Audacious Ask

There are a lot of self-styled gurus out there who will tout magic formulas for success. I don’t like to do that. I don’t feel like a guru with all the answers.

But I do like to give practical, actionable ideas that you can use to improve your own life or business. I’ve learned some things over the years, and feel like I should share them so others can benefit.

Also, one my guiding principles is to build up not just tear down. I write critical takes, as well as analyses that make some people uncomfortable. But I don’t want to fall into the trap I’ve seen many folks get caught up in where they become almost entirely negative and attacking.

Negatively sells. It gets more clicks. But there’s way too much of that in the world today. There’s always room for criticism, but we also need to be constructive and build up too. I want to be part of that building up.

So today I want to share one constructive, useful idea for you: make the direct, audacious ask.

There’s a big company whose product I really wanted to buy, but they don’t sell it where I live in Indianapolis. Although I figured it was a long shot at best, I emailed the CEO of the company - who is based in another country - and asked if there were any way I could get his product here. I offered to pay a premium.

As it turned out, his company had a secret “VIP” option to provide their product in markets that they don’t serve. I was able to get signed up for it. (I’m being vague about the company because they asked me to keep this offering a secret).

Had I not emailed the CEO and made that ask, I would not have been able to get this product I really wanted.

Shortly thereafter, my wife and I wanted to purchase a chair. We found one we really liked online, but didn’t want to buy it without sitting in it. Unfortunately, there was no retailer in down that had it in a showroom.

I did some Googling and found an article about the design of a local company’s new office that mentioned they had this chair. We decided to go to their office and ask if we could sit in it. When we got there the door was locked and there was no receptionist. But an employee walked by and I was able to flag her down and ask if she’d show us the chair. She put down her computer and personally took us to the place it was and we were able to sit in it and try it out.

If we hadn’t gone to that company and asked to sit in their chair, we would never have been able to try it out.

We ended up buying the chair. While checking the order status to see when it was expected to ship, I noticed that the vendor had put it on discount. So I emailed them and asked them to apply the discount to our order, which they of course did.

Almost any company would surely do his, but I still had to ask them first.

I’ve usually been someone who likes to avoid potentially socially awkward situations. Maybe because I’m a recovering nice guy or have a personality that is too agreeable, I’ve often avoided directly asking for things - particularly if it’s something that seems outlandish or which in my mind is something people would be unlikely to give me.

I don’t think I’m alone in this. Just as many guys are scared to ask a woman out on a date, a lot of people find it hard to ask for something directly, like a free room upgrade or a discount.

For a lot of us, we have not because we ask not. When I do directly ask for something, it’s amazing how often people say Yes and give it to me. Undoubtedly we are all failing to get a lot of things that we want simply because we didn’t ask for them.

And even if the answer we get is No, what’s the harm in hearing that? I’d have been in no worse position if I had gotten No’s in all three of the situations above.

In most cases, there is almost zero downside for asking for things, meaning that asking for things has big asymmetric upside. Which means we should be making direct asks much more often.

And making big, audacious asks too. As French Revolution figure Georges Danton put it, “Audacity, audacity, always audacity.” Asking for big things is one of the less risky audacious things we can do in life.

As I said, this one is as much more me as it is for you. I don’t make asks like the ones above nearly enough.

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