How you ask makes a world of difference. My goal in this article is to help you do your homework so you have the best chance of getting a meaningful response. Note I didn't say a positive response; 'yes' isn't always the right answer, much as we'd like it to be. You can't be too timid to even ask, but it doesn't work to be so confident you come off as a jerk.
The title and content were inspired by a post at Steven 'The War of Art' Pressfield's blog. The post, titled Clueless Asks, describes what happens when folks don't know how to ask. It might be they're just selfish; it happens. You're not selfish, but even non-selfish types confuse which type of culture they're dealing with.
Culture Clash: Askers vs. Guessers
In an interview at Lateral Action Jocelyn Glei, founding editor of 99U, describes two different cultures and how they clash: the "ask" culture and the "guess" culture. The "ask" culture is based on "nothing ventured, nothing gained, so it never hurts to ask." The "guess" culture says "better not to take chances or use up social currency, so don't ask unless you're pretty sure the answer will be yes."
These might be personal cultures, so you and your business or life partner might take opposite approaches. Here's where things fall apart: according to Glei (and my own experience) we assume others share our culture. Askers who approach guessers often overask without realizing it, and guessers approached by askers often feel pressure where, in reality, there is none. Askers accept 'no' as an answer, because they had no preconception about the response. Guessers, assuming others wouldn't ask without expecting a 'yes', feel imposed on.
Here's where the cultures don't clash: when a guesser approaches an asker. The guesser won't approach unless they think the answer will be yes. The asker assumes they're not being imposed on, because after all, it never hurts to ask, right?
From your perspective as an author marketing your book, the smart money is on being a guesser, on doing your homework and laying the groundwork so when you ask, things go smoothly, whether the answer is yes or not.
Assuming a "guesser" stance introduces limitations. For instance, the group of people from whom you might expect a 'yes' is far smaller than the group of people you're capable of asking. While you may have access to an email address for Steven Pressfield (or Stephen King, for that matter) they have no reason to spend their precious hard-earned reputation promoting your work (unless, apparently, they're married to your sister [see Pressfield's post for that wildly humorous thought.])
Wrangling an introduction to someone famous doesn't entitle you to ask for their support. Again, we're only going to ask if there's some reason for them to say yes.
On the other hand, trust is transferable, to some degree. If you know my friend Tom Bentley and he suggests you ask me, my trust in Tom extends, provisionally, to you. Don't blow it, eh?
If someone who trusts you is also trusted by Malcom Gladwell or Dan Pink, that person may well be able to make an introduction which transfers enough trust to allow you to ask.
Before that can happen, though, you have to ask your friend, which means you need to be reasonably sure they'll want to say yes. Putting them on the spot, creating a situation where they make the connection (or say 'yes' but then never do it) out of guilt or embarrassment won't serve your goals at all.
Making the Guess Before Making the Ask
Put yourself in the other person's shoes. What do they get out of saying yes? Feeling good all over isn't enough.
Are they a fellow expert in your field and do they recognize your expertise?
Are they a fan?
Will helping you further their own marketing?
Do you have a relationship already? Have you deposited enough in an emotional bank account with them that making this withdrawal will make perfect sense to them?
Are they married to your sister? (Sorry, I keep hearing Steve Pressfield's deeply frustrated tone in that line and it makes me laugh.)
Ask yourself why the other person will be delighted to say yes when you ask. Not pressured into it, not reluctantly resigned, but glad to help. If you can't some up with a reason, it's not the reasonable ask we're aiming for.
Do They Want to Say Yes?
I've been giving a short version of asking advice for years: Make it easy for them to say no, but make them want to say yes.
Once you've decided this person is likely to say yes and be glad about it, make your case. Explain why you've approached them, why this is important to you. Let them know how much you'd love their endorsement or assistance in whatever form.
But also let them know that you realize they have no obligation to you, that they probably get more requests like this than they can reasonably say yes to, and that you're not depending on their 'yes', much as you'd love to hear it. Make it clear you realize their 'yes' is a gift, not an obligation. Thank them for even considering it.
Tick, Tick, Tick
You've done your homework, identified a likely respondent, crafted a polite and professional query, and sent it off.
Time dilation sets in.
A week feels like a million years. It's tempting to follow up.
If this was a reasonable ask and you hear nothing after a week or more, send a follow up that simply mentions the earlier query, including a copy thereof, and that you realize they're a busy person and won't ask again.
And then, don't.
They'll respond, or they won't. Guess which direction they'll lean if you seem even slightly pushy? Manners matter.
C'mon, Will it Really Hurt to Ask?
If you're never going to run into George Clooney again, shouldn't you take a chance? What is he going to do, slug you?
Well, what if you shoved in front of all the people in line at the grocery store. What are they going to do, slug you?
But you wouldn't do that. Because manners matter. Good manners are one of the lubricants of society. How you treat others defines you, and if you're willing to be rude to George Clooney or Stephen King, that's not good. Somehow, some way, rude will out.
This article is far from the definitive exhaustive guide to being reasonable when asking others for help, favors, assistance. Pressfield offered a few words on what makes a clueful ask, and there are many related articles out there.
What have I missed? What questions aren't answered? What helpful tips did I forget?
Please, share your perspective and wisdom in the comments below.