In December, I led a workshop on “Designing Your 2015,” and I learned something I did not expect.

A couple dozen women had boldly sized up 2014—the victories, the unmet goals, the excuses—and envisioned the ideal 2015 and how to get there.

There was one part of the exercise, though, that gave even the most ambitious women jitters. It was a worksheet page entitled “Who can help?” You list who is able to help you, what they could help you with, and when you’re going to ask.

At the bottom of the page is a little checkbox. You can’t move on with the exercise until you ask at least one of those people, and check the box. We all have smartphones—it’s not that hard to pull one out and write an email: Hey Dan, it’s 2015! I hope all is well. My photography business has been thriving over the last 12 months, and I’d like to work with more large brands in 2015. Would you mind introducing me to the marketing manager at your firm? Here’s hoping to see more of you this year! Thanks!

Virtually every person who had completed this worksheet independently had gotten stuck at this juncture. Asking is scary. Rejection is scary. If you don’t go through life feeling entitled, where do you get off just asking for things?

That’s just the thing, though: Lots of people ask for help and ask for favors (I’ll use those words interchangeably here). If you don’t, you’re leaving resources on the table. You’re failing to capitalize on professional goodwill you’ve built up. And you’re letting more entitled-feeling people—we know who they tend to be—get ahead.

Don’t be afraid to ask for a leg up. Here’s how to start doing it.


Make the Ask Small for Them, Big for You

Some of the best favors to ask don’t take much effort from the granter of the favor, but do a lot of good for you. For instance:

I have a big favor to ask of you. I’d like to speak on a panel at conference X. I think the panel could use more diverse voices, and I have spent the entire past year working on [precise subject]. I can nominate myself, but I think it would mean a lot if you nominated me (assuming you feel confident that I’m up to the task!). Here’s a link to the form—all the form requires is your contact information and mine (which is below). Would you help?

This is asking a simple, five-minute favor of a presumably well-connected person. If the asker—say, a former intern asking a favor of her former boss—ends up speaking on the panel, it could launch her into the spotlight in her industry. Small favor for the granter, big win for the asker.

Here is a terrible favor to ask:

Would you read my novel and give commentary? I’m trying to get opinions from all the great writers I admire.

Oh, good. Not only will this favor take 14 hours, the asker isn’t even going to necessarily follow this famous writer’s advice—she’s going to consider his opinion among those of, presumably, a slate of his peers and competitors? What a little shit. Don’t do this.


Ask Well in Advance

If you want to ask for a pretty big favor, ask waaaaay in advance. Like 11 months in advance, for instance.

Daniel Gilbert in Stumbling on Happiness cites neurological evidence for why people are more likely to agree to do things if asked far in the future. For instance, if I ask you to attend my destination wedding in Thailand two years from now, that sounds really fun and adventurous! You’d love to go to Thailand, wouldn’t you? If I ask you to have lunch with me tomorrow, well—ugh, I mean, you’re sort of busy and it’s kind of cold out—maybe some other time?

When we consider doing things far in the future, we think in broad generalities: Adventure! Fun! Friendship! When we consider doing things in the near future, we think in terms of logistics: Traffic. Stress. Cost.

Do you want a pretty major professional favor from someone? Ask very far in advance. (“Dear boss, I’d like to backpack around Asia for six months and have my job saved for me while I’m gone. I’d like to leave in April 2017 and return in October 2017.”)

The person is already more primed to agree. Plus, you’ll impress them with your extreme advance planning, and the huge amount of time in between now and the actual favor gives you plenty of time to overcome objections—you can get all your work in order before you take that break, refine your product before the big pitch meeting, and so on.


Make Your Own Investment Before You Ask for Theirs

If you start a company and go looking for investment dollars, you’ll quickly find out that investors expect you to have some skin in the game. Did you put your savings into the business? Did you take out a second mortgage on your house? Have you taken on personal debt to fund the business? If you’re not willing to risk your money, why should an investor risk theirs?

Similarly, even if a favor would take your contact only a minute to grant, keep in mind that your contact may have worked for decades to get to the point where she’s able to grant it. Don’t ask actors, writers, and other creatives to introduce you to their agents like it’s no big deal. It’s a very big deal. Sure, it would only take a minute for a bestselling author to send an email, but why should she just hand that to you? (Some authors are very nice people who indeed do just that. But they certainly don’t have to.)

Make this kind of ask: “Hey, I really admire all the work you put in to become a published author. I know it takes a long time to build a platform and make it all happen. I’m going to work on a proposal this year—I’m doing interviews for the next six months and then should have the proposal finished by July. Once I do, would you take a look at it? And if it’s good, consider putting me in touch with your agent?”

A request like this makes it clear that you’re not just asking for an introduction because you’re so cool and talented; you’re going to put in six months of work before you want her to do you a favor. You’re invested. And, of course, you’ll be forever grateful.


Get Practice Asking

Do you have a lot of anxiety about asking? Practice.

Ask for a favor today. Don’t bargain—that’s not the same thing. Do you live with someone? Try, “Would you make me a cup of tea?” Don’t give a reason.

Now go to work. Ask someone to help you with something. Don’t ask someone lower down than you who might feel obligated—ask a peer or higher-up.

Say “please” or an equivalent expression of politeness (“Would you mind…”)—but don’t overdo it. Don’t say, “If you don’t mind, could you please…if it’s not too much trouble.” Too mincing. Too gendered (if you’re female). Not confident enough. This makes you look weak. You want to look like a confident and competent ally—someone anyone would want a return favor from at some future date.

A good ask should also be specific. Don’t ask someone to be or think a certain way. Ask them to do something.

For example:

“Would you include me next time you meet with him?”

“Would you help me with the Garibaldi proposal this afternoon?”

“I have a favor to ask of you. Would you cover for me on the 1 o’clock call?”


Don’t Fear Rejection—Expect it and Plan for It

If no one ever says no to your requests, you are not making audacious enough requests. Have you ever asked for a raise and been denied? Unless you’re really rich and successful right now, you’re probably not asking enough. Do you sell a product or service? If no one ever tells you the price is too high, it’s too low. You’re supposed to get rejected sometimes. That’s how you know you’re pushing forward in the world.

You can plan some responses to deal with rejection without making a big deal. “Okay, no problem. Hey, did you see the Golden Globes?” Some situations call for “Why not?” or “If you don’t mind, I’m going to [finish a project, work on a skill, whatever] and then ask you about this again in a few weeks.”



If you’re a talented worker and a decent person, there are probably already people who are inclined to help you—you just have to mobilize that resource. There are also people out there who have never thought about you one way or the other, who may or may not help you—you can’t know until you ask. There are people out there who don’t even like you who will help you out, because that’s networking; they want a wide variety of people they can call on later. Nothing wrong with that.

Don’t leave resources on the table! Ask.


Photo of help me candy courtesy of Shutterstock.