I’m fortunate to receive a significant number of emails and direct messages where someone is looking for some advice or momentary mentorship from me.

Many of these messages have this kind of structure:

Hi Dan,

I’m looking to connect with you to learn more about how I can grow as a designer.

or

Hi Dan,

I’m wondering if you’d want to be on my podcast. I’d love to have you on if you’re interested.

I try and take these for the positive spirit which I assume they’re intended. I’m honored that people reach out to learn from me or want to involve me in what they’re doing; I don’t take that lightly.

The thing that bugs me about them is that there’s no actual request here. I can certainly infer and assume what they’re looking for, but I know what happens when I assume.

I realize I’m nitpicking, but details matter. One of the most common reasons people don’t get what they want is that what they’re asking for is unclear. Here are a few tips to help you make your desires more direct.

What’s the question?

When our kids were toddlers, my wife and I would redirect their whining with this phrase, “A whine is probably a question you’re not asking. What’s your question? Is there something you want?” It was a really helpful technique in turning a hot-tempered “I don’t like peas!” to “Can I please have asparagus instead?”

Lest we think this behavior is found only in children, I was on a sales call the other day where the person on the other end spent the first 25 minutes of our call giving me “context.” Once they got to a natural pause, I asked, honestly puzzled, “What can I help with?” They spent the next 10 minutes telling me their plan. I asked again, “What can I help with?” They spent the next 5 minutes telling me what some of their personal weaknesses were. While all the info was great, I still didn’t really know what they wanted from me. I eventually left the call bewildered.

Ask an easy question to answer

When you’re asking something of someone, you probably want the result more than they want do it for you, so it behooves you to do the work. The more difficult question you ask, the less likely it is that you’ll get your desired answer.

For example, if someone were to ask me, “Can you speak to my community group?”, I couldn’t answer that question easily, even if I was very open to speaking to the group. I need a bunch of answers—both from you and from me—before I can answer yours! What would you like me to speak about? When? For how long? Who will be attending? Will you be paying me, and if so, how much? What outcomes do you want and expect for your group from having me as a speaker? Am I capable of delivering what you expect? I may choose to ask these questions to you, or, in a split second, I may decide that I’m too exhausted already to even ask these questions and instead answer a simple “no.” Either way, you didn’t get what you wanted, which was mentorship.

Instead, if you did the work to answer those questions before I even ask, that might sound something like this:

Can you speak to my community group about design systems? We meet every Thursday night and the next opening we have is January 19, which is when I’d love for you to join us. I can pay an honorarium of $200. I think we would be very inspired to hear your stories and could grow from your experience. Would you be interested and willing to speak to us on January 19? If you’re willing but can’t do that date (or Thursdays in general), let me know what days are best for you and I’ll schedule it for a day and time that works well for you

Although I might still say “no” for various reasons, I’m much more likely to say “yes” because it’s an easier question to answer than the previous one. It’s easier because:

1. Many of the questions I might have asked are answered before I even have to ask them.
2. Not only have they done the work to anticipate my questions, but they’re also offering to do more work by accommodating my schedule. This triggers a psychological factor known as the reciprocity principle: we pay back what we receive from others. The fact that you offered to do something for me makes me more likely to want to do something for you.

Rejection

A big reason that people don’t ask direct questions is to avoid rejection. As someone who really struggles with rejection, I get the strategy: if I don’t ask, then no one can say “no!” But the opposite holds true too: if I don’t ask, no one can say “yes” either.

Asking for something is risky, because you might get rejected. But all profit comes from risk. The more time and effort you spend avoiding risk, the more you delay your potential reward.

If you can, push yourself past the fear of rejection to clear ask for what you want.

You shall receive

As the saying goes, “Ask, and you shall receive.”

So, ask a direct, easy question and see how you get more of what you want!

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