The Art of Asking

Helping hand
Can you do me a favor?

If we were less relentlessly independent — a characteristic that the current western culture and environment encourages — we would find the question less intimidating. With a few exceptions — for example in a quid pro quo context, or with a family member or friend — we also hesitate or actively resist asking.

We want others “to see us once beautiful and brave,” as poet Rainer Maria Rilke wrote. But he preceded it with “perhaps all the dragons of our lives are princesses who are only waiting,” which means it is how we respond to the dire situations life throws at us that makes us beautiful and brave, not the problems themselves.

It takes work to learn to ask powerful questions, and in fact asking questions is an art. Whether we look to ourselves as the person who gives help to others or feel we can always figure things out on our own, asking is hard.

From hard to art

“Often it is our own sense that we are undeserving of help that has immobilized us,” says alt-rock icon Amanda Palmer in The Art of Asking: How I Learned to Stop Worrying and Let People Help:

“Whether it’s in the arts, at work, or in our relationships, we often resist asking not only because we’re afraid of rejection but also because we don’t even think we deserve what we’re asking for.”

Asking is an art. “Almost every important human encounter boils down to the act, and the art, of asking,” she says. More memoir than how-to guide, the stories in the book, as in her TED Talk, give us a view into human nature and the power of connection.

How do we ask each other for help? When can we ask? How often? Who's allowed to ask? Are some of the very questions we ask ourselves. She says:

“We, as 21st century human beings, have an incredibly hard time asking for certain things. Something, somehow, has blocked us from feeling like we can turn to one another for help.”


“In both the art and the business worlds, the difference between the amateurs and the professionals is simple. The professionals know they’re winging it. The amateurs pretend they’re not.”

When we approach asking as a gesture of hope and optimism, we find connection and personal growth as a result. Learning to ask restores our energy, reduces stress, clarifies relationships, and helps us solve problems. Dr. Deborah Serani, a psychologist who’s been in practice for over 20 years, says:

Asking for help creates an atmosphere of empowerment. It communicates to others that, while you may not have the answers, you are willing to find them and make things better.

Why resist? Questions do matter, and we can learn to become more effective at asking.

Asking is an acquired skill

LinkedIn used to provide forums for professionals to ignite conversations on a variety of topics and domains. An analysis of the postings revealed a lot about the person making the inquiry. For example, how a question is formulated reveals a lack of confidence in one's abilities, or when someone has not done their homework and does not share enough information about their objectives.

On the fun side, here are top ten reason why some LinkedIn questions were getting (mostly) pitches back. If we we miss the mark when we ask, it's often because we were not taught how to ask properly. Thus we do it poorly, soliciting pity when we seek assistance, asking the wrong person. Or we do it badly by using guilt and worse blackmail.

We fear rejection and that others will perceive us as weak for asking. That's because we hold onto the myth that successful people never ask. Dr. Serani says:

“Actually, successful individuals will tell you that the key to success is knowing your strengths and weaknesses. Learning how to delegate, asking for help and letting others show you the way are part of the plan. Successful people are driven and motivated — and when the going gets tough, the tough ask for help!

“Asking for help is a universally dreaded endeavor,” says M. Nora Klaver in Mayday! Asking for help in times of need. But asking is not just an altruistic gesture; it's also good for business.

Dubbed an anti-self-help book, Mayday is an exploration into the myriad of reasons why we don't ask for help, how we can benefit from asking, and how to ask the right people at the right time in the right place, thus increasing our opportunities for meeting our needs. Klaver says:

“Seven out of ten people admit they could have used help over the last week but didn't ask for it. 

The reason, says Klaver, is that we don't recognize we have a need until we are in a crisis. Often we are also unclear as to what we need. The book includes a seven-step process that starts with the important steps of naming the need — being as specific as possible — and staying open to possibilities.

Being specific is good. Breaking something down into smaller pieces is also very helpful. When I was learning to perfect English for simultaneous interpreting and the translation of panel conferences and dialogues, I used a karate-style ladder of progressive difficulty as a technique to ask increasingly bigger favors.

Ask LadderWith no agenda other than learning, the ladder allowed for modulating the level of control at each phase easing me into bigger asks. The idea came from the philosophy of master Gichin Funakoshi as expressed in Karate-Do: My Way of Life “into the empty hand falls freedom.” Karate-Do or of the empty hand is about being strong to face oneself. The philosophy stayed with me long after I stopped training for higher belts.

(I later found more examples of a similar method in Kathy Sierra's book on making users awesome.) The video of my Dare Conference talk is here.

Holding back from asking limits our opportunities

One potential reason for holding back is that we want to show we have answers, that we are experts.

In the Q&A after the talks at Dare Conference someone asked how they could reconcile the soft skills like becoming better at asking for what we need in our jobs from the expectation that we are experts in our field.

It's helpful to learn to separate the self from the task — hard on problems, soft on relationship. For one, projects require we collaborate with other experts, and asking questions is also a good way to cultivate positive relationships with colleagues.

It's the same thought process of highly successful individuals — people may respond or not to a request; but this doesn't mean it's a wholesale rejection of us as a person.


For some courage, watch Amanda Palmer TED Talk below.

Like most industries, the music business has undergone tremendous change. Artists have more opportunities to get closer to their audiences, and they are also less insulated from the business side of things. At about minute 9, Palmer says:

And the media asked, “Amanda, the music business is tanking and you encourage piracy. How did you make all these people pay for music?”

And the real answer is, I didn't make them. I asked them. And through the very act of asking people, I'd connected with them, and when you connect with them, people want to help you.

It's kind of counter intuitive for a lot of artists. They don't want to ask for things. But it's not easy. It's not easy to ask. And a lot of artists have a problem with this. Asking makes you vulnerable.


Now, the online tools to make the exchange as easy and as instinctive as the street, they're getting there. But the perfect tools aren't going to help us if we can't face each other and give and receive fearlessly, but, more important — to ask without shame.

To put in even more poetic terms, Rilke says:

“Live your questions now, and perhaps even without knowing it, you will live along some distant day into your answers.”


[image via Pixabay CC0 Public Domain]

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