For a long time, I had difficulty asking for help. I felt more comfortable on the giving side of things and feared that if I regularly asked others for help I'd take advantage of their kindness. Then I realized that most successful people know how and when to ask for help. And that most people are inclined to offer help when asked (research backs this up.)
So I started asking, and good things happened as a result of it. I got smart advice. I got support from others. And I probably made a lot of people feel good that I respected them enough to seek their counsel.
Every day I get at least one email or call asking for help with something -- a request for an introduction, a recommendation, advice on how to find a job. Some of these requests are easy to answer, and in those cases, I respond quickly, either by doing the thing requested of me or explaining why I can't. Others leave me frustrated with the questioner. And when I'm frustrated it's usually for a variation of the same few reasons. The person didn't ask a proper question; the person didn't appear to have done any work to solve the problem on her own; or she was coming to me for something that I wasn't really in a position to help with.
Based on these experiences, I've developed some guidelines for how I ask for help:
Identify the problem. This might sound simple, but it's not. Say, for example, you're not moving forward in your career. Are emotional issues distracting you? Are you unsure if you're in the right field? Are you spending too much time managing a family situation that has become tense? The answers to these questions should help you figure out whether it makes sense to talk to a career coach, a therapist, or perhaps a family member or a close friend.
Learn as much as you can on your own. Before you start contacting friends or hiring professionals, do some research on your own. I'm trained as a lawyer, yet I haven't practiced for years and am not familiar with most areas of the law. So when I have a need for legal advice, I first familiarize myself with the relevant area of the law so that I have a sense of what the issues will be. That way, when I sit down with an expert -- whether or not I'm paying for the advice -- I can be sure that I have a good sense of what the issues are.
Be direct. No one appreciates a passive-agressive plea for help ("If only I had someone to take care of my daughter a few afternoons so that I could focus on this proposal.") If you know what you want, ask outright. ("Is there any chance you could watch Lilly for me two days this week? I'd so appreciate the quiet time to finish the proposal.")
Make it easy. When my friend Sarah (yes, the same Sarah) moved several years ago, she came up with a brilliant plan to get several of her friends to help her. She divided her moving days into hourly slots and set up specific tasks (e.g. pack up all kitchen cabinets) that needed to get done. Then, any time a friend said, "What can I do to help?" she replied, "Come by for a two hour shift." I signed up. And when I arrived, the table was set up with packing materials and I was told which shelves to focus on. By the time I finished my part, I felt great for helping and unburdened by the request since she had made the job so easy.
Be clear. If Sarah's situation was a model for how to ask for help, a recent request I received (also dealing with a housing issue), was a model for how not to do it. A few weeks ago, I got a mass email from an acquaintence asking if anyone knew of any apartments for rent in New York. That was the entirety of the message. The writer said nothing about dates of availability, the location or how much she could afford. While I usually forward these kinds of requests, I didn't do anything with this one because the email was so unclear that I didn't know what to do with it. Granted, I could have written her back and asked for clarification, but with 50 other emails in my inbox, I didn't want take the time to get all the answers.
Spread it out. If you anticipate you'll be needing a lot of help, try to find a team of people to rely on rather than repeatedly going to the same person. You'll get two benefits: first, you'll hear more than one approach to your problem; and second, you won't become a burden to someone you appreciate. [An exception here is if you've decided to hire professional help. In that case, it's fine to rely on one person, as long as you've chosen wisely and still realize that you'll have to do your share of the work.]
I'm still tinkering with these, so tell me what you think. Is there anything you disagree with our that you'd add?

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