11 Ways to Ask for Help When Changing Careers

(The following is adapted from the new book, 50 Plus! Critical Career Decisions for the Rest of Your Life by Robert L. Dilenschneider, with permission from the publisher, Citadel Press.)

Maybe you love your work but you’ve suffered a setback. Maybe you’ve decided that your entire career has been a mistake and you should start all over again. Maybe your field has changed so dramatically that you’d like to get out. Maybe you’ve been pushed out. Or maybe, after years of waiting for the perfect circumstances to come along, you’ve decided to dismiss your doubts and take a leap.

Whatever your situation, it’s not too late — it’s never too late — to begin anew. One step to start, or restart, a career is to ask for help. But there are some right ways to do it and some wrong ways.

The key to asking for help is giving the people you’re asking the sense that helping you will benefit them. That can occur in many ways. They can benefit psychologically by feeling that they’re doing a good deed. They can benefit because they’re enlarging their network through you. They can even benefit monetarily. Almost everybody is willing to assist if they’re asked in the right way and at the right time.

Here’s how to do it — and how not to:

You can maximize your chances of getting the help you need if you…

Keep your request short and your demeanor upbeat. That approach is the only way to appear business-like.

Make the person you ask feel important. You don’t want to be insincere or devious or sycophantic. But let’s face it: Flattery works.

Ask for something that’s actionable. You want the other person to do something for you that will generate movement and lead to something else. Anything else is a lost opportunity.

Ask for a contact or referral. You can say: “Who can I talk to?” If the person draws a blank (which rarely happens), rephrase the question. Ask: “Is there anybody in this field who could help me take the next step? Is there someone who is knowledgeable about such-and-such?”

Sooner or later, if the person you’re talking to is in the loop, he or she will pony up. Then you ask, “What’s the best way to contact that person? Can I use your name?” Questions like that — specific and easy-to-answer — will produce results.

State your good intentions. Let the person know that you intend to help him or her in the future. Even if it’s the first time you’ve met, you can say: “I’ve heard a lot about you. I hope that this is a relationship that goes on for many years, and I can tell you, I remember the people who have helped me and I intend to reciprocate.”

Most likely, the person you’re asking will admire your attitude and decide to help.

Be clear about your timetable. Let the person know that you need the help within a certain time frame. Say that you need the help in one week or two weeks or a month, whatever’s appropriate, and ask if you can check back in then.

If there’s a specific opportunity in front of you, you might say that you need to act on it quickly. People are more likely to help you out when they have a sense of immediacy.

Offer assistance. This is important especially if your request is complicated. Offer to draft the letter, to address the envelopes, to coordinate with the secretary, to make phone calls, to do whatever research is necessary and so forth. Make it easy on the other person.

Ask for a final piece of the puzzle. It’s discouraging for people to be asked to help when they know dozens of things will have to happen before the goal of the person asking is in sight. But it’s hard to say no if the supplicant is already most of the way there. People feel guilty saying no in an instance like that — a fact that you can use to your advantage.

Spread the news. Let the people you’re asking know that you will let others know how helpful they were. Everybody wants to have a positive image.

Nail the sale. Before you leave, say something like: “What’s the next step?” Or “How do we begin?” You should never leave the room without asking for the order. If you ask, the person has a hard time saying no.

Remember: you’re probably not going to have a second chance to ask this person, so you’ve got to succeed the first time.

Be prompt with your thank-yous. Send notes of appreciation immediately. And as soon as you can, return the favor.

Unfortunately, many people don’t know how to ask for help effectively. Here’s how to avoid the nine most common mistakes:

Don’t ask for something the other person cannot — or does not want to — give. In my case, I know a lot of powerful people. Many of them are my private clients. So you can imagine how uncomfortable I feel when folks I barely know ask if I can introduce them to those accomplished, busy people. Requests like that don’t make me want to help; they make me want to sneak out of the room.

Don’t ask for too much. Keep your requests reasonable. I’m thinking of one man who has asked me for help on more than one occasion by saying that he’d like me to give him advice, to give him business leads, to introduce him to people, and, worst of all, to critique his work. To be blunt, that’s baloney! It’s a lot of work for me with no payoff in sight. That’s not the kind of help I want to deliver, and I don’t think I’m unique. When you ask for help, you want to make sure the person doesn’t feel you’re going to be a burden.

Don’t ask for an overview of the field. I’m not a fan of informational interviews. They’re time consuming and there is something disingenuous about them. I always suspect that the people who request these interviews are really hoping to be offered jobs. Since I know I’m bound to disappoint them, I’d just as soon avoid these interviews entirely.

Don’t ask someone else to do your homework. It’s a turn-off. Plus, you don’t want to waste valuable contacts by asking for something you can get easily on your own.

Don’t ask in an arrogant way. This infuriates people. The underlying feeling is one of entitlement: “I deserve to have this information (or this money or this job). I shouldn’t even have to ask.” This is not a winning approach.

Don’t beg. Presenting yourself in a pitiful way does not engender sympathy. It makes people cringe.

Don’t ask for money. That’s what banks (and parents) are for.

Don’t ask for something that intrudes on someone else’s personal time. This means: don’t ask for help at night, on the weekend or on a holiday. Call at a time when it’s convenient for them.

Finally, don’t push too hard. You need to apply some pressure, but tread lightly. You don’t want the other person to dread the sound of your voice. If that happens, you surely won’t get the help you want.