Want To Kickstart Your Career? Learn The Art Of Asking

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I was there. We all were there at one time or another. Working our butts off trying to get good grades. Packing our resumes with extracurricular activities, “leadership positions”, and awards.

And then: slam! The ivy-covered (or palm frond + sand-covered) doors shut behind you and you’re cast into the harsh cold tundra we call the “real world.”

You send off your resume and pray someone will answer. You jazz up your LinkedIn profile and hope it’ll wow someone in HR over at Whatchamacallit, Inc. (or more likely these days, “CoolStartup.ly”)

Perhaps you’re having a tough time landing a decent offer?—?or any offer at all. Or, maybe you’re in the enviable position of having several offers in hand, but struggle with making the fateful choice that could determine the trajectory of your career. Or, perhaps you’re already in a job, but you know deep down it’s not the right fit, and you’re looking to move on.

So you fire up LinkedIn and read some of posts on how to interview, how not to interview, how “work-life balance” is a myth, how performance evaluations should be abolished, how to get along with a difficult boss, and so on. Some good nuggets of advice, sure, but not exactly targeted to your unique talents and skill-set and personality and passions.

It can all feel so overwhelming. Where can you seek out some cool-headed advice, tailored just for you? How can you establish a connection with that person who knows someone who knows the guy who is hiring to fill the job of your dreams?

The good news is, there are people who can help you.

There’s an abundance of experienced people who have “been there and done that”, who possess extensive personal and professional networks, and who may be willing to give you a hand. But you’ll never tap into their wisdom and connections without first learning?—?and practicing —the art of asking.

The Art of Asking

Yeah, I know. I’ve stood in your shoes before. I know how awkward it feels to “cold call” someone you don’t know, especially those all-powerful people in HR who warn you not to call, email or otherwise approach them unless they express interest in you first. Or how about those people on LinkedIn with important-sounding titles that signal they’re probably too busy to give you the time of day.

I also know just how much you want to get that first chance to prove yourself, to put your hard-earned effort (and all that money your parents invested) to productive use, to develop your potential, to find your passion.

Tap into those feelings, take a deep breath, and start asking. Here are seven “asks” that you can consider using today to kickstart your job search:

1. Ask for advice. When you’re at such an early stage in your career that you “don’t know what you don’t know”, you should first reach out to the people you know and trust the most and ask them for advice. But you’ll benefit even more if you step beyond your inner circle, and reach out to people you don’t know. Sure, not everyone will respond with helpful tips. Some may not respond at all. But a few nuggets of wisdom from someone who knows the industry or company you aspire to join might give you the insight and data you need to make a better career decision. Or they might simply offer some helpful words of inspiration that can motivate you to keep moving forward in your search.

2. Ask to connect. One of your most important assets is your network of professional and personal connections. Be bold and ask people you are inspired by?—?or whom you think might have relevant knowledge or relationships?—?to connect on LinkedIn. Naturally, you’ll need to make sure your profile is professional and up-to-date, and you’ll want to write a thoughtful and polite note of self-introduction that explains why you’re asking to connect. Not everyone will respond. But I think you would be pleasantly surprised how willing some people are to accept invitations to connect from people like you who are just starting out on their career journey.

3. Ask for a warm introduction. Warm introductions are, of course, a lot more effective than cold calls you make on your own. You might want to ask someone to provide a short email introduction to open the door to someone you’d like to know. This generally requires having already established some level of connection with the person prior to asking.

4. Ask for a letter of recommendation. Just wrap-up a successful internship or freelance assignment? Don’t forget to ask for a recommendation letter that you can use to establish your credibility with future employers. Best to get that in writing early, before your former manager moves on to another company, or otherwise becomes too busy to draft it for you.

5. Ask someone to be a mentor. Find someone who can be your “career whisperer”, who can give you some clear-headed and objective?—? but caring?—?advice. This sounds more time-intensive for both you and the mentor, but it doesn’t have to be. It could just mean a phone call or meet-up every so often.

6. Ask for an internship. Whatever people may say about the low (or zero) pay, lack of “real” responsibility, and what not, I still believe there’s tremendous value in landing an internship at a firm, and in a function, that will expose you to the kind of work you might want to do full-time someday. It gets your foot in the door, gives you the chance to learn new things, and can be a very rewarding experience, as long as you make the most of it.

7. Ask to do more at your current job. If you’re already in a full-time position, but you're contemplating moving on, you should still make the most of your time. Learn as much as you can, build meaningful connections with your colleagues, and put in a solid performance. Even if you know you'll never return to that company or do the same type of work again. You’ll still want to secure a positive recommendation once you leave, and you’ll be glad you kept the lines of communication open with your employer in case you need anything from them after you’ve left (such as that letter).

A few things to keep in mind

It’s also helpful to keep a few things in mind as you begin to master the art of asking:

Be proactive. You’ll need to be as proactive as you can to get noticed. Don’t be shy about reaching out to people who are on your radar screen. Study their LinkedIn profile, check out their company or personal website, and start sending out your thoughtful questions and polite requests for help.

Start early. Don’t wait until the summer after you’ve graduated to start cultivating your connections and asking for advice. Get the process in motion early so you can hit the ground running when you do launch your post-graduation job search. The more “warm connections” you can cultivate now, the easier it’ll be when you approach them with one of your “asks” later.

No response? Don’t worry. If someone can’t be helpful, don’t take it personally. People are busy, and it may be hard to get even a simple reply. Don’t give up right away?—?give it some time and then follow-up with a second request. But if you still don’t hear anything, just move on.

Show your appreciation. Of course, when someone does give you a hand, make sure you follow-up with a “thank you.” That’ll make the person helping you feel appreciated for the time they invested in you, and make it all the more likely they’ll want to help you again.

I’ll leave you with one more piece of advice, something my dad once told me when I was much younger, and which I’ve put into use quite often since then: if you don’t ask, you don’t get.

Thanks for reading! Please head over to my blog and jump on my list so you can get my latest posts delivered by email. Connect with me here on LinkedIn. I’m also on Twitter @glennleibowitz.

Image credit: Davide Ragusa / Unsplash