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My Top 5 Tips: Reaching Out For Career Advice

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I love getting emails from folks looking for career advice. I also love sending them. It’s an activity in which everyone should engage, even as your goals and intentions change as your career matures.

It’s also one of those things that you can never improve upon until you try it. A few times. Maybe even a lot. You’ll learn what is more effective versus less effective based on the results. Maybe you’ll get more replies or get some helpful advice that ensures you land your next gig. Perhaps you’ll even get some advice or insight that significantly impacts your life.

So if you’ve already sent a few cold emails, LinkedIn DMs or Tweets then pat yourself on the back. You’ve put yourself out there. You’ve shot your shot. At the end of the day, that’s all anyone can ask of themselves.

But, if you’re looking to reach out to someone you admire or someone who has a job role that you’d like to pursue, I do have a few tips to help you shoot your professional shot better. These are suggestions resulting from my own experience in this effort as both a sender and a recipient.

1. Do your research as if you were studying for a test about this person.

I would’ve left the title of this tip as simply “do your research” but I feel like that phrase is said too much and successfully completed too little. I like to think of doing your research as preparing for a test about someone. And it may even be short answer, or better yet an essay test. Imagine you will have to write one to two pages about the person you are about to email. You will need to describe everything you can about how they came to be where they are, what their strengths seem to be, and the things about them that appeal to you, including their future goals and interests. You want to know facts, but you also want to understand the things they’ve written on their website, how they present themselves on tools like LinkedIn, and how they describe the work they’ve done in a portfolio or in written posts. Granted, some people will have more information to review than others, but in today’s landscape, pretty much every professional has some level of online presence. And if they don’t, well then at least you’ll be confident of that because you did your research.

2. Don’t be bashful. The recipient of your email wants to know all about you too!

This isn’t a one-way street. When you reach out to someone for career advice, whether you’ve found their email on a professional website or have a mutual connection, you’ll want to give the recipient enough background and context to explain and describe what your interests are and why they may be the right person to help. No need to paste your entire CV or life story in the body of the email. But definitely be clear about how you got their contact info, what you’re currently up to (internship, grad school, still figuring it out), and any few sentences that describe your passion or experience, whatever level that may be. Doing this before you dive into your questions or any requests helps ground your email reader in who you are as a person. It also shows that you’ve taken the time to introduce yourself just like you would do if you met this person for coffee.

3. Be specific. Like really, really specific.

If you can’t get specific, then go back to point number 1. And if you still can’t get specific go back to point number 2. What I mean is, why are you really reaching out to this specific person and what are you hoping that they can do to help you? Are you interested in landing your first job in a big corporate company and wanting to learn about the onboarding experience for product managers transitioning from startup world? Is the person you’re emailing a powerhouse product manager who used to work for a startup? Did they begin their current job recently enough to still be able to reflect on the onboarding experience? I know it can be tempting to email everyone and anyone that fits a loose set of criteria, but this leads to exerting effort without any tangible results. Tailor your emails and messages to think deeply about what you’re hoping to learn, and the possibility to forge a relationship and not to simply ask vague questions that leave both parties feeling lackluster. Try to use the specificity of your questions to highlight your greatest passions and concerns. People can connect with that. They can remember themselves being in a similar place if it’s a relevant question for them, and all the more often will take the time to answer when the question feels directed and specific. Just asking “do you like working at company X” or “how did you apply to company X” isn’t going to glean you any level of insight or invoke a sense of relationship building and rapport. Asking more specific questions like “I saw that you worked on artificial intelligence products at company X. What resources or skills would you recommend to a person with a non-technical background hoping to work in a similar domain?” Or bringing your passion to the question specificity like, “I am completing my master’s thesis about topic X and saw that you also completed a thesis in a similar area. I’m wondering if and how you leveraged that work towards your current job role and what advice you might have for someone looking to do the same.” You might think that having a longer and more detailed email will lead to a lower response rate, but in my experience on both ends I’ve seen the exact opposite. When someone reaches out with a good amount of context, a genuine sense of candor, eagerness, and specificity, I end up writing them back something pretty freaking long. Like this article for example 🙂

4. Don’t ask for a phone call or video chat. Just trust me on this.

I don’t mean to be harsh, really. I would call myself an energetic extrovert who loves talking to and meeting new people. But now, more than ever, everybody is absolutely swamped with meetings. And because these video chats or phone call requests are often so vague, I have no idea what we’re actually going to talk about for 30 minutes. It’s a bit awkward and harder for someone to coordinate scheduling, delaying your ability to get the answers you need and to start laying the groundwork for a call in the future. Note: if you are doing thesis or research work, it definitely does make sense to ask for a call, but again the same notes about specificity and research apply. But for job and career advice, give the other person the opportunity to simply reply via email or direct message. I actually had one person reach out to me and we DM’d several times on LinkedIn about her interview journey at a company I worked for in the past. I became invested in her story and her success and offered a video chat! She also got the job! Good news all around. So you don’t always need to ask for that phone call right off the bat.

5. Make sure any links or attachments are top notch and share-ready.

Your portfolio isn’t done? Don’t include the link without that context and specific requests for help to get it polished. Your resume doesn’t show your most recent academic or professional experience? Don’t attach it. Again, don’t just go through the motions you think you should do without really crafting and considering the impact they may have. I’ve had many requests to review portfolios that give me no sense of who this person is, or what they’re trying to do. Therefore, how I can be of any help to them (other than stating just that). And there’s no pressure to provide these artifacts in your first email anyway! You can always end your message by asking if they’d be open to a follow-on email, where you’d like to send your portfolio and resume. This works well becasue they have your background context, a sense of the types of specific questions you are trying to have answered, and ideas about how they may help. Their help may take the form of honest and actionable advice, a warm connection to a job opening, or an offer for mentorship. By priming the recipient with a strong and well-crafted opening message, they are more likely to become invested in your success and give your attachments the proper time and due diligence they deserve.

If you’ve sent any messages or requests recently and followed zero of my five items above, don’t sweat it. You’re already learning by shooting your shot. You’ve taken the first step, which can at times feel awkward and aimless but can also lead to some great insights, advice, and opportunities. I encourage you to play with the advice above, see what works well for you, and keep growing your professional network. Also, I’m always continuing to learn and refine the ways in which I both send and reply to career emails (big believer in Karma over here) so I’d love to hear any tips or methods that have worked well for you!


My Top 5 Tips: Reaching Out For Career Advice was originally published in Prototypr on Medium, where people are continuing the conversation by highlighting and responding to this story.