Cold calling tips: how to get strangers on LinkedIn to give career advice
They may be no such thing as stupid questions, but there are certainly smart ones
Welcome to Art Science Millennial, a newsletter for non-techies navigating the world of tech! I know the struggle because I’m one of you.
“There’s no such thing as a stupid question” — we’ve all heard this declaration used to encourage us to speak up and overcome the dread of being judged when airing our ignorance. The underlying message: When we don’t know something, don’t be afraid to ask.
As a mid-career switcher, I’ve had to ask so many more questions than at any other point of my life. When I first began this journey, I cold-messaged complete strangers on LinkedIn who made a similar transition to seek their views. Today, I periodically seek help from colleagues because as a newcomer, there are still so many things I don’t know.
The lesson I’ve learnt from these two years of asking questions: Yes, we shouldn’t be afraid to ask, but not every question gets a response, let alone a helpful answer. Here are some tips on increasing the chances of the other side hitting the “reply” button.
Never, ever ask something that can be googled
Just five minutes spent typing your question into a search engine and reading a couple of the results can save you so much grief on this one. This is especially so when the question is procedural (“when is the deadline for submission?”) — there’s usually an FAQ page out there with the answer.
One of the most mortifying responses I’ve ever received when I messaged someone on LinkedIn was simply a hyperlink with the answer to my question. There wasn’t even an accompanying “here you go” to cement my embarrassment. Needless to say, the person didn’t respond to my subsequent, feeble attempts to revive the conversation.
On a later occasion, I had to ask another person about a study grant he had benefited from. I made sure to make clear that I had tried searching for the answer by attaching several links of other similar grants that I found, and that I was reaching out only because I couldn’t find the exact one he had mentioned. This time, the contact replied with the correct link and also walked me through his personal experience of applying for it.
Don’t say: How much is the course fee for the programming bootcamp you attended?
Do say: The course fee subsidy stipulates that the recipient must find a programming-related job within six months of graduation. In your experience, is that strictly enforced?
Do your background check
When I was still considering taking a bootcamp and pursuing a data analytics career, I sought out others on LinkedIn who had successfully made the same move. But before I initiated contact, I always tried to find out more about them. Again, all it takes are a few simple steps such as checking out their latest social media posts, recent job history, and if there are mutual acquaintances. It doesn’t have to be a CIA-level deep dive vetting.
If that person writes regularly on social media or on a blog, great! Sometimes the answer might even be in one of those posts (see the point about not asking something that can be googled). Otherwise, sharing your thoughts on a particular piece and asking for elaboration on one of the points raised is a great way to start a dialogue. Few can resist the flattery that their writing is read (as a writer and someone who hangs out with writers, I should know).
Don’t say: What work did you do before you made the career switch?
Do say: I read your post where you mentioned that your past, non-tech skills can still be applied in your current workplace. Could you give some examples of how those skills are used and if you feel they are valued by your current employer?
Be as specific as you can be
Asking for help is an act of asking for someone’s time — time that can be put into something else if that someone isn’t helping you.
So be respectful of that person’s effort by being clear about what you need. If your contact expends lots of energy going in circles clarifying your question, feelings of frustration are inevitable. Instead, make the process as frictionless as possible — the less work you make the other party do, the higher the chances you’ll get a response.
The quality of the answer is also highly dependent on how specific your question is. From time to time, people who are considering a career switch reach out to me. For those who are just at the stage of maybe, perhaps, toying with the idea of trying out a new line of work, I can only give pretty generic answers hoping to spur a certain line of thought. But if someone has already sketched out a course of action and wants my take on its feasibility, I will have much more material to give constructive feedback on and usually we’re much closer to some concrete outcome by the end.
Don’t say: Do you think I should make a career switch?
Do say: I’ve been learning coding through online courses for the past six months and can now make a simple app. Am I ready to apply for entry level jobs and if not, do you recommend this course of study to take my learning to the next level?
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Prepare to answer some questions yourself
Career advice is not a one-size-fits-all kind of thing. I often ask people who approach me about their career goals, circumstances, and considerations. Often this leads to an engaging exchange about different definitions and pathways to success and I come away feeling like I’ve gained something as well.
On other occasions, I get met with a “I’m still not sure” (or some variety of vague pronouncement). Or they are unsatisfied with their current jobs but still have no clue what they want to do. Those are definite conversation killers. While I can point out the importance of beginning with the end in mind, I am really not in the position to prescribe career aspirations to people I’ve just met online.
Don’t say: There aren’t much prospects in my current industry so I’m just searching for something new.
Do say: These are the reasons why I’m considering a switch to your industry. Do you think my reasoning is sound and have I missed anything out?
Applying these lessons to the workplace
Being a rookie all over again means there are many things I’m unfamiliar with. When I ask questions at the workplace, I try to apply the same tips I’ve just mentioned. I’ve come to realise there’s a world of a difference between the two questions below:
Don’t say: Can you show me how to use the latest ABC tool?
Do say: I want to use the latest ABC tool to perform X. I’ve tried using the Y function but it isn’t working and I suspect it’s because of Z. Am I on the right track and do you know how to get past this hurdle?
When you do the latter, people are usually happy to lend a helping hand. If you do the former, you’re making it someone’s job to teach you something from scratch.
The “do say” examples I gave all require some level of homework and grappling with the topic before asking for help. This is not just beneficial to the person you’re asking, but also to yourself as you are likelier to get a response, and a useful one at that.
Maybe there are no such things as stupid questions, but there are certainly smart ones.
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