Making the leap from another industry into tech is tough, but doing your research can make for a smoother transition. One of the best ways to get an inside look at a company or career path is through an informational interview — and if you’re lucky it could even lead to a job.
Before Jared Shaner joined Trellis Commerce, a Malden, Mass.-based digital agency specializing in e-commerce, as VP of business development and later becoming the company’s CRO, he was an executive recruiter looking for a change. “I didn’t really want to be the guy trying to fill jobs anymore,” he said. “I wanted to be the guy executive recruiters were calling so they could fill jobs.”
Questions To Ask In An Informational Interview
- How did you first get into your line of work?
- What has your career path looked like so far?
- How does your role help the company reach its goals?
- What skills are most valuable in your work?
- What type of personality is best suited for a job in this industry?
- What do you love, and what’s frustrating, about your job?
How did he make the switch? It started with an informational interview. Shaner explored different companies and got in touch with Brad McCrory, the VP of sales from Chicago-based IT development agency The Plum Tree Group.
“He was nice enough to give me 15 or 20 minutes to ask questions,” he said. “I told him I was trying to land my first sales role, and that I had a few ideas I wanted to run past him.” He shared his thoughts on approaching sales and what he could do for a sales team. A week later, McCrory reached back out to offer him a job building out the east coast branch of the company, beginning Shaner’s career in sales. Of course, there’s no better outcome. But even if that wasn’t how things turned out, the conversation was valuable because it confirmed the direction Shaner wanted to take was the right one.
“Being able to learn from someone you admire who has been successful in their role will not only give you a competitive advantage with their company,” he said. “It will also help you learn what you want out of your career.”
Have a No-Pressure Conversation
An informational interview is a chance to learn — these conversations can end up being an opportunity for a genuine connection. No one on either side has to worry about being evaluated or about the company’s hiring needs.
“[There’s] no pressure to say yes or no to the person in front of them,” said Sheila Ryan, chief people officer at Reno, Nev.-based real estate tech company Clear Capital. “They are more relaxed and because they start in a mentor seat for the interview, human nature takes over. We all want to help.”
“Hearing anecdotes about their roles can help connect the dots and show how previous experiences can help you in your career.”
With that being said, if you’ve asked for someone’s time, you should be prepared to guide the conversation and ask thoughtful questions. In this format, you can candidly find out about different careers or industries. It’s important to use the time to be curious and you can even get feedback on your career so far.
“You should seek to learn about other peoples’ experiences, then apply that to better understand how you can shift into that area of work if you are interested,” said Nicholas TenBrink, senior engineering manager at New York-based Linux security company Capsule8. “Hearing anecdotes about their roles can help connect the dots and show how previous experiences can help you in your career.”
Use It as a Powerful Networking Strategy
In the short term, informational interviews are useful for deciding whether a certain career path might be for you. But that’s not all you can get out of it. Looking further ahead, it can be an effective way to build out your professional network.
“There is always potential for this person to refer you to an open role, or maybe serve as a mentor or even a boss one day,” Ryan said. “The next time they are asked ‘Do you know anyone?’ the informational interviewee tends to be one of the first on the list.”
“There is always potential for this person to refer you to an open role, or maybe serve as a mentor or even a boss one day.”
If you make a good impression, you’ll stick in someone’s mind. While this isn’t the quickest way to secure a new job offer, it’ll create connections that might come in handy down the line — you never know where someone will end up in their career.
Take Advantage of a Learning Opportunity
Thinking about the startup life? Want to get into design? Does fintech fascinate you? Reaching out and talking to people who work in these environments will give you the best opportunity to find out if it’s a good fit. So don’t be afraid to reach out to folks in a wide range of industries and companies.
Talk to entry-level engineers, product team managers and executives too. Even if you don’t see yourself leading a department or running a company, it’ll introduce you to the full scope of possibilities.
“It gives you better insight into the thought processes of bosses at bigger companies,” Shaner said. “If I’m aiming for an account executive role, I might ask to interview a VP of sales at a larger company to understand how my future bosses might think.”
It’s useful to interview executives who can give you insight into the core objectives of a company or industry, said Nick Relph, director of marketing at Engage People, a sales and customer rewards tech company based in Markham, Ontario. “You should find people who can connect you with the decision-maker or can provide you insights into an organization, so you have a background knowledge of the business and what it is trying to accomplish,” he said.
A Gateway to Mentorship
If approached the right way, informational interviews can even turn into a mentorship opportunity. Now further along in his career, Shaner appreciates when someone wants to learn more about his work. It’s a chance to pay it forward and mentor people who are new to the tech industry.
“I personally get value at this point about building people up,” he said. “As a young entrepreneur who was given an opportunity myself, it brings me intrinsic joy to help others.”
If you can offer value in return, that’ll go a long way in developing a professional relationship. You could make an introduction to someone at your company, or even share an article or book that might be up their alley. Consider how you can add to the conversation — sometimes it’s just about listening and being a fresh set of eyes.
“When someone asks why we do things a certain way or interprets our company differently, they’re pointing out areas that the company can improve,” Shaner said. “I like getting asked questions and hearing other people’s perspectives — it stimulates my thought process.”
Prepare for the Interview
Don’t limit yourself to online searches. Ask coworkers, friends, teachers and family about connections they might have in industries you’re researching. In order to get the most out of your interview, you have to find the right person.
Dig into their background — it’s beneficial to know what’s on paper and then learn what that experience was actually like. “Read your interviewer’s LinkedIn profile, and find out the schools they went to, their previous roles, and the culture of their company,” said Ryan. “Then, prepare questions to better understand that person’s career journey.”
“Some questions you could ask your interviewer are: How did you get to where you are today? What lessons have you learned? What would you recommend to someone in my position?”
It’s clear when an interviewee has done their research ahead of time, said Shaner. “Recently, someone reached out to me and said, ‘It seems like you’d be an expert on the matter — do you think BigCommerce will ever become more popular than Shopify?’” he said. “This person showed that they were genuinely interested in the space and had some high level understanding. I’m more likely to respond to that type of question rather than one that is more vague.”
Here’s what to keep in mind when you’re in preparation mode. When listing out specific, detailed questions, know that these shouldn’t have answers you can find easily find online. It’ll take time to figure out meaningful questions. A good place to start is thinking about what you want out of a job — and then tailoring your questions to find out if that’s something you can get through that career.
“Some questions you could ask your interviewer are: How did you get to where you are today? What lessons have you learned? What would you recommend to someone in my position?” said Ryan. “That way, you can ask yourself, ‘Is this what I thought it would be?’”
Wrap It Up
After the conversation, take what’s useful and leave what’s not. Jot down notes with your impressions and thoughts — it might be helpful to reference later on. “You can tailor your LinkedIn profile and resume to highlight your applicable skills and experiences,” said Ryan.
And, if you’re still left with questions, don’t be afraid to ask for an intro to another person in their network. Or see if they’re willing to give feedback on a project or your resume. It’s a good way to stay in touch and maintain your relationship.
Of course, end the interview with a thank you. If you’re sending an email add a personal detail from your conversation to show your appreciation — it’ll be much more memorable than a generic one-liner.
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