Why Smart Freelancers Use Informational Interviews
Most people hunt for remote jobs the same way—blast out applications, refresh their inbox, and wonder why they never hear back. There’s a quieter strategy that works better, especially when you’re targeting a specific company or niche. Informational interviews are informal conversations where you ask someone about their work, their industry, and how they got where they are. No resume swapping. No pressure to sell yourself. Just genuine curiosity and a chance to learn from someone already doing what you want to do. For freelancers and side hustlers, this approach can open doors that applications never will.
Get the Real Scoop Nobody Posts Online
Job descriptions paint a polished picture, but they rarely tell you what the day-to-day actually looks like. An informational interview lets you hear the unfiltered version from someone living it. You’ll learn about the tools they actually use, the challenges that come up most often, and the skills that matter more than what’s listed on a job board. This kind of insider perspective is hard to find anywhere else. Once you have it, you can tailor your portfolio, pitch, or next application to match what real practitioners say matters most.
Discover Career Paths You Didn’t Know Existed
Sometimes the best opportunities aren’t the ones you’re searching for. A twenty-minute chat can reveal a niche role, a growing specialization, or a completely different way to apply your skills that never crossed your mind. The person you interview might mention a side project, a freelance platform you haven’t tried, or a skill gap in the market that you could fill. These conversations turn into roadmaps you didn’t know were there, and they cost nothing but a polite ask and a little of your time.
Build Real Connections Before You Need Them
Networking feels transactional when you only reach out when you need something. Informational interviews flip that dynamic. You’re approaching someone to learn from them, not to ask for a job. That simple shift makes the conversation warmer and more genuine. And when people enjoy talking to you, they remember you. Months later, when a contract opens up or they hear about a remote gig that fits your profile, you’re the person who comes to mind. That’s how relationships built on curiosity turn into real career moves.
How to Set One Up Without Feeling Awkward
Keep it simple. Find someone on LinkedIn whose role or company interests you. Send a short, direct message explaining that you admire their work and would love to ask a few questions about their experience. Most people are happy to help if you’re respectful of their time. Keep the interview to 15-20 minutes, prepare a few specific questions beforehand, and always follow up with a thank-you. Whether you do it over a video call, a phone chat, or even email, the goal is the same—learn something real and leave a good impression. One conversation can shift your entire job search trajectory.
