O’Donnell: How to change careers without your resume getting lost in the black hole

I’m trying to switch industries, but I feel like my applications are disappearing into a black hole. I don’t have direct experience in the field I want to enter, and I’m not even sure my resume is being seen. How can I make a successful career transition without getting stuck in this frustrating cycle?

— Hillary

J.T.: Let me commend you for taking the leap toward a career change — it’s not easy, but it’s absolutely worth it when you land in a role you’re passionate about. You’re right to feel frustrated with the traditional application process, especially when you’re trying to pivot into a new industry. Submitting online applications without a targeted strategy is one of the least effective ways to make a career change. Let’s talk about informational interviewing, a game-changing approach for career changers like you.

Here’s the secret that many people don’t know: When you’re switching industries, the goal isn’t to apply for jobs right away. It’s to build relationships and learn as much as you can about the field and the companies you want to join.

Informational interviewing is the perfect tool for this. Unlike a job interview, where there’s pressure to prove your qualifications, an informational interview is simply a conversation where you’re asking to learn. People are more willing to share their time and insights when they don’t feel like you’re asking for a job.

This approach not only helps you gain valuable insights into your target industry but also positions you as someone genuinely interested and proactive — qualities that hiring managers love.

Here’s how to execute informational interviewing like a pro:

Step 1: Identify your target companies. Make a list of companies in the industry you want to transition into. These should be organizations that excite you and align with your long-term goals.

Step 2: Connect with one person at the company. Find someone in a role or department you’re interested in on LinkedIn or through your network. Send a personalized message requesting a 15-minute conversation to learn about their experience.

For example: “Hi [name], I’ve been researching [company name] and came across your profile. Your role in [specific department] caught my attention, and I’d love to learn more about your journey. Would you be open to a 15-minute chat to share your insights? I’m currently exploring opportunities in [industry/field] and would really value your perspective.”

This message is short, personalized and clear about your intentions.

Step 3: Focus on learning during the conversation. Once they agree, make the conversation all about them. Ask questions like:

• What do you enjoy most about your role?
• What challenges do you face in this industry?
• What skills or qualities do you think are essential for success in your field?

This isn’t the time to talk about your qualifications or ask for job leads. Your goal is to learn and build rapport.

Step 4: Ask for a referral. At the end of the conversation, ask if they know someone else at the company who might be willing to share their perspective. For example: “I’ve really enjoyed this conversation and learned so much. Is there anyone else at [company name] you’d recommend I speak with to gain more insights?”

This creates a networking chain within the company, giving you multiple touchpoints and deeper insights into the organization.

Step 5: Repeat the process. Continue connecting with other employees at the same company. By the time you’re ready to apply for a role, you’ll have a strong understanding of the organization and a network of internal advocates.

Here’s where the magic happens: When a position opens up at the company, you’re no longer just another applicant submitting a resume online.

Now, you can:

1. Write a compelling cover letter: Mention the employees you’ve spoken with and what you’ve learned about the company. For example: “After speaking with [name] and [name] in the [department], I gained a deeper understanding of [specific challenge or goal]. Their insights confirmed my enthusiasm for contributing to [company name] in a meaningful way.”

2. Leverage your internal network: Ask one of your connections to refer you for the role. Referrals significantly increase your chances of landing an interview.

This approach transforms you from an unknown outsider into a connected candidate who has already demonstrated genuine interest in the company. Hillary, here’s why informational interviewing is so effective:

• It bypasses the online application process: Instead of competing with hundreds of resumes, you’re building relationships that can get you directly in front of decision-makers.
• It shows initiative: Hiring managers appreciate candidates who take the time to learn about their organization before applying.
• It builds confidence: The more conversations you have, the more comfortable you’ll feel speaking about your career goals and transitioning into a new field.

Changing industries can feel overwhelming, but you don’t have to go it alone — or rely solely on online applications. Informational interviewing is a strategic, low-pressure way to build relationships, gain industry insights and position yourself as a strong candidate before you even apply.