How to Cold Message Someone for an Informational Interview

Tips for reaching out to strangers on the internet for design career advice.

---

Today, the job hunting process is simpler than ever. Job board websites like LinkedIn or Indeed boast thousands of available roles at countless companies. You can find exact details about when a role was posted, how many other people have already applied, and even compensation ranges for the position. And with just a few clicks, you can instantaneously send all of your information, at any time of day (or night), to each and every one of these companies. Through these modern tools, you can apply to dozens or even hundreds of jobs in a matter of days — all from the comfort of your home.

It’s tempting to think that this is the most effective way of job hunting. If your portfolio and resume speaks for itself, it often can be. But for those who are angling for their first job or trying to pivot into a new field, this mode of operating can quickly become a destructive cycle. When your applications are sent, evaluated, and rejected at lightning speed, it offers little time or feedback for reflection, improvement, or guidance. This is how informational interviews can be a powerful expansion of your job hunting process.

What is an informational interview?

An informational interview is a structured conversation with a professional in your desired role, field, or industry. 

This usually happens in a standard fashion: you find the professional and reach out. They agree to chat with you, and you agree on a date and time. Then, you meet with them (over the phone, on a video call, or over coffee), ask them a series of questions, and leave with valuable insights.

As simple as it seems, the informational interview offers many advantages:

• You’ll learn more about their history, career path, and work. Because you’re connecting with the person 1-on-1, many of these details will be more intimate than what’s available online or publicly. 

• You’ll gain a new connection in your desired field. They might make further introductions for you, answer ongoing questions you have, or even cheer you on in your future efforts.

• You’ll challenge yourself to grow out of your comfort zone. This will improve your confidence, interviewing skills, and overall knowledge of the industry. 

In my own experience, the biggest benefit is that each interview reminds me that everyone’s human. Regardless of where someone’s at in their career, they’ve overcome their own challenges and mistakes — each experience has led them to where they are today. It’s refreshing to connect with people in this way, and in the hard times, this can inspire you to continue pursuing your own path.

These advantages are often just a message away. So, to improve your chances of getting these informational interviews, let’s cover 3 tips for a successful initial outreach!

Tips for reaching out

Tip #1: Define your objective 

Before you start looking for people to connect with, outline your goals for pursuing these new connections in the first place. Depending on where you’re at in your career, your goals might include:

• Receiving career advice about how to land your first design role

• Improving your portfolio, resume, or interviewing skills in order to change jobs

• Learning more about a specific job role, like product design, or team, like design systems

The more specific you can be about your objective(s), the better. You’ll then be able to find the right people to connect with. Which leads us to the next point:

Tip #2: Reach out to the right people

Your objective will guide you to what kind of people you should contact and interview. If you’re seeking general career advice, you might want to cast a wide net for design professionals in various industries. If you need portfolio feedback, you might want to focus on designers within your niche.

When evaluating who to reach out to, always do your research on the person beforehand. Use their LinkedIn, website, or other public platforms to get a better idea of their background. Make notes on what questions you might want to ask based on your findings. What you discover here can even be used in your outreach message to make it more personable, specific, and persuasive.

Tip #3: Make your request clear and concise

When it comes to messaging someone for the first time, aim for brevity. Especially if your recipient is further along in their career, they’ll likely have more demands on their time. They will appreciate a clear, concise request — and they’ll be more likely to respond and offer help. 

To reach out for an informational interview, start your message by providing a brief introduction of yourself: who you are and what your objective is. (For more details about what to include in your introduction, check out my other article on crafting your elevator pitch.) You might also want to work in some points about why you’re reaching out to them or how you found them.

Then, get right into your ask: you’re looking for 15-30 minutes of their time to chat further. (I recommend also offering to send your questions over via writing, in case the person is too busy or prefers to answer over messages.)

As an example, here’s what that might look like:

“Hi [name],

I’m [name], and I’m a recent graduate with a major in digital design. I came across your work on Instagram and I loved seeing your latest illustration project with [company]. I’m trying to break into illustration myself, and I was curious if you’d have 15-30 minutes to chat about your work history and how you got to where you are. If not, I could send over my questions if you have any time to answer a few of them. Regardless, I’d still love to connect and keep in touch. Thank you for your time!”

When you’ve written out your message, always proofread and revise it. Can you make it more concise without sacrificing detail? Does it make sense to a complete stranger, who has no understanding of who you are? Do you need to provide more specifics?

I recommend keeping a record of your outreach messages because you’ll likely be using a similar format (with small adjustments) for each one in the future. By doing this, you can also improve your messages over time, figuring out what details are helpful to include or how to personalize your introduction.

---

In going through these steps, you’ll create a positive cycle that benefits your job hunting process. With your objective, you’ll have a better idea of what you need in order to move forward in your career. With the research you’ve done, you’ll see how other designers present their work and how you can curate yours accordingly. And by reaching out, you’ve put yourself out there in a bold, new way. Over time, you’ll find that each informational interview has the potential to lead to a new connection, which can ultimately lead to a future colleague, manager, or friend. Good luck!

---

I hope you found this newsletter helpful! If you’re interested in reading more, subscribe here for free and share it with a friend. You can also find me online at wontonface.com. To request a topic for a future article, submit it here.