Hello there 😎

For those in the US, hope you had a great Memorial Day! I spent my camped out by the splash pad at our local rec center with the kids 🇺🇸🛝

A few housekeeping items before we jump into today’s issue:

First, some personal news: the newest member of my family was born 👶 Theodore, mom, and the rest of the family are doing great.

Second, expect changes to the newsletter soon. I started The Connection in 2017(!) to share reading lists with family and friends. It’s evolved since then (obviously) and it’s finally time for a new name, design, and website.

Thanks all!

Today in 5 minutes or less, you’ll learn how I get the insider details about a company before I apply, potentially saving years of work and heartache. 

Plus, the best links and resources on remote work. You’ll learn:

• 🚢 What it’s like to work remotely for 21 days on a cruise
• 🦜 How to ask about a company’s remote work policy
• 👋 Instead of RTO, which talent is just… leaving

Let’s jump in:

The informational interview is the most invaluable tool in building your career – particularly the “messy middle” of your career.

Notice: I said career… not just landing your next role.

Yet… most people never bother to do it.

Informational interviews are how you:

• Bypass applying via job boards everyone else uses
• Do deep research about what it’s really like working at a company
• Build a robust network who can help you (and you can help) in the future

What is an informational interview?

How I use informational interviewing is a 4-step process. I’ll break it down for you, plus show you the insider details I got about a company that saved me potentially years of work. Here are the 4 steps:

1. Start With My “Career Thesis”
2. Do Deep Research
3. Learn Before I Apply
4. Evaluate The Information

Let’s dive in:

1/ Start With My “Career Thesis”

Your Career Thesis answers two questions:

With my Career Thesis defined, I compile a list of 10-15 companies. I ask myself:

• What companies have interested me for a long time?
• What industries am I interested in? What are great companies in that space?
• What industries do I have experience in? What are great companies in that space?

2/ Do Deep Research

With my list of companies, I start doing deep research. High-level here’s the information I start gathering:

• Industry
• Location (great if remote, OK if not)
• People (currently or previously worked there)
• Mission
• Products
• Customer
• Competitors
• Challenges
• Product

Traditionally, I use Google, LinkedIn, and Crunchbase in my research.

But more and more, you can use AI to get you 80% of the way there in a few minutes.

Here’s how I do that, using my Research Database (jump to 03:00):

Now, the magic really happens when you start digging into people.

I list people whom I find interesting and want to talk to. In my example, I narrowed down on a Creator Economy company and found 5 such people. Then I Google them, review their LinkedIn profiles, and try identifying one common thread we might have together.

Once that’s done, I’m ready to reach out.

3/ Learn Before I Apply

With my list of people to reach out to, I have one goal:

In other words: I want people to spill the tea.

But first, I have to get their attention.

Here’s an example script I use:

Here is what that looked like in practice:

Second, I follow up on my messages. I expect 80% of these messages to require at least one follow-up. I call this being “pleasantly persistent.” I might say:

What it looks like in practice:

With my informational interviews for this Creator Economy company, I had a 60% response rate – more than enough to get the inside scoop.

4/ Evaluate The Information

When you are open, honest, and genuinely curious, people are happy to share things they’d never share publicly. Some of the things I learned:

The Upsides of this Creator Economy company

Growth. The business is growing. Not as rapidly as before, but steadily. The unit economics make sense.

Pride. Customers are incredibly engaged and super fans of the product

The Downsides of this Creator Economy company

I wouldn’t suggest going there as a Growth person (in fact, told another one of my good friends who asked the same a few weeks before you reached out).

Under the prior VP and CPO, it was tough to succeed at all. They had little understanding of Growth, didn’t invest or care to invest much there. A lot of toxicity (many former Microsoft and Amazon folks who brought a weird culture).

It was also a low-volume product that is heavily Web. Wasn’t a great opp at the time to drive significant impact across multiple growth areas because you didn’t have enough sample. 

You only uncover this kind of detail with informational interviewing.

Armed with this information, I revisited my career thesis:

Based on what I learned from the informational interviews, and because I wasn’t in a rush, I slowed down any conversations about applying for an open role.

Conclusion

Through the informational interviewing process, I saved myself weeks of work in applying, prepping, and interviewing with this company. (And potentially years of my life by working at the wrong company at this point in my career).

If my situation changes in 6-12 months, I can revisit this decision. When I do, I’ll have a wealth of information already at my fingertips, and people to reach out to who can put me on the inside track.

That’s the power of the informational interview.

That’s a wrap. See you next week 👋