Episode 26: How to know when it's time to leave your company

Leaving a company is always scary. You’ve invested the time in building relationships, learned the product/space, and figured out your flow. And every company has problems, right? The grass isn’t always greener…but what if it is?

I’ve been on both sides—joining a new company has led to exponential growth in skills, salary, and connections. It’s also led to environments where my growth was not a priority and change was rather unwelcome (even in tech).

Every 6 months I go through a mental checklist to make sure I’m in an environment that nurtures the best version of my work self which I’m sharing with you today.

Top performers leave

I always make it a point to have regular knowledge-sharing sessions with top performers across departments. These sessions are opportunities for me to get feedback on early versions of my work and gain additional perspective on changes within the company, such as people leaving.

People leave for various reasons, so I recommend reaching out to the person who is leaving directly to understand their rationale.

👀 What you’re looking for:

- Is it an issue that affects multiple people?

- Has leaving been on their mind for some time or was it abrupt?

🚩 Red Flags

- You hear similar reasons from multiple people (across departments)

After hearing firsthand (not relying on gossip), you can decide if the reasons these individuals left affect you similarly.

For example perhaps someone is leaving because of a new manager or executive they roll up to making changes on promotion opportunities. This is a good reason for them to leave but unless it’s in your function, it doesn't make sense for you.

No new money

Companies are either making money or asking for money (raising a funding round), so it’s important that you keep a pulse on your company's ability to generate new dollars.

While companies measure many different things, here a few I look at on a weekly basis and track against the last 5 quarters:

1. Attainment vs. the quarterly goal (how many dollars coming in vs. what we hoped would come in)

2. Source of that revenue (are we bringing new customers or are we selling new things to current customers)

3. Churn (how many dollars going out)

4. Adoption of products (if you have 3 products then how is revenue split across them? E.g. 90% from product A, 10% product B, and 0% product C)

5. Margins (how much do we make on what we sell today)

That’s it. Depending on how these metrics look, there are additional metrics I will search for but these are the 5 foundational metrics I religiously watch.

For example, if we have missed our company revenue goals for 2 quarters, I know that we need to cut costs from somewhere. That means either a) stopping new hiring b) cutting program spend c) cutting people spend or some combination of all 3.

If we are meeting company goals but churn is increasing that tells me we either have a product or positioning problem. Customers don’t understand the value we told them we can offer so they decide to find another solution.

All businesses fundamentally need new dollars coming in so it’s important that you have a good understanding of how many customers you have, how much revenue they generate and how that revenue is split across your products.

Level up faster

While getting in the flow of things to the point where you can do your job quickly is nice, it’s also a good sign that you aren’t learning anymore.

If you don’t have an opportunity to level up within your role, you should seek out alternatives at the company (e.g., other departments). If you get a better opportunity elsewhere, though, it’s a good sign that you should leave.

I’m not just talking about title and salary (although that’s nice too) but more around scope of work. Do you get to run a program/initiative you want to learn more about? Are you responsible for something that helps you build a new skill? Will you learn about a new market or technology that you have been wanting to explore for awhile? All excellent reasons to leave.

I have one friend who started a crypto newsletter in 2021 as a way to force himself to become more educated about the market. Each week, he’d summarize his learnings and share, which is how he ended up an interesting company in the space. That company posted a role that was perfect for his background and he got the job!

I'm not saying you need to start a newsletter, but working in the space is often the best teacher, especially when the role requires experience you don’t have.

As always, feedback is a gift, and I welcome any/all feedback on this episode—good or bad. See you next week 👋.

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✨ Special thank you to Gigi Marquez who suggested I start this newsletter 🙏