Dear Gib: When is it time to move to a new company to advance your career? What do you lose by staying at the same company for a long time?
Short answer: Make a change when your current job satisfaction is low, and you expect that your job satisfaction at the other company will be substantially higher. Long answer: It depends.
Here’s my first question when I have a career conversation with other product leaders: “On a scale of zero to ten, where zero sucks, what is your current job satisfaction?” If the person gives a number from zero to six, we’ll have a deeper conversation about what could be better about their job. Here are the factors I focus on:
Connection. Relationship with the person’s boss, team, and other individuals in the organization.
Autonomy. The ability to self-direct— to not feel like an order-taker for their boss.
Mastery. The ability to learn and grow in their job. To get better.
Purpose. The feeling that the work they do matters— helps make a dent in the universe.
It sometimes helps to have the product leader evaluate each of these factors on the same zero to ten scale. I call this the “CAMP” model— get it? (It’s my bastardization of Daniel Pink’s AMP model, informed by Tony Hsieh’s book, “Delivering Happiness.”)
The result of this evaluation is a stronger sense of why the individual is unhappy. Some of the responses lead individuals to explore another company — to fulfill a different mission or purpose. Other diagnoses advocate exploring opportunities within the same company— because they seek a new challenge or boss.
The point is to figure out the root problem and then brainstorm potential solutions both inside and outside the company. Generally, lower job satisfaction leads individuals to take on the risk of joining another company, hoping that their job satisfaction will be eight or higher there.
If the person’s job satisfaction in their current role is seven or higher, they’re doing well. Those same questions— about connection, autonomy, mastery, and purpose — may help isolate what could be even better about their job and provide motivation to experiment with another potential opportunity.
Another perspective, based on what I enjoy: For me, career growth has always been about identifying and joining a startup with a proof of concept that is ready to scale. In almost every case, the startup’s growth created significant growth for me. But this is more an expression of what I am good at and what I enjoy, and I know that many product leaders prefer larger organizations' stability. That’s where asking questions about overall career satisfaction and digging a little deeper using the “CAMP” model is helpful.
This is a tough question to answer without context. You would be much better off having this conversation with a peer or mentor who knows you and whom you trust. The best I can do— what I am trying to do here— is to help you frame that conversation.
Nonetheless, I will do my best to answer your question directly: You should leave a company when your job satisfaction is relatively low and when you believe there’s an opportunity to find substantially higher job satisfaction at the new company. What do you lose by staying at a company too long? If your job satisfaction is high and opportunities continue to open up for you as the company grows, there’s very little potential loss.
I hope you found this helpful. Thanks a ton for asking the question — it had fourteen upvotes within an hour, so your question is very much on other people’s minds.
PS. Pro Tip: Click on the “Recent” button near the top of the list of questions to make upvoting easier.
PPS. Click here to give me feedback on this essay— it only takes one minute.