My last post was around the topic of how long should you stay in a Product Management role. While there are no hard and fast rules, in my experience it is about 3 years, give or take, before moving on to new challenges, or to be pulled up in rank.
However, turning the question around, what are the signs that it is time to move on, to begin the search for the next stop? That is a much more difficult question to answer, as the general case answer is "it depends". Realizing that no job is as great as it sounds when you are in the interviewing process, reality is often a wakeup call. But, as product managers, we are good at walking into chaos, and fixing or improving the environment. Still, there are some signs of when to look for the next stop.
Case 1: It has become routine
When you have gotten to a point where managing your products is routine. Where even a big crisis is really just another day, you know that it has become routine. Depending on the starting state, and how you have navigated, this could take a couple of years.
You have a solid roadmap, you have whipped the product line into shape, end of life-ing the products that are beyond their sell-by date, and the development team is in stride.
This is when life becomes too predictable. Some people love this state, and smart companies when this happens look for the next rung on the ladder for their product manager (director? GM?) but that is far from the usual.
For 4 of the 6 product management jobs I have left, this has been the reason. I was ready for a new challenge, and conversations with the leadership made it clear that there was no next step on the career.
Case 2: You have stayed too long
Suppose you have slayed the demons that you walked into. You have built a pipeline of products in development. You have a solid roadmap, and all the stakeholders are on board, and cheering the direction.
In short, you are comfortable. It is easy. You travel when and where you want, you are a principal in the annual strategic planning, you have different groups asking you for advice on where to go.
A smart company would promote the product manager, but this isn't a smart company. They remember the chaos before you joined, and like the calm seas. They don't want to rock the boat.
Or perhaps they want to promote you, and you just don't want that bump up. It is a very different set of skills to be a director of product management, over product managers. Perhaps you prefer the individual contributor position (there is nothing wrong with this, often the title doesn't equate to the change in responsibilities).
So you hang out. And you are bored. It isn't a challenge, but the money is good, and you just let it ride.
Once this happened to me. I stayed at least 3 years too long. I got embroiled in office politics, got burned, and really burned out. Before I left, I was on a downward spiral, in to depression, self doubt, and self loathing. It was ugly, and while we parted on good terms, the separation has negatively impacted my career in the positions I have taken since.
Case 3: You are beaten
Sometimes, you stumble into a position that is just not a good fit. Perhaps the starting state is so fouled up that it can't be fixed. Or the politics, hidden during the interview process, are too toxic. Or predecessors made some decisions in the product development that cripple the business, and the sunken costs of development mean that it can't be salvaged (if you admit the mistake, and report to the senior management, they will elect to just exit the business, rather than retrench and invest what is needed to make it right).
This is a tough place to be. You might be somewhat aware of the situation from the interview process, but you can be certain that the full on hide the disasters will be the standard portrayal.
You can (and probably should) try to fix the structural issues. However, you should be realistic about the chances of success. Sure, if you do, it is a feather in the cap, and something to brag about in the future. But, sometimes, the burden is too much, and you shouldn't beat yourself up if you cut and run.
This has happened exactly once in my career. I stayed way too long, tilted at too many windmills, and significantly damaged my psyche and reputation. The only saving grace is that I can say that I tried everything in my power, yet I was still beaten. Beaten badly.
My advice is to realize this, and to just leave ASAP. It is OK to acknowledge that you made a mistake. Better to chalk it up to experience, and move on, than to suffer needlessly. There are sure to be much better opportunities.
While the time frames might differ, there will be a right time to leave, or to move to a different position. What is right for you may differ, but the important thing is to recognize that it is time to leave.