In the nearly 24 years the Dude has spent in product management, he has learned many difficult lessons. But one that stands out is the wisdom to ask a very pertinent question.
When the Dude is interviewing for a new role, or his boss has a new task or responsibility, it is common for the sales side of it to be wonderful.
This will raise your visibility…
This is a great stretch goal…
You will get key executive exposure…
Plenty of platitudes, many promises of the benefits, to your career, your professional development, and how it will raise your stature.
Yet, all too often they become boat anchors around your neck. The job is impossible, the team is toxic, the environment is impossible, the stretch goal is unattainable.
So, how do you get a feel for the situation before saying “yes”?
Ask a simple question: “What does success for this look like?”
Short, sweet, and revelatory. The Dude’s gonna say that 99% of the time they haven’t thought about it. For a new job, it can help you uncover dysfunction that you wouldn’t have encountered until you were a couple weeks’ in. For an adjunct to your day job, it can be a forcing function to make your boss who is offering this think about what would be a win. That way, it is sure to not be an exercise in futility.
Regardless, it will cause the person you are talking to to rethink their opinion of you, and for the better.
Why it took so long for the Dude to figure this out?
Early in his career, the Dude lusted for new and exciting things. New roles, more responsibilities, different views, and he would lunge at them when they came up, assuming that the other party was being open, honest and forthright in their description of the ask.
But, after many - to put it bluntly - shitshows the Dude has learned that the grass isn’t greener, and things your boss unloads on you because he thinks you can handle it are really quagmires of political risk.
Making them tell you what success looks like can (and usually does) eliminate the bullshittery.