Tip: Ask what Success Looks Like

A long history in product management has taught me to get a handle on what success looks like. That way, you know going in what to expect, and how to execute

Tip: Ask what Success Looks Like
Photo by Eric Prouzet on Unsplash

I have been in product management for 24 years. When I began this journey in early 1998, I was the applications manager for a small optical microscope company, and the call came from the recruiter, I was intrigued. Long story short, I was in a good place to make the transition, so I took the plunge.

From that time on, I hopped a few times, each time expanding my skills and knowledge, as well as building valuable experience. But, each lily pad that I hopped to brought its own chaos and frustrations.

Often, I was asked to assume new responsibilities, and to expand my role, with many justifications that included:

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 my career, expanding my professional development, and how it will raise my stature.

Sometimes, it worked well, but all too often these assignments became boat anchors around my neck. The job is impossible, the team is toxic, the environment is impossible, the stretch goal is unattainable. Sure, I *found* ways to succeed, but it came with damage to my psyche and my mental health. During these situations, I learned to dig deeper into the expectation(s), and what was needed. I will share this nugget of wisdom here.

How to prevent a bad experience?

So, how do you get a feel for the situation before saying “yes” to these requests?

Ask a simple question: “What does success for this look like?”

Short, sweet, and revelatory. I will admit that 99% of the time leadership hasn’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  to figure this out?

Early in my career, I lusted for new and exciting things. New roles, more responsibilities, different views, and jump at them when the opportunities 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 I  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 and career risk.

Making them tell you what success looks like can (and usually does) eliminate the bullshittery. At the very least, it opens a dialog to explore what is expected, and the parameters that you will be operating under. For you, it give you a roadmap to success, and it is an opportunity to discuss the various outcomes that are possible, and to head off potential disasters.

As I have aged, I have not gotten more risk adverse, instead I view it as gaining a sage appreciation of what the ask entails, and a frank exchange of how to know when you succeed.