Optimistic PM, Pessimistic PM

“I’ve never seen a monument erected to a pessimist.” – Paul Harvey

We live in interesting times, the world around us seems to be constantly on fire – physically and metaphorically. It’s gloom and doom all around. Morgan Housel touches on this extensively in his latest book, The psychology of money. He makes a convincing argument on why pessimism appeals to our emotions more than optimism. We tend to be more fearful than optimistic as losses hurt more than happiness from gains.

Another angle on this topic is explored by Rory Sutherland in his book, Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life . Rory makes a convincing argument that forward progress is always made by ideas that seem irrational when measured by conventional (financial) means. Progress is made by crazy ideas and in organizations, you need to have the gumption to execute on these out-there ideas. He has an interesting heuristic for ideas – if your finance guy does not like it, it is a great idea!

How does this tie in with product management?

Product managers by default operate in pessimism mode. What is the first thing that you are trained to do when you hear an idea? No is the first answer. Let us gather some more data, lets flush out the idea further, let us figure out relative priorities and alignment with strategies. The default stance to an idea is pessimism. Rationally, pessimism is the right answer.

But are we looking at this the wrong way?

Digging a bit deeper, why the natural bias towards pessimism? There is a fear of being viewed as a “gut” person. PM’s (rightfully so) have it drilled into them that data is the most important currency in decision making. Crazy ideas have a huge element of instinct in them rather than cold hard data. There is also a fear of committing to something that has an uncertain payoff. PM’s are measured on the magnitude of business impact with the products that they launch. With crazy ideas there is a large standard deviation in outcomes – there is a high probability that the idea may not work. Why risk your career on a crazy idea? It is easier to say no to ideas and stick to iterating to the local maxima of your product. Pessimism is the rational response at an individual level

Is there a way to break this cycle?

I do not know of a sure-fire way to turn people into optimists. I am also aware of Goodhart’s law, any metric-based system to solve this will end up with the wrong outcome. However, some suggestions

Create a crazy ideas budget
This is similar to the 20% time concept that originated at Google. Pre- allocate resources to crazy ideas. This also creates an expectation that the organization will pursue crazy ideas. It is part of doing business.

Reduce the career harm from failure
Each PM gets a get out of jail free card once a year. They can feel free to pursue an idea without worrying about the career risk from failure. As a PM builds a track record of successfully executing on crazy ideas, they get more cards per year.

Would love to hear real-world examples from y’all. Have any companies instituted a process to work on crazy ideas in a systematic fashion?

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