I recently heard about this attitude in a podcast interview with Raylene Yung, reporting that it reflects overall company values at Stripe.
But instead of ‘only’ applying it on a business level, I think it’s also quite a suitable framework for the split of perspectives product managers face on a regular basis.
It’s kind of an analogy to the discovery and delivery separation every product manager needs to handle. While the one (delivery) focusses on execution in regards to ongoing sprint routines, details of backlog items and hitting milestones on time, the other one (discovery) focusses on customer problems worth solving and what to build next.
From my experience, optimism is key for going into a product discovery. That doesn’t necessarily mean to be overly enthusiastic about a certain feature.
Furthermore, you should be looking forward to the digging into customer or business problems and the creative journey that you’ll identify something valuable you can build up on with your team.
On the execution side, I found the ‘right’ degree of pessimism helpful for staying on track. That doesn’t mean that you should doubt the success of your team on a regular basis, but challenging (your own) priorities and decisions at least during every sprint planning.
Don’t take yesterday’s decisions for granted – As long as corrections still fit into the overall product vision.
Remain skeptic that the path you chose for the next sprint will still be the right one when looking back at it into the retrospective. This way, you’ll stay hungry for ongoing improvement and avoid a ‘now we just need it build it’ attitude.
Your macro perspective should always be mostly positive. This will give you the confidence to question decisions on a micro level more regularly without becoming scared that you’re losing touch with the big picture.