Why pros and cons will fail you

Satyajit Rout
2 min readDec 21, 2022


Almost always the first, and often the last, decision-making tool that you will pick up is one that will fail you miserably.

That tool is the good old pros and cons list.

I’ve seen long-term org decisions being made on the basis of a pros and cons list. And I’ve tried to emulate what I’ve seen by faithfully listing pros and cons to make a choice.

But that’s like squeezing a lemon harder to get honey.

Photo by Kelly Sikkema on Unsplash

Here are what pros and cons won’t tell you.

❌How bad can bad be, or how good can good be (payoff)

For a VC making an investment decision, the upside is way bigger than the downside–something that a pros and cons list won’t reveal.

❌What’s the likelihood of bad or good (probability)

For a manager making a hiring decision, a competent hire can be a risky choice if their record suggests they’re likely to leave in 6 months.

❌What is most important to you (preference)

For your choice of holiday, the rains can be both a blessing and a curse. If you want to lock yourself up to catch up on your reading, rains are your best friend to keep you in. If you want a week of sightseeing, rains are your worst enemy.

A pros and cons list is better than nothing the way a hammer is better than your fingers. But as the saying goes, ‘To a man with a hammer, a screw is a defective nail.’

Hammering means you’ll break things often. Don’t just walk around with a hammer. Get a toolkit for yourself.

A good decision-making toolkit should care for about what Annie Duke calls the three P’s: payoff (how much you’re getting), probability (how likely it is), and preference (what’s most important to you).



Satyajit Rout

I write about decision-making, mental models, and better thinking and things in between