Beware: results-oriented thinking

If you talk to expert poker players, one thing you’ll hear them talk about is the trap of results-oriented thinking.

Results-oriented thinking is when we overreact to a probabilistic result, blaming or crediting our process or strategy when, in a sample size of 1, we got an outcome we did or didn’t want.

We took a huge risk, and won.¹ Or, we did everything right, but still lost.²

Results-oriented thinking is a bias our lizard brains evolved to keep us alive from danger — we don’t approach bears, we don’t eat the purple plants — but at work, it no longer serves us.

It’s important to ask yourself, did we just get (un)lucky or was this the result of our process or strategy?

There’s two kinds of protection against this bias.

1. Have a hypothesis-based mindset. Instead of just barging ahead with an idea, take a beat and write down what we think our hypothesis is. That way, when we get the results of our test (or launch), we can go back and see whether it confirms our hypothesis or not.

2. Regularly do “5 Whys”-style root cause analysis, where we ask Why five times. When something goes wrong (or right!), ask Why. And then, inspect your first-level Why and ask Why that first-level Why happened. Then repeat that — why did the second-level Why happen? And so on, until you feel like you’ve really gotten to the bottom of the issue.

Sometimes rolling the dice on a low probability strategy is the right thing to do. And sometimes we don’t get the outcome we wanted even though we did everything “the right way”. If we can maintain process-oriented thinking, we can better look back in retrospect and see what we could have done better vs. where we just got (un)lucky.

The Workshop

This is a newsletter-only section where I share a half-baked idea in hopes that y’all who are smarter than me can work it out with me.

Many thanks to those of you who reached out wishing me well with last Friday’s interviews. They went great! It’s been a whirlwind last 7 days: I’ve got from first round interview last Tuesday to 2.5 hours with the CEO (Wed/Thurs), 4.5 hours of interviews with other execs (Fri/Sun), and a 90 minute case presentation (yesterday). Offer decision to come tomorrow. Fingers crossed.

Back to The Workshop — one of questions asked in my case presentation interview yesterday got me thinking about how, at both of my last two companies, one of the product problems that we got really stuck on was getting users to convert through a funnel when they had a significant deficit of knowledge and expertise.

At Buoy Health, it was medical knowledge — I know I’m not feeling well, this article (or AI symptom checker) suggests it might be [x], but I’m not confident enough to take an action like booking an appointment.

At The Knot Worldwide, it was wedding planning knowledge — I know I need to book a florist or photographer, but I don’t know what I like or what questions to ask to figure out who’s worth the money and who’s not.

And so I got to wondering if a conversational AI experience would have been really helpful. This is definitely giving me Clippy from 1990s Microsoft Word flashbacks, but I wonder if there is something to having a “no dumb questions here” AI buddy at the ready to answer all of your questions and your “I still don’t get it” follow up questions might have helped our overall funnel conversion.

I could be totally wrong here but seems like it might be worth a look.

1  Superstitions are an example of this: Imagine if, when getting dressed for a big interview, you reach into your sock drawer and grab a pair of purple socks. You go on to pass the interview! And then you start to wonder — are these lucky socks? So you start to wear your lucky purple socks to every interview.

2  My least favorite example: We’re doing all the “right” customer discovery agile product management stuff, but our numbers are not getting any better. CEO concludes that all this process is a waste of time, and we should get back to the old way, where he would just dictate what to build next.