I told you sos. And putting your money where your mouth is

Catching up on Podcasts after a few months ‘reading’ audiobooks and came across another great Surprisingly Awesome titled ‘I Told You Sos’ which is pretty much the point I was making in a post a few years back titled Haters say I told you so. Ergo, I totally told you so, that it was an interesting thing to think about!

Granted, my post was a bit of rant, given 10 years into running With Associates, at which point we had witnessed a few common ill scenarios repeating time and time again, despite various efforts to alert new clients about the challenges we had already experienced. Unable to make them believe our words, we would end up in the uncomfortable position of being able to say ‘I told you so’. Not actually saying it, but clearly in a situation were the elephant in the room was mouthing “YOU SO TOLD THEM SO!”

Now. Pause here for a moment and realise, just how the act of me suggesting that I could once have told someone “I told you so”, feels kind of yucky. You dislike me a tad don’t you? Or think a little less of me at least? Well that’s my point and the one that’s more articulately explored in the podcast. I told you sos suck for all involved. 

They even mention the Cassandra curse as per my post, which is still one of my favourite project management similes. That awful feeling, or utter conviction, that you know what’s going to happen but you just can’t make the colleague / client / board members / investors believe you. 

To this day though, no matter how frustrating it feels and how many memories I have of these scenarios, I believe that you only have yourself to blame if you find yourself in a position to tell “I told you so”. Or at least, that no one really does everything they possibly can to ensure that their point is taken before it’s too late. 

Even if it’s just finding a new and more open way to frame the “I told you so” opportunities, so that they’re not always about you getting your comeuppance, but a way for everyone to put their money clearly where their mouth is. 

What I mean by this is the idea to apply a more scientific bent to running a project and managing a team, where everyone openly documents their ongoing micro-hypothesise about potential outcomes so that they can be reviewed and learned from, even when wrong. “I told you so” and “Oh, I was wrong that time”. 

Having both potentials documented, rights and wrongs, all sitting together for the whole team to review would lessen the cherrypicking nature of remembering only the times where people were right. And with everyone openly fallible as well as occasionally right, it could create a better environment for all to learn from mistakes and stop dwelling on hindsight.

I can imagine it being an interesting Slack app or some sort of Github or Trello integration. You record a hypothesis as part of your regular workflow, a sort of a hypothetical branch or meta card, and set a reminder for a review date. 

This general idea also comes up in the podcast at 31min 10sec, though again, they’re more funny and articulate than me, and their version contains more of a gamification edge:

COLIN: …I’ll tell you exactly what the solution would be. If every time you said something, any time anyone made a prediction, they had to bet on it. Like financially, you had to lay out money.

DAVIDSON: And say like, on this date we’re gonna check. Like in 2028, we’re gonna have a check in, did Tiger Woods ever win another golf tournament.

COLIN: Exactly, then it’s like you go to the window, the racetrack, and instead of saying I told you so, you collect like 800 bucks, you don’t have to say I told you so, because you won 800 bucks, and everybody else lost.

DAVIDSON: I love this idea.

COLIN: It would be great.

DAVIDSON: LIke I think there could be an app.

COLIN: And you put everybody’s win/loss record online, so that everyone can see, so whoever you’re talking to, you’re like are you kidding me? Why would anyone listen to this person, you lost like 80,000 dollars, you know.

This version reminds me of the incredible longbets.org which I’ve always loved the idea of. And more generally and recently of the exciting work happening with alltrials.net and cos.io. Basic, classic scientific methods. Here’s my idea. Here’s how I’ll test. Oh look I was right/wrong. Now, what does that teach us?