Fail Thoughtfully, Not Just Fast

I've noticed a trend in my bubble of startups of taking complex concepts (Radical Candor, Pivoting, Talent Density) too literally without considering the context / all of the other culture bits that prop up these concepts.

I call this cosplaying as a startup - you're using the right words, but aren't executing fully like these concepts were intended. So you're not actually Charizard, you're a person cosplaying as Charizard; you're not actually Meta, you're a startup cosplaying as Meta.

Now let's apply this concept to Fail Fast, a common startup trope. The intention of Failing Fast is to counter what we'd been seeing in larger, more bureaucratic organizations where change is slow, and projects that everyone knows will fail are often still seen through to completion without much retrospection until the end, wasting time and money when they do fail. But without the large company resources, startups don't have the luxury to take 2 years to decide to pivot or fully fail - so the thought was to fail faster and try more.

What this actually means is that you need to have stage gates in place to monitor the project and identify when you need to pivot, iterate, or abandon while using the minimum resources possible.

What I've seen in the current startup ecosystem is that we call it quits as soon as a stench of failure comes our way. I've seen startups so afraid to actually fail that they pivot every 2 months, or after talking with one new stakeholder, or immediately after discovering a new competitor, and nothing ever gets a fair shot to succeed. I've seen startups approve projects that never should have been approved because they know they can shut it down in a month if it shows any sign of not working. When it's easy to get rid of things, we're less thoughtful with the decision in the first place - think of buying clothes you know you can return, or the US concept of at-will employment ( 😬 )

So let's not just focus on failing fast. Let's focus on what the intention was - fail thoughtfully:

Only approve projects/products that you truly believe have a chance to succeed. Approving projects that you think will fail, and then shutting down once they show any trouble only disengages and demotivates the team while costing resources.
Set check-ins / stage gates to review results and decide a path forward (iterate, pivot, abandon) trying to be as objective as possible with measurements.
Postmortem each failure so you can learn from it, and get better with each launch - it's not a failure if the team learned something that improves the business overall.

To complete the actual quote - Fail fast. Learn fast. Improve fast.

Since at this point startups already have the "fast" part down, I think it's time we went ahead and pivoted this one to simply "Fail Thoughtfully."

Manage Expectations, Not Performance