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”How can you get lucky more often?”

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A friend of mine who’s Sr. VPEng at a mid-side SaaS company in a competitive market told me a story, and I’ll share it with their permission.

“This weekend I decided to sign-up for our tool, as I’m playing with some startup ideas. I went through sign-up and on boarding, and was shocked at how disconnected the process felt. Conway’s Law was obvious!”

”For example, the first screens in the sign-up used one design pattern and language, and all of a sudden I was dumped into something different. It was jarring, and personally frustrating.”

”I took my experiences to the team, and we’re working on improving it. It was lucky I tried that when I did, or we might never had known.”

And me, being eternally curious, asked: “Wow, how can you get lucky more often?”

This caused a bit of giggling until we both realized what was at risk.

For example…

  • What if they hadn’t signed up that day?
  • What if they’d been interrupted before they completed it, and never finished?
  • What if they’d been distracted and hadn’t noticed the disconnection?
  • What if they’d been too busy to share their notes with the team?

The what-if’s go on, and all of them end up with the answer “our competitors might win.”

All of this made us consider how important the ‘luck factor’ is.

And how we can increase our ‘luck surface’ – the possibility that they will get lucky.

They continued…

“Five years ago I don’t think this would have happened. The people who worked here were much more like our target customer. Our company was smaller, scrappier, and less experienced. We were like our customers in size our expertise.

But then we started hiring ‘real’ experts from larger companies, and we started growing really fast. Now our company doesn’t look anything like our target customer.

I wonder this change made a difference? Maybe we stopped looking for what our customers look for? Maybe our luck surface got smaller?”

I wonder, indeed.

Hiring experts and growing isn’t wrong, of course.

But, never forget that in a Complex Adaptive System (CAS), it’s impossible to anticipate all the consequences of our actions.

Not just ‘hard,’ but impossible.

The moral of our story


Okay, now you’ve seen a mini-case study for getting lucky and unintended consequences.

Always check if an improvement in one area causes problems in another part of the system.

And don’t assume that fixed things will stay fixed, or that “unrelated” parts of the system won’t be impacted.

If it’s important, keep checking, as the effects of a change may take some time to show up.


What unintended side effects can you spot where you work?

How does your team talk about their ‘luck factor’?



About Marcus Blankenship

Where other technical coaches focus on process or tools, I focus on the human aspects of your Programmer to Manager transition. I help you hire the right people, create the right culture, and setup the right process which achieves your goals. Managing your team isn't something you learned in college. In fact, my clients often tell me "I never prepared for this role, I always focused on doing the work". If you're ready to improve your leadership, process and team, find out how I can help you.

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