Using Safe-to-Fail Experiments in Continuous Planning

Annual Planning Nightmares

It feels strange to admit this today, but I thrived in this environment. Each year during annual planning, as the leader of our Internal Tools, I would check in with the company’s Senior Leadership Team and give them a choice of 4 or 5 big strategic projects that my team could tackle the following year. It was always important to me that my team was working on things that mattered to the business. Once I knew what was most important, I would work with my team to set ambitious goals that might take 6 or 8 or 10 months to deliver. We put our heads down and we delivered on them. Year after year.

A sarcastic gold star award given to someone who does what they said they will do

From Annual to Quarterly

Moving from an annual planning cycle to quarterly was much harder than I expected it to be and requires a fundamental psychological shift, otherwise you’ll find yourself doing all the work of the annual cycle, but repeating it every 3 months.

  1. Accept the unknowable. (Mindset)
  2. Know what’s important, aka your guiding North Stars (Strategic)
  3. Embrace Safe to fail experiments (Tactical)

What is a safe to fail experiment?

A safe to fail experiment is exactly as it sounds. It’s just an experiment you can run where no matter the results or what happens as a result of the experiment, nothing too bad can happen.

What does experimentation have to do with business?

We know experimentation is important to science. The scientific method is based on hypothesis and experimentation for the purpose of discovery. Scientists run experiments to learn what they don’t or can’t otherwise know.

Tips for conducting safe to fail experiments

The key when designing experiments is to make sure they are safe to fail. The goal of running an experiment is to learn something. So, the cheaper, faster and safer, the better. If something is not going to work, the sooner you know the better.

  • Can it be reversed?
  • What is the worst thing that could happen?
  • How much will it cost?
  • What might we learn?
  • Will we actually change based on results?
  • Is there a smaller, cheaper, safer way?
  • What objective does this advance?

A way of life

Designing and conducting safe to fail experiments was a critical piece to our successful shift away from an annual cycle with its emphasis on being “correct” towards a quarterly cycle with its emphasis on “what can we learn” and “what value can we create today”.

A graphic with the quote “Computer science without conducting experiments is just computers”



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IT Executive, Engineer, Enterprise B2B SaaS. Interested in innovation, cloud, devops, agility. Passionate about making tech more inclusive.