“The first rule of holes: when you’re in one, stop digging!” Thoughts on Answering a Deceptively Tricky Question

February 20, 2020
Less than a Minute
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In SaaS businesses, operating results are earned every single day; and good businesses are made, not found. Writing here about building organizations, learning from the experience, and appreciating the ride.

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The “law of holes” was drilled into my head as a kid; and it is sound advice. The problem, of course, is proactively identifying whether and when you are actually digging yourself a hole.

I was recently reminded of this dynamic while visiting with the impressive leadership team of a 40-ish person SaaS company. We had met to discuss a range of topics relating to the life cycles of growing businesses. One person posed a seemingly straightforward question to the group that resulted in an immediate and spirited exchange: What do you do when it’s not working?

As a rich discussion unfolded, I remained silently stuck in the subtle, complexities of the question. While the debate whizzed past, I did what I often do when stranded in such situations — start to draw. The graphic below is a more formalized version of my notes and thought process from that session. It’s also an attempt to offer a simple approach to tackling this deceptively tricky question, and potentially others like it that prove surprisingly elusive to wrangle.

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