Knowing How, Knowing Whether

How do you navigate that moment in a career when people stop asking what you know and start asking whether it makes sense?

There are days when I sit down to type this newsletter, and my head is brimming with ideas. Then there are days like today, where there’s nothing.

I think it has something to do with a broader shift in thinking from a focus on knowledge to wisdom. Typing that feels uncomfortable, so let me explain.

How it begins

When I started in my career, I knew little but had boundless energy and a desire to learn. Impatient to be older, taken more seriously, and accumulate grey hairs (crazy really). I, like many others, felt compelled to try to demonstrate knowledge. Some of that was ego, some conditioning. The ‘knowledge economy’ rewards relentless acquisition of the adult equivalent of gold stars in school. Some folks wear them as streams of acronyms at the end of their names, others in our bios and introductions.

But there comes a time when that knowledge is expected. You know this moment when people start asking you to solve problems with the presumption that you’ve done it before.

The shift

I’m still learning. Sometimes at an overwhelming pace. But this is a different type of learning. It’s a bit like how I observe my father. When younger, he’d use brute strength to do the heavy work that comes with smallholding (and running a B&B). Now, he’s in his 80s, and the learning is more around how to do that same work while navigating some truly testing medical conditions. A system of winches, levers, and wheels emerges, working with (not against) gravity.

That’s what I meant by wisdom.

Knowledge is knowing how to do something. Wisdom is knowing whether it’s worth doing, and how else it could be done.

Professionally, that’s the transition I’ve been experiencing for a few years now. The conventional knowledge around many things - how to assess risk, how to interview, how to train people, etc. - does evolve, but marginally and glacially. More interesting and more relevant now are questions around whether it makes sense and how else things might be done.

An example

A first step in most investment due diligence is document review. Does the investee have in place the things the investor keeps on a list? That list was probably written years ago and has since been treated as a sacred text with no interrogation of provenance or relevance. Comparing what sits in a data room to what a list says should exist requires some knowledge, but it’s unwise. Risk management doesn’t (often) fail at the policy level, but in the gap between accurate identification, calibration, implementation, and appropriate response (decision-making).

So, instead, it might be wiser to begin with an analysis of future contextual risk. As in, if this company secures this funding, what will that look like (where are they, what are they doing, how do they operate, with whom, etc.). In that setting, what risks can we sensibly expect (knowledge) and what controls and culture might actually help mitigate (wisdom)? That exercise helps triage terabytes of stuff into megabytes of relevance. (And yes, AI can accelerate some of this if trained properly, tasked properly, and overseen vigilantly.)

But what next?

There’s a time in the not-too-distant future when wisdom (and its sisters, judgment and empathy) will become the new professional currency. Churning stuff out has lost its lustre as we all drown in data.

Wisdom is harder to write about, as it’s more of a conversation (requiring context, by definition). So, rather than go on (I managed to write this far, which surprised me), I’d ask:

“What knowledge have you swapped for wisdom?”