There’s a whole set of things that feel concrete and objective and are easiest to talk about: writing, financial modeling skills, project management, writing a decent PowerPoint deck, etc.
And then there a whole set of “softer” skills – skill in building relationships, how well you manage a meeting, whether or not you successfully deal with uncertainty.
And then the real biggies: Are you a great judge of talent? Do you consistently build trust? Are you courageous? Does your presence and do your actions make people better at their jobs? Do you inspire people?
The challenge is that there’s an inverse relationship between how important a skill is for long-term success and how easy it feels to talk about it.
“You’re still not where you need to be in building a cash flow statement” feels safe.
“I’ve not seen you show consistent success in gaining a sense of shared ownership around your good ideas,” feels like emotional thin ice, so we don’t go there enough.
On some level we know that the second conversation is orders of magnitude more important than the first, but since it feels (inter)personal, less objective and harder to talk about, we avoid having it and stay in the safe (today) but dangerous (in the long-term) space of “stuff that you can learn in a textbook.”
Sooner or later, we have to learn how to talk about the real stuff.