Wishful Leading

Imagine having an IC whose manager describes like so:

  • Doesn’t follow up.
  • Doesn’t communicate when things are taking longer than expected.
  • Rarely even estimates and commits to a time frame.
  • Cannot show tangible results over the past six months.

Sounds terrible, right? I’m sure you wouldn’t want to thatperson’s manager. It sure doesn’t seem like it would be a fun 1:1 to have.

Oddly enough, this sort of behavior is something I witness in many tech executives, though it is usually less obvious in their case. Here are a bunch of examples from the last six months:

Me: “What was your agenda during the last year in this position?”

CTO: “Create a great team.”

Me: “And what initiatives did you put in place to achieve that?”

CTO: *Blank stares*

VP R&D: “We’ve been working on changing our organization to do X.”

Me: “For how long?”

VP: “Five months…”

Me: “And how much did you think it would take?”

VP: “Two.”

Me: “Would you say most of your initiatives are done on time?”

VP Engineering: “That’s hard to say.”

Me: “Why?”

VP: “We don’t really set a timeframe.”

Me: “So how do you know you’re not investing in it more than it is worth?”

VP: “That’s a good question.”

CTO: “We got the whole team together and tried Scrum/Squads/OKRs/Whatever.”

Me: “… and?”

CTO: “We kind of never followed up on it after announcing it, so it died slowly, and now everyone is skeptical of any new initiatives.”

It’s a bit longer than I had planned, but I think it drives home the issue. Leaders don’t have any discipline in order to do the leading. It’s not possible to simply hire good people and let them be. Without providing them with a framework, an expected pace of improvement, and a steady rate of learning, productivity will continue to decline as the organization grows and becomes slower.

Your toolkit/operating system should consist of several essential tools for you to be an effective leader:

Accept that you cannot merely wish good things to happen. You have to set up your organization for success.

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