The Leaflet #114
1. Upskill through example and exposure 2. Overcoming disgust 3. Prompts for good skip-level conversations
Onboard and upskill through example and exposure
For a new leader, most of what they will learn to do effectively they will learn by example and exposure. The overall headline I bring to the onboarding / upskilling challenge is: how do I immerse them as quickly but as comfortably as possible in the experiences he’s going to eventually be responsible for?
Onboarding a new teammate using positive peer pressure and exposing them in as many ways as possible to excellence around the team is good but not sufficient. It’s important to add and accept that they’re going to have to take on responsibilities for which they’re probably under-equipped and they’re going to have to do this before they feel ready. Articulate that reality, that future state; make it clear and expected. If your new leader expects those responsibilities and is spending time with the people who shoulder them now, watching them do what they do, that will maximize the speed at which they will take on and succeed with those responsibilities.
This shakes out into roughly two stages. One stage where they shadow you in every meeting that you’re in, followed by maybe a five-minute debrief about what they took from that each time. At a meta level, they’re stamping what they learned and what they’ve taken away from the shadowing.
Then there’s the second stage where they’re doing more themselves, which will bring up new questions for them. They’ll think they’ve directly, fully modeled you, but then they go into a meeting and they’re stumped a few times, and now have more questions for you, and maybe need to observe you a little bit more. Then they’ll do that observation and go back into trying out your moves on their own.
If you want this process to be fairly robust, you could plan for the first stage to unfold over the course of two weeks. In the first week, they observe and name takeaways. In the second, you let them dive into the independent practice of stage two, with you observing a little bit at the outset to make sure they’re handling it well.
I don’t think there’s any chance they spend an entire week shadowing you at meetings where they don’t come out quite evolved in their ability to handle the things you’re handling there.
-ben
Moving on from disgust
It’s unfortunate that most bosses’ immediate response to underperformance — mine included — is disgust. That’s obviously not the state of mind from which we should operate to solve underperformance.
I also think there’s an adjacent problem: when we do feel aversion, personal grumpiness towards somebody, to what degree is that a sign or anti-sign of them actually being a bad fit or not performing?
In my best moments, when I’m checking that for myself, what I’m doing is looking ahead to the future and saying: in six months, if this is a high-performing employee, what am I seeing that is different from what I’m seeing now? And is my answer to that question something idiosyncratic and particular to me only, or something I genuinely want to develop people to have in the organization?
So if my answer would be, like, Eric is just less annoying — and by that I mean he’s more considerate of people’s time, he’s more thoughtful in how he frames his negative commentary — okay, now I’m thinking, yeah, that is something he should improve. And if he’s not improving on that in six months, I know the stakes of that and I might not keep him around.
But if I can’t really identify an actual trait that is worth developing, then I have to pause and say: am I just in a mood about this? Do I need to balance my aversive reaction with some more data about his actual performance?
The bigger question is: am I going to invest in developing this capacity in this person? Is that doable for me? Can that happen here?
-ben
Three prompts for good skip-level conversations
When I was using skip levels most effectively, making my way through the full cohort every quarter, there were three purposes.
One was to establish relationships with people I wouldn’t see as frequently. It wasn’t like talking to them for a half hour every couple of months was enough for a robust relationship all on its own, but it often opened the door to more conversations, and that was helpful.
Two was gathering feedback for their manager. I always said to the person in the skip level meeting: I’m not bound to confidentiality on any of what we’re talking about today, but I do want to learn what you think would help me help your manager succeed.
And finally, the third was to ask: What are you thinking — and what are others maybe thinking — about the organization that I might not know, that would help me to know? Usually, having gotten warmed up on the first two prompts, they are fairly candid about that.
-ben
COMPELLING QUOTATIONS
Whole earth cataloguer Stewart Brand on maintenance and precision:
Although precision in manufacturing was initially driven by the quest for conveniently interchangeable parts, it soon proved to be about something far deeper than maintenance and repair. The progress from efficient steam engines to an efficient assembly line to the extreme density of nanoscale microchip fabrication is a saga of multiplying capabilities for humanity. Simply by becoming masterly at doing ever more with ever less, again and again, we live in a time of such potency that we have to be careful about what we wish for. Maybe considerations of long-term maintenance of the whole process can help us frame our desires judiciously.
Butterfly enthusiast Vladimir Nabokov on place and memory:
As if feeling that in a few years the tangible part of her world would perish, she cultivated an extraordinary consciousness of the various time marks distributed throughout out country place. She cherished her own past with the same retrospective fervor that I now do her image and my past. Thus, in a way, I inherited an exquisite simulacrum — the beauty of intangible property, unreal estate — and this proved a splendid training for the endurance of later losses.
Observer of places Tony Hiss on simultaneous perception:
Normal waking consciousness adn our sense of separateness from the world protect us from harm by allowing us to focus instantly on any source of danger… So for simultaneous perception to emerge, we need a place that seems safe, where the information presented to each sense is complex but not overpowering. If louder signals appear, they will tend to drive simultaneous perception underground. That is why we lose touch with it when we leave Grand Central and walk over to Fifth Avenue.






