GCR Problem #9: Keeping (and cultivating) senior talent
In many organizations in the sector, one or two senior people hold the place together. Those same essential leaders are flight risks. I intermittently track departure risk in coaching sessions, asking coachees to estimate their likelihood of leaving the team, and I regularly hear numbers like 40, 75, 80 percent.
The same folks offering these estimates often have no designated successor or defined opportunity above the one they currently hold. If they quit, there’s no one to replace them; if they stay, they’re stuck in place indefinitely. Understandably, mission-driven people in this situation feel unhappy, unappreciated, and despite themselves will start looking for a job elsewhere.
To their credit, the executives I coach recognize the importance of these senior folks and the risk of losing them. In my experience of the last few years, retention of one or two people consumes more coaching session time than any other operational topic in this cohort.
Let’s assume you’re also in a sector with small organizations, breakneck growth, for-profit orgs pulling talent up and out, and a labor pool of mission-aligned people that all your peer orgs are also fishing within. In these conditions, how do you keep your best folks?
More likely than not, you cannot out-pay frontier labs, eg, so it’s better to compete along two axes you do control: ceiling and belonging.
Ceiling: The reason a strong number two feels unappreciated is usually structural, not emotional. There is literally no bigger job for them to grow into and they are savvy enough to have seen and felt this. So one option is to fix the structure: define a role above/beyond their current role and build the path to it with them explicitly. A known path up can matter much more to a high-performer than a raise thrown at them to stay put.
Belonging: Retention in mission-driven work hinges on whether someone feels seen and ~irreplaceable. One cheap lever managers have to achieve this is regular, direct, career-focused conversations. The convos that build that sense of belonging are not flat “are you happy?” prompts (or spicier “how likely is it that you leave in x months?” prompts) but conversations that include takes like “here’s where I think you could go, here’s what I’d invest to get you there, here’s why it’s important for the org that it’s you that does this.” Most leaders have this conversation far too rarely with the people they can least afford to lose. Your all-stars burn bright but they’re not fires to put out, so they get ignored.
In addition to building a tractable future for your current senior folks, you need to build a bench with those same senior people. Many in this cohort resist investing in the next layer before it’s obviously necessary. That investment usually looks like giving real, stakes-y responsibility to less-proven people and coaching them through it. You bite the bullet of some shaky work from them in the near term so you can have a robust pipeline of leaders over time.
-ben
Relevant:
Teach 12 people, train 100
For seventeen years, while I led a school and then a network of schools, I taught a leadership class at 8am on the first Saturday of the month. The class was open to anyone, from assistant principals to custodians. You just had to put in the time. Over the life of that organization we never once hired a school leader externally; every one of them started in an entry-level role. Those same leaders stayed in their roles longer and performed better than their counterparts nearly everywhere in the country.
The best outcomes of leadership class came from the structure and requirements more than any particular set of insights I imparted. In other words – leadership class transformed the organization due to what the leaders were asked to do after class more than what I said in class.
Here’s the structure and the requirements:
Structure: You take 12-18 of the most influential leaders in the organization (this was ~1-5% of our total headcount; you can adjust numbers accordingly for your team). You choose participants based on their influence, not their title. For us, the meant cohorts that included C-suite, principals, assistant principals, and many people several rungs down whom everybody listened to. This group did one session a month, one objective per session, for six sessions.
Requirement: Between each session, every participant has to reteach the objective they just learned to four or five people who weren’t in the room. To be clear - summarizing it doesn’t count. Forwarding notes with an email that says “check this out” doesn’t count. Teaching it, observing implementation and giving feedback on that implementation - that counts.
With the numbers above, by the end of six months, the organization trained close to a hundred people in the material and — more importantly — had 12-18 trained trainers who could run cohorts of their own without me.
An obvious win here is getting a leadership pipeline that includes folks who aren’t yet in senior roles. A less obvious win is that you’ve assembled a cross-hierarchy group that shares a common language for leading people. Change management happens dramatically faster. There’s a built-in bat signal that lasts for years. People feel like leaders, feel seen and appreciated and upwardly mobile, because they are.
-ben
Quick wins as permission slips
For coaches, for product designers, for new managers: identify and deliver a quick win for your new/prospective client. If you’re good at what you do, you probably have a robust mental model of a high performer. You have a catalog of best practices and a catalog of interventions that can achieve those practices. You may even have a curriculum, where those interventions are sequenced and stacked.
Very likely, the full sequence, the whole stack, is hard. Doing it hurts. If it were quick and easy, your client would have done it already. Everyone else would have, too.
Your client may never take on the hard, painful parts of the curriculum that can transform their performance without evidence that you know what you’re talking about. Your glittering record of success may not be enough. Your client will think, with some justification, that their situation is unique and that any template you have in mind is Not For Them.
Win the trust you will need for the challenging curriculum by solving something observable now. Consider doing this for the low low price of free. The quick win isn’t fake or cheap, in the broad pejorative sense. It’s immediate and it shows that you know what you’re talking about and you get what they’re struggling with. You get it, so you give it.
-eric
COMPELLING QUOTATIONS
Poet Andre Bagoo on experience machines:
All art forms are experience machines. But unlike films, plays, and paintings, poems are mainly constituted by language. And language is everything. “There is what we say there is,” said W.V. Quine. Because I also think poems can be made of things, I sometimes feel poems can control me, and that we are all living inside a poem. A poem contains what contains it. Perhaps this is why we need to believe in higher things like gods, biscuits or spirits – to close Pandora’s Box.
Writer Jeanie Riess on horses in New Orleans:
One summer night, when I was twenty-five, I was sitting on my porch and a horse galloped by without a rider, headed for the river. I’m not sure what happened next. Horses gallop by sometimes in New Orleans, and no one writes an article about it for the newspaper.
Poet Jack Gilbert on love and Pittsburgh:
By insisting on love we spoil it, get beyond
affection and wade mouth-deep into love.
We must unlearn the constellations to see the stars.
But going back toward childhood will not help.
The village is not better than Pittsburgh.
Only Pittsburgh is more than Pittsburgh.