At Work with The Ready

Sam Altman and Elon Musk built some of the most valuable companies on the planet while doing nearly everything we would advise against. So a listener wants to know: if ego and raw self-belief keep landing people at the top, is all this talk of trust and participation on our show worth it?

In this mini episode, Rodney and Sam get honest about survivorship bias, why colorful founders get all the ink while quietly thriving companies get none, and how the frontier game selects for a very particular kind of human. They also make the case for a bigger definition of success, one that counts the experience of the people doing the work right alongside the profit.

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Mentioned references:

Sam Altman article

survivorship bias

Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.

If you hired a chief of staff to be your leadership team’s star athlete, don’t let them languish on the bench. At many organizations, chiefs of staff are meant to execute high-wire strategic work. But the job is often reduced to: glorified project management, executive cat-herding, and catering to the CEO’s whims. They compensate for bad work design through effort and influence, carrying big expectations with no real authority.

In this episode, Rodney and guest co-host, Sam Rothkopf, lay out the first move toward becoming an organization built to benefit from change: Recharter your chief of staff as the leadership team's work designer. They dig into the three jobs most chiefs of staff currently hold; why the role should serve teams, not single leaders; and the authority they need to put business strategy into motion and free up executives to do the work only they can do.

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Mentioned references:

Miraval Rosé

Casamigos

"built to benefit from change ep": AWWTR Ep. 52

"failure of the ways of working ep": AWWTR Ep. 50

Mia Wise

00:00 Intro + Check-In: Favorite Celebrity Endorsed Product
03:13 The chief of staff already exists, but does the wrong work
06:49 The chief of staff today: admin, project manager, influencer
11:02 Why chiefs of staff are prone to burnout
16:46 Chiefs of staff are everywhere in tech orgs, with no power
22:26 The reframe: serving the team, not the leader
25:44 Building your “shelves”
28:57 Operationalizing strategy, for real
32:47 Playing “favorites’ around who is leading the strategy
37:21 The CEO's first hire
42:07 The authority the role actually needs
46:07 Tooling, comms, and where the team does its work
49:17 Wrap: more moves next week

Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.

Every org has process that started as protection and calcified into performance: boxes we check to prove nothing bad happened, rather than to help good work happen.

In this mini episode, Rodney and Sam respond to a listener trying to resist the "checklistification" of their org. They draw a line where good checklists turn bad and explore the limits for what checklists can—and can't—solve in your team's Twilight Zone.

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Mentioned references:

"Sunshine and Twilight Zones": The Ready's Depthfinding

Atul Hawande, author of The Checklist Manifesto

complicated vs complex

MECE (Mutually Exclusive, Completely Exhaustive)

Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.

Volatility is just the new normal, and it's crushed everyone's appetite for complexity at the exact moment complexity demands attention. Executives who used to love a whiteboard now say "just tell me the answer." Five-year plans read as fiction within months. Employees trust leadership less than ever and with AI in the mix the old moats (talent, pricing, product, position) are eroding or gone.

So what's left? In this episode, Rodney sits down with Sam Rothkopf, co-steward of The Ready, to lay out the firm's new thesis: durable competitive advantage is the ability to execute in complexity, and the organizations that win will be the ones built to benefit from change. They get into why discernment beats endless experimentation, why execution is strategy now, and what it looks like when a company gets it right.

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Mentioned references:

Sam Rothkopf

"stewardship": Miniseries episode

Jon Roth

Sky & Depthfinding

IKEA's AI and virtual design transformation

"Transfo A and Transfo B": AWWTR Ep. 43

"Action Meetings": BNW Ep. 80 with Sam Spurlin

00:00 Intro and Check-In: what have you completely changed your mind about?
05:09 The moment: volatility has killed our appetite for complexity
06:39 "Just tell me the answer"
09:30 AI speeds you up, but doesn’t change your direction
12:54 The old playbooks are defunct and leadership trust is at an all time low
17:41 Built to benefit from change is the future
21:42 Experimenting that leads to new outcomes
23:48 Finding your business’ spark
27:16 Example: IKEA finding their spark
30:44 Finding your spark doesn’t have to be a journey
37:04 Where The Ready’s thinking has evolved
38:00 What "execution is strategy" actually means
42:00 Treat volatility as a resource + the transfo A/B conversation
43:34 Sam’s disposition towards change and volatility
47:16 The inner work: creativity needs a grounded self
48:00 Wrap up—Leave us a review

Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.

You can see it clearly: the project is FUBAR, the reporting is rosy, and the people with the power to do something about it are several levels above you. But sending a flare up the chain feels risky—especially when your boss's boss's boss is the one you need to reach. So what do you actually do?

In this mini episode, Rodney and Sam respond to a listener stuck in that exact spot and offer a few moves that don't involve career-ending emails or anonymous screeds nailed to the CEO's door, and explore whether you can quietly reshape the data story being told upstream in a way that's helpful rather than accusatory.

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Ready to change your organization? ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Let's talk!⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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Sound engineering and design by Taylor Marvin of ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Coupe Studios⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.