At Work with The Ready

53. The Chief of Staff’s Real Job: Turning Strategy Into Action

July 27, 2026·51 min
Episode Description from the Publisher

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. -------------------------------- Ready to change your organization? ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Let's talk.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Get our newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Sign up here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow us: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -------------------------------- 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.

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