The Outsiders Playbook:
Why Unconventional Leaders Are Winning (And How You Can Think Like One)
By Bryan J. Kaus
Three CEO announcements hit my inbox last week that made me stop scrolling:
Harley-Davidson picked Artie Starrs, the CEO of Topgolf.
Jaguar Land Rover chose P. B. Balaji, Tata Motors’ Group CFO—who will become the first Indian CEO in JLR’s history.
A telehealth startup tapped Linda Yaccarino, the former CEO of X, to run a GLP-1 weight-management platform.
On paper, these moves look random: a golf-entertainment operator running motorcycle culture; a finance chief steering a luxury auto brand; a media/ads veteran leading a healthcare platform. Look closer and you see the same logic boards use when they get it right: hire for the constraint you must solve next, not the résumé you celebrated last. Think Eric Schmidt joining Google to complement the founders with operating discipline and scale literacy; Alan Mulally bringing aerospace-grade systems leadership to Ford’s turnaround; and Larry Culp, the first outsider to lead GE, doing the difficult work of breaking a sprawling conglomerate into focused entities to survive and win.
When “Wrong” Becomes Right
Early in my career, I said yes to roles that looked lateral: public affairs → sales → pricing → analytics → commercial strategy. It didn’t dilute me; it gave me range. I learned to connect the micro to the macro—how regulatory shifts hit P&Ls, how channel choices move unit economics, how capital structure shapes competitive latitude.
William Thorndike captured this dynamic in The Outsiders: the CEOs who deliver extraordinary returns rarely look the part. They’re not the most symmetrical résumés; they’re the leaders whose capabilities match the job to be done.
Mulally at Ford didn’t win by being “more automotive.” He won by running a system—cadence, clarity, and one enterprise plan. Schmidt at Google didn’t replace founder vision; he amplified it with operating judgment and scale literacy. Culp at GE didn’t chase optics; he made the hard capital allocation and portfolio calls. That’s the pattern.
Why Last Week’s “Odd” Picks Make Sense
Harley-Davidson → Artie Starrs (Topgolf).
Harley isn’t just selling bikes; it’s selling experience, community, and new-to-brand customers. Starrs brings franchise/format scaling, guest acquisition, and brand activation muscles—exactly where Harley’s constraint lives.Jaguar Land Rover → P. B. Balaji (Tata Motors CFO).
JLR’s EV pivot is a capital-allocation + operating discipline problem as much as a product one. A finance-first leader who has steered group-level tradeoffs is a logical fit for the disciplined course necessary to navigate the immediate future —also - he’ll be JLR’s first Indian CEO.eMed Population Health → Linda Yaccarino (ex-X).
The GLP-1 wave is an ecosystem + go-to-market challenge: payer partnerships, acquisition funnels, retention, and trust at scale. That’s an ads/media operator’s playbook more than a pure clinical one.
The throughline: boards are optimizing for fit to constraint—experience design, capital allocation, or platform orchestration—over industry tenure for its own sake.
The Pattern Behind the Pattern
Most succession processes still worship the checklist: rotation A → rotation B → division → region → corner office. That builds strong specialists—and often misses the integrators who see across functions, make hard tradeoffs, and redesign the operating system when the world shifts.
It’s also why companies routinely promote their best player into head coach and then wonder why execution stalls. Different game. Different skills.
The AI Accelerant
AI sharpens this talent problem:
Mask: A mediocre performer can now ship polished work. If you evaluate by artifact alone, you’ll get fooled. The human factor becomes more important than ever before.
Multiplier: A true integrator with an AI co-pilot separates signal from noise and makes better, faster calls.
The premium on discernment—asking the right questions, spotting the real constraint, making integrative judgments—is about to skyrocket.
Make Talent a Strategic Discipline
Throughout my career and in my advisory work at 23.5 Strategies, we don’t treat talent as an afterthought. We start with three questions:
Which 5–7 decisions will define the next 12–24 months? (pricing, capacity, product cadence, channel, capital allocation)
Which capabilities are non-negotiable to make those decisions well?
Who has them now—and who can learn them quickly?
From there, we design for adaptability:
Hire for decisions, not titles.
Look for spike + slope: one unmistakable strength and visible learning velocity.
Dual tracks for mastery and management—so great ICs don’t have to lead people to advance.
Planned tours of duty to develop integrators without breaking accountability.
A light operating rhythm (weekly exceptions, monthly decision logs) that makes judgment legible.
When to Bet on an “Outsider”
The model is shifting (product → platform; manufacturing → experience).
Culture needs a reset (candor, speed, accountability).
Capital allocation is central (portfolio, M&A, buybacks/dividends).
Customer experience has drifted from the brand’s promise (stores, service, digital).
The status quo has stalled or is inadequate for the present.
Different backgrounds—same logic: fit the constraint.
If You Don’t Do This…
You’ll promote the wrong profiles (players to coach), stall execution, and burn political capital.
You’ll over-index on dashboards and miss the human reality (context, culture, trust).
You’ll freeze in the middle—the layer that turns strategy into movement.
Competitors who hire for learning velocity will lap you quietly before you know what has happened.
If You Do…
Your org becomes decisive (fast tradeoffs, fewer reworks).
You surface real leaders earlier (the integrators, not just the polished).
AI becomes a force multiplier—not a mask—because judgment sits on top.
Strategy stops living on slides and starts compounding in operations.
What This Means for Managers at Every Level
Principle: hire and develop for decisions, not titles; reward spike + slope (clear strength + learning velocity); make judgment and operating cadence teachable, visible, and repeatable.
Frontline & First-Time Managers
1:1s that build range: goals → obstacles → “what did you learn this week that changes our plan?” Capture in 3 bullets.
Make work legible: keep a simple decision log (what, why, owner, by when). It teaches ownership and systems thinking.
Promote mastery without forcing management: publish an IC progression with pay parity.
AI as co-pilot, not mask: require a POV-first draft before AI assist; ask “what did the tool miss?”
Mini pre/post-mortems: 10 minutes before/after key deliveries. Normalize learning velocity.
Middle Managers (the cross-functional glue)
Map capabilities to decisions: staff to capability gaps, not boxes.
Install tours of duty: 12–18 month rotations across ops/product/commercial to create integrators.
Measure execution quality, not activity: track cycle time, rework, % decisions documented, defect recurrence. Review monthly.
Build a bench on purpose: keep a live slate with (a) insider integrator, (b) spiky outsider, (c) master-IC path.
Ritualize dissent: one slide per meeting—“What we’re probably wrong about.”
Senior Managers/Directors (portfolio & culture shapers)
Simple rhythm: weekly exception review (red/amber only), monthly decision audit, quarterly capability review tied to strategy.
Price talent like capital: treat senior roles as capital allocation—what’s the return if we deploy this leader here vs elsewhere?
Always include an orthogonal candidate: one outsider or insider-with-range whose spike matches the constraint.
Codify judgment: publish 5–7 heuristics (e.g., “two-way doors go local,” “favor reversible tests over big bets”).
Coach multipliers: reward leaders who create leaders—measured by their team’s promotions, cross-org pull, and idea flow.
Cultural Micro-Habits That Compound
Two-way door default: reversible decisions go fast at the edge; one-way doors get deliberate review.
Narrative over decks: 1–2 page memos for big calls; forces clarity and exposes tradeoffs.
Shadow boards & reverse mentoring: rotate emerging leaders to pressure-test strategy; senior leaders take quarterly “learner” roles.
Talent as a standing agenda item: include people moves, capability gaps, and learning wins in every ops review.
A One-Week Activation Plan (for any manager)
Day 1–2: Map your next 90 days. List the 5–7 consequential decisions.
Day 3: Start a decision log; assign owners.
Day 4: Identify your spike and your slope.
Day 5: Find one integration opportunity across functions.
Day 6: Draft a learning agenda for next year’s constraints.
Day 7: Write your decision heuristics—share with the team.
The Bottom Line
The companies winning the next decade will pair clear strategy with adaptive talent—depth where it’s non-negotiable, range where markets move, and leaders who know what game they’re playing.
The most dangerous sentence in business remains: “That’s not how we do things here.” The leaders who thrive will look at Harley hiring from Topgolf or JLR elevating a finance chief—and see strategy, not randomness.
If your organization is wrestling with this, my team at 23.5 Strategies helps boards, founders, and operators align human capital to the jobs that actually matter—and build the systems that keep it aligned when the game changes.