Opinion
What defines great leadership? There are many answers, but one is surely the ability to deliver a challenging, long-term goal. Setting the right objectives is rarely the hard part.
The challenge is implementation, where aspirations collide with limited resources and irritating constraints, and too often wither.
When we set out to achieve something ambitious and hit a wall, we are often quick to classify the obstacle as a permanent feature of a system we can’t change. But sometimes we are wrong. The obstacle can be overcome, but at a price. A constraint that looks immovable is often just a cost we haven’t tried to reduce.
Unlikely as it may seem, Taylor Swift provides the master class (pun-intended) in tackling a catch-22 familiar to many leaders: a combination of systemic constraints and available resources obscuring the path an important goal.
Swift did not own the master recordings of her first six studio albums, and their value had grown to the point that even one of the world’s most successful musicians was unwilling to pay the asking price.
Disputes between artists and their labels are common, and the artist rarely wins. Swift’s dilemma? Future success that grew her wealth would also increase the value of the asset she wanted to buy.
When the dispute became public, her first move was to “release the Swifties”, hoping negative publicity might extract better terms. Strategically deploying a valuable but low-cost asset is the obvious place to start.
It was never likely to succeed, and it didn’t. That is where ambitious goals often end in organisations. “We gave it a go.” “The system was against us.” “Luck wasn’t with us.” We review how we executed, note the lessons and move on.
What we seldom do is review the higher-cost option we dismissed, not to ask, “Should we pay that price?” but “Is there something we could do to lower it?” The barrier is usually real, an external system we can’t change, or staff time we can’t spare.
But we rarely test whether the cost can be reduced to a price we would be willing to pay. The internet being what it is, there was no shortage of suggestions, including one from fellow musician Kelly Clarkson who suggested Swift re-record the six albums.
At first glance that looks like high cost for low return, the kind of idea dismissed with “yes, that would work in theory, but it’s just not practical.” Swift however, found way to make it practical.¹
Re-recording devalues the original masters, lowering the price of the thing she ultimately wanted to buy. But Swift’s time is her most valuable resource, and re-recording old material carries a large opportunity cost against writing new music or touring.
She had to reduce that cost too. With a large and loyal fan base, an incentive to buy the new versions would recoup much of the cost. She added previously unreleased songs “from the vault” and issued each as “Taylor’s Version” so fans could tell them apart.
Rather than tackling all six albums at once, she started with one, which let her test the real costs and benefits before committing further. The re-releases were framed around a compelling narrative: Swift as the wronged artist fighting back against an exploitative industry.
In buying “Taylor’s Version” her fans were able to participate in that fight. She refined the approach as she went: the re-recorded Red included a 10-minute version of the fan favourite All Too Well, which reached number one on the US Hot 100 nearly a decade after the original.
What evidence do we have that she did genuinely lower the opportunity cost? During the same period, she released four albums of new material and staged the record-breaking Eras tour.
The campaign to reclaim her masters ran alongside the most successful stretch of her career to date, not at its expense. In May 2025, nearly six years after she began, Swift announced she had bought the original masters outright, on her terms.
There are, of course, important differences between a solo artist and someone leading a large team, and two of them matter here. The first is control: Swift’s most valuable asset is entirely hers to direct.
Few leaders have that authority over their key resource, and none have it over people. The second is motivation: she wanted this outcome with an intensity that sustained six years of deliberate execution.
The second point is where the real challenge lies, and why this is harder for those of us leading teams than it was for Swift. She only had to convince herself to stay the course.
A leader has to carry a group whose beliefs will vary, whose patience will be tested by a strategy that takes years to show results, and who can’t be ordered to care. Careful, iterative strategy of the kind Swift executed is necessary, but it isn’t sufficient.
The harder and more interesting task is sustaining a team’s engagement through a long and uncertain implementation when you can’t command their conviction, only earn it. That, more than the strategy itself, usually determines whether an ambitious goal is achieved or quietly abandoned.
¹ Kevin Evers, There’s Nothing Like This: The Strategic Genius of Taylor Swift (Harvard Business Review Press, 2025), gives a fuller analysis of Swift’s career as innovation strategy; my focus here is the narrower, transferable question of how she made an impractical option practical.
Professor Simon Ellingsen is Executive Director of the International Centre for Radio Astronomy Research (ICRAR) at The University of Western Australia.
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