Is Steve Ballmer the Most Underrated CEO of the 21st Century?

Original Article ↗ Hacker News Discussion ↗

Overall View of Ballmer

  • Many argue Ballmer is underrated: he left Microsoft extremely well‑resourced and oriented so a stronger product leader could thrive.
  • Others say he is correctly rated or even overrated: under him Microsoft went from “the” software company to one of many large incumbents, with rivals like Apple, Google, and Amazon outpacing it.
  • Some see him as essentially a co‑founder who deserves credit “as much as anyone” for Microsoft’s long‑term success.

Windows and Consumer Products

  • Mixed assessments of his Windows era:
    • Longhorn/Vista seen by some as a failure of management; others say Vista was good on properly specced hardware, but many recall it as slow, complex, and user‑hostile.
    • Windows 7 is widely cited as a success; Windows 8/Metro and removal of the Start button are viewed as disasters.
  • Several commenters say current Windows (10/11) is being “enshittified” with ads, telemetry, and complexity, especially for power users.

Mobile Strategy and Phones

  • Strong consensus that Microsoft “whiffed” on mobile:
    • Went from significant smartphone share to near zero during Ballmer’s watch.
    • Incompatibility between Windows Phone 7 and 8 APIs alienated developers.
    • The Nokia acquisition and failure to capitalize on Maemo/Meego are cited as strategic blunders.
  • Some argue abandoning phones freed Microsoft to focus on more lucrative enterprise segments; others say missing the primary new computing platform is an unforgivable CEO error.

Enterprise Pivot and Cloud

  • Broad agreement that Ballmer decisively backed enterprise:
    • Elevation of “Enterprise Business” and “Server and Tools” over the Windows/consumer side is credited with seeding Azure, Office 365/M365, and security offerings.
    • This positioning helped Microsoft defend against Google Apps and iPad+iWork and later enabled Nadella’s cloud push.
  • Debate over whether enterprise/B2B “has more money” than consumer/B2C; examples and counterexamples (e.g., Apple) are raised without resolution.

Comparisons, Metrics, and Wealth

  • Critics note Microsoft’s stock stagnation relative to peers during Ballmer’s tenure, contrasting with Apple’s ~20× rise in the same period.
  • Others emphasize revenue growth, Xbox and Azure as big wins, and diversification into many “pies.”
  • Ballmer’s immense net worth is used to question the idea that he is “underrated,” including comparisons to typical lifetime earnings of teachers.

Current Microsoft and Nadella Era

  • Nadella is widely credited with:
    • Releasing previously shelved Office for iOS.
    • Fully embracing cloud and keeping Microsoft from IBM/HP‑style stagnation.
  • Yet Nadella’s Microsoft is criticized for:
    • Spyware‑like behavior in Windows, aggressive monetization, and ads.
    • Buzzword‑heavy “vision” (AI, metaverse, web3).
    • Fractured developer platforms (WPF, WinUI, MAUI, Blazor) while internal teams favor React Native.

Other Notes and Side Topics

  • Debate over how much Skype’s tech underpins Teams/O365; some claim it’s foundational, others say the real lineage is Office Communicator/Lync. The exact technical inheritance is unclear.
  • Several comments highlight the famous “developers, developers, developers” focus as directionally right, though later layoffs of developers are lamented.
  • Thread also touches on broader CEO overrated/underrated debates (e.g., Jack Welch, other tech CEOs) and Microsoft’s historical “flexible” business ethics.