TThe Diary of a CEO
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Leadership

Operate-Before-You-Hire Rule

Do a critical job yourself when repeated hiring misses expose ignorance

Difficulty
Advanced
Time to result
~months to results
Steps
5
Confidence
96%

After two failed appointments to lead Expedia.com, which Khosrowshahi says produced half of the company's profits, he concluded that another search using the same understanding was too risky. His diagnosis was not simply that two candidates were poor; it was that he did not know the job well enough to identify the right person. He therefore took the operating role himself, initially expecting six to twelve months. Direct responsibility taught him how to organise, set goals, assemble a team, and run the business, although he ultimately stayed in the role for years. The transferable rule is to treat repeated critical hiring misses as evidence about the assessor. A bounded period doing the work can generate a more accurate role model before the next hire.

Origin

Extracted from The Diary of a CEO. Dara Khosrowshahi describes taking charge of Expedia.com after two failed leadership hires because he believed he did not understand the job well enough to choose a third person.

Core principles

  • 01Repeated hiring misses can reveal that the manager does not understand the role
  • 02Direct operating experience exposes the work's real demands
  • 03Role knowledge improves both selection and organisational design
  • 04A critical business cannot absorb unlimited learning-through-mishire

How to run it

  1. 1

    Recognise the Pattern

    Treat repeated misses in the same critical role as a systemic signal. Quantify the role's importance and the cost of another weak selection.

    Pro tip Review whether the assessment criteria predicted actual performance.

    Watch out Do not infer a pattern from one unlucky hire alone.

  2. 2

    Test Your Understanding

    Ask whether you can describe the role's recurring decisions, operating demands, and success conditions from evidence. If not, acknowledge the assessor gap.

    Pro tip Compare the written role with what the failed hires actually faced.

  3. 3

    Take Bounded Ownership

    Assume the work directly for a defined learning period when you are qualified to do so. Make continuity arrangements for the responsibilities you retain.

    Pro tip Set explicit questions the operating period must answer.

    Watch out Do not step into work that requires credentials or expertise you lack.

  4. 4

    Capture the Job Model

    Document the decisions, interfaces, capabilities, and behaviours that produce results. Use observed work rather than inherited job language.

    Pro tip Record surprises that would change candidate assessment.

  5. 5

    Rebuild the Selection

    Turn the new job model into clearer assessment and onboarding. Delegate when a candidate has demonstrated the capabilities the work actually requires.

    Pro tip Use realistic work evidence where appropriate.

    Watch out Temporary ownership can become a bottleneck if no exit condition exists.

In the wild

Khosrowshahi Runs Expedia.com

Khosrowshahi says he was zero for two in hiring leaders for Expedia.com's largest business. He told the board that a third miss should cost him his job, then took the operating role himself because he believed he lacked enough understanding to make the next selection. The experience became his practical education in operating a technology business.

He developed a direct model of the role and discovered that operations and leadership were the part of the chief executive's work he most enjoyed.

Common mistakes

Running the Same Search Again

A third search built on the same incomplete role model can reproduce the earlier error.

Assuming Every Miss Is Your Ignorance

The rule fits a repeated pattern in a critical role, not every isolated hiring failure.

Never Giving the Role Back

The purpose is to learn the job well enough to improve selection, not to accumulate permanent operating control.

Is it for you?

Best for

It is best when a leader can competently step into a high-impact role and the organisation can define a bounded learning period.

Not ideal for

It is not ideal for regulated or specialist work the leader is unqualified to perform, or as a permanent excuse to avoid delegation.

From the transcript

Obviously, I don't understand enough about the job

Dara Khosrowshahi · (37:30)

I've got to take the job myself for 6 months to a year

Dara Khosrowshahi · (38:00)

From the episode

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