MMarketing Against The Grain
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LeadershipAlex Lieberman

Earned Right to Challenge Test

Audit whether genuine human care has earned you permission to demand more.

Difficulty
Moderate
Time to result
~weeks to results
Steps
6
Confidence
98%

The Earned Right to Challenge Test is a private leadership scorecard built around one counterfactual question. For each direct report, imagine that the employee is speaking behind closed doors to a trusted friend or family member with no possibility that the answer reaches the company. Would that employee honestly say the manager cares about them as a human being? The manager must answer using the employee's likely evidence, not personal intentions or formal authority. A credible yes indicates a strong foundation for direct accountability. A no means the manager should build genuine understanding, support, and trust rather than merely intensifying criticism. The output is a relationship-specific assessment and a concrete plan to earn the permission required for candid leadership.

Origin

Alex Lieberman offered this test as his closing leadership advice on Marketing Against The Grain.

Core principles

  • 01Authority alone does not create trusted accountability.
  • 02Employees judge care through behavior, not managerial intent.
  • 03Intellectual honesty is required when auditing a relationship.
  • 04Demonstrated care earns permission for stronger challenge.

How to run it

  1. 1

    Select the relationship

    Evaluate one direct report individually rather than judging team trust in aggregate.

    Pro tip Start with the relationship where difficult feedback feels most strained.

    Watch out A strong relationship with one employee says nothing about another.

  2. 2

    Create the private scenario

    Imagine the employee answering a trusted friend, sibling, or parent with complete protection from workplace consequences.

    Pro tip Remove politeness, hierarchy, and performance-review incentives from the imagined answer.

    Watch out Do not substitute what the employee says publicly.

  3. 3

    Ask the care question

    Determine whether the employee would say you genuinely care about them as a human being.

    Pro tip Use a binary initial answer before adding nuance.

    Watch out Do not reinterpret an uncomfortable no as “they know I care in my own way.”

  4. 4

    Audit the evidence

    List concrete actions the employee could cite for and against the answer.

    Pro tip Include support for their career and personal well-being.

    Watch out Good intentions that were never expressed or enacted are not evidence.

  5. 5

    Match challenge to trust

    If the answer is yes, use the relationship to hold the employee accountable; if no, repair the foundation while still maintaining necessary standards.

    Pro tip Tell the person directly that their growth matters and demonstrate it through action.

    Watch out Care must not become a transactional tactic for obtaining compliance.

  6. 6

    Retest over time

    Repeat the exercise after meaningful interactions or changes in the reporting relationship.

    Pro tip Look for changes in the employee's willingness to raise problems and receive feedback.

    Watch out Trust can erode even after it has once been earned.

In the wild

Audit before a performance conversation

A manager preparing to address weak execution realizes that the employee could name many deadlines but no occasion when the manager invested in their goals or checked on their well-being. The manager still clarifies the immediate standard, then schedules career-development conversations and follows through on practical support before relying on increasingly direct challenge.

Accountability continues, but the manager also repairs the missing foundation of trust.

Common mistakes

Answering from intention

A manager may feel caring while the employee has seen no behavior that would support that conclusion.

Using care as leverage

Performing concern solely to gain permission for criticism turns a human relationship into manipulation.

Averaging across the team

Trust is relationship-specific and cannot be inferred from overall engagement or popularity.

Is it for you?

Best for

It is best for managers preparing to give difficult feedback or assessing the trust within each reporting relationship.

Not ideal for

It should not postpone legally required action, urgent safety intervention, or immediate responses to serious misconduct.

From the transcript

does this person actually give a s about you as a human being? What would they say?

Alex Lieberman · 43:00

And if the answer is yes, to me, you're in an amazing spot to have the permission to hold them to account.

Alex Lieberman · 43:00

If the answer is no, you have not earned the right to challenge them directly.

Alex Lieberman · 43:30

From the episode

Framework Thinking for Success With Alex Lieberman

Alex Lieberman