Ask the Amys: Sabotaging Bosses, Irritating Employees, and More

What It Covers

Amy Bernstein and Amy Gallo answer listener questions about workplace challenges including pushing for better performance review systems, deciding which workplace battles merit engagement, handling manager sabotage, navigating toxic dynamics with departing bosses, addressing gender inequality in medical training, transitioning from tactical execution to strategic leadership, and coaching employees with difficult interpersonal behaviors.

Key Questions Answered

• •Building case for organizational change: When advocating for new processes like formal reviews, assemble a coalition of supporters and address specific leadership concerns around cost, bandwidth, and bureaucracy. Propose time-limited experiments in one division rather than company-wide rollouts. Reframe requests away from formal bureaucracy toward creating a feedback-rich culture where managers and employees regularly exchange input outside annual review cycles.
• •Strategic objection framing: When raising concerns about policies or decisions, recast moral or fairness objections as business cases focused on organizational impact rather than personal or small group effects. Research shows this approach proves especially effective for women seeking to be heard by leadership. Always assume positive intent and gather information about behind-the-scenes context before declaring something wrong.
• •Managing political capital: Avoid raising every concern that arises, as becoming known as an alarmist diminishes credibility when genuinely important issues emerge. Apply the energy management framework by asking whether problems have long-term organizational consequences or represent one-time occurrences. Consult trusted colleagues to pressure-test concerns and identify blind spots before escalating issues to leadership.
• •Documenting manager undermining: When managers actively sabotage career growth by spreading false narratives about performance, immediately document the situation with HR to protect reputation and create a paper trail. Focus energy on strengthening relationships with other colleagues and potential mentors rather than trying to repair the damaged manager relationship. Build networking opportunities that provide alternative paths for advancement and protection.
• •Shifting to strategic thinking: Develop strategic perspective by working future-back from desired outcomes rather than present-forward from current details. Study organizational competitive environment using frameworks like Porter's Five Forces and understand how leadership defines winning. Write detailed first drafts as appendices, then extract two to three top-level takeaways for executive audiences. Frame all suggestions in terms of long-term organizational health.