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    2.5 Having Difficult Conversations 2.0

    February 18, 2026

    If you’re the one always delivering bad news, rejecting PTO requests, and handling every performance issue — even for people who don’t directly report to you — there’s a problem. Your managers are avoiding the hard conversations by passing the uncomfortable stuff up to you, which means you’re stuck doing everyone’s job instead of actually leading your business.

    This episode is about why difficult conversations keep landing on your desk, and how to shift that responsibility back to where it belongs: with your managers.

    Listen in to hear:

    • Why copying someone else’s leadership style makes you less effective in the moment.
    • The three questions every manager should be able to answer without hesitation.
    • Why PTO approvals are a capacity planning tool, not an admin task.
    • What bottom-up accountability actually looks like in practice.
    • The real cost of managers who dodge difficult conversations.

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