For short-term mentoring to be impactful, it must be painful. The goal isn't gentle guidance but to make an overlooked opportunity or flaw so painfully obvious that the mentee is jolted into action, partly to prove the mentor wrong. It's 'crash therapy'—uncomfortable but highly effective at driving change.

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The founder received harsh 360 feedback, with colleagues labeling him 'Hurricane Ben' for his disruptive behavior. Instead of being defensive, he recognized the feedback as a critical inflection point, forcing him to fundamentally change his leadership style to effectively scale with the company.

The biggest professional and personal problems often stem from a lack of candor. Withholding honest feedback to "keep the peace" is a destructive act that enables bad behavior and builds personal resentment over time. Delivering the truth, even when difficult, is a gift that addresses problems head-on and prevents future failure.

To give difficult feedback, use the Situation-Behavior-Impact (SBI) model. Instead of making accusations, state the situation, the specific behavior, and crucially, the impact it had on you. This approach prevents triggering a defensive, fight-or-flight response in the recipient.

A leader won't address their limiting beliefs until they feel a palpable tension. This dissonance arises when their actions conflict with desired results (like a promotion) or their own values. This feeling of 'something's not working' is the essential starting point for genuine change.

Effective coaching requires a two-step process. First, directly confront an individual's flaws ('poke the zit'). Then, immediately reframe their negative self-perception by explaining they are 'hurt,' not broken. This prevents them from spiraling into self-loathing and opens them to change, turning a harsh truth into a constructive catalyst.

Orlando Bravo argues valuable mentorship isn't found in occasional calls. It's cultivated through daily work with colleagues who have direct context on your challenges. Proximity allows for the deep, nuanced guidance that scheduled, low-context conversations cannot provide.

Feedback often fails because its motivation is selfish (e.g., 'I want to be right,' 'I want to vent'). It only lands effectively when the giver's genuine intention is to help the other person become who *they* want to be. This caring mindset dictates the delivery and reception.

When confronting a high-performing but abrasive employee, don't just criticize. Frame the conversation around their career. Offer a choice: remain a great individual contributor, or learn the interpersonal skills needed for a broader leadership role, with your help.

Instead of trying to find the perfect words, preface difficult feedback by stating your own nervousness. Saying, "I'm nervous to share this because I value our relationship," humanizes the interaction, disarms defensiveness, and makes the other person more receptive to the message.

In difficult conversations, leaders fail when focused on their own feelings or ego. The real work is to get to the absolute truth of the situation. This involves moving past your own reaction to understand why the person acted as they did, if the behavior is correctable, and what would truly motivate them to change.