Senior clients may bypass formal reporting lines to deliver sensitive or embarrassing feedback directly to junior staff. This can happen when they are uncomfortable discussing a topic with senior managers, putting the junior employee in the difficult position of relaying awkward but critical information up the chain.

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People won't bring you problems if they fear your reaction. To build trust, leaders must not only control their emotions but actively thank the messenger. This reframes problem-reporting from a negative event to a positive act that helps you see reality more clearly.

Innovation is stifled when team members, especially junior ones, don't feel safe to contribute. Without psychological safety, potentially industry-defining ideas are never voiced for fear of judgment. This makes it a critical business issue, not just a 'soft' HR concept.

A leader's failure to deliver difficult feedback, even with good intentions, doesn't protect employees. It fosters entitlement in the underperformer and resentment in the leader, leading to a toxic dynamic and an inevitable, messy separation. True kindness is direct, constructive feedback.

When internal teams like operations or IT make critical errors that impact a client, the salesperson must bear the full force of the customer's frustration. Despite being blameless, the rep is the face of the company and is held responsible for managing the crisis.

A key stakeholder within a client account may actively create friction and gaslight your team, not for legitimate business reasons, but to steer the contract towards a competitor where a friend works. This form of psychological warfare can derail renewals despite strong performance.

Don't be afraid to surface problems to executives, as their job is almost entirely focused on what's not working. Withholding a problem is unhelpful; clarifying and framing it is incredibly valuable. Your champion isn't offending their boss by raising an issue, they're demonstrating strategic awareness.

Leaders often avoid sharing negative news to "not scare the children." However, this creates an information vacuum that teams will fill with the "darkest ideas available" from other sources. Leaders must compete with misinformation by providing clear, honest context, even when it's difficult.

To get truthful feedback, leaders should criticize their own ideas first. By openly pointing out a flaw in their plan (the "ugly baby"), they signal that criticism is safe and desired, preventing subordinates from just offering praise out of fear or deference.

Instead of offering unsolicited advice, first ask for permission. Frame the feedback around a shared goal (e.g., "I know you want to be the best leader possible") and then ask, "I spotted something that's getting in the way. Could I tell you about it?" This approach makes the recipient far more willing to listen and act.

Bypass C-suite gatekeepers by interviewing lower-level employees who experience the problem daily. Gather their stories and pain points. Then, use this internal "insight" to craft a highly relevant pitch for executives, showing them a problem their own team is facing that they are unaware of.