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To avoid alienating mid-level managers, leaders must inform them before and after conducting a skip-level meeting with one of their reps. This frames the conversation as a collaborative effort to help the rep, rather than a secretive performance check that undermines trust.
Trust is not a given; it's the outcome of being trustworthy. Leaders build this by consistently demonstrating accountability, transparency, and a willingness to receive feedback. The focus should be on modeling trustworthy behavior, which in turn inspires the team's confidence.
To move beyond status updates in one-on-one meetings, managers should open up about their own challenges. Asking a team member for their perspective on a decision the manager is making fosters trust, shows respect, and can uncover valuable insights you hadn't considered.
Lower-level contacts often block access to leadership for two main reasons: fear you will waste their boss's time (hurting their credibility) or take their power. Proactively address these fears by positioning the C-suite meeting as an informative session that will make *them* look good, not a sales pitch that undermines them.
As leaders rise, direct reports are less likely to provide challenging feedback, creating an executive bubble. To get unfiltered information, leaders should schedule regular one-on-ones with employees several levels down the org chart with the express purpose of listening, not dictating.
As an organization scales, some leaders become skilled at managing up while being poor managers to their teams. Executives must conduct regular skip-level meetings with frontline employees to get direct, unfiltered feedback and catch these bad behaviors that would otherwise be hidden.
Hold two distinct meetings with reps. Use weekly "deal reviews" for tactical inspection of data, risk, and next steps. Reserve separate, bi-weekly "1-on-1s" for relationship building and career pathing. This prevents surprise forecast discussions and builds trust.
Always leading with good news causes unresolved problems to pile up, eroding trust. Instead, start meetings by addressing challenges and presenting a clear solution. This builds credibility and ensures critical issues get the attention they deserve.
To get reps to open up about their development areas, a new manager should first be vulnerable about their own shortcomings. This lowers the rep's defenses and transforms the conversation from a review into a collaborative effort to improve together.
When meeting with senior leaders, shift the focus from your status updates to their priorities. Ask what's top of mind for them, what challenges they face, and how you can help. This reframes you from a direct report into a strategic ally, building trust and social capital.
When asking to see a rep's calendar, they may feel scrutinized. Defuse this by framing it as a way to help them achieve their goals. Phrases like "I don't care what's on there, I just want to help you" build trust and encourage the transparency needed for effective coaching.