There's a right way and a wrong way to have skip level meetings. But meeting with staff members who report to one of your direct reports is a great way to ensure that you have open communication with your team and that you understand the issues that your team may be encountering at a very personal level. While trust is a critical part of the relationship between a manager and an employee, I've always relied on "trust and verify" as the way to ensure that the trust remains solid. The verify part, is to hear what's going on right from the horse's mouth, so to speak.
Sometimes managers are reluctant to enable conversations between their boss and their direct reports. Usually this is due to a lack of confidence or perhaps this trust issue that I mentioned. But getting to a place where these meetings are part of a regular schedule is a very helpful process.
As I said at the outset, there is a right and wrong way to go about these meetings. The right way involves building trust, setting this out as a standard process, and implementing it well by spending your time listening. These go wrong when the manager begins to migrate from listening to telling. When a manager skips a level and "tells" an employee what to do or directs them to a different place than perhaps their direct manager was suggesting, things can go awry.
Skipping a level and directing an employee is a clear way of disempowering the manager. By introducing direction from a skip level above, priorities can change, authority becomes foggy, and the manager caught in the middle may likely be damanged. Accepting negative comments about your direct report from their subordinate, even without acknowledging or acting upon them, can erode the foundation that a manager requires to with her employees. So your conversation should be directed at gaining a clear understanding rather than imposing your way or offering up your authority.
Assuming you can pull this off without negatively impacting other management level relationships, you can learn important information about your organization that you might not otherwise receive.
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