If you think the conversation is difficult now, try waiting a few weeks, because difficult conversations rarely stay the same size while we avoid them. The original problem will still be there, but it will probably be joined by a few more examples, some frustration you haven’t expressed, assumptions about why the other person keeps doing what they’re doing, and perhaps a growing irritation with yourself because you knew, somewhere along the way, that the issue needed to be addressed sooner. There’s nothing groundbreaking about telling managers to deal with problems early. Most experienced managers have heard that advice countless times, and most could probably give it to somebody else without much thought. What makes the lesson feel more important is discovering how different it looks when the consequences are personal, particularly when the person you need to manage is someone you knew long before either of you expected there would ever be a reporting relationship between you. Workplace friendships aren’t inherently a problem. They’re often inevitable, and they can be one of the better parts of working life.
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