If you were to ask executives how well they believe their managers handle hard conversations, 74% are confident that they can handle them alone with ease. Yet when managers reflect on their own experience, 42% said they knew exactly what to say but couldn’t land it. Another 26% couldn’t predict how the other person would respond. And 20% could plan for everything except the moment the conversation went sideways.
CEOs and managers, describing the same moment, are reaching entirely opposite conclusions about how well those tough conversations go. Leadership confidence in their managers quietly redirects budget and attention elsewhere, away from the managers still learning how to handle a conversation that doesn’t go according to plan.
Data from PI’s AI and People Leadership Report shows just how consequential that can be. When leaders overestimate how prepared their managers are, they risk missing the support managers need.
Are CEOs solving the right problem with AI?
There are several layers to what managers struggle with most when preparing for a difficult conversation, including delivering criticism constructively (23%), anticipating employee reactions (20%) and remaining objective (14%).
Each of those struggles comes down to managers not knowing how the specific person across from them
