You can avoid being blindsided by developing a relationship founded on trust, in which your reports feel that they can be completely honest with you because they have no doubt that you truly care about them.

My reports regularly bring their biggest challenges to my attention.

A hallmark of a trusting relationship is that people feel they can share their mistakes, challenges, and fears with you. If they’re struggling through an assignment, they tell you right away so you can work through it together. If they’re having issues collaborating with somebody, you hear it first from them and not through the people in other team. If something’s keeping them up at night, they tell you what it is.
Here is a simple litmus test for assessing the health of relationships: If you ask your report how things are going and the answer for multiple weeks is “Everything is fine,” you should take it as a sign to go further. It’s much more likely that the report is shy about getting into the gory details than that everything is consistently rainbows and butterflies.
If your report does work that you don’t think is great, are you comfortable saying that directly?
Similarly, would your report tell you if he thinks you’ve made a mistake?
Strive for all your one-on-one meetings to feel a little awkward. Why?
Because the most important and meaningful conversations have that characteristic. It isn’t easy to discuss mistakes, confront tensions, or talk about deep fears or secret hopes, but no strong relationship can be built on superficial pleasantries alone.
There’s no wordsmithery that gets around the awkwardness of expressing a sentiment like, “I don’t feel that you recognize when I’m doing a good job” or “Last week, when you said X, it made me feel as if you don’t really understand my project.” But these things need to be said in order to be addressed, and with a bedrock of trust, the conversations become easier.

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