DEAR HARRIETTE: I have some negative history with a woman who is now back in my life through work. We worked together years ago, and it didn’t end well. I didn’t like the way she handled certain things, and I let her know how I felt. Now, here we are again, working together on a project. I wonder if I should clear the air and acknowledge that things didn’t go so well last time. Should I say that I hope we will work better this go-round or just leave it alone? As I recall it, I was the one who complained before. But I know it was awkward for both of us. -- Awkward
DEAR AWKWARD: If it feels potentially awkward now, you can say something positive to her about this new experience. You can tell her you look forward to working together on the project at hand. You may also recommend that you two come up with a way of working together that is mutually beneficial for both of you. If there is something specific that didn’t work before, you may want to suggest that you both agree to take a different approach this time.
While in the moment, this could feel extraordinarily uncomfortable, stepping up and actively working to find a way for the two of you to work well together creates the space for a positive outcome. Let her know you are sincere, and then see what happens.