Holiday Follies: RIA Edition

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Dear Bev,

We have a team member who has been really struggling to step into who she is and what she is capable of doing. She was in our industry for about seven years. She stepped back to have her children and now has returned (12 years later). She is attentive, responsive, smart and eager to contribute. However, I fear she is suffering a lack of confidence after being out of the game for so long.

Most recently, my partners and I asked her to plan our holiday party. Every year we have done a big gala for our team members, and we invite a number of outsiders who work with us – vendors, strategic partners and so on. We typically have about 75 people come, and it is a really nice evening with dinner, often a speaker (last year we had a comedian) and music and dancing.

We have a well-organized way of doing things, but we thought we’d let her run with it this year to give her a chance to shine. It was a disaster. She didn’t want to spend our money, so was very cautious with the budget. She also puttered around with invites for so long that by the time she had approved what needed to be sent, people had made other plans. We had 35 people come, and while everyone likely enjoyed themselves, many commented on “how different” the experience was from our past events. I interpreted this to mean it wasn’t nearly as good. The turnout certainly was disappointing.

I know we should not be upset since we were trying to get her to step up, and she did. However, now we have to give feedback saying how poorly it went when the whole point was to build her confidence. Do we congratulate her anyway? Tell her she can’t do this again? Ask what went wrong?

I admit that the people aspect of this business is challenging for us. We don’t like dealing with tears and upset, so I don’t want to confront her. That said, one of my partners says we will be remiss if we don’t – hence, the note to you.

Anonymous (because I don’t want her to read this and know I wrote in)