Advice column: I'm embarrassed about the Secret Santa gift I bought for my boss

Dear Ash

This year our department decided that we should start a secret Santa gift giving event, as it seemed like fun and others in our firm already follow this office tradition. However, I perhaps naively presumed that any gift giving would indeed remain secret and therefore when I picked my boss’s name from the hat I thought it would be hilarious to buy him a book on bad management!

Unfortunately, when we all exchanged and opened our gifts at the Christmas lunch, it was evident that nearly everyone seemed to have picked gifts that the other person would like rather than pick gifts with a funny angle… like me. To add to the awkwardness, many of my colleagues began to guess who had bought their gifts and this resulted in most people confirming who they had bought for.

Although my boss did not guess it was me who bought him his present and I did not say anything, he probably would not find it difficult to guess that it was me and this is making me feel really apprehensive about going back to work after the holidays as I certainly don’t want this to be held against me.

Ash replies:

The run-up to Christmas is one of those times of the year when people tend to lower their guards and mistakes can be made in the office environment, such as drinking too much at the office party or buying inappropriate presents for colleagues, so in short you will not be alone in feeling the way you do.

I suggest that you try to put this behind you and just focus on your work in the new year. If you do attempt to raise the issue with your boss, then it may just cause unnecessary awkwardness between you, especially as he may not have even guessed it was you in any case and indeed may have forgotten about the whole thing by the time you return to the office.

Just learn from this for the future and remember that the festive time is certainly a time for giving, but not necessarily a time for giving out such home truths, especially when it comes to your boss!

All the best for the New Year!

Send your queries to Ash

“Ash” is a solicitor who is willing to answer work-related queries from solicitors and trainees, which can be put to her via the editor:, or mail to Studio 2001, Mile End, Paisley PA1 1JS. Confidence will be respected and any advice published will be anonymised.

Please note that letters to Ash are not received at the Law Society of Scotland. The Society offers a support service for trainees through its Education, Training & Qualifications team. For one-to-one advice contact Katie Wood, head of admissions on 0131 476 8162 or by email: 

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