Workplace dilemmas: do I tell my boss I found his personal document on the work computer?

Each month, our resident agony uncle deals with your workplace concerns. This month, protecting a colleague’s confidentiality

Dear Tim,

At work, we have a fairly simple method for demarcating documents that we’re happy for everyone in the company to see from those that we want to remain private.

    We’re discouraged from using our work computers for personal stuff, but most of us do.  

Most documents are saved on the Public Drive (known as the “P-Drive”), to which everyone has access. But if you’re working on something that you want to keep under wraps, you save it locally on your computer, meaning that you’re the only person who can access it.

We’re discouraged from using our work computers for personal stuff, but most of us do. When you’re working 40-odd hours a week, it’s often only possible to deal with personal correspondence while you’re in the office. Most of us keep a USB stick or external hard drive in our desk drawer on which we store personal documents. This ensures that they don’t (a) clog up the work computer, and (b) fall into the wrong hands.

This is the reason for writing. Today, as I was searching for a letter on the P-Drive, I came across a document with a title I didn’t recognise. I’m the office manager and administrative lead for our company, which employs around 70 people. So it seemed appropriate for me to open the document to find out what it contained.

      “I don’t want him to think I was snooping, or feel embarrassed that I know so much about his personal life.  

When I did so, I got something of a shock. The document was a personal letter, written by a senior manager to his solicitor, in which he details his wife’s infidelities. It’s clearly a part of his divorce proceedings – something that a handful of us know about, but which certainly isn’t common knowledge.

I should say that even those of us who know about the marriage breakdown don’t know any detail. Needless to say, my colleague would be highly embarrassed if the information contained in the letter were known publicly.

So, I have a problem. I want to let him know that he’s accidentally saved the file in the wrong place, meaning that anyone in the company could open it, as I did. But to do so, I need to let on that I’ve read it.

I don’t want him to think I was snooping, or feel embarrassed that I know so much about his personal life. I’m also mindful of his seniority in the business, and worry that he’ll feel awkward hearing the news from me, who is very much his junior.

Which means I don’t really know what to do. Shall I stay quiet and hope he discovers his error himself? Or do I have a conversation, knowing that it could be very tricky indeed?


I think you must have the conversation, even though it’ll be challenging for both of you. You need to put his status as a senior manager to one side. If anything, that makes his position all the more serious, and exacerbates his vulnerability. If the letter were discovered by someone less discreet than you clearly are, it could cause no end of embarrassment to its author.

My advice is simple: ask for a quiet chat with your colleague. Tell him it’s about a confidential matter. When you’re in a private space, explain that you were looking for a document and opened something that looked unfamiliar and out of place. Upon reading its content, you felt mortified to have encountered such privileged information. But because it’s on the P-Drive, you feel compelled to tell him, so that he can remove it as appropriate.

It’s my instinct that your colleague will be so relieved that only you have read the letter that he’ll not have time to feel anything other than deeply grateful for your kindness and discretion. As you say, it’s not as if you were snooping. He clearly just made a careless mistake while saving his personal correspondence. You’ve helped prevent no small amount of exposure. I don’t doubt he’ll thank you for that.

Published: 31 May 2019

© 2019 Just Recruitment Group Ltd

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