Should I try to speak to my boss on the train? NICOLA HORLICK replies

Published on: May 10, 2025

By NICOLA HORLICK

Updated: 21:50 BST, 10 May 2025

Working life today is full of constantly evolving challenges and pitfalls. When is it OK to date a co-worker?

Can you tell your team to get back into the office five days a week? Whether you’re a baffled Boomer, a muddled millennial, or a confused Gen Z-er, our brilliant columnist Nicola Horlick can help.

Dear Nicola,

Every day I travel to work on the same train as my boss and I have no idea whether I should strike up conversation or leave him alone with his phone or his tablet.

On the one hand, I might be able to impress him in the hope he’ll remember me during the next round of promotions.

But on the other, should I respect his right to privacy outside the office environment?

Would it play against me if I approached him on the train?

Yours, Simone

Talking shop: Every day, Simone travels to work on the same train as her boss

Dear Simone,

THIS is a really difficult question. The one thing I have found as a ‘boss’ in a large organisation is that it’s very lonely. This is because, in order to be the best boss you can, you need to keep your distance and ensure that you treat all team members equally. It’s a bit like being a parent of more than one child – you can’t have favourites.

On the other hand, looking at it from your point of view, it would definitely be helpful if you were able to interact with your boss on a regular basis and let him know what you’re working on and how you are helping the organisation to progress.

In order to determine whether there’s an opportunity to talk to your boss on the train, you need to try and catch his attention with a nod and a smile and see how he reacts. If he nods back and then returns to his reading, then that will be a signal that he wants to retain his privacy.

If he greets you and invites you to sit with him, you will have the opportunity to chat. If this does happen, you will have to be careful not to presume that it will always be okay for you to sit next to him on the train. You could repeat the process of nodding and see how he reacts after a decent interval.

It is undoubtedly the case that if you want to be promoted, you need your boss to know what you have achieved and appreciate that you are ambitious and want to take your career to the next level. But there’s a fine line between coming across as confident and enthusiastic, and being too pushy.

The one thing that is certain is those who sit in the corner, work hard and don’t make senior team members fully aware of what they have done will not get promoted. It is important to sell yourself.

So, next time you get on the train and your boss is there, take a deep breath, nod and smile and see if he is open to having a chat.

Yours, Nicola

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