Workplace Doctor: Be brave and raise lipstick on teeth issue with the boss

Red lipstick wearing boss needs a quiet word in her ear about teeth stains. Ignoring the issue won't make them go away.

The lack of care over lipstick could affect personal brand and image especially if she is in an environment where she is client-facing or people are judgmental about appearance.
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My boss slathers on red lipstick every day. It suits her and it looks good. However, she sometimes slathers on a little too much and it ends up on her teeth. This is where I find myself squirming in my seat. Do I speak up and have an awkward conversation or stay quiet to avoid offending her? BA, Dubai

Awkward conversations are something no one wishes to have. However, it seems you may actually have a genuine need to think about having one with your boss. The possibility of offending her may be outweighed by saving her some embarrassment in front of clients, senior internal stakeholders and colleagues.

If your boss is in an environment where she is client-facing or people are judgmental about appearance, then this lack of care over lipstick could affect her personal brand and image. Professional presentation is about paying attention to details, especially in certain corporate environments.

Speaking to her in a private setting, where the conversation won’t be overheard, may raise her awareness and stop something that seems small and trivial from potentially damaging her credibility among others. It would also show your willingness to speak up and put her best interests first, showing your support for her. But there is clearly a way of communicating the message so it is well received; here you need to be specific, keep the conversation positive and it may help to attach the feedback to a business issue (such as an upcoming client meeting). It is also up to you to consider the consequences if you say nothing.

This leads me to a broader point about difficult conversations in organisations. If the intention is genuine, which I suspect yours is and the message is communicated in a considered, fair and sensitive manner, having a difficult conversation has the potential to strengthen the quality of a relationship. This especially works if you think about how you communicate the message and explain why you want to communicate it. It shows integrity, trust and a willingness to speak up, to support another person and their credibility, which can take a career to build but an instant to erode.

We have all been in situations where we feel uncomfortable and awkward raising an issue. This is particularly challenging when it is with our boss. However, overcoming this and thinking about how something so small could potentially affect all the good work that your boss and the team have done, should help you find the right words. Also, when it comes to your own career development and the day you lead your own team, then difficult conversations will become more frequent in your daily work life.

Good luck if you do decide to mention it.

Doctor’s prescription

Dealing with challenging conversations is a common part of working life for people who care about their role, and learning to cope with these effectively is essential for managers today. It is tempting to dodge difficult conversations, but you should consider the wider implications of failing to tackle this seemingly trivial issue and the impact on the other person. Handling this well will set you in good stead for your future career.

Alex Davda is a business psychologist and consultant at Ashridge Business School based in the Middle East. Email him at for advice on any work issues.

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