The other day I was asked what features I like in my new flat. It is terrible, but I could instantly list a few things I didn’t like before I answered positively (the sofas too close to the telly, the dining room table is in a weird place etc.) I think it is human nature to think about your dislikes rather than all the things you adore; it just seems more natural – especially when it comes to work! I always say that assistants should try to remain positive at work and not moan too much and I do honestly stand by that.. but what if we could use our colleagues’ natural negativity to enhance our productivity and value in the company? Instead of asking our managers ‘what can I do for you?’ ask ‘how can I ruin your day?’

How can I ruin your day?

Asking what your manager doesn’t want is as important as asking what they do want.

I think this approach works particularly well when you first start a new job especially if your manager hasn’t had an assistant before or isn’t sure how to work anew with you. If you have been in the role for a while but are struggling to develop your relationship with your manager or a colleague this approach might also be worth trying too. Here are a few questions you can ask your manager that will provoke honest answers and will help you understand their needs and add value also.

  • Is there anything you do not want me to go near or change in any way? 
  • What is your biggest distraction?
  • What do you dislike in your daily routine?
  • Is there anyone that you don’t want to talk to… ever?
  • Are there any points in the day when I should just leave you alone?
  • What personality types do you dislike working with?
  • Are there any aspects of my role that you don’t need me to do?
  • What do you least value in an assistant?
  • Are there any forms of communication you dislike?
  • What details bother you? What doesn’t?

If you have been in the job for a while, these questions are still relevant as you will probably gain a different insight into how your manager likes to work. Remember we are taking their dislikes and making them disappear! 

I would say that asking negative questions rather than asking what success looks like is certainly refreshing and I think if you are honest with your manager and say you want to try a different approach they will go along with you and find it a fun way to develop your working relationship. As we all know it can be cathartic moaning about your least favourite parts of the day and I bet your managers get very little chance to do that!

If you are new to the Assistant role, you can also take a look at our eBook – Starting out as a new Assistant.

How can I ruin your day?

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