Holly is Executive Assistant to a CEO, and each month she arranges the company board meeting. She compiles and sends out the board papers, arranges the catering, and corresponds with the directors about arrangements.

It is over this correspondence, however, that her stress begins, and it’s possible you have sometimes been in a similar position.

The majority of the directors fly in for the meeting, and so one of Holly’s tasks is to book a hotel for those who need to stay overnight. She always finishes her email to the board with: ‘Please let me know if you need accommodation.’

Many months of the year, almost no-one replies to that question. Holly worries that a director will ask her to book a hotel at the last minute, when the best places are already full. And her CEO often asks her, ‘Is anyone staying over I should know about?’ But although a few directors ask her to make a booking, the dearth of replies occasionally leaves Holly wondering if the directors are a tad rude.

The problem is that Holly is unlikely to trigger more replies through the question she asked. That’s because her question, using ‘if’, is a conditional one. ‘Please let me know if you need accommodation.’ This means that only those directors who do need accommodation are required to reply, whereas Holly, for peace of mind, wants to hear from all the directors.

Holly, like many people emailing in a similar situation, would do better to use ‘whether’ in place of ‘if’: ‘Please let me know whether you need accommodation.’ The word ‘whether’ indicates that two alternatives are possible. The directors are required to reply whether they do or whether they don’t.

Once Holly asks this question, she receives a full swag of replies:

Graeme wrote, ‘I’m alright thanks, Hol. I’ll be flying out again that evening.’

Maya said, ‘No need for the hotel, but thanks for checking.’

And James replied, ‘I’m right for a bed, thank you. My Mum still lives in town so I’ll stay for the long weekend.’

Now Holly is reassured. The directors do read her emails, and when the CEO asks, ‘Is anyone staying over?’ Holly can tell her James will be in town all weekend. ‘Excellent,’ the CEO replies. ‘Just the person I need to see.’

Holly’s careful now to use ‘whether’ when she wants to hear back from someone either way. So when her CEO flies in from overseas the following month, Holly texts her: ‘Let me know whether your flight is delayed.’

Reassuringly, in comes the reply: ‘The flight’s on time. We’re boarding now.’