Messaging the Boss – how to get results and fast!

In a recent workshop, the topic of messaging in the workplace came up. Whether via WhatsApp, Skype, Slack, FB Messenger or even general phone message – how do we know what’s best practice?

Email has its place for many reasons, one being that it creates a digital paper trail and many people can be cc’d or forwarded the information, and you can include a lot of detail and attachments.

However, busy inboxes means often people don’t get to an email in time, or the email may have too much information and detail to bother being read properly. (Which is why unnecessary meetings are set, but that’s a whole ‘nutha story).

‘Urgent’ emails aren’t even really a thing anymore, but we send them in the knowledge that ‘Well, I’ve done my part, if they don’t see it that’s on them’.

But, as an EA, it’s your job to make sure the exec does see it!

YOU can’t just leave it and hope for the best as that means you just aren’t being as effective as you could be, and if you do usually leave them, perhaps rethink if you are in the right position.

Well, enter ‘Messenger Mode’.

How much easier is it to get an answer from an exec via message!!

In my role as an executive, I often asked my Assistant to message me if things were important or urgent, and particularly if a deadline coming up. I was out in meeting or on site projects most days, and so I relied on them to filter the noise and be able to succinctly ask me for what was actually needed.

So, here is my advice from having worked both sides of the industry:

Firstly – COMMUNICATE with your exec how you are going to interact and ensure they are on board with it. No point using an app like WhatsApp if they aren’t ‘phone’ people. Also,  they would know if there is a company-wide policy on how sensitive information can be sent, so always best to clarify this.

Secondly – if it’s important to have an email trail, send an email with ALL the detail – plus you can include those you need to. Then, send a message to your exec to let them know in a succinct way exactly what you need from them. It could be:

‘Please read carefully, this belongs to case XYZ, which so-and-so is waiting on your judgement from. I need an answer by the end of today please to ensure project goes ahead’

Thirdly – Perhaps it doesn’t need an email trail at all. Think efficiency – e.g. ‘I just need you to please confirm you have resolved the issue and the staff wide email you sent me yesterday can now go out at 2pm today.’ A simple text with this will often garner a very quick response.

Now,  a few words of advice.:

  • Always be careful – you don’t want to send a message to the boss that was meant to go to your spouse or friends. That could be VERY awkward.
  • Keep tone professional, avoid emojis unless necessary (we had a company culture of using emojis that was fun, but then people thought you were angry if you didn’t use them. So just forgo, or stick to a simple smiley.)
  • Potentially use screenshots to ensure if any big decisions are made over message, you have them to reference. You can then put them into an email and forward to the relevant parties to show the exec has confirmed.
  • Also if anything inappropriate is messaged to you, screenshots are a good idea.


Thoughts? Do you or do you not message your exec for answers?

If you don’t, I suggest you start as you may find things happen a lot faster – but obviously be careful and use these guidelines for ensuring a professional and well maintained working relationship.

Feel free to email for further discussion – I’d love to know what you think!

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