June – Flipping the 9-5: the 5 steps to outsourcing all of your email

6 - Flipping the 9 to 5-01

As part of this month, I have outsourced my email inbox to a new personal assistant, Sam.  I have had a few PA’s in the past.  They have generally all managed my diary (which is a massive relief for me since I seem to have a mental blank when it comes to the detail of dates and schedules and hence this reduces a lot of time and stress), but I’ve never gone that step further into having the whole inbox managed.

However, with only 5-9pm to play with, I wanted to see if there was a way of making this kind of outsourcing much more sustainable – as opposed to my month of only working an hour a day, which is deliberately too extreme to do on a regular cycle.

So how would you go about outsourcing your inbox?  Here’s my 5 step process, based on the learning of how Sam and I started this month…

1. Find the right person! 

I had previously tried this with a VA company I’ve worked with a lot and whose work for us in other areas has been good (websites, etc).  However, that company was in India and less experienced both in UK office life (humour, etc) and crucially, less experienced in this particular kind of outsourcing – outsourcing your inbox is as close as you’ll ever get to handing over your soul, so you need a very high level of trust here.  I found Sam using People Per Hour, a site I’ve used for a few different projects.  Her hourly rate is higher than you might pay for someone from overseas, but it’s worth it to get this right.

2. Set up an initial ‘chemistry call’. 

This person will be working with you and interacting with you several times a day.  Make sure this is someone you can trust and can enjoy working with too.  At the end of this call, if it’s potentially a go-er, suggest a 1 month trial with some boundaries/limits.  Mine was basically to say “do an hour a day, 5 days a week.  When you get to the end of the hour, tell me”.  That way, I’m trialling something with a fixed cost and everyone’s clear.

3. Orientation. 

Spend at least an hour (probably closer to 2), on a Skype call where you can both see and administer your email inbox.  Have your PA go through each email, and discuss with you where stuff might go.  This is a great way to establish and recongnise what your current habits are, how you currently like things done, how you think, and so on.  So much of this is engrained behaviour, that it’s important to have an open conversation – there will be situations where both of you need to compromise how you would usually do it to suit the other.

4. Structural Inbox Tweaks.

Be prepared to challenge your own status quo and make changes to how you work.  I operate a very simple folder structure.  I have 3 processing folders (@action, @read, @waiting – with the ‘@’ symbol ensuring they’re top of my inbox).  I then have a small number of 6 - Flipping the 9 - 5-03‘library folders’ (Think productive, Friends & Family, Confirmations etc).  I also have a library folder called ‘Circulars’ which is where I set up rules for low-level noise emails such as newsletters and so on will automatically file into.  We created two new processing folders – one permanent and one temporary – in order to work together more efficiently:

– @grahamtoread: this folder is where Sam will put stuff that I do actually need to read.  Then, every day at 5pm she calls me and we run through what’s in here.  This is really the power of the whole system: by having Sam do 80% of the processing, it leaves me to focus only on the 20% that need my decision, thereby freeing up a lot of time.  We can run through the whole folder in 20 minutes or so, and Sam will also flag a small number of items in this folder to bring my attention quickly to the ones that require immediate responses.

– @Sam2DeleteOrFile – we’ve also set up a temporary folder, which is so that Sam can have license to file or delete stuff without me seeing it.  If it goes in there, she’s made the decision I don’t need to see it, and whilst we’re both still learning the ropes with this system, I check this once a day, and just mention to her anything that I feel I should have seen.  It’s a good way of us both learning safely.

5. Write the rules down. 

Once you start to develop a reasonable set of ‘rules’, write them down.  I’m using a simple word document in Dropbox so that we can both access and update, but you could equally use a wiki or google doc.  If you’re stuck in thinking of rules, think about…

– who’s important?  are there people who you ALWAYS need to read their emails?

– what information do I need to make a decision?  So if someone is asking me to write something for them, or meet them for coffee, what are the circumstances in which I would give them an hour of my time… versus not!  We are now working on Sam being the one who goes back to people asking for the additional info that I would have previously done myself.

– where does the conversation stop?  if you can get clear on where conversations finish, it means you no longer need to read the final emails that wrap things up or simply say ‘thanks’

– what happens with ‘set piece’ and repetitive items such as diary and calendar appointments, tickets, and other set types of admin?  Diary appointments for me always trigger this little process (1. add the event to the calendar, 2. save the postcode, phone number, website and conversation within the calendar appointment, 3. move the original email to ‘confirmations’ folder).

There are many more ‘rules’ you can establish here.  But writing them down promotes clarity, allows a firm basis for regular discussion and review and keeps the conversation collaborative rather than judgemental.


With all of that set up, my inbox has gone from being something I’d have turned on in the background for at least half the day, to something that take me no more than an hour of my time each day.  And by creating space, we can get beyond email and start focussing on creating the things that really matter.


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