From Clutter to Control: 5 Ways to Better Manage Email Attachments

We have discussed folder strategies before. We have discussed colour coded emails before. BUT…

We are yet to discuss managing attachments in Outlook. Email attachments often are pushed to the side in the email world, seen as nothing more than basic requirements of business but there are strategies to make the attachment experience MUCH better, in fact, I have five of them. We will discuss each of these five strategies in detail and in order of least impactful to most impactful. The strategies are as follows:

1.) Using the ‘Preview Attachments’ function
2.) Removing attachments from emails after you download them
3.) Setting up ‘Auto-Delete’ and ‘Auto-Archive’ functions
4.) Compressing attachments that you send

And last but certainly not least:
5.) Creating an attachment naming system

These five tips will make sure you will never have to worry about attachments ever again.
So lets begin…

1 | Preview Attachments Function

The first and simplest part of managing our attachments is the preview attachments function. This is automatically enabled in Outlook and helps you avoid downloading attachments unnecessarily. It is as easy as clicking on the attachment and a preview will pop up showing you the contents of it, allowing you to read or print it without needing to download it.

This is a very basic tool and one that most people are aware of but an important one nonetheless. The time and storage savings by not having to download files is a big deal. DO NOT underestimate it. Even if it saves you only 3s of time per attachment and you deal with 50 files a day and only on weekdays, it will save you around 10hrs and 50mins a year. This seems like a small difference, but if you compound it with just 9 other small differences, you have now saved yourself almost THREE full-time working weeks every year.

2 | Removing Attachments

Moving on to something with a little more substance, we have the ‘Remove Attachments’ capability. This feature of Outlook is a nice addition to help us with managing emails, but it’s most powerful nature comes when you combine it with some VBA coding to automate some of this. But first, we will go over what it is, what it does, and why you should care.

The remove attachments feature in Outlook allows you to do exactly as it sounds, remove attachments from emails in your inbox. The reason this feature is interesting however is how you can use it. This feature can be used to effectively make sure that you never run out of space in your inbox ever again. The caveat to this is that you need to make sure you have a good folder system on your device in place to manage and keep track of all the downloaded attachments since they will no longer be accessible from your inbox. There are a few different strategies on how to utilise this depending on how ruthless you are which are listed below:

1.) Remove each attachment as soon as you download it
2.) Remove each attachment after something is resolved
3.) Remove each attachment after a given time period

The first example is true ruthlessness and requires you to make sure all other systems are in place to avoid losing things or making mistakes. The benefit of this strategy however, is that you know that all emails that have attachments remaining are ones that have not been downloaded. This strategy will also maximise your available inbox space. I would not recommend this for legal documents and tax invoices because they require timely attention and tracking but if you are confident in yourself and your system, this is the best option.

The second option represents a more refined solution that is not directly tied to the downloading of the attachment but instead to the process the attachment goes through. The perfect example is an invoice. You receive an invoice for a company and download the invoice. From there, you send it to the accounts team and they organise payment. You then receive a receipt from the original company, marking the end of the invoices journey. Therefore, you would set it up a little automation so that once you get a receipt from a company in reference to an invoice, you remove the invoice attachment from the original email. This is the sort of stuff that is a little more complex to set up but can run in the background and if done correctly is very easy to manage, update or change in the future.

Finally we have the last example. This is actually the one I use the most. The reason for this is simply that it has the ruthless generalisation of the first option but has a bit more of that refined nature with the time component like the second one. This time period does not have to be the same for every attachment. You could have it that all attachments in regards to quarterly reports, sales and financials are removed after 12 months (assuming you have a proper system to track these effectively). Another example would be invoices to customers. If you have a credit policy or payment plan, you can set that they delete after the maximum payment period. There are many other ways you can set this up to be as relaxed or ruthless as you like, but I find most people settle for the broad approach of removing all attachments after 60 days, 90 days, or 365 days.

While the above rules are pretty easy to set up if you know some VBA, creating a tutorial for those who do not know VBA is a bit beyond the reach of this post and would instead be its own post entirely.

3 | Auto Delete & Auto Archive

Following the ‘Remove Attachments’ function, we have a more simple strategy for dealing with attachments (and excess emails), auto-delete and auto-archive. The Auto-Archive function is more practical than the Auto-Delete function due to still having the ability to access the emails afterwards, but both can be utilised depending on your goals and type of business. While these do not target attachments directly, they can be a great way to manage the size of your inbox.

The way Auto-Archive works is by allowing you to designate a folder on your device where old emails get sent to in the form of an Outlook archive file. This file can be viewed using Outlook and will appear like any other normal inbox folder when opened. The emails in this folder are now no longer part of your inbox and are only stored on your local device saving you a lot of space and can help speed up searching for emails. However, because these emails are now only stored on your local device, make sure to back them up regularly to avoid losing them when things go wrong.

But how do I set this up?

Setting up Auto-Archive or Auto-Delete is actually more confusing then it should be so let me go through the steps to get this done.

The default ‘archive’ button you see in Outlook, found either in the tool bar or in your ‘mailbox settings’, does NOT clear your inbox from these emails. This archive button instead, just allocates a folder in your inbox for emails to go to when you press ‘Archive’. We do not want this.

Instead we are looking for the actual Auto-Archive setting. To get there, we have to follow these steps in order:
1.) Click on ‘File’ at the top left of Outlook
2.) Find the small ‘Options’ button down in the bottom left and click on that
3.) Navigate to the ‘Advanced’ section from the ribbon on the left
4.) Find the ‘Auto-Archive’ portion and click ‘Auto-Archive Settings’

Now that we are here, you have the ability to choose how frequently the Auto-Archive takes places along with how old the emails have to be for them to be archived. Additionally, you will also have the ability to either select a folder on your device for them to be archived to or set it that they are deleted instead.

The details of this will be discussed in a later post about managing email volume. For now, just remember to be practical about how often the Auto-Archive function runs and how long before an email gets archived.

4 | Compressing Attachments

Now we are starting to get into the more juicy strategies with these last two. This one is probably the highest ROI on your time and effort given how easy it is and how big the difference is. It is a basic one but can make a MASSIVE difference to small and medium businesses. Having smaller attachments not only means less storage demand, but it means a better experience for the clients you work with. I STILL… even with today’s endless storage available, regularly see company inboxes almost maxed out on storage, and STILL… even with today’s super fast internet, regularly have to wait an extra few seconds for an attachment to download. But I get it, compressing every single attachment before uploading sucks… It is tedious and feels like a waste of time. So let me teach you a hack that will make this 100x easier… NXPowerLite!

This little add-on will revolutionise your email attachment game! What it will do is automatically compress any attachment you ever send. No more will you ever have to about attachment size. As soon as you press send, NXPowerLite will AUTOMATICALLY compress any attachments you have; whether it is a PDF, Powerpoint presentation, Word document, PNG or JPG file, Excel document or any other common file type. There is no sponsorship or affiliate deal going on here. I am just a big fan of this undderated piece of software.

5 | Attachment Naming System

Now onto the finale, the attachment naming system. This one is a sneaky one because it seems simple on the surface but will change how you view managing attachments entirely.

I see it all the time… emails popping up in my inbox with some PDF attachment, but when I look at the attachment, it ends up being titled something like ‘fgp_15032024-TUIHN invoice copy’. How on earth am I meant to know what this file is unless the sender has made it clear in their email; but then after I download it, I no longer have this context. So unless I then rename it, I will NEVER be able to find this file again. Don’t be like this, we can do better.

The Who:
The first part of your naming system is the ‘who’. Make sure that when you name your attachments, you are able to identify who it is from, who it is for, or who made it. Which one of these you use depends on what you plan to do with them and where the attachments came from originally; see below:

Who it is from = Think sending a file from one company to another company
Who it is for = Think sending credits, invoices, contracts, etc.
Who made it = Think sending designs or marketing material within your company

This part of the naming system will make it incredibly easy to find these files and their email threads, and will make your emails feel just a touch more professional, but there is more…

To make it clearer, let’s go over the three options in more detail.

For ‘who it is from’, I most often see it used as a way to advise generally where the file originated from. This is helpful when you are sending files between contacts, not only making these messy interactions easier to track for you, but also making it easier to track for those you plan to send it to.

For ‘who it is for’, this is used when important information is being shared by you and stops at the receiver, like an invoice for example. This has some crossover with the first category, since putting your business name in the file will be useful to the other party in keeping track of their invoices, but only helps them. We need something on our end as well. This is where we would put the receiving company’s name in the title allowing us to track these invoices on our end.

And lastly, ‘who made it’. This one is a bit more unique but definitely has its use cases. The best way I can describe the use for this one is when you are providing some sort of reference material, whether you are providing a resource to another company, or if you are sharing a piece of design work within the company. Having who specifically made it in the attachment name will mean that you can easily locate all of this person’s work that has been sent via email, and allows the receivers of said attachments to easily identify who’s work it is beyond the company that provided it like in the ‘who it is from’ section.

The What:
This part is exactly what it sounds like. It makes sure it is clear WHAT the file is. People get lazy with this part… Welll… People get lazy with all of the parts, but people get ESPECIALLY lazy with this part. ‘The what’ is the most important part of all this once we get to the end and bring it all together. I will address that soon.

For ‘the what’; we are wanting categories, not specifics. The specifics are covered by ‘the who’ section mentioned previously, and ‘the when’ section that is coming up. In ‘the what’, it should be PREFEREABLY identical to whatever category folders you have, whether that is implemented in the ‘Action Orientated Sorting’ or ‘Category Orientated Sorting’ method. The reason will become clear later, but what we are doing here is making it easy to track what type of attachment we have provided. Most people I see already do this for something like an invoice, but they do not always do this with stuff like presentations or employee ID pictures, etc.

The When:
Finally we have the when. The strategy here is to track the timeline of attachments: the date the file was created, the date it was sent, or the time period the attachment represents. We will use these three in different scenarios, as seen below:

When it was sent = Think legal documents and contracts
When it was created = Think invoices, receipts and tax documents
When does this attachment matter = Think reports, monthly sales figures and regular announcements

The importance of the ‘when’ comes into play when we are trying to manage timelines and create a clear paper trail of documents. As an example for ‘when it was sent’, lets say you get into a legal dispute with one of your suppliers. They claim that you took too long to send the contract, so the terms are no longer satisfactory meaning they refuse to sign. In this case, naming the attachment with the date it was sent is an easy way to keep a digital paper trail beyond just when the email was sent, building a legal safe guard through redundancy. It is a small change, but a helpful one. Therefore, in the above situation you could pull up the file, compare when it was made with the name used for it, then matching it up to the email you sent and its attachment, you could then be 100% sure of the timeframe from when the contract was made to when it was sent.

The second way of using ‘when’ is ‘when it was created’. I use this one to track important documents that need storing. As an example, most people need to keep receipts for tax reasons, putting the date it was made into the name of the file makes this much easier.

Lastly we have ‘when does this attachment matter’. This use case is less for tracking timelines of a specific file or keeping track of particular documents, but to log a history of stuff. For this example, think of a regularly released announcement like a monthly customer stories newsletter. There would be no reason to use a specific date in the name of the file since it represents the whole month, but titling it ‘This month’s customer stories’ would make it impossible to locate the particular newsletter in the future. Now… I know most people already do this, but that does not mean this is not worth mentioning: put the month and year into the name of the file, e.g. “January 2025’s Customer Stories”. This makes sure that at any point in time, you or any of the people that receive this newsletter can instantly find an issue from a particular time.

There is one final part of this equation to create your naming system and that is how to format it. Then we can finally talk about my secret tip that pull all of this together.

The Format:
This is where we pull all of the above together and make a coherent file naming system to make sure everything is perfectly consistent and easy to manage and track. To do this, I find that the ordering should be optimised for readability and understanding for both the sender and receiver of the attachment. The ordering when doing this however can vary a lot depending on what the file is being used for and in what context. Therefore it becomes far more practical as a business owner to not over optimise and just make sure that you use the same ordering for everything and that the who, what and when is always included. This way the consistency itself will make it understandable and highly readable. As both you and the people you send to slowly become more exposed to the system, the naming will become more recognisable and easier to understand.

THE SECRET:
I have not seen many people mention this but once I reveal it, it will enlighten you to as to why the attachment naming system is so powerful. The secret sauce I have is… that Outlook lets you create inbox rules based on properties of attachments in emails. You may be thinking, “So what?” or “Why are attachment properties a big deal?”, so let me elaborate…

If you use the who, what, when framework I have outlined above, you can set any number of rules to sort emails you send based on this naming system you have created. Including what the attachment is about, what financial year it relates to, who made it and any combination of the above. As an example, you could very easily set up a rule to forward all emails that have an attachment that includes: “company 1”, “2025” and “invoice” in its title to your accounts team.

Don’t let the work scare you though, with a little bit of elbow grease to figure out your own naming system and rules, you will never have to manually sort emails that have attachments ever again.

Best of luck with your inboxing journey, and lets organise!
Cheers, Nathan.