Capturing Via Flagged Emails In Outlook

[Baz]

Hi,

I have Outlook at work and receive the vast majority of my input via email.

My process since implementing GTD c3 years ago has been to review my Outlook inbox in the morning and at regular intervals throughout the day.

I'll open an email and if it's not something that can be done in two minutes or trashed I flag it for follow up without no date.

I then move that email into reference folders in Outlook. I have a portfolio of c17 customers and have a dedicated reference folder for each customer.

Those flagged emails then show in my list manager - Microsoft To Do.

At the end of each work day I'll go through those flagged email in To Do and add a hash tag that links them to a particular project if needed and process them into the relevant contexts.

I quite like this method as the To Do I have created has a snapshot of the email which I can scan for more info. before deciding whether it is something I want to action at that moment.

If i do decide to action it there and then To Do has a link straight to the email which opens in Outlook Web. I therefore don't have to go looking for an email in Outlook if I need more information or need to reply to it.

If an outgoing email has a waiting for, I'll flag the outgoing email for follow up and move it into my waiting for list in To Do.

This seems to work well for me but are there any drawbacks?

In some sense I am having to double decide as I make decision in my Outlook inbox and another decision when I open the flagged email in To Do.

However, to me the first decision is a very high level decision as whether the email is actionable. When processing the flagged emails in To Do I know I'm only looking at actionable items and will make a more in depth decision about what the next action is and where it needs to be done at that point.

This helps me keep my Outlook inbox at zero for most of the time which I find less stressful.

I would welcome people's thought's on my approach.

 

[PlunkRock]

I've been wrestling with the exact same workflow challenge recently.

I use Microsoft To Do at work, and I've tried a few different approaches:

The flagging method you describe - I used this before, but stepped away from it. Like you note, there's definitely a double-handling element (flagging to get it into To Do, then still needing to process it properly). It's been a while since I last used this approach, but I recall running into technical issues where moving flagged emails between lists would sometimes break the links. Might be worth revisiting if that's not the case!

Dragging emails from Outlook to the To Do sidebar - I experimented with this more recently but hit some annoying glitches. I can't drag emails that are currently selected - I have to select a different email or hit escape first. Also, if I edit the task title too quickly after creating it, it reverts back to the email subject line after a few seconds. Both irritating, and it still suffers from the double-handling issue!

My current approach is the simplest but requires the most discipline: I create the task directly in To Do with a clear next action (and project, if required), then archive the email immediately. I'll include a note about when the email was sent or reference the subject/sender if I think I'll need to find it again.

I stopped maintaining a dedicated "action support" folder in Outlook because I got tired of the cleanup overhead - I'd either fall behind on clearing it out or discover I hadn't touched it in weeks. That said, it was handy to just write "see email AS" in my actions and know exactly where to look.

The question I'm sitting with right now is whether we actually need that quick link back to the email as much as we think we do. When I reflect on it, I find I go back to emails for three reasons:

1. I need specific details/attachments (genuine reference material)
2. I didn't fully clarify what the action was (incomplete processing on my part)
3. I need to reply to it (need the thread)

For #2, the "problem" isn't really the system - it's that I haven't captured a clear enough next action. For #3, I can usually find the email quickly enough by searching the subject or sender in my archive.

#1 is where I go back and forth. I can see how having an organized folder structure would help here - you'd know exactly where to find particular reference material. But that comes at the cost of ongoing folder maintenance. On the other hand, search has come a long way (particularly with Copilot now), so maybe the folder structure is less essential than it used to be?

Anyway, I'm really curious to know what others do. Recently, I've been trying to be ruthless about keeping my system as simple as possible. It's definitely my tendency to introduce complexity and elaborate structures, but I'm trying to be honest with myself about what I actually need versus what feels satisfying to set up. Right now, I'm enjoying having less "drag" on my system by not maintaining extensive linkage between projects, actions, and reference material.

 

[bobusa]

GTD doesn’t dictate what tools to use, and the method itself is flexible. If it works for you, that’s great! I think it aligns well with GTD’s Capture, Clarify, Organize, Review, and Do. You’re using the 2-minute rule, even if it happens in your inbox and in To-Do. I’m curious how you handle your weekly review. To-Do has the drawback of not showing the next action(s) linked to projects, except by using tags, and the only way to keep them together is through search, which doesn’t group them well. That’s just my take on To-Do—it’s not very GTD-friendly. Still, I like the feature that links back to the original email, making it easy to jump right to it. Using lots of customer folders in Outlook also makes it quick to find emails. I use Nirvana HQ, which lacks that feature, but I don’t miss it.

 

[bobusa]

I've been wrestling with the exact same workflow challenge recently.

I use Microsoft To Do at work, and I've tried a few different approaches:

The flagging method you describe - I used this before, but stepped away from it. Like you note, there's definitely a double-handling element (flagging to get it into To Do, then still needing to process it properly). It's been a while since I last used this approach, but I recall running into technical issues where moving flagged emails between lists would sometimes break the links. Might be worth revisiting if that's not the case!

Dragging emails from Outlook to the To Do sidebar - I experimented with this more recently but hit some annoying glitches. I can't drag emails that are currently selected - I have to select a different email or hit escape first. Also, if I edit the task title too quickly after creating it, it reverts back to the email subject line after a few seconds. Both irritating, and it still suffers from the double-handling issue!

My current approach is the simplest but requires the most discipline: I create the task directly in To Do with a clear next action (and project, if required), then archive the email immediately. I'll include a note about when the email was sent or reference the subject/sender if I think I'll need to find it again.

I stopped maintaining a dedicated "action support" folder in Outlook because I got tired of the cleanup overhead - I'd either fall behind on clearing it out or discover I hadn't touched it in weeks. That said, it was handy to just write "see email AS" in my actions and know exactly where to look.

The question I'm sitting with right now is whether we actually need that quick link back to the email as much as we think we do. When I reflect on it, I find I go back to emails for three reasons:

1. I need specific details/attachments (genuine reference material)
2. I didn't fully clarify what the action was (incomplete processing on my part)
3. I need to reply to it (need the thread)

For #2, the "problem" isn't really the system - it's that I haven't captured a clear enough next action. For #3, I can usually find the email quickly enough by searching the subject or sender in my archive.

#1 is where I go back and forth. I can see how having an organized folder structure would help here - you'd know exactly where to find particular reference material. But that comes at the cost of ongoing folder maintenance. On the other hand, search has come a long way (particularly with Copilot now), so maybe the folder structure is less essential than it used to be?

Anyway, I'm really curious to know what others do. Recently, I've been trying to be ruthless about keeping my system as simple as possible. It's definitely my tendency to introduce complexity and elaborate structures, but I'm trying to be honest with myself about what I actually need versus what feels satisfying to set up. Right now, I'm enjoying having less "drag" on my system by not maintaining extensive linkage between projects, actions, and reference material.

Processing should ideally happen in just one tool, in this case To-do. I’d only send actionable emails there, though I believe that only works by flagging them, which is the problem. Capturing and clarifying in two places puts extra strain on your brain and can lead to inconsistent results. Managing both Outlook and To-do is also quite stressful. Try doing the 5 steps entirely in To-do, or consider switching to Nirvana HQ, which is more true to GTD than To-do. I’ve tried To-do myself, but it takes a lot of effort to make it fully GTD-compliant.

 

[PlunkRock]

One other thought on your folder structure - have you considered using Search Folders instead of manually moving emails into customer folders?

You could set up a search folder for each of your 17 customers that automatically shows all emails from/to that customer. This gives you the same organized view without the filing overhead - emails stay in archive, but you get instant customer-specific access when needed.

I also recently experimented with a different approach to speed up email processing - using Outlook categories based on this Jeff Su video. The system involved categorizing emails as Follow-up, Waiting For, or Reference and archiving them. It was genuinely fun and fast at first.

The problem? It skipped GTD's clarification step. I'd end up with emails tagged "Follow-up" and then have to work out what I actually meant every time. What's the next action here? What does "follow up" even mean? It got tedious quickly.

That's why I went back to proper GTD - defining the actual next action during processing. Takes a bit longer upfront, but saves time and mental energy later because I'm not constantly re-deciding what past-me meant.

 

[PlunkRock]

Processing should ideally happen in just one tool, in this case To-do. I’d only send actionable emails there, though I believe that only works by flagging them, which is the problem. Capturing and clarifying in two places puts extra strain on your brain and can lead to inconsistent results. Managing both Outlook and To-do is also quite stressful. Try doing the 5 steps entirely in To-do, or consider switching to Nirvana HQ, which is more true to GTD than To-do. I’ve tried To-do myself, but it takes a lot of effort to make it fully GTD-compliant.

I agree with your processing point, this is exactly why I do what I do at the moment. I dislike the two step approach of:

1. Is it actionable? If yes, send to To Do
2. Review actionable emails in To Do and clarify the action/project

My preference is just to capture straight into To Do and archive the email.

I've used Nirvana in the past and have a lifetime license, but I must say I prefer To Do. I think it's perfectly serviceable for GTD, but I just use flat lists with no hashtags, etc.

Hopefully I've not doomed another thread to getting bogged down by the benefits/drawbacks of linking Projects and Next Actions

 

[bobusa]

Hopefully I've not doomed another thread to getting bogged down by the benefits/drawbacks of linking Projects and Next Actions

As long as your lists make sense to you, that’s what matters. They don’t necessarily need to be linked. But I do wonder how you do the weekly review. It's so much easier to have a link between the next action(s) and the project and areas. And there Nirvana fits perfectly.

 

[PlunkRock]

I used to think the same way, but find that following the steps of the weekly review in order means I can bear the relevant things in mind and get through it with no problem.

I find the limitation keeps me more honest, I could probably maintain a greater number of projects in Nirvana, but not necessarily get more of them done!

I found it more annoying selecting projects when capturing/clarifying, and feeling like I had to park every action not only in the right context, but also the right project. But as always, each to their own - I certainly understand the benefits, particularly during review!

 

[Baz]

The question I'm sitting with right now is whether we actually need that quick link back to the email as much as we think we do. When I reflect on it, I find I go back to emails for three reasons:

1. I need specific details/attachments (genuine reference material)
2. I didn't fully clarify what the action was (incomplete processing on my part)
3. I need to reply to it (need the thread)

For #2, the "problem" isn't really the system - it's that I haven't captured a clear enough next action. For #3, I can usually find the email quickly enough by searching the subject or sender in my archive.

#1 is where I go back and forth. I can see how having an organized folder structure would help here - you'd know exactly where to find particular reference material. But that comes at the cost of ongoing folder maintenance. On the other hand, search has come a long way (particularly with Copilot now), so maybe the folder structure is less essential than it used to be?

Sounds like we're in a similar boat!

One the one hand I like having easy access to the email in To Do. On the other hand using flagged email adds a further step to processing,

An alternative is to create a task with an attachment from the email there and then. The link to the email is still there in To Do but you don't get the preview like you do with a flagged email.

However, I'm starting to think that if I've fully clarified what the next action is then the preview isn't actually necessary.

 

[Baz]

I’m curious how you handle your weekly review. To-Do has the drawback of not showing the next action(s) linked to projects, except by using tags, and the only way to keep them together is through search, which doesn’t group them well.

In my projects list in To Do each project has a hashtag on the front. I work in banking. If I have an annual renewal of facilities to do for "CustomerX" then the project title will look like:

#CustomerXRenewal - Complete The Customer X Annual Renewal by 28/2/26.

I then add that hashtag to any next actions which I put in the correct context list e.g.

#CustomerXRenewal - Call Alastair To Discuss Annual Renewal.

I review each context during my weekly review as there will be next actions that are untagged due to not being part of a project.

When I review my project list I left click on the hashtag and it provides a list of the To Do's (next actions) which have the same hashtag.

I rarely use the search function unless I'm speaking to someone on Teams and want to see if I have anything that's a Waiting For from them.

 

[Baz]

One other thought on your folder structure - have you considered using Search Folders instead of manually moving emails into customer folders?

You could set up a search folder for each of your 17 customers that automatically shows all emails from/to that customer. This gives you the same organized view without the filing overhead - emails stay in archive, but you get instant customer-specific access when needed.

Thank I'll take a look at search folders.

I find that having a folder for each customer makes it easy to find any email that related to them as I make sure that any email related to that customer goes in that folder. That's just a case of left clicking and dragging so there's minimal effort.