Stop Using Your Task Manager as a Project Manager

I almost added this to the What we’re reading thread, but it’s better here.

I’m currently reading Software Estimation Without Guessing by George Dinwiddie. It’s really good, and I’m someone who has thought about estimation for decades. The goodness inside isn’t limited to software.

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In my project management career, I’ve never wanted to use this kind of delegation - there’s no point in my giving someone a task until Ive established:

  • They understand its content and priority, in relation to the other commitments they have
  • They’ve accepted the task, and responsibility for it
  • They have the time and resources to do it

If I don’t do all of that, I’m simply setting them (and myself) up to fail. I’ve seen many “blame culture” organisations where that’s the whole point - fail to deliver and have the scapegoat ready.

I’ve very frequently been in the position where I’m forced to use client systems - in those cases, I always maintain my own, separate system (paper/iPad/laptop) for my own planning. It introduces a major overhead in duplicating and reformatting data, but my own experience is that that’s less of a cost than attempting to do my job with systems that just don’t fit it.

Ironically, some of the clients where I’ve the worst problems are those who’ve established MS Project as their PM tool of choice. It’s not because of shortcomings in Project - in my experience, it’s a pretty good tool - but because the setup is designed to support project office processes. They care about tracking time, resources, spend etc. They’re not concerned with actually getting the project done - so I end up with two separate project plans - one to achieve the project goal and another to provide reports

4th law of thermodynamics - “Everything takes longer and costs more”

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But late to the conversation, but I came across this method years ago and have tried it out (on myself, using spreadsheets and some R scripts) for legal work like contract drafting. It seems to work, but that may just be because breaking things into small chunks and actually working out what’s needed in advance helps you to make better estimates. The actual time recording is being done anyway (hey, we bill by the hours, so sure we know how long it took!).

Has anybody else had experience with this approach? All I know is that Fog Creek implemented it in 2007 and it’s apparently still in their product 15 years later, which is a data point in favour. On the other hand, I don’t see it being implemented in other project management tools, which is odd because quite a few implement stochastic modelling and it’s really just another way of generating a distribution for the Monte Carlo model to use.

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I watched this video today, after reviewing a few Todoist how-to videos in the channel of the author, Carl Pullein. His main point seems to be that your notes app is often better for project management, as you can provide more context there. And that many things that hardcore GTDers label as projects really aren’t, even if they do take multiple steps and hours to complete.

Tasks can be one-offs, some taking hours—“clean the garage,” for example—or a task might simply be “work on Project X.”

I like it.

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Reading this thread, my thought is that “projects” encompasses such a diversity of endeavors that discussing project management without further specifying what kind of project we’re talking about isn’t very useful.

For example, the biggest project I’ve managed was a rewrite of the regional long range transportation plan for a sizable metropolitan area. Unlike some of the examples discussed here the project was quite well defined from the beginning (the federal government even provides a checklist of everything your plan needs to cover). On the flip side, it came with a rock-solid federally mandated deadline two years hence, so the very first step once I was assigned the project was to back-plan from the deadline (and find out we should have started at least six months earlier). So, not something you could manage with just one next action.

Projects come in all shapes and sizes, and the project management solution needs to fit the project. For some projects a task manager might be a great fit, others need some other tool, whether it’s a notes app, some sort of team communication system like Basecamp, dedicated project management software like OmniPlan or Microsoft Project, or something else entirely. For the aforementioned project I went through four or five different project management setups over the course of those two years (the project actually lasted long enough that OmniPlan added some features that made it a much better fit by the end of the project than it was at the beginning).

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This has been an issue for me. I used a combination of Omnifocus, DEVONThink, Aeon Timeline and folders of files in the Finder to manage complex multi year projects. As long as I had good separation I could find things but there was always, in spite of trying to implement shortcuts etc, a lot of friction between the project management and support materials in DEVONThink and the tasks in Omnifocus. The timeline in Aeon timeline often went totally by the wayside and rarely got used past the initial development/planning for the project.

An interesting development for me is that now that I am using Obsidian for all the stuff DEVONThink used to do, and am slowly moving all my task management from Omnifocus into it as well I’m finding MUCH less friction in how to track and manage all the disparate pieces for complex projects.

What’s key for me is that I use different capabilities in Obsidian for the different types of things. So I have notes with the overall project plan, but tasks get flagged with context per GTD and get automatically pulled into my GTD dashboard for work by context. Complex projects have all the Obsidian notes contained in a single folder that I can share with teammates easily by setting it up as its own separate Git repo. That also has the advantage of handling the version control so as we are all working on the project we can see who did what. Dependencies are more difficult to handle but I am prototyping a simple way to do that that seems to be working well. Time will tell if it is actually able to handle the complex projects that have multiple task dependencies. A schedule or gantt chart has typically been only useful for me to explain a project to a manger but far less useful in actually working with the team so I am not missing my aeon timeline project in my new Obsidian workflow. I can get 90% of the way there by using a kanban note in Obsidian with the columns being timeframes. And that granularity is good enough for all my current major projects.

@MitchWagner points out that

And for those types of problems I am using a combination of written user stories to describe the problem and brainstorming. The team and I share in an Obsidian Canvas where we throw ideas up like a whiteboard that we can play with and review later. Those can get fleshed out into more formal project notes with links and finally to tasks assigned to each person as needed.

Over the lifetime of a major project or major pieces of a project I am using all sorts of different tools and features of Obsidian. One huge benefit is that the more I use it the more I become proficient in its use so I can devise faster and easier ways to make my use more efficient. I also now have a single place to go for the information which in and of itself reduces the friction of managing and working on complex projects.

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An interesting development for me is that now that I am using Obsidian for all the stuff DEVONThink used to do, and am slowly moving all my task management from Omnifocus into it as well I’m finding MUCH less friction in how to track and manage all the disparate pieces for complex projects.

Obsidian natively supports Markdown, plain text, audio, video, and PDFs. But it can contain any document type. I use Obsidian as a container for managing Office documents. I feel like this is a powerful benefit to Obsidian that is not discussed a lot.

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I wonder what effect dumping all kinds of files into an Obsidian vault will eventually have on performance? I’m happy to keep my Markdown Notes in an app dedicated to that, and collecting all sorts of other types of (relatively static) documents in an app dedicated to that.

Although I can see why people might think they want this.

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Can you share what your “GTD dashboard” is / how it’s set up?

It’s a simple note that pulls tasks by tag in sections with a header. The header is the context and is a nested tag in Obsidian so entered as #Context/DownTheHill or #Context/Internet

Obsidian

not done  
tag includes Obsidian
short mode

AnimalTrakker

not done  
tag includes AnimalTrakker 
short mode

A typical task uses the tasks plug-in and is formatted like this. This example is from a meeting note where I add the actions that came out of that particular meeting.

# Oogie Action Items
- [ ] #task Add birthdates to LambTracker database #Context/AnimalTrakker  ⏫
- [ ] Email the updated DB to Mitch #Context/Internet 
- [ ] #task Search for how to calculate inbreeding from relationship matrix #Context/Internet  ⏫

And here is a quick view of what part of my GTD dashboard note looks like when I am reading it.

Screen Shot 2022-12-28 at 1.05.38 PM

I must admit that I did not read every post on this thread. However, despite the title “Stop uisng your task manager as a Project Manager”, I see only few mention of project management software. I could be missing some key discussions but GTD methodology does not direct support good projext management core requirements

To me, project management needs to have the following key ingredients

  • time management - especially what is the critical path
  • resources management - what are the supply and demand of resources to complete the project
  • financial management - budget , cash flow (super important)
  • option study - delay analysis and how does other options will perform will time, resource do not go with original plan (almost always happen)
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It will be interesting to see. I know of one test of plain markdown files where the vault had 20,000 files. Initial opening on an Android took 5 minutes to index but then it was fine. There were some tests of 100K files, IIRC the issues were the graph view, some dataview queries and I’d expect tasks to also have problems. Basically slow but as far as I remember not crashing.

I consider myself a fairl heavy user and I expect to be in the 8-10K note range when everything si finally converted over.

Are you equating GTD methodology with the task lists themselves, or perhaps general implementations of task management software?

Other than the fact that GTD uses “project” differently than you’re using it (GTD is more broad - “project” is “anything with more than one step required to complete” in GTD), the GTD methodology isn’t prescriptive regarding things like project management methodologies. It has the Natural Planning Model:

1 | Defining purpose and principles
2 | Outcome visioning
3 | Brainstorming
4 | Organizing
5 | Identifying next actions

and the stuff you’re talking about it missing is mentioned explicitly in the “Organizing” phase:

This is the stage in which you can make good use of structuring tools ranging from informal bullet points scribbled on the back of an envelope to heavy-horsepower project-planning software. When a project calls for substantial objective control, you’ll need some type of hierarchical outline with components and subcomponents, and/or a Gantt-type chart showing stages of the project laid out over time, with independent and dependent parts and milestones identified in relationship to the whole.

So it’s definitely referenced - GTD is just non-prescriptive regarding the specific tools. It leaves them up to you.

And of course Step 5 means that after you’ve done the planning, the lists themselves in GTD hold the records of the next action(s) that need to be taken to move the project forward.

So if you’re doing something that requires a critical path analysis, budgeting, resource management, feasibility studies, etc., David Allen is all in favor of you doing that stuff (step 4, above). And once you’ve done it, you translate “what’s next?” into one or more actions that go on a list somewhere (step 5).

But again, the lists contain the immediately actionable items - not the whole project plan. And that’s by design.

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what I meant ( perhaps poor choice of words) is that GTD is great for Task management but not really suitable for Project or Programme management

Also GTD may be great for planning but AFAIK, it does not help on progress, financial and resource monitoring and tracking.

I am not saying GTD is no good, but for effective Project or Programme management , it needs a lot more special tools (as a minimum, like MS Projects, and Oracle Project Management for large infrastructure projects /program. Project Controls is another specialised tool that is essential to keep large projects in check)

I think it is horses for courses, GTD in todoist or Obsidian may be great for task management but for project management , it requires a different set of tools. I am just responding to the title of this discussion

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I agree 100%. It gives a high-level planning model, and leaves the specifics to you.

By the same token though, it’s a perfectly useful system for the people tracking the progress, financial, and resource stuff to use for keeping track of the many things they have to do in those areas. :slight_smile:

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I have not found performance to be a problem. My vaults may be small compared with many folks.

What app do you use for non-markdown documents?

EagleFiler, a Mac-only everything-bucket app, is my choice.

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More on separating task management and project management:

I’ve choose to keep all referenced files in the vault structure. There is something about keeping it all together in the same structure that is comforting. I don’t imagine accessing the files outside of Obsidian so I don’t see the value of storing external or is this strictly a DevonThink thing