Open Thinkering


Tag: project management

AI for boring project tasks

Yesterday, WAO ran a pre-mortem for a new project we’re kicking off. We used Whimsical, but wanted the results to be in a spreadsheet for easy reference. This is the kind of thing that used to take probably an hour of my life and was a boring task. LLMs like GPT-4o make it easy:

Screenshot of Whimsical board with the instructions:

We ran a pre-mortem activity and I've attached the output. Working step-by-step, I'd like you to:

1. List all of the risks (yellow sticky notes), grouping them by theme (blue stickies). The sticky notes are grouped horizontally.
2. List all of the preventative measures (orange stickies) for each of the risks
3. List all of the mitigating actions (green stickies) for each of the risks
4. Create a table that I can copy into a Google spreadsheet that has the following columns:
- Theme
- Risk
- Preventative measures
- Mitigating actions

A few minutes later, I had this:

As Ethan Mollick says in his book Co-Intelligence: Living and Working with AI, it’s worth experimenting with AI in almost every corner of your life. Being able to outsource boring stuff, and using it as a thought partner for things you may have missed can be transformative.

For example, I asked a follow-up question as part of this conversation for things that we might have missed. It surfaced things around cultural (mis)understanding, data security, and policy changes, among other things.

At the moment, the main point of friction for me, whichever LLM I seem to use, is that it forgets context. Sometimes, that can be even within the same chat — and even sometimes when I’ve created a custom GPT. I haven’t used Amazon Titan, nor have I done much with Google Gemini, so I should explore those further.

Ideally, what I’d like is for an AI assistant to conversationally implement workflows that we’ve agreed upon in kick-off meetings. That may also involve my AI assistant talking to a client’s one for scheduling, updates on progress, etc. I think it would be a huge improvement to the hodge-podge of systems involved in multi-organisation projects.

(A)synchronous project updates within organisations

As a consultant, I find that there are, broadly speaking, three types of teams and organisations when it comes to project updates:

  1. Synchronous updates (only)
  2. Aynchronous updates (only)
  3. Asynchronous and synchronous updates

The purpose of this post is to explain why the third of these is by far the better option.

1. Synchronous updates (only)

The most popular (the default, even!) are those only doing synchronous project updates. This means that the team, group, or other unit of organisation finds out the whole picture of what’s going on in the weekly team meeting.

Advantages: every project update can come with full context and, if someone doesn’t understand, or has a question, this can be addressed immediately. If the project team is meeting face-to-face or via video then facial expressions and body language can convey additional information.

Disadvantages: if the project team is only receiving updates on the day of the meeting, then the information they have can be up to six days out of date at any given time. Also, anyone who misses the meeting has to rely on the notes.

2. Asynchronous updates (only)

Other teams, groups, or other units of organisation only do asynchronous project updates. This means that meetings are rare, and the main way to find out what’s going on is to check the place where updates are made.

Advantages: anyone with the necessary permissions can get involved, which is why this approach is common to Open Source Software projects. What you see is what you get, and combined code repositories and issue trackers (e.g. GitHub) provide a decent workflow to get things done.

Disadvantages: with the human element removed, it’s difficult for the full context (including relative importance) of an update to be conveyed, and for serendipitous links to be made between projects.

3. Asynchronous and synchronous updates

The best teams I’ve come across do a combination of asynchronous and synchronous project updates. They meet regularly face-to-face or by video and provide updates in a dedicated space between meetings.

Advantages: everyone on the project gets full context around an update, either in the dedicated space or by asking a question about it in the meeting. There is now more time in meetings for forward planning and innovation.

Disadvantages: none that I can think of!

N.B. Workplace chat solutions such as Slack are great for many things. Given the potentially low signal/noise ratio, project updates are not necessarily one of them. Instead, I recommend using a dedicated space — e.g. Trello or Nextcloud Deck.

This post is Day 64 of my #100DaysToOffload challenge. Want to get involved? Find out more at

PRINCE2 for schools (or, why don’t schools have project managers?)

I spent last week studying for and taking my Foundation and Practitioner PRINCE2 examinations. Programme and project management is an expected part of the world I now work; in fact, funding and facilitating projects too risky for institutions to take on individually is pretty much what JISC does.

PRINCE2 logo

PRINCE 2 is a project management method standing for PRojects IN Controlled Environments. It’s generic and applicable to everything from painting and decorating your house through to the machinations of multinational corporations. Granted, at first the rather abstract concepts seem needlessly convoluted (‘dis-benefits’ anyone?) but the commonality of language and ability to tailor a workable organizational structure make sense in the end.

What I can’t understand is why most schools shun formal project management methods? More than any almost any other type of organization, schools have to deal with constant change: personnel, curricula, buildings – so many different elements! Whilst it would be overkill (and the cost prohibitive) to have everyone within an organization PRINCE2-ceritified, I would definitely recommend the following:

Senior & Middle Leadership – full PRINCE2 Practitioner status

Teachers, Learning Support Assistants and Site staff – PRINCE2 Foundation status

If tied to professional development activities, the 7 PRINCE2 principles could really make a difference to organizational efficiency:

  1. Continued business justification
  2. Learn from experience
  3. Defined roles and responsibilities
  4. Manage by stages
  5. Manage by exception
  6. Focus on products
  7. Tailor to suit the project environment

The three I’ve highlighted would in particular benefit schools and make them much less frustrating (and much more productive) places to work. To explain those three:

  • Continued business justification – at the end of each stage the Executive (usually be the Headteacher) decides if the ‘business case’ is strong enough to continue the project.
  • Defined roles and responsibilities – project roles are based upon the ability of the person’s role within the school to allocate resources and carry out the task (and not on personalities).
  • Manage by exception – once each stage plan is agreed with specified tolerances, the project manager gets on with it, only raising exceptions to the Project Board if the tolerances (time, cost, scope) are exceeded.

I’ll explain more about PRINCE2 if there’s enough interest. I may not be qualified to give the training, but I am qualified to write explanatory blog posts. 😉