I’ve come across two very different approaches to making plans over the years (OK it’s more than two, but I’m trying to keep it straightforward)…

The first approach is where someone locks themselves in a darkened room with some ‘gantt chart software’… they think about the sequence of tasks; they phone people up and say “how long will it take to make a “; they work out all of the intricate dependencies. Some time later they emerge with a massive file of paperwork which contains ‘the plan’.

The second approach is where a team get together in a room and work out what needs to be delivered, roughly when things are required and who is going to get on and do them. Usually there is lots of scribbling on whiteboards – the plan may not be nicely wrapped up in a document, but is more likely a collection of phone-snapped pictures of flipcharts and whiteboards.

So which one is best?

Of course, the answer is… it depends.

Next time you need to make a plan answer these two questions…

* Can I precisely describe the ‘thing’ this project is meant to deliver?
* Have the people I’ll be working with delivered one of these ‘things’ before?

If the answer is a resounding YES to both of these then you can stop reading now – go and find a darkened room and start making gantt charts.

If you’re not so sure you can answer yes to both of these questions, then its time to book a meeting room…

Here are four questions to tackle with your team. Don’t worry about getting them exactly right first time – it may take a few iterations before things become completely clear.

Why is this thing so important that we going to spend lots of time, energy and money on delivering it?

Sometimes grown-up organisations call this ‘The Business Case’ and make you jump through all sorts of hoops to have it ‘approved’. However, the real reason for answering this question is that it starts to shape the approach you are going to take to the project. Are you going to go out of business if you don’t deliver? Will doing this increase the number of customers you have? Will it reduce costs? Will it be fun and exciting? etc

How will we know when the ‘thing’ is finished?

This one needs some imagination, but its important. By working out – if you like – the ‘test criteria’ for your project you are moving toward defining the outcome (which is a handy thing to know). So it could be… “at the end of the project we’ll count the number of widgets we make per day and that number will be twice as big as it is now” or “we’ll have released a new version of our software to all our customers with no additional calls to our support centre”… and/or “our boss will be so delighted that we’ll all be taken out for a massive celebratory dinner”

What are the smaller ‘things’ that we know we need to finish the bigger ‘thing’ AND Who is going to get/buy/make each of the ‘things’ by when?

OK its a big long question, but this is the one that’s going to make stuff happen. Break the project down into chunks. If you don’t know what all the chunks are right now, then at least you’ll identify some things that you can get on with while you are working out what the rest of the chunks are. For each chunk have an initial stab at who is going to be delivering it and when it’s going to be needed by. Don’t worry too much about getting dates right first time – as your plan starts to take shape you’ll want to shuffle dates around anyway.

Write this up somewhere – a flipchart or whiteboard with post-its that you can move around will work. Even better (and here’s a plug) use Milestone Planner with a projector and start putting each of the chunks on the timeline as Milestones. With everyone looking at the same screen its then easy to assign people to milestones and move things around on the timeline as you work out what needs to happen. (As a bonus, at at the end of the meeting, Milestone Planner can send you a pic of your plan which you can then circulate to everyone so that everyone stays on the same page !!)

What are we going to do when stuff goes wrong?

Anyone who thinks that reality will pan out exactly like the plan is kidding themselves. Use some of your workshop time to ask ‘What if…?’ type questions. Try and get a feel for where the risky areas of the project might be and start to work out what your response might be.

Wrapping Up

Its important to document the answers you got to… and agree what the next steps are.

If you’re lucky and you’ve got to the point where all the answers are clear you might want to ‘write it up’ into some impressive document. If things are still fluid then it might be better just to take lots of photo’s of the flipcharts and whiteboards and send them around to everyone. Of course if you’ve used Milestone Planner you could just invite everyone to the plan and ask them to update their milestones as they work on them!