Project start checklist

What do you need to have thought through before you start a project?

In a large organisation, like I left last year, there’s often a lot of heavyweight project management overhead. The downside is filling out lots of paperwork, but the upside is that it does make sure that the project is in good shape at the start. If it’s good project management paperwork, of course.

Working in smaller contexts lets you be much more agile and swift. Now I’m an independent consultant, I can start a project the moment I think it’s a good idea.

But how do I know it’s a good idea, and how do I know it needs more work, or is better not done at all? Obviously, using my skill and judgement developed over many years of working on projects. And that tells me that if it’s more than a teeny tiny bit of work, it’s well worth spending some time up front, to systematically work through what needs to be in place at that stage.

Some people would be happy to simply do that in their head and be done. But I am a huge fan of checklists. This post isn’t about the wonders of checklists. Suffice to say, the more experience I get, the more I think they are wonderful. They help make sure that the obvious things actually do get done.

So I have found myself wanting a project start checklist: a list of things that need to be thought through before I start a new project. It’s here, at the bottom of this post.

The checklist is deliberately skewed towards freelancing and consultancy, rather than internal projects inside large organisations that already have more project management overhead than they perhaps need. So, for instance, it doesn’t have any of the “set up project board” and “identify project sponsor” things you’ll find on other project start checklists. If you need to do those things, you (should!) already have a formal project management process. This checklist is for when you don’t have that. It would also work for small-scale guerilla projects inside a large organisation that don’t need official sign-off. It assumes the project is highly custom and not a standard one, which covers pretty much everything I do, but it is way more than you’d need if you are a freelancer doing well-established work – like, say, you’re a graphic designer and simply doing another logo for a new client. (Although even then some of the elements will be useful.)

The way I use it is to go down the list, systematically, and make sure I have a good answer to each question. To work the checklist magic, it is important to do them in order and not to skip any of them. (Obviously, if you don’t think an item belongs on the checklist, ever, delete it and never worry about it again.) If I don’t have a good answer to a question, a good argument for why it doesn’t matter in this context will also do. If I can’t answer a question with no good excuse, that’s a prompt to find out more before I start. Not knowing can be a red flag that this project is ill-conceived. Sometimes it’s the right decision to start a project before it’s all tied up and thought through. But better to do so having that potential risk in mind, and even better to mitigate that risk before it happens.

On to the list itself!


Is this project worth doing?

Ideally, it’s worth doing because I believe it will make the world a better place.

The underlying idea here is to avoid doing things that would be better not done. I like Peter Drucker’s distinction between “doing the right thing” and “doing things right”. Most of project planning and delivery is focused on “doing things right”. It is all too easy – and indeed necessary a lot of the time – to forget about the big picture, get your head down, and get it done and delivered. But the time before a project starts is a golden opportunity to pause and ask the big questions, like “What’s the point of this? Why bother?”.

Even if you think the project’s a terrible idea, it may be worth doing for other reasons. Not everyone can afford to be picky about what work they do, in which case, “it is worth doing because it will pay me money I need and I don’t have a better alternative” can absolutely make it a yes here. But if you’re doing that, it’s good to be aware that you’re in it for the cash (or the exposure, or the experience) not for the project itself. That way you’ll be in a better position to work to get more of what you want and minimise what you don’t.

Who actually wants this project to happen? Who directly benefits?

This is related to the first question, but different. I draw a distinction between someone who actually wants a project to happen because they themselves want the results, and someone who wants a project to happen so they can say that something like it has been done, for presentational or organisational reasons. So, for example, an organisation might want to be seen to be doing something about an issue, but they don’t actually care about it. They set up a little project, perhaps engaging an external consultant, so they can point to that as having done something, but they are not engaged in the issue. That doesn’t make it a no, but it is a different context to one where there are actual direct beneficiaries.

Fundamentally, it is often the case that people who are intent on doing something for someone else’s benefit have a different view of what would constitute a benefit to the  person themselves. I might sincerely want you to do good for you, but you will usually have a better insight in to what is good for you than I do.

This isn’t to say that I’m against building new things that people don’t yet know they want: far from it. (Think of the apocryphal story of Henry Ford saying that if he’d asked people what they wanted, they’d have said better horses.) But you need to know when you’re doing that, and how you will know that you have given them something that they do want.

Who are the other stakeholders and what should happen to them?

To many British people of a certain age, banging on about stakeholders makes you think about Tony Blair and the 1990s, or about frustrating project management paperwork, or both. It can be a little overworked, but I do think it’s worth thinking through who else will care, or ought to care, about a project you’re involved in, and what you’re going to do to them. Or with them. With them, totally.

Where is the value generated? Where is the money coming from?

This is again related, but may give different answers. For working in the commercial sector, it’s vital to understand where the business makes its money and how the project will impact on that. For other public and third-sector work, it’s vital to understand how they are funded and for what purposes, and how the project will impact on that. Grant funders – whether that’s the European Union, a research council, a foundation or a charity – will have a set of conditions on their funding, but there will also be a more a more implicit set of ideas about how projects they fund ought to work.

Will I get paid, and when?

This is, of course, the freelancer’s main question.

The obvious thing is to make sure the mechanics are in place. Is there an agreement to pay me? Does there need to be a purchase order, and if so, has it been raised? Have we agreed the invoicing pattern, and do I know who is responsible for paying the invoices? I don’t need much paperwork: I log every potential client, and I log every project. But the client and/or funder may have paperwork or processes to follow before the project can start. I can start work on my own initiative, but that may raise the risk that the project never officially happens, and I don’t get paid.

Underlying the mechanics (or overlaying them?!), there’s the question of whether they will pay when the invoices come in. What’s their cashflow situation? What’s their payment track record? This can crop up at all levels. A small company may have cashflow problems and have to defer paying you. A large company may have an imperative to juice this quarter’s financials and defer paying you. A university may defer paying because it is extremely bureaucratic and it’s nobody’s job to make sure you are paid in a timely manner.

Why do they need me?

Usually, this is because they need to get something done but don’t know how to do it, and so they’re bringing me in because I do. That will usually mean part of my role will be explaining what I’m doing and why. Sometimes it might be that they do have the skills but they don’t have the capacity, in which case there’s less need for explanation.

There are also projects with an aspect of management consultancy to them. Anything involving organisational change falls in to this category, but so too does most work on training and development. Here, it’s very important to understand the political context within the organisation before starting.

Do we have a shared vision for the final outcome?

If they’re bringing me in because I have skills and knowledge they don’t, my experience will be very different to theirs, so it is almost certain that what I imagine will not be quite the same as what they imagine. We need to do the work to ensure we agree what we’ll have at the end.

I can be happy to go without this, so long as the project plan has some way of bringing our visions together – although if that’s the case, I’ll usually prefer to have a break or review after the converging-vision phase.

Does the project plan make sense?

This is the bread-and-butter thinking through the project and planning it, or understanding the plan if someone else has produced it, and working through what my role will be. I need to work through what I’ll be doing, and how, and exploring all aspects of the project iron triangle (quality/scope, time, resource). This also includes how it will dovetail with my other commitments.

This question is where most of the planning effort goes in, but it doesn’t need extensive reminders on a checklist.

What is out of scope?

Obviously, a complete list of things out of scope of any given project is going to be pretty large. However, I do like to explicitly write down the things that one might reasonably think were included, but are not. This can be really useful to clarify with the client or funder, particularly if I can get it in to the paperwork.

What will you end up doing anyway?

Sometimes I want to do something to a certain standard of work and the client doesn’t want me to spend all that time (and/or pay me for it), so they say don’t bother with that. In many cases that’s fine. It can be important part of making sure we’re getting best value out of the work. Not everything has to be done to world-class research standards, and outside academia, done quickly is usually more valuable than done perfectly.

However, there are some things I simply can’t shortcut. One example for me is preparing for a presentation, talk or speech. I will always put the work in to be prepared to my own standards, even if that means skipping things I really want to do or staying up absurdly late. And I have tried but failed to make something without checking what similar things other people have done already. I don’t need to do a full lit review before starting a project, but if I havent spent at least a few hours exploring what’s been done in the area recently … I know I will end up doing that anyway. And I am an incorrigible data nerd, so if I collect some data, whether quantitative or qualitative, I know I will spend a fair amount of time getting to know it, regardless of whether I’m being paid to.

It’s better if I know to expect this than have it bite me yet again.

What if things are harder than expected?

A bit of thought ahead of time can help a lot here, and again the iron triangle (quality/scope, time, resource) applies: What aspects of quality or scope could I cut? Where could I find extra time? How could I get extra resource? How would I communicate and renegotiate if I can’t address the issue myself?



What could go wrong?

I like to do a project pre-mortem. This post isn’t about the wonders of pre-mortems, but they are a very useful tool. The idea here is you imagine that the project has failed and you’re working out what went wrong. How did it happen? It’s a cognitive flip: instead of only thinking about how it will succeed, you assume that it has gone wrong, and come up with ideas for how that could have happened. This can be very useful for spotting things that you are half-deliberately hiding from yourself because you don’t want the project to fail.

I’ve done a bit of flying in light aircraft, and like many aviators, I read a lot of air accident investigation reports. Often, when you these reports, you can see that bad judgement was present at the start. So a useful question to ask when preparing to fly is “How would this look in an accident report?”. That can keep you on the straight and narrow, and out of obvious, well-known mistakes.

So, in this context, how would you talk about this phase of the project if it later turned out to be a disaster? What were the red flags, the early warning signs, the classic blunders, the usual procedures avoided?

What would huge success look like?

This is a question I picked up from a cheesy talk some time ago. It’s not my usual style: I’m quite undramatic and practical. I think a lot of massive success is luck. But I do believe in making sure you’re keeping the door open to runaway success should it show up, and not closing it off as a possibility so it never does. This often leads to practical decisions like making things easily scalable, being open, and so on.


What are the Benefits, the Risks, the Alternatives, your Intuition, and what would happen if you do Nothing?

This checklist has already covered the benefits, but the risks and the alternatives need to be explored, as does the do-nothing option. This should also cover the opportunity cost of taking this project on. If I didn’t do this, what would I be doing instead?

And I always need a reminder to check what my intuition says. What does your gut say? What does your heart say? I am very much a brain sort of person, but instincts arise for a reason, and it’s worth paying attention if my analytical brain is saying this is a great idea but my emotional brain is reacting like it’s a terrible one.

(BRAIN is an acronym/method I have shamelessly stolen from decision-making around childbirth. It’s fair to say I have more experience of bringing new projects in to the world than new people, but I have found this exercise to be a useful one when faced with any major decision.)
Brain Waves

What about personal information?

This is the GDPR question. What personal information will be generated, used, and managed in the project? And what needs to be done about that? This can be a very big question, and can roam well beyond a quick checklist, but it needs addressing on pretty much any project.

Luckily for me, this is one of my interests, so it’s not too hard for me to do. If you don’t have that background, it’s worth getting some advice if you’re not sure.

What about intellectual property?

The main IP in my projects is copyright. Almost everything I produce in the project – writing, code, interfaces, graphics, diagrams – will have associated intellectual property rights. What is going to happen to them? The client is paying for me to produce them, but what scope will there be for me and them to use them later?

I am a big fan of free and open source software and of Creative Commons licensing. As an idealistic youth, my first enthusiasm for them was about the value of increasing access to things. But as my experience has grown, my main enthusiasm now is about the immense value of an open license in making sure that everyone involved will be able to build on their previous projects in the future.

A project brings people together. If the products of that project are available only under a closed license, it can be difficult to all but impossible to get the necessary paperwork together to prove that it is Ok to build on those products to make something even better. But if it was licensed openly, there’s no such problem: the license says anyone can build on them – and anyone includes the original contributors!

However, I’m a pragmatist and I’m very much of the view that not all projects are suitable for release under an open license. If so, how are we going to manage the IP generated?

As well as the stuff generated by the project, it’s worth thinking through what is happening with pre-existing intellectual property: the stuff that I am bringing in, and stuff that others are bringing in. Do we need an explicit agreement about that?

In my line of work it’s less common for patents, designs, and trade marks to be involved than copyright, but it’s worth thinking through if anything in that area is going to come up and deal with it up front.

Again, this can be a complex area, but luckily for me it is one of my particular interests. This does vary considerably between jurisdictions – for instance, I know the US has work-for-hire laws that set a very different context.

What will I learn?

One of the things I enjoy most is learning about an entirely new-to-me area of human endeavour, so if there’s an opportunity to do that and get paid for it, I’m going to be very keen.

But even when it’s well within areas I’ve worked in before, there’s almost always the opportunity to learn something new, pick up a new tool, get better at a particular task, or something in that line.

My hope is that using this checklist will help increase the chance of learning positively from a project, and decrease the chance of it being the old joke of “another bloody learning opportunity”.

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