I have seen many projects fail; often despite the best intentions of of the people sponsoring and working on them. Often they fail because they change in small steps over time until they are no longer capable of delivering on the outcomes they were established for.

The Standish Group produced the chaos report a number of years ago that examined the reasons for project failure. It’s an eye opening read and I have seen many projects fail for the reasons outlined in the report.

To my mind though, these projects failed because people didn’t ask good questions at the right time.

A large part of good governance is asking good questions. The following are 5 questions that I think are great to ask at any time on a project. People with governance responsibility for a project (i.e. project boards or steering groups or whatever) should definitely these questions and more. But anyone can ask them, at any time.

If you are new onto a project, these can be quite a good way to get a feel for the project. If you are working on a project and you ask one of these questions and can’t get a straight answer, then I’d suggest that’s a warning sign that the project is in danger of going off the rails.

Why are we doing this project?

As a proud dad I have answered many “why” questions; often frustratingly many. But it seems to me that we grow out of that desire to know why. We need to recapture the power of “why”. “Why” is one of the most powerful questions you can ask.

“Why are we doing this project?” If you are new on a project this is a great question to ask. Start with the project manager. If they can’t tell you very succinctly then they may not really know the answer themselves. If you are the project manager ask your sponsor.

But ask other people too. Ask the people doing the work; whatever it is. I have often found many of the people in a project team don’t actually know why the project exists. They know why they do their work; but they don’t know why there’s a project that wants them to do their work. If the team don’t understand the why then it is very easy for them to make small decisions everyday that slowly take the project off course.

People sometimes get upset with “why” questions. That’s usually also a sign that they don’t know. I have found that people who do know usually love to tell you. My experience is that projects where everyone understands the why (and aligns to it) are much more likely to be successful. And they are often much more fun to work on too.

Who are we doing this project for?

There are many answers to this question, we need to know them all, but some are far more important than others.

One often overlooked answer to this question is “our customers”. I have seen many projects fail, not because they didn’t meet their business stakeholder and sponsor needs, but because they failed to meet customer (internal or external) need.

Again, if the people working on the project don’t know who will be using the solution this should be a warning sign for you.

Who is paying for this project?

I once worked on a project that was paid for by one part of the organization delivering changes to another part of the organization primarily to provide benefit to users in another part of the organization.

When the person paying is so far removed from the people mostly affected by the work the project is in trouble. With out very effective and clear governance and project management that includes clear and strong representation from the people most affected by the project’s efforts there is a considerable risk that those end users will be steam rolled by a project that is likely to make their life worse.

Who else is doing, or has done, something like this?

A project is a temporary organization set up to deliver to some set of outcomes. The temporary nature of a project means that it generally doesn’t have a past to learn from. This is a key question to ask at the beginning and then throughout the life of the project. Basically you want to know if there are lessons others have learned the hard way that you can benefit from.

I often find project teams become very insular. They become solely focused on what they are doing and become blind to what is happening around them. This is a great question to ask to get a feel for whether a project team succumbing to this insular mindset. If people answer: “I don’t know” then they are probably starting to zoom in.

In my opinion; if people answer “no-one” it’s even worse. This is an implicit sign of hubris. If they think no-one else in the world is doing something like they are doing they are probably mistaken. Sure; the specific details might be different, but my experience is that most projects have more in common that not. And the “no-one is doing what we are doing” response implies that they feel like they couldn’t learn off other things that are going.

“Why don’t we stop doing this project?”

You have to be a little careful with this question, I’ve found people can be quite offended by it. Most projects had to be fought for to get started in the first place. Funding had to be found from somewhere (possibly meaning other people lost out on that funding). Business cases of some description had to be developed. People become invested in it. They develop a kind of confirmation bias. Because they have given their blood, sweat and tears to get this far, they fight tooth and nail to carry on; even as the business case they developed to do the work erodes from underneath them.

This attitude gets worse the more money they spend as well. “We’ve already invested a million dollars, we can’t just walk away from that?” is something I’ve heard all too often.

People reactions to this question will give you an insight into whether or not they are slipping in to this kind of confirmation bias.

My view is that it’s never a bad time to ask these questions. Many times I’ve asked them I don’t actually care that much what the answer is. What I care about is that there is a clear answer. Because that is evidence that people have done the thinking, analysis, planning, consulting etc that you need to have a successful project.

Matt Mansell HeadshotMatt Mansell is an organizational change provocateur who uses lean change techniques to help organizations grow and evolved. He’s also a part time philosopher and theologian and a full time dad. You can connect with Matt on his personal website: CultivateChangeConsulting.com  Or via email @ mattmansell@cultivatechangeconsulting.com