The Valley of Doubt

Managing creative projects through uncertainty

I used to think it was me. That soon I would be exposed as a terrible project manager. My team was lost. The challenge was seemingly insurmountable, looming on every side as the deadline approached. How had I got us here? How had I led us to disaster?

I call this place “The Valley of Doubt” and when I think back, I’ve rarely delivered a genuinely creative project that at some point hasn’t gone through it. Because coming through The Valley is to be expected, even celebrated.

Unfortunately, The Valley looks very similar to the “Desert of Death” — and the former can very quickly become the latter if you plough on aimlessly. Not only is it right to be attuned to that danger, but it’s the very thing you should be protecting your teams from.

The problem is, we’re on unmarked paths. The greatest creative breakthroughs can come when all others have abandoned hope, and yet we’ve all seen weeks and months lost to noodling around in the pursuit of nothing valuable.

Don’t panic!

You might not go full Corporal Jones, but you’d be surprised how teams can see the fear in your eyes. While your emotional response can be an important tool in your toolbox, don’t weigh others down with it until you know it’s the right thing to do.

Creating new things isn’t linear, although we (especially the ‘organisers’ amongst us) too often expect them to happen as if they are. We set deadlines and milestones to track progress and to hold people to account, but while these are valuable tools, we need to understand their limitations in giving us a true picture of progress.

Ultimately, if we want to step into the unknown and go to the edges of what’s possible, then there has to be a risk. That risk comes with that feeling in the pit of your stomach that this time it might just not work.

This is normal. It’s ok to feel like this. You now need to do something productive with it.

Look up

I’ll never forget the hill-walking expedition where having scrambled the final metres to the peak, we looked up confused and wondered where the sign saying ‘Snowdon’ was. In fact, wasn’t there meant to be a cafe? It slowly dawned on us that we’d climbed the wrong mountain.

Somewhere, about an hour earlier, we’d unknowingly forked in the wrong direction, but convinced we were making progress by our continued upward movement we kept going until we stood windswept and hungry on the wrong summit.

It’s easy to do this on projects — to lose ourselves in the daily progress and forget the big picture. Ensuring there is a shared understanding of the objective is a good place to start. If your team are in agreement on the challenge ahead of them, then the tensions are more likely to be the ones expected as part of a creative process. If you’re not sure: clarify and if necessary, reset.

My only word of caution is that too much time debating the objective in the abstract can sometimes lead to unhelpful navel-gazing and a bit of “what-does-it-all-mean-anyway?”. Remember that in managing this conversation, you’re only looking for a ‘good enough’ sense of where you’re heading. There’s still plenty more to learn along the way.

Create space

I remember from my early days as a project manager, creating space was something traditional advertising used to be incredibly good at. Creative teams could be given weeks of space to tackle a challenge (oh, the budgets!). And while you could say that the freedom was abused at times, with weeks spent in the pub followed by a couple of all-nighters just before the deadline, there was a truth in it. To think creatively you need time and space.

Give space to your teams. Allow them to think in a non-linear way. Relieve them of the burden of constant updates (even to you!). Creative thinking often looks like nothing we’d regard as ‘productive’. But build trust with them, and understand that sometimes you just need to ignore the (occasionally terrifying) concerns you feel as a manager.

Find a balance

While these ideas are hopefully helpful, they aren’t hard and fast rules. Part of becoming better at leading creative projects to success is learning to manage the tensions, and to balance all of the factors involved — who your team are, their personalities, their experience, your relationship with them, your organisation style, the tolerance of failure… The list goes on.

Unfortunately, it’s the project manager’s curse to see every potentially impending disaster before it happens. It’s like living constantly in the opening scene of Casualty. While you won’t get it right every time, in time you’ll get better at understanding what risk you can live with. You’ll become comfortable with feeling uncomfortable and learn to differentiate between when it’s just part of pushing your boundaries or something going truly awry.

There aren’t any easy solutions, but tackling The Valley is part of the adventure.