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What The Princess Bride Can Teach Us About Project Management

Note: This post was originally published on Applied Intuition

By Will Sullivan

I watched The Princess Bride over the weekend, and I found it contained a few interesting lessons about about working with clients through the travails of production management. In particular, how to deal with that inevitable down period during a project we lovingly call “the pit of despair.”

You all know these pits well – they appear precisely at the point in every project when people stop having fun. Negative fun, to be exact. This period represents the sausage-making of any project where you start to drift into the weeds, feel overwhelmed by decisions and pressures, feel like it’s all more than you bargained for, that you’re losing sight of the purpose. It’s the point in the project where you’re looking for a glass of wine frightfully early in the day. Conveniently, these pits of despair always seem to occur smack dab at the point where full-swing content production meets design, meets development, meets executive approvals.

We know this period well. We’re usually the people who have brought you to the pit of despair, grabbed your hand, and plunged into it with you. Thankfully, we know the way out.

And this is why a few quotes from the Princess Bride struck me as so familiar. First, read this direct dialogue from the movie:

Westley: Where am I?
The Albino: [raspy voice] The Pit of Despair! Don’t even think…
[clears throat]
The Albino: … don’t even think about trying to escape. The chains are far too thick. Don’t dream of being rescued, either; the only way in is secret. Only the Prince, the Count, and I know how to get in and out.
Westley: So I’m here till I die?
The Albino: Until they kill you, yeah.
Westley: Then why bother curing me?
The Albino: Well, the Prince and Count always insist on everyone being healthy before they’re broken.
Westley: So it’s to be torture?
The Albino: [nods enthusiastically]
Westley: I can cope with torture.
The Albino: [shakes head enthusiastically]
Westley: Don’t believe me?
The Albino: You survived the Fire Swamp, so you must be very brave, but no one withstands The Machine.

Now let’s reimagine it by replacing all the above instances of Westley with “You” and all the instances of The Albino with…Us – The Consultant.

You: Where am I?
Your Consultant: [raspy voice] The Pit of Despair! Don’t even think…
[clears throat] : … don’t even think about trying to escape. The chains are far too thick. Don’t dream of being rescued, either; the only way in is secret. Only the production manager, the chief technical officer and I know how to get in and out.
You: So I’m here till the project is over?
Your Consultant: Until we kill you, yeah.
You: Then why bother prepping me for all this?
Your Consultant: Well, we always insist on everyone being very well informed before they’re broken in the pit of despair.
You: So it’s to be torture?
Your Consultant: [nods enthusiastically]
You: I can cope with torture.
Your Consultant: [shakes head enthusiastically]
You: Don’t believe me?
Your Consultant: You survived the project ramp up and the content phase, so you must be very brave, but no one withstands this period of a product launch.

Not that I like to compare us to Creepy Subterranean Henchmen, but it does sound a little familiar, doesn’t it?

And, just like the Princess Bride, this is where we typically start talking to you about True Love – or maybe just truebelief: Belief that a project will end up in a far better place than you ever imagined.

If you don’t happen to have the desire or ability to have this particular movie clip playing on loop in your office, here are a few specific things to remember as you approach, enter, and leave the Pit.

  • No Surprises.  The fewer surprises there are by the time you reach the pit, the shorter your trip. Surprises are reduced and eliminated by engaging in the process (being present during meetings, actually reading and commenting on milestone documents), and taking the time to understand how the process leads to the result. This means paying attention and asking a lot of questions early in the process, making sure you think about the approval process, understand risks and ramifications, etc.
  • Understand physics. For every action, there is an equal or opposite reaction. This is true whether you’re attempting to find the Higs boson or whether you’re building a blog. When you make decisions in the Pit – be sure to have conversations with your counselors about what those changes mean late in the process.
  • Slow Down. Take a deep breath before every decision. And then take another one. And then sleep on it. Knee-jerk reactions in the Pit tend to lead to broken pelvises – and no one likes that.
  • Have a little faith.  “To Believe” means you trust the people you’re working with – and hopefully even like them. Trust comes from a solid relationship based on open communication. Look for this when you’re hiring people and imagine how they’ll react when you’re in the Pit together facing the evil Prince Humperdink and the Six-fingered Man.

Every single project has a unique Pit of Despair. Being prepared, having true belief in your counsel and, let’s face it, being able to put up with a little bit of pain, are the keys to getting through.

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