How to Project Manage Even the Worst Kind of Work

I love solving problems. And pretty much every kind of work I do — from marketing to copywriting to project management to video production to creative writing — is, at its roots, the act of creatively solving a problem.

But solving problems requires a clear understanding of every variable involved… and sometimes that’s not always possible.

In fact, there’s one type of work that I hate to do, but it’s also the only kind of work that will help me grow and accomplish new things. What a perfect catch-22, right?

So what is this nightmare type of work?

Any work whose scope I don’t know completely before I begin.

In project management terms, this could mean a gig that involves any of the following:

  • No clear deadlines
  • No clearly-defined responsibilities for each team member
  • Highly subjective components that will need to survive multiple rounds of review
  • “We thought we needed X, but it turns out we really need Y.”
  • “We thought we needed X, but it turns out we really need X+Y.”

Whether I’m doing these as an independent contractor, a consultant, or an employee, each of these situations is a recipe for an ulcer. (If you’re nodding right now, it’s because you’ve survived your fair share of these same types of projects and you’re hoping you’ll never end up in those leaky boats again. Keep reading; there’s a solution at the end.)

But there’s one more aspect to a project that’s even worse for me than any of those, and I bet you feel the same:

Any work where I don’t yet know what I don’t know.

I’ll give you an example.

At my last day job, I was put in charge of getting our company set up for a huge trade show. There was just one problem: I’d never done that before. Not only did I not know the answers to a whole lot of brand new questions, but I didn’t even know what questions I should be asking.

Was this an interesting challenge? Absolutely.

But it also felt like a crushing black hole, because I literally had no idea where the edges of this task were, and all those “unknown unknowns” made me feel like I was completely out of control of the situation.

Now, I should mention that I’ve also done a slew of crazy and complicated things in my life. I became a radio DJ with zero experience, I moved across the country in a car by myself, I filmed a series of safety training videos in active steel mills, and I launched a web series years before YouTube existed. Figuring out the unknown is not beyond me, and it can often be exhilarating.


In each of those cases I mentioned, I had two very important things: help, and a clear understanding of the scope (or lack thereof).

When I became a DJ, I was trained by people who’d already been doing it. It was new and unknown to me, but they gave me hands-on experience and clarified the scope of what we couldn’t and couldn’t do (or get away with).

When I moved across the country (in 1999, before the days of smartphones), I had maps. I may not have driven down those roads before, but I understood the scope: I knew where I was headed, where the roads led, and where they ended.

When I was filming videos in steel mills, I may never have been inside one before, but I had a corporate contact who was escorting me around and who could negotiate certain filming details with the machine operators, and I had a clearly-defined shot list so I knew exactly what we had to get done each day.

When I started a web series, there were no rules about what you could or couldn’t do online, so the sky was the limit… and I probably would have been paralyzed by choice at that point, but the cast I’d assembled and our access to specific locations helped define what the show would become.

In other words, although there were plenty of unknowns, and plenty of skills I’d need to learn in order to be good at these new gigs, I had access to help and I could see the borders of what was possible / necessary, so I viewed all those unknowns as fun experiments to conduct and interesting problems to solve, rather than sources of misery.

Thus, when I had to make sense of our trade show task, I did the same thing that had made sense for me in all those previous instances: I found help, and I established a scope.

In that particular case, I managed a team of sales reps, product managers, trade show booth designers, and liaisons from our PR agency. We each had clearly-defined roles, and every time a new question came up the responsibility of finding out an answer was assigned to one of us. We had a weekly progress call in which every action item was reviewed, and we shared documents where all our sub-tasks and their statuses were clearly visible — and if a new task popped up, it got added and delegated.

Did we need to develop new skills or strengthen existing ones in order to get the job done? Of course — but we did so within a clearly-defined context.

Did everything go completely smoothly? No, but we learned as we went.

Was the trade show a success? Yes. We even repeated that effort on a smaller scale at two more shows thereafter, because now the whole process was no longer an unknown: now it was just a series of variables with a clearly-defined scope.

Now it was manageable.

Now the unknowns were all known.

What Does This Mean for You?

If you only ever take jobs or do work that you’ve already figured out, you’ll never grow. You’ll just keep running in place until you’re obsoleted. But taking risks and trying new things can feel daunting for a variety of reasons, including that terrifying haunted house of unknown unknowns.

But those unknowns only seem scary because they’re nebulous and ill-defined — so defang them by defining them.

If, like me, your stomach drops when you realize you don’t know everything you need to know in order to complete a job, there’s a way to fix that. (And it’s not “defer the whole thing for as long as humanly possible,” which is still my first reaction almost every time it comes up.)

Here’s what I do when I find myself in this situation now:

  1. Figure Out What Success Looks Like — and Get Specific. Is a client’s goal to “develop a marketing plan,” or to “develop an 18-month marketing plan with must-have and nice-to-have budget variations”?
  2. Figure Out the Hierarchy. Who’s in charge, who’s here to help, who absolutely must sign off on what along the way, and who can be ignored or overruled if push comes to shove?
  3. Set Deadlines. Even if no one is asking for them. (And especially if people are asking to not have them.)
  4. Get Everyone Using the Same Documents. On one recent gig, we had a 5-person team and a series of Word docs that were ballooning in size and variation — v2, v2b, v3edit — all flying back and forth through email. I asked if there was a reason why we weren’t using Google Docs to eliminate versioning. “We’ve never done that before.” Was there a rule against it? No. So we used Google Docs and saved our sanity.
  5. Figure Out What We Don’t Have Answers for Yet. These are the “known” unknowns. Your trade show booth space is 24 feet x 24 feet? Great. So how large are your booth components? Who’s working at which demo station at which demo times? Which direction will most foot traffic be coming from? Those are known unknowns, because you know which variables are in play.
  6. Figure Out What We Don’t Know at All. These are the “unknown unknowns.” You don’t have a name for the product we’re demonstrating yet, so you don’t have a marketing plan or even a color scheme in place? Okay, those are a lot of unknown unknowns, and that’s dangerous because those are the ones that can screw up your scope and force even your known unknowns to shift. FIX THESE AS SOON AS POSSIBLE.
  7. Figure Out If I Need to Learn Any New Skills. You want me to rewrite your website’s copy? Sure. You want me to also publish that copy by accessing your CMS which I’ve never used before? Hang on, let me grab this online tutorial and some Ibuprofin…
  8. Break the Process of Answering Unknowns or Learning Skills into Schedule-able Sub-Tasks. You don’t know what your entire marketing plan is yet, but you have a trade show coming up in ten weeks? Great; here are all the specific steps between “I don’t know what my marketing plan is” and “Hey, here’s my finished marketing plan.” Get each of those steps scheduled into your master checklist and assign the accomplishing of each sub-task to an actual human. Now, instead of a black swirl of confusion, you have a concrete list of answerable questions with deadlines attached.

Life is still full of unknown unknowns, but at least now you have a blueprint for scoping them.

Doesn’t seem so scary in the light, does it?

Image: “Nightmare” by Michael Koralewski via Flickr Creative Commons License

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