Choking on an Elephant


This morning, I was going to riff on some tired tripe about “eating an elephant… one bite at a time.”

And then realized: I would hate reading something like that.


Even so, tackling seemingly unassailable – and impossible-seeming – projects has been very much top of mind for me these days. And honestly, it is making me put my best problem solving, King Solomon decision making skillz to the test.

Without falling back into tired homilies, then – how does one begin managing the unmanageable?

Identify the “big problem.” First, you must understand the big problem needing to be solved. Surprisingly, many projects go off the rails at this very step. Correctly identifying what the big problem to be solved is, and keeping it at the center of every conversation in the project, is vital to having a successful outcome on the other end of the process.

Break the big problem down. Once you identify the “big problem”, begin deconstructing the process by which you will obtain a solution. Draw pictures. Paste stickies to the wall. Create user personas and user stories. Create tasks that are understood by the team, and make sure everyone on the team understands how each task leads to the completion of the big problem.

Assign responsibility. Once the big problem has been deconstructed into manageable chunks, the next step is to assign responsibility to the oversight of each element in the process. Maybe it’s a project lead, or engagement manager. Perhaps it’s even a user. Someone, or a collective group of someones, must ultimately be accountable to each element of work.

Set milestones. As travelers, we know where we are, by the milestones we pass along the way. The same is true of our projects. Milestones are those events in the life of projects, by which we gauge our progress – or the lack thereof. Defining milestones is not a passive activity – it requires careful thought and communication, and may not be strictly defined by individual sub-projects within the project. It might be when “minimal viable product” is reached. Or, when you can invoice for the next payment. Whatever your milestones are, they should be broadly visible, universally understood, and tied directly back to those held responsible (see previous paragraph).

Monitor progress. If you adhere to an Agile development process, you monitor your progress through your scrums and by what is accomplished through each run. If you are less formal, perhaps you simply check in with your team on a regular basis. Whatever your style, methodology, or philosophy, you need some form of continuous feedback to let you know where you are. And by monitor, I don’t mean show up when a milestone is supposed to be complete, and expect everything to be hunky-dory. Be engaged. Be attentive. Be proactive.

Adjust as needed. This is a natural consequence of monitoring progress. Because – surprise, surprise – all our well laid plans have to exist in the real world, where vacations, life, unforeseen events, and plain old human frailty conspire to bring our projects to a screeching halt. You need to be flexible, and make mid-game adjustments, if you ever want to foster your behemoth project to a successful end.

Now, your mileage will definitely vary. And, if you’re fortunate enough, you will live through many iterations of current management style, speak, and methodologies throughout the course of your career.

What your project management success will ultimately boil down to, is mastering how to go about solving “intractable problems”, regardless of the fact-dependent and unique circumstances of each individual project – and applying those lessons learned from each engagement, toward the betterment of the next project you encounter.

Go, and be you.