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Advice / Succeeding at Work / Productivity

How to Get Started on an Incredibly Daunting Project


“Get rid of all the paper.”

I was a project manager working in the New York City Mayor’s Office, and this was the task I was assigned to accomplish. In a bureaucracy with hundreds of thousands of employees, thousands of paper-based processes, and a limited budget for new technology, I was asked to develop a plan for digitizing just about everything.

This was a daunting project if ever I’d seen one. It was, in fact, next to impossible given the constraints within which I was working. But I couldn’t throw my hands up and say no. I had a job to do and I had to begin somewhere.

Project Paper Elimination was not an unqualified success. In fact, it was closer to an unqualified failure. If you walk into any New York City office today, you will most definitely find paper piled up on desks, in inboxes and outboxes and recycle bins.

Yet, the project taught me more about how to begin an overwhelming task than any success I’ve ever had. Here’s how I learned to take something seemingly insurmountable and tackle it in bite-sized pieces.

1. Take Stock of the Big Picture

New York City has dozens of departments, each of which has dozens of divisions, each of which has its own internal processes. There is paper that already exists in file cabinets and boxes, and paper still to be created when customers and employees fill out forms and applications. It was impossible for me to know where to start before I took stock of all the paper-creating processes out there. Which ones generated the most paper? Which ones lent themselves to digitization, and which ones had complicating factors, like the need to accept money? Which would produce the biggest bang for the lowest buck?

I spent a solid few weeks canvassing every department to get a feel for the scope of the endeavor. Doing this initial assessment can help to define your scope, as well as what belongs inside and outside of it. It can help you communicate to your higher-ups the breadth of the task and get their feedback about what they care about most. And it helps you navigate your way to a logical starting point.

2. Find an Example of Success on a Smaller Scale

In the case of Project Paper Elimination, the Health Department had recently undertaken a paper reduction project prompted by an office move. They didn’t want to take all their paper records with them if they didn’t have to, but they didn’t know which ones to take and which to leave behind. So they implemented a multi-phased project: Define what legally needed to be retained, destroy what didn’t, and scan anything for which a hard copy wasn’t required. They’d implemented the technology and the staff to make it happen, and they had the results to show for it.

One size doesn’t always fit all, and new considerations arise when you increase the scale of a particular project. But an example of success not only offers proven methods to achieve the same goal you’re out to achieve, it can also allow you to learn from the failures of others. It provides a model you can use as a starting point. You might need to modify, expand, or adapt it to fit your own objectives, but it’s easier to react to something than to start from a completely blank canvas.

3. Identify the Low-Hanging Fruit

Yes, “low-hanging fruit” is surely on a list of overused office jargon somewhere, so let’s call it what it is: the easy stuff. The stuff that costs the least and takes the least amount of time to do. In the case of Project Paper Elimination, this meant things like getting rid of obsolete paperwork, creating simple online forms, and disposing of records long past their expiration dates.

There are a few reasons to start with the easy stuff. First off, it gives you some notches on your belt. This feeling of forward movement, minimal as it might be, is an important psychological win. It gives you momentum, fuel for the more challenging work ahead. And second, it allows you to demonstrate progress to the project’s stakeholders, generating faith in your ability to deliver on future phases of work.

4. Lay Out Your Biggest Obstacles

Even as you tick off the little successes, it’s important to take that feeling of an impossibly looming challenge and break it into concrete obstacles. Without naming them, it’s so much more difficult to develop strategies to overcome them. In the world of paper elimination, one obstacle was the complexity of capturing data entered into an online form, and another was accommodating legal requirements for electronic signatures.

Laying out these obstacles might lead to the discovery that a perceived obstacle is not as big a challenge as you initially assumed. It might, alternatively, bring to light a major roadblock you’d previously thought to be minor. Knowing what the hurdles are early on will prevent you from being blindsided when you’re already knee-deep. It can also help you to line up the resources you’re going to need to tackle them, whether it’s political support, funding, or expert guidance.

5. Phase Out the Work

The Chinese philosopher Lao Tzu famously said, “a journey of a thousand miles begins with a single step.” It is also true that a journey of a thousand miles consists of four smaller journeys of 250 miles, or 10 journeys of 100 miles. Breaking your daunting project into manageable phases makes it that much less daunting. And it gives you realistic interim milestones to aim for between step one and step done.

Trying to digitize paper-based processes in New York City government, there were several options for phasing out the work. One approach was to tackle a certain number of departments at a time. Another was to start by determining which paper could be eliminated, continue by implementing the technology to digitize it, and conclude by training staff and advertising the new technology to customers. The most logical way to phase out an overwhelming quantity of work will vary depending on the nature of the work itself, but it’s always worth tackling before you get in too deep.

6. Set Expectations

Whatever you do, don’t over-promise what you’re not confident you can deliver. Ask for what you need to make it happen. And if you can’t get it—whether it’s people, money, or technology—then explain the ways that might affect your timeline. Sometimes an executive will ask for something without a nuanced understanding of the work required to achieve it, but once you’ve pulled together your assessment and identified the obstacles, you’re in a position to communicate this nuance.

Shaking your head and running in the other direction is a common, and sometimes justified, reaction to the most overwhelming projects. But it’s guaranteed to get you nowhere. Even the most daunting task can be wrangled with the right outlook, a solid understanding of the work ahead, and a set of realistic and achievable milestones to check off along your way.

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