I remember singing the song “ Going on a Bear Hunt ” as a little kid. For the uninitiated, the song is about some folks going out in search of a bear and coming across a variety of obstacles on their way: tall grass, oozing mud, a cold river. With each hurdle, the hook repeats: “Can’t go over it, can’t go under it, gotta go through it!”
Working in city government brought these lyrics to mind time and time again. In government, as with large, bureaucratic organizations of any kind , there are often structural elements that slow the pace of progress (more on that, here ). In many cases, rules were put in place decades earlier to prevent corruption or manage a problem specific to that era, but the outdated regulations remain on the books, thanks mostly to inertia.
I often felt that I was not only unable to go over or under the obstacle before me. Sometimes I couldn’t even go through it. Sometimes there was no route I could think of to get from point A to point B. And that’s when I got creative.
Here are the three most frequent obstacles that threatened to derail my work throughout the years, how I managed to get through them, and my advice for anyone who needs to do the same.
1. It’s Too Expensive
“It’s a great idea, but it’s too expensive.” In many businesses—but especially in government—money is almost never not an issue. The very first question someone’s going to ask about an idea that’s even mildly plausible is whether there’s budget for it. No matter how brilliant the proposition may be on its face, it can’t be done if it can’t be funded.
No, money doesn’t grow on trees , but sometimes you can find it in unexpected places—even after you’ve gone back to the budget countless times, scrimping everywhere you possibly can. The first thing to do when your budget’s been denied is to take a step back from the whole thing and ask yourself which aspects are must-haves, and which are merely nice-to-haves. How to know the difference? Eliminating a must-have would completely derail the endeavor, while ditching a nice-to-have will still allow you to achieve your central mission. It would be nice, for example, if those new handheld devices for building inspections had turn-by-turn navigation and high-resolution cameras. But if neither of these is required to get the inspection done, then neither one is a must-have. See if cutting out the nice-to-haves helps you shave off a few dollars.
Next, think through whether any elements of the plan can be implemented at no cost. Sometimes there are process changes, for example, that can get you well on your way to your desired result without all the expensive bells and whistles. And if you get enough momentum with those no-cost changes, you might be able to make a better case that an investment is worthwhile.
If the money’s simply not showing up, you’ve got two more options to try to make it rain. First, see whether there’s anywhere you can find cost savings that can then be redirected to your initiative. If that fails, look into whether there might be a partner who would benefit from donating goods or services to the cause. In New York City, for example, the Mayor’s Fund works with outside donors interested in testing unproven ideas. It’s good PR for them, and it gets the job done for you.
2. It’ll Take Too Long
Passing new laws. Registering contracts with new vendors. Either of these can plague a project timeline, whether you’re working inside government or working outside of it on anything that brushes up against it. These can be some of the most rigid and structural hurdles, so how do you get around them?
The first order of business is to start digging for loopholes. Not the kind of loopholes that get one in trouble, but totally legitimate alternative approaches to the standard way of doing things. For example, when my team was working to find new ways for New Yorkers to pay their taxes and parking tickets, we learned that a new contract could take a year. We just didn’t have the time to wait. So we found a little-used contracting method that shaved at least half a year off our timeline. All it took was a little digging in the rulebooks and a bit of pestering at the procurement office.
Another approach is to divide what you want to do into a series of smaller initiatives. Rank them from easiest to hardest to enact. At the top of your list, you have your low-hanging fruit: the items you can get done in a day or a week, at little cost and minimal effort. Start here. Begin to prove the value of your idea. Sometimes the more complex pieces will take longer, but if you’ve set the machine in motion as you pursue the longer-term goals , you’ll see steady progress that wins you champions who want to see your project succeed.
3. But We’ve Always Done it This Way
In the tech sector, companies thrive on innovation: Keep doing things the old way and you fail. In more traditional sectors, like government, the status quo is often held close, like a child holding onto a life preserver even though she’s fully capable of swimming. This obstacle may not seem insurmountable, but it can be very difficult to convince the powers that be to embrace change if they believe the current situation is working just fine.
The trick is to challenge your naysayers’ assumptions without being insensitive . You might begin by finding examples of other organizations—cities, states, or companies—that implemented a similar idea and met with positive results. If someone else served as a guinea pig, you can reach out to them to understand the challenges they faced, and the improvements the changes brought to bear.
Another way to get holdovers to see the light is by showing them the benefits in real time. The proof, as they say, is in the pudding. You may not be approved to go ahead across multiple divisions and hundreds of employees, but a limited pilot project can bear out your idea on a small scale. It moves your bright idea from the theoretical into reality. It will also uncover whether there are any flaws in your thinking, or weak spots you hadn’t thought through. Seeing is believing, and success in the baby pool may get you the green light to move into deeper waters.
Of course, there are only so many ways you can get creative while keeping things totally kosher. Situations will arise when you hit a wall, and the only way around it is to back up and take a different route. But that wall is too often imagined when it doesn’t exist. Train yourself to run through all the alternatives. Where the bear hunters have their across, between, and beside, you should have a stable of questions at the ready for roadblocks. Ask yourself these questions and map out all the scenarios you can think of, even if they seem ridiculous. Sometimes the ridiculous idea comes just before the brilliant one. And sometimes, it actually works.