Business leaders like Richard Branson and Mark Zuckerberg are famous for making quick decisions to launch and grow their companies. “Move fast and break things” has become a Silicon Valley mantra that permeates all of business.

But since not everyone is superhuman like the Bransons and Zuckerbergs of the world, you might struggle to make those decisions. When there are 15 good possibilities, how do you know which is the best one?

There’s an old (hopefully apocryphal) story that perfectly illustrates the analysis paralysis many of us feel on a daily basis. It goes something like this:

A donkey is very hungry and very thirsty. The assumption is that if offered both food and water, each placed in opposite directions, the donkey will go for the closest one first. However, if the hay and the water are placed equidistant apart, the donkey will be unable to decide which way to go and slowly starve to death.

What an ass.

To be honest, the incident never happened, and the theory was never a serious one, but maybe you can identify with the donkey anyway.


  • Do I take the job I hate for more money or the job I love with lower pay?
  • Do I live in the city, where my kids can experience urban life? Or the country, where they have room to ride their bikes?
  • Do I hire Candidate A or Candidate B?
  • When my company is ready to grow, do I buy off-the-shelf software or custom software?


American business values the fast moving, quick thinking decision maker more than other type. But even the best of us can wake up one day and find ourselves paralyzed with all the options.

The Danger of Analysis Paralysis in Business

As a business leader, your daily decisions could make or break your company. How do you know which way to go when time and resources are limited? 

Analysis paralysis–or the paradox of choice–never happens when there is a clear cut winner. You won’t ever choose being trapped in a burning building over taking a vacation, but deciding between the beach and the mountains can paralyze you so much you never pack your bags.

Let’s take the analogy one step further. What if escaping from the burning building relied on your choice between the beach and the mountains, but you don’t know which choice will get you out of the flames?

That’s how it can feel in business. There are only limited resources, and many roads might lead to success. But there’s no concrete way to know ahead of time which those are.

We experience this as a company all the time. Should we focus on building websites or more robust apps and products? Should we spend marketing capital on sponsorships or on hosting our own events?

Should we have turkey or fried chicken for Thanksgiving dinner??

(Come on, team. This answer is so obvious.)

Our Secret Solution to Analysis Paralysis

Terrible menu choices aside, what do you do when you can’t decide which way to go? At Centresource, we have our own unique way of moving forward.

Whenever we find ourselves in a loop–and in a holacracy, this happens a lot–someone always pipes up to ask one of two questions:

  • Is it safe enough to try?
  • Will this bring us harm?

Whether it’s an internal initiative or we need a client to make a decision, these two questions focus in on the things we can really answer.

Is it safe enough to try?


The certainty effect is a key component of the prospect theory, developed by Daniel Kahneman and Avery Tversky. Basically, it says that we are more likely to gravitate towards choices with certain outcomes, even if those certain outcomes aren’t as beneficial as the probable outcomes of a different choice.

We’ll choose safety over risk.

But here’s the thing we forget: there are no certainties. (With medical advances and the current tax structure, we can’t even be sure about death and taxes anymore.)

Choosing an option for “certainty” isn’t always the best, and looking for certainty is likely to hinder you from ever moving at all. That’s why we ask ourselves, and our clients, “Is this safe enough to try?”

There are sometimes real reasons that a solution is not safe enough to try. When a product doesn’t meet user’s needs, don’t launch it. That’s not safe.

When the answer is, “no,” it’s time to figure out what’s keeping it from being safe. Then we can address that issue and move us closer to launch.

Internally, we faced this last year when it came time to replace a project manager. We decided that rather than incurring the expense of hiring, we could distribute the responsibilities to two of our strategists. After a lot of thoughtful planning, we decided it was safe enough to try.

It turned out not to be. The strategists quickly became overwhelmed, and we discovered that the skillsets didn’t align. But, in the interim, we also discovered that one of our favorite PM’s from earlier days was willing to come back to the team. If we hadn’t tried the other tactic first, we could’ve missed out on a great rehire.

Louis C.K. talks about “safe enough to try” in his own brilliant way:

“These situations where I can’t make a choice because I’m too busy trying to envision the perfect one—that false perfectionism traps you in this painful ambivalence: If I do this, then that other thing I could have done becomes attractive. But if I go and choose the other one, the same thing happens again. It’s part of our consumer culture. People do this trying to get a DVD player or a service provider, but it also bleeds into big decisions. So my rule is that if you have someone or something that gets 70 percent approval, you just do it. ’Cause here’s what happens. The fact that other options go away immediately brings your choice to 80. Because the pain of deciding is over.

“And,” he continues, “when you get to 80 percent, you work. You apply your knowledge, and that gets you to 85 percent! And the thing itself, especially if it’s a human being, will always reveal itself—100 percent of the time!—to be more than you thought. And that will get you to 90 percent. After that, you’re stuck at 90, but who…do you think you are, a god? You got to 90 percent? It’s incredible!”

“Will this bring us harm?”


Our second question is the other side of the coin. When we get stuck with the “safe enough to try” mentality, we ask, “Will it bring us harm?”

Sometimes you think you know the answer, but you don’t. (See project manager story above.) But often, the very act of asking the question mitigates the risks. If you understand the potential dangers, you can make a plan to meet those challenges when they come.

The Third Secret…

There is one more element to breaking analysis paralysis in business: a great team.

About halfway through writing this article, I stalled. I was suddenly gripped with burning questions.

“Do I take this angle or the other one?”

Do I use the donkey example or do I talk about the Target CEO?”

“Speaking of donkeys, can I say ‘ass’ in a blog post….”

Yup, while writing an article on analysis paralysis, I found myself paralyzed. A couple of quick talks with teammates smoothed it out, though. Without them, I would probably still be clicking through Google articles, with a dose of Facebook when I needed a breather.

The right team around you will keep you honest. If you get into the habit of asking yourselves, “Is it safe enough to try,” and “Will it do us harm,” all the smart brains in the room with find the answers.

 Then all you have to do is jump.

So, you think you need custom software. Everyone’s doing it, and you’re wondering if it’s time to take the plunge.

But you’re also a little afraid this might be a case of “If all your friends jumped off the Brooklyn Bridge, would you jump, too?”

The custom software question is a big one for all growing companies. It’s expensive, but there’s usually a tipping point at which the ROI becomes worth the upfront costs. The question is, how do you know?

While there are a lot of moving parts in making such a big decision, it really comes down to process and commitment. Are you truly familiar with your process, and are you ready to commit to owning software?

Defining Your Software Needs

The first question you need to ask yourself is, “What do I really need this software to do?” Maybe it’s an internal process or a customer-facing app, but either way, you need a clear idea of the features and benefits of any piece of software.

Off-the-shelf (OTS) software is the way to go if you aren’t clear on those. One of the benefits of OTS software is the ability to help define processes. (It’s also one of the cons, but we’ll get to that in a minute.)

If you are still new to the space, or if the particular process you want to automate is not yet fully defined, chances are good you aren’t the first person to have this problem or need this solution. An off-the-shelf solution will help you define the process and develop a workflow that would be too overwhelming to develop from scratch.


Remember how we said that process-defining ability is a pro and a con? OTS solutions are rigid. Good if you need to define process. Bad if you have outgrown the prescribed workflow.

Let’s take Shopify as an example. Shopify is a robust e-commerce solution that equips a lot of e-commerce businesses. It’s a great solution because of easy integrations and lots of features. As an OTS platform, it’s one we highly recommend in the right circumstances.

It’s not perfect, though. One of the biggest issues Shopify customers experience is the inability to set up recurring payments for customers. Bundling products and easy organization of the front-end are also concerns.

Shopify is just one example of an OTS solution that is great in the early days but is likely to be outgrown over time.

Let’s say you’ve been working with just such an OTS solution for awhile now, and you’re beginning to find its limitations. Maybe it doesn’t give you the freedom your team wants, or it doesn’t perform one little function you’ve discovered you really, really need. What now?

At this point, you can reach out to the company providing your solution and request the feature you need. The problem is, if that feature doesn’t meet the needs of most of their clients–or doesn’t make sense for them financially–you won’t ever solve your issue.

You could also cobble together another third party solution to that one issue and incorporate it into your workflow. This might work beautifully, and you’re off to the races.

Until it doesn’t. Third party software doesn’t always play nice, and you could quickly discover that nothing will integrate seamlessly. Even if you make it work, this cobbling together of solutions will eventually become cumbersome and time-consuming.

While an OTS software is a great way to get started in something new or unfamiliar, once you define your own processes, you’ll probably discover that you need something custom. The bellwether question to ask:

Is my team actually using the software?

If you have a great team in place, and they are constantly dragging their feet to use the software at their disposal, chances are really good that it’s no longer working for them.

Making The Commitment to Custom Software

Let’s be very clear about this: custom software is a long term commitment. It’s expensive on the front end, and you have to budget time and money to maintain and iterate it over time.

That said, much like when you find the right life partner, that long term commitment isn’t scary as much as it is exciting.

With a custom software solution, you will exercise full control because it’s literally made for you. That means you define the features you need instead of the software dictating what you can do. With the right development team, you’ll be able to iterate quickly when it’s time to innovate or update.

Custom software will likely save you time and productivity over the long haul, and as your software gets older, you’ll also need to commit to caring for it. There’s regular maintenance required with any product, but there’s also the need to stay on top of user needs.

But, honestly, there’s regular maintenance and licensing fees with OTS solutions as well. The beauty of investing this money in custom software is that you can build it just for you and your team/users. As needs change, you won’t be beholden to the OTS you’ve always used. Instead, you can adapt your own software as your needs adapt.

The upkeep of a custom software solution never ends, but there is a tipping point where even that upkeep is more cost-effective than inefficient cobbled together solutions.

No really…how do I know?

Okay, so there are lots of pros and cons to both OTS and custom software. When you’re at the decision point, how do you know when to pull the trigger?

Here are 10 ways to know you’re a good candidate for custom software:

  • You’ve tried the best off-the-shelf solutions and still need more.
  • Your current custom software has stopped meeting your needs.
  • You know going custom will give you a true competitive advantage.
  • You spend a significant amount of time and budget on adapting an OTS solution.
  • You know building custom software is expensive, but you also know it will eventually save you time and money if you do it right.
  • You’ve got the budget to build at least a portion of what you need. (Stay tuned for a guide to custom software pricing.)
  • You’ve got buy-in from all the necessary stakeholders.
  • You are committed to maintaining the software over the long haul.
  • Your business model demands custom software (i.e. the custom software IS your business.)
  • You’ve exhausted all other options. No, we really mean ALL other options.

Building custom software–whether you hire developers or outsource to a vendor–is an intense, expensive experience. It’s not for the faint of heart, but it is for anyone who is ready to level up their processes, either internally or for your customers.

If you’ve read all of this, and we haven’t scared you off, you might be ready to dive into the deep end of custom software.