What Could Possibly Go Wrong?

What CEO’s Need to Know to Prevent Existential Mistakes

I’ve yet to meet a software developer that says “You know, that’s not really in our wheelhouse.”

Why?  Because, when you have a hammer… 

Software developers build their business on proficiency in a given technology stack. (A set of software development tools designed to work together, that from here forward I’ll refer to as “toolkit”. )

But, it’s not so easy for a company to change their toolkit. They’re heavily invested in the employees and skills needed to use the tools they have. Their employees have spent hundreds of hours learning and getting certified in the tools; and thousands of hours applying that knowledge. So, developers continue to leverage their investment for as long as possible. Often, well past the toolkit’s shelf-life. Other major factors contributing to this tenacity include the “Sunk Cost Fallacy” whereby continued investment is justified by the amount of previous investments in a given project; A.K.A. “Throwing good money after bad”. And, cognitive dissonance (the theory that the mind cannot hold  two contradictory beliefs at the same time): 

  1. I’m smart = I make great decisions
  2. Changing course = my prior decision was bad

These dynamics affect executives on both sides of the vendor-customer relationship. Aggravating the situation is the likelihood that the same people who built (or recommended) an association’s existing software are often the association executive’s trusted advisors in matters of technology. But, asking your trusted advisor whether or not you should be looking at other technologies would be like asking your mechanic what he thinks of you buying a Tesla. Regardless of whether it’s in-house IT; or a trusted vendor; you can rest assured that your business priorities are almost their top priority. 

By now, It should be clear to everyone that the future of business will be played on a digital landscape. Association executives can no longer afford to delegate when it comes to matters of technology. 

Here are some ways to protect yourself:

  1. Buy before build: First and foremost, ask do you absolutely, positively have to custom build it? Your search for existing commercial-off-the-shelf (COTS) products should be exhaustive. Even if you can only find 80% of the desired functionality, the result will be far less painful and costly buying it, than building it. Building software is extremely expensive. Moreover, it’s never one-and-done. You will have to continually invest in the solution until a COTS product that does the job comes along; or your custom solution dies from irrelevance.
  2. Consider using a platform: If you have to build it; find out if it could be built on a platform like Salesforce, Microsoft CRM or NetSuite. Building on a platform is like building with a Lego set. The platform may provide 70% or more of what you need right out of the gate. With a platform, you’re configuring, not creating from whole cloth. If the app is centered around people (B2C), organizations (B2B); and relationships, that’s already baked in. Platforms provide ad-hoc reporting, custom fields, forms, workflows, dashboards, member portals and mobile apps. Platforms allow you to extend the functionality via their app store and existing integrations. Most widely used applications already connect. And platforms have hundreds, if not thousands of certified partners who can jump in to help you enhance or update your system down the road. With a custom solution – there’s only one.

The biggest problem with non-platform-based solutions is that while you can add features and functions, modernizing the foundation is cost prohibitive; as it requires rebuilding the entire application. With technology evolving at an ever-increasing pace; older foundations simply lack the dexterity to keep up. The AMS market is a perfect example. The companies that have dominated the market for the last 20 years have all been put out to pasture. Why? Not one of them invested in rebuilding their foundation.

With platforms, the platform is the foundation. the companies that build them have staked their reputations on keeping the tech current. So, in addition to economies of scale; you will always have a modern foundation. 

  1. Call references to verify the tech is their core competency: If your developer says they’re technology agnostic, ask them for recent references from each of the primary tools in which they claim proficiency. Call references and ask them who, when and why the specific toolkit was selected. If the particular toolkit is not their primary; you’ll often find that it was selected by the customer. They may even outsource your work. I know an association that spent $1M on a new website; only to discover that the entire job was outsourced to a single developer in India for about $30K.
  2. Get the advice of an outside expert who can prove they don’t benefit in any way from the choice you make.
  3. Read the vendor’s reviews on Glassdoor.com and Clutch.co. Glassdoor tells you what their employees think; and Clutch.co tells you what their customers think. Both are important.

I don’t mean to imply that there aren’t any developers that have successfully migrated from one toolkit to a more modern toolkit. Nor am I saying that there aren’t any developers that support more than one toolkit. However, if they do; they’re usually migrating from one to the other. A quick Google search should tell you which is which – hint: they’re moving to the newer one

If this article has convinced you not to build a custom app; my work here is done. However, if you’re still determined to forge ahead; do your homework. Do not trust the recommendation of any single source – especially if that source is in-house IT or a vendor you have used in the past. Don’t confuse liking them with getting good advice. You are about to get major surgery, get several opinions. Most importantly, do not use the same selection process you used last time. If we’ve learned anything in this age of digital disruption; it is that the past is a lousy guide to the future. 


David Schulman is President of Associations Rewired. With over 30 years of experience in business technology strategy consulting for over 80 associations. For years, he has been preaching to anyone who will listen, that digital transformation is the single greatest opportunity to land on your doorstep in the last century. Prior to starting Associations Rewired, David built and sold two technology companies.