The Harsh Reality of Your Software Purchasing Dreams

Choosing the right software to solve a business problem is a big job—especially when the problem is complex.

🔎 “We don’t have enough pipeline visibility to forecast accurately.”
🔎 “We’re losing customers, but we aren’t sure why."

It’s tempting to:

🤓 Jump right into researching and comparing tools 
👀 Click through ads promising the world and following you around
🗣️ Talk to a few peers and see what they would/wouldn’t recommend
📆 Do your due diligence and book several demos 
🌟 Cherry-pick a couple of success stories 
📈 Build a business case for getting a green light
🟢 Get buy-in from your decision making committee 
💸 Sign on the dotted line 
♻️ Run your traditional software training playbook

…and call it a job well done. 

But if you do that, you gloss over some of the harsh realities of your software purchasing dreams.

1. Software can’t magically understand your business 

Before you start looking at software options—or buying licenses—you need to get very clear on the “why” and “how” of your operations. 

Why? Because true problem solving starts with understanding the underlying business processes causing your biggest business problems. 

Say you’re struggling with pipeline visibility and customer retention. You buy point solutions to improve those two things…and two months later, you have to go back to your boss and admit: 

🤦🏼 “X tool hasn’t helped us with pipeline visibility because it’s still cumbersome to convert leads to opportunities.”

🤦🏽 “Y app isn’t teaching us anything about churn because we still haven’t been able to make time to analyze tickets.”

A better order of operations starts with:

• Understanding formulas for success at an operational level
• Working backwards to create suitable systems and rewards
• And then buying software to add efficiencies 

2. More tools = less productivity 

It’s no secret that the number of tools for knowledge workers has skyrocketed in recent years. According to Okta, large companies continue to roll out new software with an average of 231 apps (up 10% this year).

But what we don’t talk about enough? How much people hate 99% of the tools designed to make their jobs easier—and how much time they’re wasting trying to learn them all.

ICYMI, the majority of your end users are:

• Not excited about your new productivity tool
• Overwhelmed by the number of standard operating procedures they need to do their jobs
• Frustrated by constantly evolving user interfaces and business processes
• Failing to use your tech stack to “work smarter, not harder”

The best thing you can do for your organization is be the voice in the room encouraging everyone to think about software purchases all the way through. Try asking questions like:

↳ How many other tools have we asked employees to learn this quarter, this half, and this year?
↳ How many tools are people already using on a daily basis?
↳ How effectively are we taking advantage of the software we already have?
↳ What are the odds our end users will adopt this tool successfully enough for us to see real return?

3. Not all software startups make it 💔

It’s natural to be interested in the most cutting edge software tools, companies, and vendors. Which often means straying away from the incumbents and finding the new startup that's doing something different. 👏🏽

But 2023 research from Peter Walker at Carta paints a pretty grim picture about startups shutting down. 

The TL;DR? 238% more startups that had raised over $10 million or more in capital shuttered in 2023 vs. 2022. This trend is likely to continue, with even more startups closing their doors in 2024.

So if you’re an operations, enablement, L&D, system admin, business application, change management, or training manager evaluating new software vendors…you have to look at the numbers and see around the corner. 

You're trusting these vendors with your data. Your processes. Your most critical workflows. And your reputation as a Change Enabler. Finding a solution that fulfills your feature requirements isn’t enough.

Before you start championing a product internally, ask yourself questions like:

↳ What’s the longevity of this company?
↳ How much runway do they have?
↳ What's their foresight into their next fundraising round?
↳ What's the confidence level that they'll be able to hit it?
↳ Are there enough customers/revenue supporting this company for me to trust it?
↳ What are the chances that they’ll suspend service because they’re going out of business?

4. Change management is the name of the game

If you’ve dealt with a failed software rollout, you know this sequence of events all too well. 👇

🤖  A new tool pops up with some pretty magical promises 
✍🏾  Stakeholders see an opportunity to stay current and solve a business problem, so they buy it
🫠  They underestimate the change management and end user training needed to drive adoption
👎🏿 Change enablers like you struggle to convince end users to learn yet another software
🤫 Everyone who hates change finds ways to keep doing what they’ve always done 
💸 No matter how good the solution is, no one gets anywhere near their anticipated ROI

TL;DR → You won't get the value you’re expecting if you don't factor in end user change management and how many people will actually adopt the new tool (especially if you have lots of ambivalent adopters!).

5. Traditional software training isn’t cutting it

If you’re still asking your end users to:

❌ Train when it’s convenient for you
❌ Sit through long meetings
❌ Memorize dozens of procedures
❌ Search multiple knowledge bases 
❌ Read through walls of text
❌ Watch boring videos

…it won’t matter how amazing your new software is. Because you’re taking an outdated approach to teaching people how to use it.

Real-Time Enablement (RTE) is a more modern, employee-first alternative to traditional software training. 

With RTE, you can: 

• Stop training your end users on software—and start freeing them up to learn how to sell more, build better products, and delight more customers   
• Embed process knowledge and pro tips into the tools employees work in every day, so everyone can learn how to use software while using it (without breaking flow)
• Make succinct instructions easy enough to follow on autopilot (while dramatically improving your process adoption metrics) 

At the same time, your end users can:

✅ Access information in their moment of need
✅ Leverage “just enough context” to quickly complete the task at hand
✅ Save more mental energy for the job they were hired to do

6. Your training and enablement tool of choice matters more than you think

Tango customers have created over two million walkthroughs to teach people how to use software. 

Regardless of industry, company, or function, there’s one thing that holds true. Not all training and enablement tools are created equal.

You might hear people talk about some of the most popular options interchangeably. But the reality is: 

💪 Knowledge Bases are good for centralizing reference information 
⏩ Learning Management Systems are good for video training courses
🎯 Only Digital Adoption Platforms (DAPs) are purpose-built to enable software process adoption with the least amount of change for end users 

Click here to learn more about DAPs—and how to ensure a successful software rollout post-purchase.