Business Software Adoption Strategy (1): Know Your Enemy — Software Selection Principles for the AI Era
After nearly 20 years of developing, marketing, selling, and implementing software, I found myself for the first time on the other side of the table — as an evaluator considering a purchase. What struck me was this: things that seemed completely obvious as a seller looked entirely different as a buyer.
Sun Tzu’s Know Your Enemy — Applied to Software Adoption
“Know your enemy and know yourself, and in a hundred battles you will never be in peril (知彼知己 百戰不殆).” Apply this principle to software adoption. If you encounter serious difficulties during implementation and use after adoption, that’s a signal that your pre-investigation was insufficient in at least one of two areas: knowing the other (知彼, Jipí) or knowing yourself (知己, Jigi).
“The enemy (彼)” carries multiple meanings here. It could be your competitors, or it could be the software vendor you’re evaluating. Poorly adopted software can, like the Trojan Horse, create chaos from inside your organization. “Yourself (己)” refers to the departments and individuals who will actually use the software, and the entire organization driving the adoption.
Common Patterns of Software Adoption Failure
Through my experience in IBM marketing automation sales and Adobe Marketing Cloud implementation partnerships, I’ve repeatedly witnessed the same failure patterns:
- Senior leadership makes a unilateral decision without input from actual end users
- Competitors’ adoption stories are given excessive weight in the decision
- Internal user resistance and low actual usage rates after adoption
- Insufficient changes to work processes after implementation is complete
Software Selection Has Gotten More Complex in the AI Era
In 2025, the choices have become even more complex. Every SaaS solution promotes itself as “AI-powered,” and new generative AI-based solutions hit the market every month. In this environment, making adoption decisions based on AI features alone — without the discipline of Know Your Enemy and Know Yourself — will only create greater confusion.
| Area | Key Question |
|---|---|
| Know the Enemy – External | What problem were competitors trying to solve, and what did they choose? |
| Know the Enemy – Vendor | Are this software’s AI features genuinely validated, or are they marketing language? |
| Know Yourself – Internal | Who will actually use this, and what is their digital skill level? |
| Know Yourself – Organization | Is there a leader who will drive change management after adoption? |
This series examines software adoption strategy by separating Know Your Enemy (知彼) and Know Yourself (知己). In the next post, we’ll cover the traps that appear when you ask for competitors’ case studies.