Your AI Why
Outsell partner, respected colleague, and AI strategy advisor Jennifer S. Ives, often speaks about the importance of a company’s “AI Why,” a question every leadership team must be able to answer before launching AI initiatives.
Starbucks got the memo this week and others are sure to follow. Score one for humans. Zero for the machines. Yes, AI does a lot of things well and right. But it still requires humans in the loop and thankfully the leadership team at Starbucks listened to their front-line staff who were advocating for the other way as a better way.
There is also little doubt that the cost of tokens is starting to bite and a reckoning between experimentation and real outcomes is on its way. Enterprises are built around budgets and variable pricing that is unpredictable and is the bane of any CFOs existence. At some point token pricing breaks driving further focus on AI Why.
In the Outsell Accelerate A! Benchmark™ we look at five dimensions of deployment, and the first one is AI Strategy — What is our defensive and offensive plan for deployment? What moats do we intend to keep, build, and protect? What are inherent risks? How are we both sustainably differentiating from competition? And so on and so forth. It’s about having your AI Why and aligning the CXO team around it.
We discussed these topics in our recent digital council meeting for CXO leaders and had a strong discussion about what our benchmark is finding and what they are seeing inside their own organizations and in the market.
The conversation was most valuable when participants moved beyond the data into sharing practical examples, challenges, and lessons learned — the alchemy inside Outsell where the magic happens.
A quick highlight from each dimension:
- AI Strategy: The biggest point of engagement was the gap between high executive focus on AI and the limited number of organizations that have documented an AI threat model. This prompted a strong discussion around disruption risk and how companies are rethinking their business if they were starting from scratch today.
- Organizational Readiness: Governance and training generated the most discussion here. Members responded well to examples of putting clear guardrails in place early and treating workforce enablement as a structured capability-building effort rather than expecting employees to self-teach.
- Internal Operating Use Cases: This was one of the most practical parts of the session. Attendees shared specific examples of productivity gains across sales, marketing, research, and editorial workflows, while also acknowledging that most organizations are still early in formally measuring ROI.
- Revenue from Product Use Cases: The clearest takeaway was that simply adding AI features is no longer enough. The discussion focused on whether AI is truly changing customer workflows, creating differentiated value, and supporting a credible commercial model.
- Revenue from Licensing to LLMs: This section sparked strong interest because of the mix of new revenue opportunity and legal uncertainty. The discussion centered on the importance of being proactive about licensing strategy rather than relying on unsettled fair use outcomes.
Overall, the session reinforced that the market is moving quickly, but maturity is uneven. The most engaged discussion came from the areas where organizations are shifting from experimentation toward governance, measurable impact, and commercial execution. In the words from a MasterCard commercial the discussion was priceless. In the view of one attendee:
Thank you so much for the opportunity to participate in the A! session. The content is so relevant to everything we’re doing, and it’s helpful to understand from others what they are experiencing as well. This is all evolving rapidly, and we have to stay on the forefront of innovation to enable customers to accelerate (their) innovation. What I love most about Outsell is the forward looking dynamic and community engagement, and your session delivered! I anticipated listening and learning, but it was also enjoyable to contribute to the conversation, so thank you for that.
It doesn’t get much better than that and like the inquiries we wrote about last week — working with CEOs and their execs to grow revenue and mitigate risk in this next era of transformation is our AI Why. More next week with highlights from our F2F meetings with CEOs this week and last. Anonymized, private, meaningful — where hard conversations are had and good decisions are won. Searching for your AI Why? Reach out to Jennifer or me. We’re awaiting your call.