#31: Dear AI: We Need to Talk About Your Boundaries

Chip Royce, Flywheel Advisors

The promise of autonomous AI applications is seductive: “Set it and forget it” automation that handles everything from email follow-ups to customer engagement.

But here’s an uncomfortable truth: these tools are creating more problems than they solve.

Just last week, a CEO shared a cringe-worthy story. Their AI sales tool automatically sent a “Sorry I missed you” email to a prospect… hours after they’d shared drinks at an industry event. The AI didn’t know about the in-person meeting because it wasn’t logged in the CRM.

Ouch.

This isn’t a rare occurrence. The gap between AI’s promises and its actual performance is getting bigger, and it’s taking a toll on business relationships.

Here’s why autonomous AI often fails:

Here’s why autonomous AI often fails:

• Missing Context: AI can only work with data in your systems. Phone calls, hallway conversations, and informal meetings often go unlogged
• Incomplete Information: Critical business context lives in human relationships, not databases
• Over-promised Capabilities: Many AI tools claim to “fully automate” processes that require nuanced human judgment

The Better Approach: AI as Force Multiplier

Instead of pursuing full automation, smart companies are implementing AI co-pilots that:

Work Alongside Humans

• Flag potential opportunities in real-time
• Suggest next best actions based on available data
• Draft content for human review and refinement

Ask Smart Questions

• “Have you considered reaching out to [contact] who viewed your pricing page?”
• “This account’s engagement has dropped 40% – worth investigating?”
• “Three people from this company attended your webinar – time for a coordinated approach?”

Highlight Blind Spots

• Surface trending topics in your market
• Identify patterns in customer behavior
• Alert you to competitive movements

Real-world Success:

A B2B software company recently shifted from autonomous email campaigns to an AI co-pilot approach. Their sales team now uses AI to draft personalized outreach, but each message gets human review.

Result? Response rates increased 3X, and embarrassing context mistakes dropped to zero.

The Bottom Line:

Your AI tools should strengthen your team’s abilities, not take the place of human judgment. When choosing AI solutions, ask yourself: “Does this improve my team’s performance or try to replace them?”

At the end of the day, human connection builds successful B2B relationships, supported by technology – not the other way around.

Action Items:

1. Audit your current AI tools: Are they working alongside your team or operating in isolation?
2. Identify processes where AI can augment (not replace) human decision-making
3. Ensure your AI tools have feedback loops for continuous human input and improvement

Remember: The goal isn’t to remove humans from the equation – it’s to make them exponentially more effective.