4. A Surprised Client is Rarely a Happy Client

When my daughter was four, she was obsessed with a show called BeatBugs. It’s a cartoon where bugs go on adventures and sing Beatles songs. One day, they did "A Day in the Life," and she was floored. She looked at me like she’d just discovered fire.

I just shrugged and said, "The classics are the classics for a reason, kid."

Years ago, back when I was a management trainer for a bank in Colorado, a boss handed me two “classics” that I still lean on today. One was the Performance Management cycle: Expectations → Tools → Coaching → Feedback.

I think about "Expectations" more than anything else. In the agency world, we usually miss the mark because we’re stuck on a hamster wheel. We’re running so hard just to keep the lights on that we forget to check if the client is even on the same track. Whether it’s spend, timing, or risk comfort, a surprised client is rarely a happy client. This is not to be confused with a delighted one, that’s the goal; surprises are just landmines you didn't see because you were sprinting.

The other "classic" that was mandatory reading: Covey’s 7 Habits. The one that haunts me in agency life is "Seek first to understand, then to be understood." We put our people on a relentless cycle, meeting to meeting, client to client. Eventually, they stop listening and start just waiting to speak so they can move to the next call.

Your New Digital Wingman

Most agency folks are brilliant practitioners, but they aren't always great at guiding a client through the fog. At Black Propeller, when we had people juggling a dozen accounts across global teams, it was easy to miss the "vibe shift" where a client starts to sour.

This is where AI became our essential wingman. If you’re recording calls on a Gong or Gemini, stop relying on your "wait, what did they say?" notes. Feed that transcript into an AI and create reliable, reusable scripts to get a reality check:

• The Expectation Audit: "Are the client and my team actually aligned, or are we nodding at different goals?"

• The Sentiment Scan: "What did the client not say? Did we leave any questions hanging?"

• The Commitment Log: "Draft a follow-up email with our priorities and timing so there’s zero room for 'surprises' next week."

Moving from Weekly Tasks to Quarterly Strategy

That’s the daily grind. But to really stop the surprises at the monthly or quarterly level, you need to use your wingman for the big picture:

• The Virtual Planner: At the end of the month, feed in the last four weeks of transcripts. Ask: "Based on these conversations, what are the three biggest roadblocks the client hasn't explicitly named yet?" It’s like having a silent partner who’s been paying attention when you were too busy to think.

• The Risk-Adjusted Recommender: Every client has a different stomach for risk. Use a prompt like: "Here is our Q2 strategy and the client’s historical risk tolerance. Critique this plan, where are we being too aggressive for their comfort, and where are we being too timid to hit the goal?"

• The "Surprise" Forecaster: Upload your quarterly data and ask the AI to play devil's advocate: "If this project fails in 90 days, what will be the likely cause based on our current communication patterns?"

The End Game: Sophisticated Retention

The goal isn't just to use AI because it's the "new shiny thing." Part of getting more sophisticated with these tools is about keeping your clients and growing them. At HITLStrategies.com, I’ve built a diagnostic to help agencies move from "surviving" to "scaling" by focusing on Client Success & Value. It’s about defining how value is measured and ensuring it drives commercial renewal. Using AI, we can finally answer the hard questions that stop churn in its tracks:

• The Churn Post-Mortem: Why did we actually lose those clients in the last 12 months, and what patterns is the AI seeing that we missed?

• The Value Proof: Can we prove the financial ROI to an executive buyer, or are we just reporting on "marketing KPIs"?

• Predictive Expansion: Which data points allow us to predict an expansion opportunity with over 90% accuracy?

By letting the machine handle the "hamster wheel" tasks, like communication volume and data benchmarking, your team is freed up for high-level executive consulting and innovation. That’s how you get off the wheel, stop the surprises, and actually get back to the classics.