The Fresh Start Trap (and how to avoid it)

Hey there,

I'm writing this as I restart my own newsletter after months away – which makes me either the perfect cautionary tale or the ideal guide for what I'm about to tell you about product team transformations.

"We're going to start doing proper user research this quarter."

"This time we're really implementing OKRs."

"We're moving to a more data-driven approach."

Sound familiar? These are the battle cries of product teams everywhere, launching their latest attempt at transformation. The truth, however, is most of these initiatives are dead by Week 4.

Product team "fresh starts" are organizational theater disguised as strategy.

We're addicted to the dopamine hit of kickoff meetings, new processes, and the intoxicating belief that this time our team will magically embrace change. But after both personally experiencing and watching product teams attempt transformation, I've learned something many leaders miss: The magic doesn't happen in the energetic Week 1; it happens in the unglamorous Week 4.

Here's the pattern that usually plays out:

• Week 1: Revolutionary energy. "This new process changes everything!" Your team is performing enthusiasm.

• Week 2-3: Reality friction. The new user research process feels slow. OKRs seem bureaucratic compared to "just shipping stuff."

• Week 4: The enthusiasm cliff. Someone suggests "just this once" we skip the retrospective because of that urgent deadline.

• Week 6+: Only the initiatives designed for human psychology, not human idealism, survive.

The Enthusiasm Cliff

The sophisticated insight most product leaders miss:

You're not managing a process change in Week 4. You're managing neuroscience. The brain's novelty bias has worn off, dopamine levels have normalized, and your team's cognitive load is fighting against the new behaviors you're trying to install.

Most leaders treat Week 4 like a failure of execution. Smart leaders treat it like a design problem they should have solved in Week 0.

Instead of asking "How do we launch this new process?" ask "How do we succeed when this stops feeling revolutionary?"

Because what Week 4 actually looks like in product teams is this: The new user research process feels like it's slowing down delivery. Writing OKRs feels like busy work when there are features to ship. Your daily standups start running long because people aren't used to the new format yet. The old way of working—chaotic but familiar—starts looking efficient compared to this new "overhead."

This isn't failure. This is Tuesday.

The product leaders who successfully transform their teams design their initiatives to work when motivation is low, when the new process feels clunky, and when "the way we used to ship" starts looking reasonable again.

Three tactical shifts that separate lasting transformation from expensive theater:

1. Engineer the reality check – Don't schedule a "how's the new process going?" meeting. Schedule a "here's exactly what Week 4 will feel like and why your brain will rebel against this change" conversation before you start.

2. Normalize the psychology – Tell your team that around Week 4, the new process will feel slower and more annoying than the old way. Make the dip predictable, not shameful.

3. Architect micro-victories – Design specific wins for Week 4 when "becoming more user-centric" feels abstract compared to the very concrete bug that needs fixing today.

   
   

What product team transformation are you planning right now that you're secretly worried won't stick? Email and tell me – I'll share the specific Week 4 design patterns that separate lasting change from well-intentioned process theater.

Speaking of designing team transformations for human reality (not human idealism), this is exactly how I approach building sustainable AI capabilities in product teams. If you're tired of AI initiatives that fizzle after the initial excitement, my next cohort of “Build an AI-Confident Product Team” starts July 21.

Your Week 0 assignment: Design your Week 4 strategy before you need your Week 1 energy.

Here's to engineering lasting change…

Break a Pencil,

Michael

P.S. The most dangerous words in product leadership: "This time will be different." The most powerful: "This time we planned for it not to be."

P.P.S. If you found this useful, share it. The best referrals come from people who’ve lived through their own Week 4.