Executives crave predictability, which feels at odds with agile discovery. Bridge this gap by making your learning visible. A simple weekly update on tested assumptions, evidence found, and resulting decisions provides a rhythm of progress that satisfies their need for oversight without resorting to rigid plans.
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AI initiatives often require significant learning and iteration, which can derail a roadmap. To combat this, PMs should dedicate a fixed percentage of development bandwidth (e.g., 5-10%) specifically for iteration on high-priority AI projects. This creates a structured buffer for discovery without compromising the entire plan.
A dual-track launch strategy is most effective. Ship small, useful improvements on a weekly cadence to demonstrate momentum and reliability. For major, innovative features that represent a step-change, consolidate them into a single, high-impact 'noisy' launch to capture maximum attention.
True agility isn't just about sprints; it's psychological. By breaking massive projects into minimal viable products (MVPs) or small features, the team creates a steady stream of "quick wins." This builds a sense of progress and happiness—a "dopamine type of reward"—that keeps the wheel of innovation turning and prevents teams from getting bogged down.
Don't let the importance of a piece of content, like a sponsored newsletter, lead to analysis paralysis. It's better to ship consistently and learn from each deployment. This agile approach of weekly "at bats" allows for constant calibration based on real audience feedback.
In the fast-moving AI sector, quarterly planning is obsolete. Leaders should adopt a weekly reassessment cadence and define "boundaries for experimentation" rather than rigid goals. This fosters unexpected discoveries that are essential for staying ahead of competitors who can leapfrog you in weeks.
In a rapidly evolving field like AI, long-term planning is futile as "what you knew three months ago isn't true right now." Maintain agility by focusing on short-term, customer-driven milestones and avoid roadmaps that extend beyond a single quarter.
Go beyond visual roadmaps. Create a monthly written document for executives that explains *why* the roadmap changed, details priorities, and includes data from recent launches. This forces intentionality, builds trust, and fosters deeper, more accountable conversations with leadership.
To prevent rigid plans that break, maintain consistency in your high-level strategic pillars for the year. However, build in flexibility by allowing the specific tactics used to achieve those pillars to change quarterly based on performance and new learnings.
To bridge the gap between a product's long-term vision and its current state, focus on "progress, not perfection." Deliver a quick, meaningful win for the customer—like a single workflow or integration—to build the trust and momentum needed for them to stay invested in the unfolding roadmap.
Adopt the private equity board meeting model: circulate a detailed brief a week in advance. This forces attendees to consume updates asynchronously. The meeting itself can then be dedicated entirely to debating critical, forward-looking decisions instead of wasting time on status reports.
