OKRs, SMART goals, V2MOM and Balanced Scorecards were all designed with one purpose: to bring clarity, focus, and alignment to teams. Yet in practice, they often generate confusion, drag, and disillusionment. Many Chiefs of Staff and operators find themselves trapped in a quarterly cycle of goal theater; going through the motions of implementation and enforcement without real traction.
The problem isn't the frameworks themselves. It's how we implement and maintain them.
Why These Frameworks Break
The failure points are consistent across companies:
- Goals are misaligned or poorly cascaded.
- Updates are manual, irregular, or forgotten.
- KPIs lag behind real progress.
- Teams feel burdened, not inspired.
- Accountability becomes performative.
As Product Leader & OKR coach, Evan Hammer noted during a Chief of Staff Network event, “Using OKRs with Better Alignment” last year, "We had 40 OKRs at one point. It became noise. No one could remember what actually mattered."
These systems work well in theory, but too often collapse under the weight of human bandwidth.
Where AI Makes the Difference
AI doesn’t replace the frameworks. But it will finally make them usable.
Real-time assistants and dashboards reduce overhead. Generative AI tools summarize goals, surface blockers, and synthesize progress from existing tools like Notion, Asana, and Slack. Instead of updating progress manually in a spreadsheet, teams can auto-generate check-ins based on actual work output.
Former Chief of Staff, Caitlin Bartlow, on another CoS Network panel, put it clearly: "The challenge with OKRs isn’t always setting them, more often it’s tracking them in a way that is useful to the team without being a burden.”
Until recently it would take a small data team weeks, if not months to set up automations and reporting dashboards so employees could properly track their key results. AI tools given appropriate access to company systems are much more efficient helping teams see the gaps faster and course-correct in real time.
From Static Goals to Living Systems
AI enhances these frameworks in four key ways:
- Contextual Tracking – AI systems can integrate with tools like Slack, Linear, or Notion to connect day-to-day activities to overarching goals without additional human input. Instead of relying on manual status updates, AI passively monitors workstreams and logs activity that aligns with goal metrics. For example, Brev.io automatically pulls relevant data from integrated tools to keep OKRs updated in real-time. This enables Chiefs of Staff to spend less time chasing updates and more time evaluating progress.
- Smart Summarization – Chiefs of Staff often act as translators between executive strategy and team execution. AI tools now analyze project documentation, meeting notes, and internal chats to produce high-level summaries tailored for leadership. This reduces the need for weekly syncs or slide decks and helps operators identify key themes and blockers. Tools like Notion AI or Glean surface these insights on demand, turning noise into clarity.
- Proactive Nudges – AI excels at pattern recognition. When it sees a task languishing or detects a mismatch between effort and objectives, it can prompt teams with helpful nudges. These nudges can re-surface neglected priorities, recommend collaborators, or suggest next actions. For Chiefs of Staff, this acts like an always-on assistant helping maintain momentum and accountability without micromanagement.
- Dynamic Prioritization – Traditional goal frameworks assume priorities remain static for a quarter or more. AI, on the other hand, can ingest signals from across tools and update recommendations dynamically. If one team is blocked or ahead of schedule, AI can suggest resource shifts or reprioritization. Agent-based models, will help teams reallocate attention based on actual execution, making it easier for Chiefs of Staff to lead through complexity and course-correct early.
The New Role of the Chief of Staff
This evolution changes the CoS remit. Instead of acting as a manual router of updates and facilitator of status meetings, Chiefs of Staff can focus on orchestration: defining success, interpreting signals, and steering momentum.
With AI assisting with the "what" and "how," the CoS can focus on the "why" and "when."
This shift opens the door to new responsibilities: designing adaptive systems for learning and iteration, overseeing cross-functional impact measurement, and leading strategic sensemaking during times of ambiguity.
Legacy frameworks may even end up by the wayside as CoS leaders start to pilot alternative goal methodologies that move beyond traditional OKRs such as rolling priorities, impact loops, or mission-based progress tracking better tailored to high-change, high-context environments.
As frameworks become more fluid and contextual, the CoS becomes the steward of organizational coherence, ensuring that strategy remains grounded in real-world conditions and execution momentum.
Don’t Ditch Your Framework. Upgrade It.
If OKRs or V2MOM aren’t working, it might not be the framework’s fault. It might be your system. AI offers a way to transform rigid goal-setting into dynamic execution support.
The result will be a living, breathing source of truth that aligns, motivates, and adapts in real time. Instead of abandoning your frameworks, let AI make them work the way they were always intended to.
Want to hear how other Chiefs of Staff are integrating AI into their planning systems? Listen to the Chief of Staff Network Podcast for real-world insights from leaders on the front lines.
