OKRs in the Age of AI: Supercharging Strategy Execution

I recently joined an OKR mentors panel on Strategy, Execution, and AI alongside some amazing practitioners: Elie Casamitjana , Harry Siggins , Natalie Webb , and Peter Kerr . Even though I can’t share the full recap here (you can go purchase it as part of the full [and excellent!] OKR Forum event recap), I wanted to pass along a few highlights that really struck home for me—especially on how AI supercharges OKRs (Objectives & Key Results) and strategy execution.

AI + OKRs: A Perfect Match

One of the points I hammered home (and wholeheartedly believe) is how well AI dovetails with OKRs. OKRs are all about continuous learning, experimentation, and focusing on outcomes that matter. AI is basically an accelerant for these processes—it lets you spin up new products and prototypes faster, handle enormous amounts of data in real time, and reduce the tedious overhead that often stifles creativity.

I like to say I’m practically a cyborg these days, using AI for everything from drafting complex pieces of code to analyzing meeting transcripts. Why? Because AI transforms mundane “information tasks” into strategic learning moments.

Two Concrete Examples

1. Front-End Intelligence: Before setting each quarter’s objectives, I love to gather insight directly from frontline folks or customers. Instead of sending out forms or relying on multiple reporting layers, I spin up an AI-powered voice agent (think of it like an automated interviewer with excellent follow-up questions). I’ll send out a phone number, let employees and customers dial in, and collect nuanced feedback that a static survey can’t capture. It’s faster, more natural, and you can analyze the transcripts right away.
2. Prototyping on the Fly: Once OKRs spotlight a new opportunity (say, a potential product feature), you can turn those verbal “what-ifs” into actual working code. Just feed a transcript or a bulleted list of requirements into a generative model—o1 Pro, Claude 3.5 Sonnet, or whatever powerful tool you like—and get a near-instant draft of the concept. You don’t have to assemble a full dev team just to see if something is valuable (and possibly even technically feasible). That allows you to execute at unprecedented speed.

Privacy, Policy & the (Inevitable) Shadow AI

Of course, all this capability comes with serious responsibilities. One big watchout is privacy. You can’t just drop proprietary or regulated data into a free, consumer-grade product and hope it stays confidential. Corporate policies matter—so leaders need to anticipate how employees will use AI rather than trying to lock it down. Because here’s the thing: if you don’t give people the right sanctioned tools and guidelines, “shadow AI” will pop up anyway (as Peter Kerr mentioned, just like those “shadow IT” Excel macros we used to see everywhere).

Decentralize Innovation—and Then “Show & Tell”

A big theme that came up in our panel is the tension between centralized IT policy and the grassroots user-driven innovation that AI makes possible. My take is that we should welcome decentralized experimentation—within guardrails. Let your people flex their creativity and find new AI hacks, but set up an internal “Show & Tell” rhythm. Every week or two, let those folks share what they’re building, how they did it, and what results they’re seeing. That’s how you unstick knowledge from individual silos and spread it throughout the company.

My Favorite Prompt to End Each Week

Here’s a hack I’ve been using lately: Every week, I take transcripts from my key meetings, feed them into a robust large language model (like o1 Pro with the expanded context window), and ask:

1. “What’s the most important thing nobody’s paying attention to?”
2. “Give me three hard-hitting questions I should be asking.”

Those answers force me to think deeper about risks, missed opportunities, or blind spots that never surfaced during the live conversation. It’s like having an ever-present coach who’s constantly challenging me to raise the bar.

Accelerating AI Adoption

AI can absolutely supercharge OKRs and strategy execution—but only if we stay human at the helm. The best results come from pairing good AI prompts and frameworks with real human intuition, curiosity, and a willingness to challenge the status quo.

If you’re ready to explore how AI could transform your organization—from quick wins to a deeper strategic overhaul—I’d love to connect. I’m offering a free 30-minute Accelerated AI Adoption consultation to help you:

? Identify your most promising AI opportunities

? Outline practical, low-risk pilots or proofs of concept

? Draft a roadmap for AI integration that aligns with your key objectives

Reserve your spot here: https://calendly.com/gsdatwork/free-consult