Harnessing AI for Effective Technology Investment Evaluation

Ever wonder what's really happening in the OKR world beyond the hype?

Join Sara Lobkovich, Maria Rowcliffe, and Natalie Webb for a candid, no-BS look at where OKRs are heading in 2025. This isn't your typical "here's how to write an objective" conversation. Instead, you'll get insider insights from three veteran practitioners who've been in the trenches, helping organizations navigate the messy reality of goal-setting and alignment at scale.

In this first part of our quarterly update, we dive deep into the generative AI revolution (spoiler: it's not as revolutionary as everyone claims), the evolving art of OKR localization across complex organizations, and why your retrospectives might be the most important OKR practice you might be doing wrong. Whether you're an OKR skeptic, a seasoned practitioner, or somewhere in between, this conversation will give you practical insights you can't get anywhere else.

Episode Highlights:

• Generative AI in OKRs: why draft quality is improving, but real strategic impact is still lagging behind
• TRV (Technology Realized Value): the Big Five’s new metric for linking OKRs to actual tech investment outcomes
• The “Two Lists” Problem: how teams are secretly working off dual strategies—and why it’s undermining OKR focus
• Cascading and Localization: evolving models for aligning across global teams, even amid geopolitical complexity
• Culture-First OKRs: tailoring implementation to readiness, from transformation-driven overhauls to scrappy gradual rollouts
• Retrospectives that matter: how deeper reflection—not just review—builds quarter-over-quarter OKR maturity

Key Concepts Explored:

• Generative AI in OKRs: Where it's accelerating strategy work, where it's falling short, and the risk of generic, uncontextualized models
• Technology Realized Value (TRV): A new metric used alongside OKRs to measure the tangible impact of tech investments
• The “Two Lists” Problem: How parallel strategic workstreams outside the OKR framework dilute focus and undermine accountability
• Localization & Alignment: Why clear, bottom-up contribution is critical in global, matrixed organizations—especially in high-stakes geopolitical climates
• Culture-Responsive Implementation: Tailoring OKR rollouts based on organizational readiness, risk appetite, and transformation goals
• Iterative Learning over Perfection: Why OKR maturity builds quarter over quarter—and how learning from retrospectives is more valuable than writing the “perfect” OKR
• Leading vs. Lagging Indicators: The power of AI to help surface potential leading indicators clients may struggle to define on their own
• Transformation & Change Management: How OKRs, when paired with transformation strategy, become powerful drivers of organizational evolution

Notable Quotes:

"Is this really driving the value you wanted to achieve? How do you know who cares? So what happens if this is done or not done? These things that don't get asked are so critically important to make sure that people are focused on the right work." — Natalie Webb [00:12:00]

"If I could only tell clients one thing about OKRs, it would be we spend all of our time focused on writing them and then way too little time focused on learning from them." — Sara Lobkovich [00:23:00]

"I think the best way to use OKRs initially is always the way that the company is willing and able to adopt it. Me talking about the gold star way of doing OKRs isn't gonna help clients that are at the crawling level and not a hundred percent convinced yet." — Maria Rowcliffe [00:21:00]

"OKRs are really hard. We're talking about change - really hard for people to stick with when it gets challenging." — Sara Lobkovich [00:28:00]

Chapters:

[00:00:00] Introduction: Welcome to the OKR Dream Team Q2 Update

[00:03:00] Book Launch Celebration and Team Introductions

[00:05:00] Generative AI in OKR Practice: Separating Hype from Reality

[00:06:00] TRV (Technology Realized Value): The New Complementary Metric

[00:08:00] Practical AI Applications: Interview Analysis and Leading Indicators

[00:12:00] The Risks of Anonymous OKR Generators and Untrained Models

[00:14:00] OKR Localization: Navigating Global Complexity and Geopolitical Challenges

[00:16:00] Alignment Strategies: KRs vs. Full OKRs at Lower Levels

[00:18:00] Culture and OKR Implementation: One Size Doesn't Fit All

[00:21:00] Meeting Organizations Where They Are: The Quarterly Improvement Approach

[00:23:00] Retrospectives Revolution: Beyond Basic Questions

[00:26:00] The "Two Lists" Problem: When OKRs Fail to Drive Focus

[00:27:00] Transformation Expertise: The Secret Weapon in OKR Practice

[00:29:00] Wrap-up and Part 2 Preview

Upcoming Events:

• Q3 Strategic Achievement Intensive is now registering!
• Join for a No-BS approach to strategy and goal-getting with Sara: saralobkovich.com/nobs-strategic-achievement-intensive
• Catch Sara at the World OKR Summit! She’ll be speaking this October 30–31: okrsummit.org

Book Update:

• You Are A Strategist: Use No-BS OKRs to Get Big Things Done: New book available in print and ebook. More info is here!

Natalie’s Links and Info:

• Company: Cloud Peak Enterprise Group (Founder)
• Specialization: Global OKR consulting (8+ years experience)
• LinkedIn: https://www.linkedin.com/in/nataliejwebb

Maria’s Link and Resources:

• Chief of Staff & Business Operations: 10+ years experience
• Specialization: OKR implementation, transformation, and program revitalization
• Linkedin: https://www.linkedin.com/in/mariarowcliffe

Sara’s Links and Resources:

• Email: sara@thinkydoers.com
• Website: thinkydoers.com
• Podcast: Thinkydoers Podcast (available on all major platforms)
• Social Media: Sara Lobkovich (across platforms)
• Newsletter: Subscribe at findrc.co/newsletter
• Contact: findrc.co/contact or hello@redcurrantco.com

Programs and Services:

• No-BS Strategic Clarity Workshop: More info here
• No-BS OKRs Workbook: PDF download available at saralobkovich.com/no-bs-okrs-workbook-pdf-tc
• Speaking and Event Facilitation: Now booking!

Find full show notes and the episode transcript via https://findrc.co/thinkydoers !

Mentioned in this episode:

Join the Strategic Clarity Workshop Waitlist for Early Bird Access

Are you ready to not just set goals, but actually change behavior to achieve them without overwhelm, shame, blame, or overthinking. Join me for the Strategic Clarity Workshop. A No-BS hands-on experience, where you'll turn your vision into a reality proof plan for real measurable results in a calm, supportive space. We're opening up the June dates very soon, and the early bird sale will be limited, so learn more and join the wait list at findrc.co/scwtd or look for the link for the Strategic Clarity Workshop on findrc.co or saralobkovich.com.