Leading with OKRs

Welcome and Introductions

Rina Alexin | 00:00–02:03 OK, so welcome and thank you so much for joining us today. Today, we’re bringing you a fantastic webinar — one that Ryan has been called back to due to its high reception last year: *Leading with OKRs*.

Now, for many of you, we’re in the second half of the year. Everyone’s on different calendars, but this is the perfect time to reflect on how the year has gone so far — and what big goals and objectives you want to carry into next year. Annual planning is coming fast, so this is a great webinar to not just listen to, but repeat when you’re doing that planning.

Rina Alexin | 02:04–03:52
For those of you who don’t know us, at Productside we pride ourselves on being an outcome-driven product partner. We deliver results, not just training — helping our clients transform through consulting, coaching, and implementation. We focus on understanding each organization’s gaps, tailoring solutions to mature their product practices in both skills and process.

Rina Alexin | 03:53–04:14
These webinars are for you — so please stay engaged! Use the chat, talk to one another, and share your perspectives. I’ll monitor Q&A while Ryan presents. If you’re wondering, yes — you’ll get the recording afterward.

Rina Alexin | 04:15–04:50
Also, if you haven’t joined our LinkedIn group yet, we have over 60,000 product professionals sharing insights daily. It’s a great space to connect and grow your network. Product management is hard — don’t do it alone!

Setting the Stage – The Power of OKRs

Ryan Cantwell | 04:51–06:19 Thank you, Rina! Hello everyone — I’m **Ryan Cantwell**, Principal Consultant and Trainer here at Productside, calling in from Pittsburgh, Pennsylvania. Let’s dive right in.

We’re here to talk about a tool product managers can use to achieve more — OKRs: Objectives and Key Results. Today, we’ll explore best practices, common pitfalls, and how OKRs can transform not just teams, but leadership effectiveness.

Story: Regan’s Journey with OKRs

Ryan Cantwell | 06:20–08:36 Meet Regan — a results-driven product leader working in a fast-paced environment. She’s overwhelmed by constant change and shifting priorities. One day, she learns about OKRs and realizes they might help her bring order to the chaos.

Initially, she’s hesitant — she can’t change her entire organization. But she discovers she doesn’t have to. By starting small and applying OKR principles in her own work, she quickly becomes more focused, more organized, and starts getting noticed for her impact.

What Are OKRs?

Ryan Cantwell | 08:37–10:47 OKRs stand for **Objectives and Key Results**. – **Objectives** are aspirational — they describe what you want to achieve. – **Key Results** are measurable indicators showing how close you are to reaching that goal.

When combined, they bring focus, alignment, and transparency. OKRs help teams connect strategy to execution — turning lofty visions into measurable progress.

Breaking Down Objectives

Ryan Cantwell | 10:48–12:10 Objectives should be **clear, inspiring, and action-oriented**. They’re qualitative statements describing a future state the organization or team wants to achieve. Think of them as the “north star.”

For example:

Reach the top of the highest peak this season.

Ensure all team members safely reach the summit.

They motivate, align, and inspire.

Breaking Down Key Results

Ryan Cantwell | 12:11–14:28 Key Results are **quantitative**. They measure progress toward the objective. They’re time-bound, tangible, and assigned for accountability.

Example:

Achieve weekly hike durations of 10 hours.

Complete three intermediate hikes with at least 2,000-foot elevation.

100% gear check success before each hike.

Each key result moves you closer to your goal.

Discussion: Selecting the Right Key Results

Rina Alexin | 14:29–15:00 Ryan, we often see teams struggle with too many key results. What’s your advice on choosing the right ones?

Ryan Cantwell | 15:01–17:07
Great question. Start with feasibility and strategic connection. Ask: can this team truly influence this metric? Does it link to the objective? Keep only what’s essential — the “key” in key results matters. And don’t be afraid to refine them as you learn.

Poll #1 – What’s Your Experience with OKRs?

Rina Alexin | 19:00–21:06 Let’s see where everyone stands. How experienced are you with OKRs? Most of you seem familiar but still experimenting — perfect. This session will deepen that understanding and give you tools to use OKRs strategically.

Best Practices for OKRs

Ryan Cantwell | 22:13–25:25 OKRs are flexible and adaptable. The Harvard Business Review found people who write down goals are **10x more likely** to achieve them. Write your goals, but keep them dynamic. Adjust as conditions change.

Avoid rigid planning — OKRs should motivate, not overwhelm. Use only a few measurable key results, and connect them clearly to outcomes.

Connecting OKRs to Strategy

Ryan Cantwell | 25:26–27:42 OKRs should cascade from strategy. Business objectives stem from mission and vision, product objectives stem from those business goals, and initiatives drive execution.

Imagine Dunder Mifflin’s regional manager aiming to become “the most customer-centric paper supplier.” The Scranton branch can align by setting its own localized OKRs that ladder up to that vision.

Product Objectives and Initiatives

Ryan Cantwell | 27:43–29:45 Product objectives define how your product delivers value to users. They’re the customer-facing side of business goals. Initiatives — epics, features, user stories — represent how you’ll achieve those results. Together, they create a full strategy loop: strategy → objectives → key results → initiatives → outcomes.

Poll #2 – Which Best Practice Helps You Most?

Rina Alexin | 39:12–40:48 Which best practice do you think would benefit you most? Aligning OKRs with strategy? Clear communication? Cascading objectives? Most of you selected alignment — no surprise. Alignment is what makes OKRs powerful and sustainable.

When Good OKRs Go Bad

Ryan Cantwell | 41:00–44:22 The most common failure? Confusing outputs with outcomes. Outputs are activities; outcomes are results. Hosting a dinner party isn’t about how hot the meal was — it’s about whether your guests enjoyed it.

OKRs should measure impact, not just activity.

Why OKRs Shouldn’t Be Performance Metrics

Ryan Cantwell | 44:23–46:42 OKRs work best for teams and products — not individuals. Using them as personal performance tools limits creativity and transparency. Even **Spotify** abandoned OKRs for individual performance, realizing they distracted people from *why* they were working.

The “Deadly Sins” of OKRs

Ryan Cantwell | 46:43–48:29 Avoid these traps: – No alignment to strategy. – Leaders dictating OKRs without team input. – Vague or uninspiring objectives. – Overly rigid plans with no flexibility.

Keep OKRs connected, motivating, and revisited often.

Q&A and Closing Remarks

Rina Alexin | 50:41–End Thank you, Ryan! Let’s take a few questions before we wrap.

Q: How are key results different from KPIs?
A: KPIs track ongoing health. Key Results measure progress toward a specific objective — they’re temporary and contextual.

Q: What if my company doesn’t have a goal-setting process?
A: Start small. Apply OKRs within your team. Pilot the approach, then expand as it gains traction.

Rina Alexin | Closing
If you enjoyed today’s session, join our next webinar, Getting Real Product Management Work Done with AI, hosted by Dean Peters and Joe Ghali. And don’t forget — use code OKR500 for $500 off any Productside instructor-led course.

Thank you for joining us today — and remember, product management is hard. Don’t do it alone.