Summary:

Forget the frameworks that gather dust in your Google Drive. This is how one CEO used OKRs to rebuild trust, reduce chaos, and create clarity for her team—without losing the human side of leadership. If you’ve ever set goals that didn’t stick, this one’s for you.

What’s in it for you:

You’re drowning in competing priorities and need clarity on what to do next.
You’ve tried OKRs (or something similar) and they didn’t stick.
You want a goal-setting system that builds trust and makes decisions easier
You’re looking for something that actually works in practice—not just in theory.

Helia’s Perspective

First, know that I’m a BIG fan of OKRs. Out of all the things I’ve tried to help teams align and move forward—reading, listening, experimenting—they’ve made the most sense to me. (Thanks especially to my former Chief of Staff Emmy DeFigueiredo who brought these into my world and stayed side by side as we brought them to life!). And still, even while I sing their praises, I’ve never quite cracked how to make them feel alive—like a living, breathing part of how we work and make decisions every day.

So when Libby Fischer—someone I deeply admire—offered to share her story, I jumped. She didn’t just use OKRs. She lived them, during some of the hardest moments of her leadership. She brought OKRs into a team that had been through the wringer and made them a trust-building, problem-solving rhythm that actually stuck. When she told me her drag name would be “Sub-Bullet to Infinity,” I kind of fell in love.

If you've ever felt like frameworks are more fluff than function, I think you'll really appreciate the way Libby does this. I certainly did.

From Chaos to Clarity: Libby’s Story

Libby Fischer didn’t have a founder’s fairytale. No garage startup. No vision board. Just a company that was in trouble—and a team that needed someone to step up. "The company was failing, no one else wanted the job, and I was still there," she told me, laughing a little. "That’s how I became CEO."

She didn’t have an MBA. She hadn’t run a company before. She didn’t even know what she should be working on most days. “I was constantly reacting—whatever was on fire got my attention. I wasn’t floating, but I wasn’t leading either.”

Then came 2018. Their tech platform collapsed. Customers were furious. Employees were exhausted. Morale was in the gutter. They were in survival mode.

"We had been chasing revenue and saying yes to everything the last four years. Custom requests, side deals, anything to close. But all of that led to a giant pile of spaghetti code behind the scenes, and eventually it broke us."

Someone handed her Measure What Matters by John Doerr. Libby read it in a single weekend and came in Monday morning with a decision:

“I said to myself, ‘We’re doing OKRs.’ I didn’t have a full plan, but I had energy, and I needed a way to rebuild trust with my team. I needed to show them that I saw how hard it had been—and that I was serious about changing the way we worked day to day.”

This wasn’t about checking boxes. This was about getting out of survival mode and transforming into a business that was in charge of its own destiny.

*Libby + her husband Kyle marching in their last* *Krewe of Red Beans* parade as New Orleans *residents. New Orleans was Libby’s and Whetstone’s home for nearly a decade.*

What this Looks Like in Practice

It had taken four years to create the problems that Libby and her team were now solving.
“I had to believe that it wouldn’t take us four more years to right the ship. I felt confident that, if we worked strategically, we could turn things around in a year.”
So, she started with the end in mind.
"I thought, ‘One year from now Whetstone is thriving. We’ve hit our growth goals, our day to day is not chaotic, and our infrastructure is set up to carry out our future vision. How did we do it?” That’s the story we had to write.”
Then she worked backward. Each quarter became a chapter. Every team had its plotline. Objectives weren’t just goals—they were the turning points. And the Key Results? They were the threads that tied the story together.
Libby’s superpower is clarity. And it shows up in how she writes OKRs.
“We got into this mess because we hadn’t thought about the details. Thinking about the details was what got us out of it.”
Once she set clear objectives for the business on its path back to stability, she didn’t let them just float at the strategic level. Everything got broken down into Key Results by her Leadership Team, and then sub-Key Results by their teams, and sub-sub-Key Results by the cascading levels of the business until the path to achieving that objective was visible. (Note: John Doerr calls sub-KRs and sub-sub KRs “initiatives.”)
“Saying ‘Increase application uptime to 99% ” is a decent Key Result but it’s not enough. I made my team go further: What’s causing the downtime? What new technology do we need?Do we need new team members with specific expertise? When do we need them? How will we onboard them quickly enough to hit our timeline? How will our build and release processes look with an expanded team?

OKRs became a tool to push beyond assumptions. To spell out what needed to be true—not just what needed to be done.
“People in leadership always talk about "getting into the weeds" like it's a bad thing. And yes, you should not be in the weeds every single day as CEO, but how do you expect a garden to flourish if you don't know for certain that your gardeners have a plan for treating the weeds and the tools to do so?"
Coming out of the organizational crisis, Libby’s sales team was struggling. New business wasn’t closing. They were leaning on existing customers for growth—what should’ve been natural renewals were getting pushed into the new deal pipeline just to meet targets. Pipeline numbers were “squishy” at best.
"When I asked what was going wrong, I got a long list. Marketing wasn’t sending good leads. Customer success wasn’t passing intel. The website wasn’t converting. The deck was outdated. New features weren’t released fast enough."
Instead of trying to pep talk her way through it, she documented every excuse—and made it someone’s objective.
"Some of their objections were excuses (and I pushed back on those), but some were valid. Turning them into OKRs was a way to say, ‘I hear you—and we’re going to fix this as a team.’”
Acknowledging that the Sales Team’s success depended on the actions of other departments unlocked something.
“They didn’t feel like they were out on their own anymore. We made their success the company’s success."
Traditional Method: You miss your Sales numbers → You invest more money into the team → You’re frustrated when nothing changes → You replace your Sales Leader or live with mediocre results.
OKR Method: You miss your Sales numbers → You identify the gap(s) causing this → You and Sales Leader refine the Objective → Sales Leader and Team set Key Results → Everyone measures weekly → Adjust until it starts working.
The result? No more finger pointing. Just shared ownership. And they hit their numbers.
No new meetings. No OKR standups or special check-ins. Libby just wove OKRs into the meetings that were already happening.
“We set OKRs in our annual planning. Reviewed them in our Quarterly Business Reviews. And tracked progress at weekly Leadership Team meetings on our red/yellow/green KR Scorecard.”
Pre-existing team meetings used OKRs to prioritize; 1:1s used them to focus on the highest leverage activities. It wasn’t extra work. It was the structure underneath the work.
"After a few weeks, we started ending meetings early. Not because we rushed—because we were all good. That’s when I knew it was working."
Check out the Want to Try This section for all the details!

Libby’s Secret Sauce

After using this approach, Libby transformed her company from crisis to acquisition in just a few years. Here's what made the difference:

Think BIG Picture – Start with where you want to be a year from now, then work backwards. OKRs are the story for your year. Libby says, "Don't just focus on the next 90 days – make sure you're moving the business in the direction of your big vision!!"

Example: When Libby talks about OKRs, she says "For me, I have to start a year out and work backwards. I always think about what are our overall objectives and map out the whole year... and then align to the quarter." This approach helped her team see each quarter as part of a larger story, not just isolated sprints.

Get Specific – If meeting your Key Results doesn’t guarantee you’ll hit your Objective, you’re just making a wish list. “If you look at the Key Results list and can’t see the path to success, you’re not done with your list.”

Example: With marketing, Libby moved beyond vague goals like "drive more leads" to specific metrics: "Optimize landing page conversion rate to 5%" with sub-bullets for value proposition, page layout, and content formats. When that created the wrong leads, they could immediately see where to adjust for the next quarter.

Don’t get hung up on terminology – Call them whatever works for your team. Goals, targets, priorities, big rocks – the structure matters more than the name. Libby found, “Sometimes people get weird about ‘OKRs’ but are totally fine with ‘goals’.”

Example: Libby shared how she had a CEO who resisted the term "OKRs" but was completely on board with the exact same structure when they just called them "goals" instead. The design stayed the same, but changing the language removed the mental roadblock until folks were comfortable with the process.

Transform team pushback – When you hear the same excuses over and over, turn each one into an OKR owned by the right person. This shifts the conversation from “We can’t because...” to “Here’s how we will.” (introducing OKRs for the first time? HERE are a few scripts you can adapt and build from!).

Example: When Libby's sales team complained that sign ups for website demos weren’t from qualified buyers, instead of folks being frustrated, the team were able to ask questions and then create key results to help target. “It’s a way to say, 'I hear you—and we're going to fix this as a team.'"

OKRs become a feedback loop – Every quarter brings new experiments, and every experiment makes you better. This creates a system to make small bets and adjust in real time rather than getting stuck when things don't work out perfectly.

Example: When Libby's marketing team hit their numerical targets for demo sign-ups but found half were from the wrong industries, OKRs gave them a framework to adjust. "Before, I'd just get frustrated. Now we could say: 'Here's what's not working. Let's build a KR to test a new approach.'" They tightened personas, changed copy, and updated targeting—all within the OKR framework rather than throwing everything out and starting over.

*Libby traded New Orleans for the forests of Pennsylvania in 2022 and took on her greatest (and cutest and sweetest) challenge to date: Sylvie. Read more on Libby’s Substack,* *Outfoxed*.

Questions to Ask Yourself

Are you using OKRs?

Is everything keeping you up at night integrated in?
What excuses do you hear over and over? Could you turn them into OKRS instead?
Do you have any meetings NOT on OKRs? If so, what and why?
How are you tracking them? Is your system visual enough that anyone can see progress at a glance?
Are folks on your team bringing up OKRs without you asking?

Not yet using OKRs? Thinking about whether this could help?

How confident are you that you’ll hit your goals this year?
Does everyone on your team know how their daily work connects to your big goals?
Are your current meetings moving things forward in a way you feel great about?
Do you have a story about where you're headed—or just making a to-do list?

Here are some ways to get started:

Want to Try This?

Templates & Guides:
- Check out these actual OKRs for Libby’s edtech company (post-crisis and before acquisition!) and for Helia in 2025 (the real live working doc!) as we’re getting going that go DEEP. Have fun with the sub-bullets.
- If there's one thing you should do, it's: Make OKRs part of your regular meetings. Don't create special "OKR meetings"—just build them into what you're already doing. Here’s what this looks like:
- OKR Scorecards - HIGHLY recommend to see and track all the pieces
- ChatGPT Prompts for Writing OKRs - put the right things in and get a really solid draft in 10 minutes(!) so you get to spend your time refining and sub-bulleting(!) with your team versus trying to get things down or getting stuck wordsmithing.
- Introducing OKRs for the first time?!?!!? HERE are a few scripts you can adapt and build from.
Recommended Reads:
- Measure What Matters by John Doerr - THE definitive guide to OKRs (and their website WhatMatters .com - with oh so many resources)
- Strategic Planning Framework (Libby’s!)
- Traction by Gino Wickman - Similar framework with practical implementation advice (though Libby hates that he calls OKRs "big rocks"!)
Connections:
- Libby helps mission-driven orgs and leaders use OKRs to build trust, clarify direction, and get results. To work with Libby, send her an email at ElizabethCFischer@gmail.com with the subject line “Helia Help.”
- Have a person or org you recommend for help with strategic planning? Tell us about them!

About the Library Contributor

Libby Fischer Connell is a former accidental CEO who took a struggling tech company and turned it around by getting very clear about what mattered. Today, she helps mission-driven orgs and leaders use OKRs to build trust, clarify direction, and get results.

She’s been a barista, a teacher, a grocery store clerk, a corn detasseler, and a CEO. She lives in Pittsburgh with her husband, their magical daughter, and Sylvie, the world’s most anxious (and beautiful) dog. You can read more of her writing here and at Outfoxed.

This article comes from a coffee chat with Libby Fischer in April 2025 - and then lots of hours of her pulling resources and examples together! We've learned the most from doing and from talking with other doers willing to share their wisdom. We share these stories in the Helia Library because we don't need to start from blank pages or do it all alone.

As always, take what's helpful, leave what's not, and make it your own.

Love this article? Have a suggestion? We want to hear it all. Share feedback on this article here, and on The Helia Collective as a whole here.

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