Strategic Planning: From Reacting to Leading
Summary:
Forget complicated strategic plans that gather dust in your Google drive. This is how one leader uses a two-day process to create a two-page plan(!) charts a clear path for forward-progress and that you can actually use to get unstuck when things get chaotic.
What’s in it for you:
You’re tired of "plans" that don't change anything
Your team feels busy but not focused
You’ve entered annual planning sessions with your team saying, “so, what do we want to accomplish this year?”
You need a living plan that fits on two pages—not a two hundred page PDF that sits in a Google Drive.
Helia’s Perspective
The reality is - every leader has a responsibility to think ahead and make sure their team has a plan to operate against. There are times I’ve done this really well - and times I’ve failed terribly. And when I have failed, I take full accountability for ALL the things that happened - the lack of clarity, the distractions, the wasted time, the lack of progress, the confusion, the inefficiencies, etc. I own it and it’s real!!!
Libby's been there too. Her approach combines her hard-earned lessons with advice from trusted mentors into something beautifully practical. It's a process I wish I'd known earlier and now want to share with every leader and every org to be able to actually follow, as honestly, the greatest gift for your work and your teams and what you're trying to accomplish.
Strategic Planning doesn’t have to take fifty pages or hundreds of hours or $100K+ of consulting or fancy-ness, which is often where folks go (myself included) because they fear if their process is simple, they’ve done it wrong. With Libby's approach, you can create a two-page plan in just a few days that actually guides your team's daily work - not another dusty document in your Google Drive.
From Reacting to Leading: Libby’s Story
"Before I discovered a real strategic planning process, my approach was pretty much 'pick a revenue number and hope for the best,'" Libby told me, laughing a little. "We'd throw in whatever operational headaches were on our minds that day as 'priorities' and call it a plan."
Despite having a great product, Libby's team was in constant firefighting mode. The company was growing, but at a painful cost. "I didn't sleep for about four years," she admitted. "We were saying yes to everything, constantly reacting, and everyone was exhausted."
At the same turning point when they adopted OKRs (read the story HERE), Libby found the book Traction, by Gino Wickman. “It’s essentially a strategic planning process designed to illuminate what your OKRs should be, and it’s not done until the OKRs are mapped out.”
"I followed it almost to the letter," she told me. "What made the difference wasn't the specific framework, though I think it’s a great one - it was having a clear process with separate meetings for different topics, clear agendas, and a consistent way to document decisions."
The result was a simple two-page plan that, alongside her OKRs, were the foundation AND the north star. "It wasn't just another document in our Google Drive," she emphasized. "It became the tool we used at every moment of tension or tradeoff. When you're stressed and not thinking clearly, you can pull it out and remember what you decided matters most."
And then she and her team started having fun again.
Did Libby organize a neighborhood pickleball tournament to raise money for the local community center? Or did she do it so that she had an excuse to use a megaphone?
Libby’s Key Takeaways
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Strategic Planning sounds straightforward but quickly derails without structure. Libby discovered that using a consistent approach across eight targeted meetings made all the difference.
"I've sat in meetings where the CEO opens with, 'Hey guys, what should we do this year?' No surprise - we'd leave without a plan, and chaos would follow."
Instead, Libby's process breaks planning into distinct conversations with clear purposes:
Core values and organizational focus (What principles guide our decisions?)
Long-term vision (Where are we headed?)
One-year plan (What must we accomplish this year to be on track to our vision?)
Quarterly priorities (What must we accomplish in the next 90 days to be on track to our one-year plan?)
"The magic is simple: you're not done until the template is filled out."
What's unique about Libby's approach is its simplicity. "When I was preparing for this conversation, I looked at a bunch of different strategic frameworks and got super overwhelmed," she admitted. "I worried my process was too simple."
But that simplicity is precisely what made it work. "You don't need every team to come with a slide deck; you don’t need an overwrought process. You need the four key things that will actually drive your organization forward: a long-term target, a detailed plan for the year, a detailed plan for the next 90 days, and articulated values or focus to filter decisions."
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After years of rapid growth, Libby's startup hit a crisis point. Their platform was crashing regularly, frustrating both customers and the team.
"Our new CTO was clear – we needed a complete front-end rewrite and database restructure," Libby explained. "But this meant sacrificing all new feature development for a year."
Despite it being May – not typical planning season – Libby gathered her team. "I said, 'We just survived a crisis. Our year starts now.'"
With about 20 competing priorities across departments, the decision was challenging. Sales wanted new features, major clients expected custom development, and different teams had their own urgent needs.
"Previously I would have said, 'Let's do it all!' But that's how we ended up in crisis. This time, we agreed resolving our tech debt was most important, second only to retaining customers and employees. Those became the top 3 priorities.”
Through her structured process, the team realigned on values, clarified their focus, and created a motivating 10-year vision.
“At the end of Day 1 I thought to myself, ‘This is too easy. We’ve got to be missing something.”
But they weren’t missing anything. On Day 2, they mapped out all the details and left with a clear plan based on what they were uniquely good at.
“The Focus meeting was the key to success. We got into our mess because we tried to be all things to all people. The session was designed perfectly to get everyone to agree that we needed to focus on what made us successful – a product that makes life easier and amazing customer relationships – if we wanted to reduce the chaos we’d come to dread.”
Within a year, they resolved their tech debt, reduced hosting costs by 80%, positioned Whetstone to scale to 100,000 more users, and doubled revenue – all with zero customer or employee churn related to our tough choices."
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Libby recommends completing strategic planning in 2-3 intensive days rather than spreading it across weeks or months.
"When you spread it out, whatever happens between day one and day two can completely disrupt your thinking," she explained. "You forget what you talked about, or new crises pop up that render everything you’d previously discussed moot."
This intensive approach forces everyone to get their thoughts organized and creates a clear boundary between working "in" the business versus "on" the business.
"Strategic planning is working on the business, not in it," Libby emphasized. "It's hard to go from thinking about high-level strategy on Monday, then being in the weeds Tuesday through Friday, and then trying to lift back up to strategy the next Monday. I just can't do it."
The short timeframe also creates productive pressure. "If you're going to be offsite or unavailable to answer emails for two straight days, it forces you to get your stuff together. People come prepared because they know this is their window to influence the direction."
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The difference between a good plan and a great one isn't what's in it - it's how you use it. Libby transformed her strategic plan from a static document into a dynamic tool by connecting it directly to how the team works.
"You know that feeling when you finish strategic planning and then nothing changes?" Libby asked. "That happens because most plans don't become part of your regular meeting rhythm."
She solved this by translating her strategic plan into OKRs (Objectives and Key Results) that became the backbone of every meeting:
Annual planning set the year's direction and priorities
Quarterly meetings reviewed progress and set next steps
Weekly leadership team meetings tracked progress through a simple red/yellow/green scorecard
One-on-ones focused on individual contributions to the larger goals
"The ‘plan’ is the OKR list," Libby explained. “They’re not two separate things. And when you weave it into meetings that were already happening, it's not extra work - it's the structure underneath the work."
When Libby brought this approach to Open Literacy,one year into its new business model, the impact was immediate. "The first week I was there, I just listened," Libby said. "A question I heard over and over was, 'What should I be focusing on this week?'"
After running her strategic planning process with leadership, "I never heard that question again. There was a roadmap for curriculum development, a plan for coaching tutors – and all it took was creating the space for a targeted discussion with a clear agenda and a ban on tangents."
This integration transforms day-to-day operations. "We had fewer urgent customer emails, fewer disruptions to our product roadmap, and less tension in cross-departmental meetings," she shared. "Suddenly our regular meetings weren't about firefighting but about becoming leaders in the market."
The Secret Sauce
If there's one thing you should do, it's: Use a clear process with separate meetings for different topics and stick to it. Don't try to cover everything in one marathon session.
Tangents are the enemy of good strategic planning. - "Avoiding tangents doesn't mean you won't go deep—it means you'll go deep on the right things." How to do it: Have a clear agenda for each meeting, and when a tangent comes up say, “We’re on a tangent. Let’s add that to the “Issues List” and we’ll cover it during the Issues Session.”
Keep it simple!!! – You don't need to leave with a 40-page document to have done Strategic Planning. Four key elements matter most: long-term target, one-year plan, 90-day plan, and values/focus. How to do it: Create your two-page strategic plan by having separate sessions to cover each topic.
Two Days = Exactly right – Do it in intensive sessions, not spread across weeks. How to do it: Follow this itinerary for the two days.
PRIORITIZE – If everything is important, nothing gets solved. How to do it: Schedule a 2-hour “Issues Session.” Start by having the team list every issue with the business they can think of. Then, set a timer for 3 minutes and tell the team: “Decide on the top two issues.” Spend the rest of the time solving those issues. If you have time left over, set the prioritization timer and do it again.
Building Trust - The human impact of this approach is powerful. As Libby experienced: "We went from a working environment with all the ingredients for burnout to a place where nobody worked nights and weekends just to survive. Nobody feared opening their laptop on Monday morning. And our numbers were better than ever! We finally had time for the creative work we'd dreamed of but never had space for. The trust that builds when you go from playing defense to playing offense is the difference between a thriving business and a surviving one."
A snapshot of Libby’s daily hikes with her beloved dog. Sylvie, in The Slags (a Pittsburgh thing!). You can read all about how The Slags are changing and Sylvie’s hijinx as a puppy on Libby’s Substack, Outfoxed.
Questions to Ask Yourself
If I asked five people on my team what our top priorities are, would they all give the same answer?
What's the biggest fire we keep putting out? Could better strategic planning prevent it entirely?
Do we have a plan we actually reference when making tough decisions, or just vague directions?
When was the last time we worked "on" our business instead of just "in" it?
What's preventing our team from shifting from defense to offense?
Want to Try This?
Templates & Guides:
Strategic Planning Process - The FULL process - all the structured agendas for the eight strategic planning meetings
Strategic Plan Framework - The two-page template Libby uses to document decisions and keep priorities visible
Check out Helia’s initial Strategic Plan Framework (as of May 2025) to see what it looks like in action
Sample Emails to send the team pre and post planning sessions
Recommended Reads:
Traction by Gino Wickman - The strategic planning process Libby follows "almost to the letter"
The Five Dysfunctions of a Team by Patrick Lencioni - Helia’s FAVORITE leadership fable I’ve ever read - beautiful and SO SO SO helpful - and you can pretty read it in an afternoon. Noting Libby also recommends his book The Advantage which focuses on clarity and alignment for leadership teams
Helia’s article - also co-written with Libby!) on Getting to Clarity: OKRs for Results!!!! (with a bonus of reading Measure What Matters by John Doerr on how to connect strategic plans to OKRs
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 through strategic clarity and operational excellence. Today, she helps mission-driven organizations create plans that actually drive results rather than gather dust.
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.
