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(!) that charts a clear path for forward — a plan 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
It’s rare that Helia takes a strong stance on how organizations should operate, but if we have one, it’s this: Every leader has a responsibility to look ahead and make sure their team has a strategic plan to guide their work. There are times I’ve done strategic planning really well and times I’ve failed terribly. In the years I’ve fallen short, my teams have felt it: the lack of clarity, the distractions, the wasted time, the lack of progress, the inefficiencies. It feels like everyone is working constantly and nothing meaningful is getting done.
Libby's been there too. Her company nearly fell apart when years of working without a strategic plan led it to a crisis point. She brought it back from the brink with a 2-day strategic planning process that 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 everywhere as, honestly, the greatest gift for their work and their teams and what they’re trying to accomplish.
Strategic Planning doesn’t have to take fifty pages or hundreds of hours or $100K+ of consulting or fancy-ness. Folks often go there (myself included) because they fear if their process is too 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 just another forgotten 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."
Eventually, the business hit a scaling cliff and was at serious risk of falling off the ledge (read the whole story HERE). A mentor handed Libby the book Traction, by Gino Wickman, just in time. “It’s a strategic planning process that can be done in two to three days and fits on two pages. There’s no fluff. It’s designed to illuminate what your OKRs should be, and it’s not done until your 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 step-by-step process with separate meetings for different topics, concise agendas, and a consistent way to document decisions."
The result was a simple two-page plan that codified the company’s vision (page one) and everything they needed to do that year to move toward that vision (page two). "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 we were stressed and not thinking clearly, we would pull it out and use it to make decisions."
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 (yes, eight!) targeted meetings made all the difference. (Are you meeting-phobic? Read our article on How to Run Good Meetings.)
"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:
Day 1: Vision
Core Values (Re-)Definition (What values will guide our decisions?)
Organizational Focus (What Business Are We In?)
10-Year Target (What’s the BIG GOAL we’re aiming for?)
Market Positioning (Who do we serve and how?)
Day 2: Operational Strategy (Plan of Action)
3 Years From Now (What will the org look like in 3 years if we’re on track to our 10-Year Target?)
1-Year Plan (What are the big Objectives that, if achieved, will mean we succeeded?)
Next Quarter (Key Results – What is everything that needs to be done in the next 90 days to be on track to those objectives?)
Issues (What are the current opportunities and challenges that need to be tackled along the way?)
"Each meeting guides you to make the decisions needed to fill out the Strategic Plan Framework. If you follow the process, it’s hard to finish without a good plan.”
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 key things that will actually drive your organization forward: a long-term goal, a clear definition of success in 12 months, a detailed plan for the next 90 days, and an agreed upon definition of your business and market to filter tough decisions."
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After years of rapid growth, Libby's startup hit a crisis point. Their software platform was crashing regularly, frustrating both customers and the team. Despite it being May – not typical planning season – Libby gathered her team. "I said, 'We just survived a crisis. Our year starts now.'"
Libby knew that the strategic plan her company needed would not be the plan everyone in the business wanted. "Our new CTO was clear with me before our strategic planning meeting – we needed a complete front-end rewrite and database restructure," Libby explained. "This meant sacrificing all new feature development for a year." Sales wanted new features, major clients expected custom development, and different teams had their own urgent needs.
Scaling back was not going to be a popular decision. "There were about 20 competing priorities across departments. Previously I would have said, 'Let's do it all!' But that's how we ended up in our crisis. I knew if we were going to move forward with a plan that was best for the business as a whole, that I’d need to get every member of my team to agree to prioritize the business over their department.
Through her structured process, the team realigned on values, clarified their focus and market, 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 agreed that resolving their tech debt was most important, second only to retaining customers and employees. Those became the top 3 objectives for the year, and they used the rest of the time to map out the key results they needed to accomplish in the next quarter in order to be on track.
“The Focus meeting on Day 1 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."
The next year? They got acquired at a valuation beyond their dreams.
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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’ve been forced to delegate to their teams. They can fully focus.."
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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. Page two of the Strategic Plan is the OKR list," Libby explained. “They’re not two separate things. When you weave the OKRs into meetings that are already happening, the strategic plan naturally gets integrated into the day to day.”
She solved this by calendaring out meetings at a “just right” cadence to track progress on the Objectives (1-yr Plan) and Key Results (Next 90 Days) sections of the strategic plan.
Quarterly meetings were used to track progress to OKRs at the end of each quarter and set new KRs for the next quarter
Weekly leadership team meetings tracked leading indicators of OKR progress through a simple red/yellow/green scorecard & enabled cross-functional teams to work together to remove barriers that threatened OKRs
One-on-ones created a space to dig into key results that were stuck or tradeoffs that needed to be made
These regular touchpoints gave her team a space and a process to respond to the inevitable challenges that came up throughout the year.
“If you make a strategic plan in January but funding gets cut in June, you need to adjust the plan. You don’t have to redo the whole thing, but you absolutely need to take a look at the 1-year Objectives and say, ‘Are these still feasible given the new situation? If yes, what are all the extra things you’re going to have to do to overcome that challenge? If no, then let’s redefine success and make a plan to hit that.’”
Integrating the strategic plan/OKRs into her company’s existing meetings transformed 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 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."
The Secret Sauce
If there's one thing you should do, it's: Use a clear process and stick to it. Libby like’s Traction but use whatever you like! Just stick to it.
Two Days = Exactly right – Do it in intensive sessions, not spread across weeks. How to do it: Follow this itinerary for the two days.
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.
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.”
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.
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