Long Story Short
Long Story Short: A revenue target and a random list of initiatives is NOT a strategic plan. AND, a 100-page strategic plan that nobody ever looks at is just as useless. If you don’t have time to read this article, we built you a Strategic Planning Toolkit based off the book Traction to help you thread the needle with a 2-day strategic planning process that fits on 2 pages.
How to Jump!
Libby here!
“Pick a revenue number and hope for the best.”
That was my strategic planning “process” for years. To say I’m not proud of it is an understatement.
Every year it was the same story: I’d gather my leadership team, someone would throw out a number that felt ambitious but not insane, and then we’d list out whatever operational headaches were on our minds that day as “strategic priorities” and call it a plan.
Because this plan wasn’t really a plan, it naturally led to chaos, and I didn’t sleep for about four years.
We had a great product. We had a great team that worked insanely hard. But we were constantly in firefighting mode. We were saying yes to everything — every client request, every new feature, every shiny opportunity — because we didn’t have a clear strategic plan that told us what to say no to. Everyone was exhausted.
And then the business hit a scaling cliff. Our software platform was crashing regularly. Customers were frustrated. The team was demoralized. We were at serious risk of falling off the ledge entirely.
What I learned the hard way is that if you don’t invest the time in real strategic planning up front, you’re going to spend time putting out fires on the backend. And, thankfully, there’s a better way to do it than a month-long process that ends with a 100-page plan you never look at again!
The book that gave me a strategic planning process I actually use
A mentor handed me the book Traction by Gino Wickman right when I needed it most. It laid out a strategic planning process that could be done in two to three days and fit on two pages. My first reaction was: this can’t be right. It’s too simple. Real strategic planning takes months and consultants and a document nobody actually reads, right?
Wrong.
What Traction taught me is that a simple plan doesn’t mean we did strategic planning incorrectly. It means we took the time to ask the right questions and make tough choices so that everything could fit onto two pages; to distill everything down to the stuff that really matters so that we knew what to focus on and what distractions to avoid for the rest of the year.
What makes the difference isn’t just the framework itself — it’s having separate meetings for different topics, concise agendas, and a consistent way to document decisions. No sprawling off-site. No hundred-page deliverable. Just a clear process that, if you follow it, is hard to finish without a good plan.
In addition to Strategic Plans, Libby is an expert wedding officiant!
The Key Takeaway
Most strategic plans fail before they’re even finished. Not because the people making them aren’t smart or don’t care — but because the process is either so complicated it never gets finished, or so vague it produces a document that sits in a Google Drive and collects dust.
Two things have to be true for a strategic plan to actually work: it has to be simple enough to remember and structured enough to finish. A two-page plan that your team references every time there’s a tough decision beats a fifty-page plan that nobody uses. And a two-day intensive process with clear agendas beats six months of scattered meetings where you keep starting over.
Libby’s DIY Version of the Traction Process
If you’re a “just tell me what to do and let me get started” kind of person (aka Helia’s COO, Libby), our Strategic Planning Toolkit gives you the process, the template, and an example to get started.
If you’re a “tell me why this works” kind of person (aka Helia’s Founder, Jess), read on. Here’s what we’re going to cover:
- Day 1: Vision — Define your values, your focus, your 10-year target, and your market positioning
- Day 2: Operational Strategy — Build your 3-year picture, your 1-year plan, your 90-day priorities, and surface the issues standing in the way
- Days 3-363: Make it a living document — Connect the plan to your existing meeting rhythm so it actually drives decisions instead of gathering dust
How this Strategic Planning Process Works
Day 1: Vision — get aligned on where you’re going before you talk about how to get there
Day 1 is made up of four conversations, each with one job — get your team aligned on the fundamentals before you touch anything operational.
- The Core Values Meeting
- The Organizational Focus Meeting
- The 10-Year Target Meeting
- The Market Positioning Meeting
The sequence matters. I’ve sat in meetings where the CEO opens with, ‘Hey guys, what should we do this year?’ No surprise, we’d talk about none of the above, leave with a crappy plan (if you could even call it that), and the rest of the year would be miserable. When you skip the vision work and jump straight to priorities, you end up with a list of competing agendas dressed up as a strategy.
The Core Values Meeting isn’t a feel-good exercise. It gets you the answer to a critical question: what environment will enable our success? This conversation is about naming the values that are actually true of your organization today — not the ones that look good on a website or the ones that were true when you were half the size. Organizations evolve, and when your team can articulate shared values clearly as it grows, it becomes much easier to make decisions together, hire the right people, and call it quits when something feels off. These are the foundational norms that make it possible to run your organization without constant whiplash or headaches.
The Organizational Focus Meeting asks what ‘business’ you’re actually in — which sounds obvious until you’re in a room with five people who have five different answers. This is the conversation that gets everyone aligned on what you do, who you do it for, and why it matters. It’s also the session that saved my company. We got into our crisis because we tried to be all things to all people. The Focus conversation was perfectly designed to get everyone to agree that we needed to focus on what actually 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. Without that alignment, Day 2 would have been a fight.
The 10-Year Target Meeting gives your team a big, motivating goal to aim at — something far enough out that it feels ambitious, but specific enough that you’ll know if you hit it. This isn’t a revenue projection or a strategic objective. It’s a north star. Having it changes how you make decisions in the short term, because every quarterly priority can be evaluated against it: Does this move us toward the 10-year target, or away from it? It also has a way of clarifying what you’re not trying to do, which is often just as useful.
The Market Positioning Meeting closes out Day 1 by going deep on who you serve and how — and what makes you the right choice for them. This conversation is where you get honest about your niche. Not who you wish you served, but who you actually serve well, and what they value about what you do. It becomes the filter for the tough decisions that come up throughout the year. When a new opportunity shows up that sounds exciting but doesn’t quite fit your market, this is what you point to when you say no. (Easier said than done for most CEOs, but critically important.)
At the end of Day 1, you might find yourself thinking: this is too easy. We must be missing something. I had that exact thought. But we weren’t missing anything! We were just finally asking the right questions in the right order.
Libby and her dog, Sylvie, who is often as much work as running a business.
Day 2: Operational Strategy — translate vision into a plan your team can actually execute
Day 2 is where the vision becomes a plan. Four more conversations:
- The 3-Years From Now Meeting
- The 1-Year Plan Meeting
- The Next 90 Days Meeting
- The Issues Meeting
The 3-Years From Now Meeting asks a simple question: what will your organization look like in three years if you’re on track to your 10-year target? Revenue, team size, programs, reach — whatever the meaningful markers are for your organization. It’s a bridge between the long-term vision and the work you’re about to plan for the next 12 months. It doesn’t need to be complicated. It just needs to be specific enough to know if you’re on track.
The 1-Year Plan Meeting is where you identify the big objectives that, if achieved, will mean you succeeded this year. This is also where the hard calls get made — and where a good process earns its keep. Before we started our planning session, our new CTO was clear with me: we needed a complete front-end rewrite and database restructure. That meant sacrificing all new feature development for a year. This was a tough pill to swallow because there were about 20 competing priorities across departments. Sales wanted new features. Major clients expected custom development. Our Ops Team wanted better tracking. Previously I would have said, “Let’s do it all!” But that’s how we ended up in our scaling crisis. I knew that if we were going to move forward with a plan that was best for the organization, I’d need to get every member of my team to agree to prioritize the business over their department. And, through the process, we did. Resolving our tech debt became the top priority, second only to retaining customers and improving employee satisfaction. Those became our top three objectives for the year.
The Next 90 Days Meeting gets specific about, well, the next 90 days. Essentially, it asks, what needs to happen to be on track to those one-year objectives? This is where plans either get real or fall apart. It’s specific enough that people can’t hide behind vague language. For us, coming out of our crisis, the 90-day conversation was about immediate stabilization — what exactly needed to happen in the next three months to stop the bleeding and start rebuilding trust with customers and the team. Things like:
- CEO leads partner success calls with all clients <$50,000 ARR within 3 weeks.
- CS, Product, and Engineering audit all custom development requests, choose critical work to complete within next 6 weeks, and manage expectations with clients about rejected requests.
- Hire two new AI-native software engineers and 1 QA person by end of quarter.
If you can’t name what needs to happen in the next 90 days, you don’t actually have a plan yet — you have a wish.
The Issues session is last, and it’s not an afterthought. It’s where you surface the opportunities and challenges that need to be tackled along the way — the things that could derail your objectives if you don’t address them head-on. For us, this meant naming the things we were worried about: client relationships that might not survive a year without new features, team members who were skeptical the rewrite would actually work, and the internal communication plan we’d need to bring everyone along. Putting them on the table didn’t make them scarier. It made them manageable. Plus, having a dedicated meeting where we knew we’d go deep on these things meant that our other conversations didn’t get sidetracked. When an issue surfaced, we’d just say, “Add it to the Issues List” and get back to the discussion at hand.
If you can’t name what needs to happen in the next 90 days, you don’t have a plan yet — you have a wish.
Days 3-363: Make the Strategic Plan a living document — or it’s just another file in your Google Drive
Here’s where most strategic plans die. Not in the making — in the not-using.
You know that feeling when you finish strategic planning and then nothing changes? That happens because most plans don’t become part of your regular meeting rhythm.
The fix is simpler than it sounds: the Strategic Plan is the OKR list. They’re not two separate things. When you weave the OKRs into meetings that are already happening, it’s not extra work — it’s the structure underneath the work.
Here’s what that cadence looked like for us:
- Quarterly meetings tracked progress on OKRs at the end of each quarter and set new key results for the next 90 days.
- Weekly leadership team meetings tracked leading indicators of OKR progress through a simple red/yellow/green scorecard and gave cross-functional teams a space to remove barriers together.
- One-on-ones were where we dug into key results that were stuck or tradeoffs that needed to be made.
And when things changed — because they always do — we used the plan to respond. If funding gets cut in June, you don’t redo the whole thing. You pull out the 1-year objectives and ask: are these still feasible? If yes, what extra things do we need to do to overcome the challenge? If no, let’s redefine success and make a new plan to hit that.
The human impact of this was the thing I didn’t expect. We went from a working environment with all the ingredients for burnout to a place where people no longer had to work nights and weekends just to survive. Nobody feared opening their laptop on Monday morning. 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 organization and a surviving one.
When to do this Yourself vs Bring Someone in
The honest answer is: most people can do this themselves. The Strategic Planning Process and Strategic Plan Framework are designed to be followed without a facilitator, and if you have a leadership team that’s reasonably aligned and willing to do the work, you have what you need to get started.
That said, there are times when bringing someone in makes sense:
- Your leadership team has unresolved tension that tends to derail conversations before they get productive
- You’ve tried strategic planning before and kept ending up with a document nobody used
- You’re at a genuine inflection point — a crisis, a merger, a leadership transition — and the stakes are too high for a process that might stall
- You want someone in the room whose only job is to hold the process, so you can actually participate instead of facilitate
If You Need Help
Libby, Helia’s COO, works with organizations on strategic planning — from first-timers who want a thought partner through the process to teams that need a facilitator in the room for the full two days.
Libby and Helia are a good fit if:
- You want to follow this process but would feel better having someone hold the structure so your whole team can participate
- You’ve done strategic planning before and ended up with a document that didn’t stick — and you want to figure out why
- You’re navigating a significant moment of change and need a plan that’s built for the reality you’re actually in, not the one you had six months ago
- You want help connecting your strategic plan to your OKRs and meeting rhythm so it actually drives decisions
Connect with Libby!
Try it Yourself
- 01 — Strategic Planning Day 1: Vision: Use this first, before anyone touches a single operational priority, to get your team aligned on the fundamentals that everything else depends on.
- 02 — Strategic Planning Day 2: Operational Strategy: Use this after Day 1 to translate your vision into specific OKRs and 90-day commitments that your team can actually act on.
Recommended reads:
- Traction by Gino Wickman — The strategic planning process this article is built on
- The Five Dysfunctions of a Team by Patrick Lencioni — A leadership fable you can read in an afternoon that will change how you think about team dynamics
- The Advantage by Patrick Lencioni — Lencioni’s follow-up, focused on clarity and alignment for leadership teams
- Measure What Matters by John Doerr — The definitive guide to connecting strategic plans to OKRs
Go deeper:
- Check out Helia’s own Strategic Plan Framework to see what a completed two-pager looks like in practice
Questions to Sit With
- If I asked five people on my team what our top three priorities are right now, would they all give the same answer?
- What’s the biggest fire we keep putting out — and could a clearer plan prevent it entirely?
- When was the last time we worked on the business instead of just in it?
- Do we have a plan we actually reference when making tough decisions, or just a document we made once and forgot about?
- What would it feel like to stop playing defense?
This article comes from a coffee chat with Libby Fischer in April 2025. These conversations form the heart of the Helia Library — because we’ve learned the most from doing and from talking with other doers willing to share their wisdom. We don’t need to start from blank pages or do everything alone.
Not sure Libby‘s the right fit? Talk to Helia directly!
About Libby
Libby Fischer Connell is a former accidental CEO who took a struggling tech company and turned it around through strategic clarity and operational excellence — and then watched it get acquired at a valuation beyond her dreams. Today she’s Helia’s COO and works with mission-driven organizations on the kind of planning that actually drives results. She’s been a barista, a teacher, a grocery store clerk, and a corn detasseler. 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 at Outfoxed.
