Rethinking Strategy Planning When Clarity Feels Out of Reach
I’ve learned something after too many years in business planning: most of us are winging it. Not when it comes to goals, or vision—those, oddly enough, tend to be clear. But process? The system? Total improvisation. People nod, scribble, murmur about “market dynamics” and “operational bottlenecks.” Then they leave the room, unsure what just happened. I know this because I’ve done it—too many times.
Here’s where it gets weird: everyone accepts this. Strategy planning is broken, yet we pretend it works. Why? Habit, mostly. Planning looks productive. Whiteboards fill. Sticky notes multiply. Someone says, “We’re getting somewhere.” Are we? Probably not.
You’ve been there too, right? Maybe. Maybe not. Maybe your team gets through those sessions cleanly. If so, congratulations. But most don’t. Most people leave those rooms drained and not clear.
Clarity. That’s the word. Not progress, not insight. Clarity. That gut feeling that you know what matters next. That was missing, and I didn’t realize how badly I missed it until I stumbled on something stupidly simple. But I’ll get there.
First, let me describe how things usually went. Picture a table. Seven people. Coffee is going cold. Ideas scatter. Someone draws a quadrant, vaguely. Strengths? Silence. Then a half-hearted answer. Someone writes it down. The rest of the team nods, but they’re not engaged. They’re waiting for their turn to say something obvious. This goes on. Strengths, Weaknesses. Opportunities. Threats. Same pattern. By the end, it feels like we built something. We didn’t. We listed things we already knew. No clarity. Just clutter.
One night, tired and frustrated after a session like that, I stopped. Not because I wanted to. It was late because I didn’t have the energy to fake it anymore. I opened my laptop—no grand plan. I just wanted to dump my thoughts somewhere, anywhere.
And that’s when I did something strange.
I opened a simple quadrant tool, but no account was required. No setup. Four boxes. I typed. No structure. No method. Just typing. Strengths. Weaknesses. Threats. Opportunities. Whatever I thought of. At first, it didn’t feel very sensible. But as I filled those boxes? Patterns appeared. Real patterns. Connections I’d missed in those polished meetings.
That surprised me enough that I paused. Then I kept going, adding, moving things around, assigning names to problems, marking risks, and labeling tasks without even noticing.
When I looked up, two hours had passed.
Next morning, I showed it to my team—not as a process, not as a solution, just as a tool to try. They resisted at first. Then something shifted. Not dramatically, not visibly, but people contributed—honestly, quickly, without waiting for permission.
Ideas stopped being statements and started becoming tasks.
Not a perfect session. But real. Focused.
After that, I kept using it quietly because I wasn’t sure it would hold. Maybe it was a fluke, but it wasn’t. Every session, solo or with a group, the pattern repeated. The thought dump became clarity, and clarity led to action.
Let me be clear about something: this wasn’t magic. It didn’t solve problems. It just showed them to me, plainly. It made me face what was on the table, not what I hoped would be there.
And over time, that changed how I approached planning entirely.
You’re probably thinking: “It’s just a quadrant tool. A grid.” You’re right. That’s all it is. But that’s why it worked. It didn’t try to do more. It didn’t layer complexity over clutter. It just sat there, waiting to be filled like a conversation that didn’t need small talk.
I hesitated to share this. Not because it’s proprietary. Because it feels too simple to be valuable. But the more I used it, the more I realized: simplicity was the value.
Most of us aren’t stuck because we lack insight. We’re stuck because we’re buried under process. Under expectations of how planning should look. So we perform strategy. We don’t do it.
I’m tired of performing.
That’s why, these days, I open the tool before every major session—not because I think it’ll save the day, but because it stops me from pretending.
And it works.
What hit me weeks later was how much energy I used to spend just preparing to look prepared. Agendas that read more like checklists for checking in. Recaps are written more for optics than outcomes. Nobody admits that, but you know what I mean.
This tool didn’t make me smarter. It made it harder to hide. Harder to coast through a session with buzzwords. The boxes don’t care how good you sound. They wait for you to say something real.
And in a way, that’s all I needed. Not inspiration. Not motivation. Just something that required honesty.
I still keep notes the old way sometimes. Pen, paper, sketchy diagrams. But when it counts—when there are real decisions to make and no time to waste—I return to this. Not because it impresses anyone, but because it doesn’t try to.
So much of leadership is learning to get out of your way. That’s what this helped me do.
That’s all.
If you want to try what I did?
This SWOT Analysis Tool.
https://swotanalysistool.vwcg.app/
I’ve learned something after too many years in business planning: most of us are winging it. Not when it comes to goals, or vision—those, oddly enough, tend to be clear. But process? The system? Total improvisation. People nod, scribble, murmur about “market dynamics” and “operational bottlenecks.” Then they leave the room, unsure what just happened.…