“Failing to plan is planning to fail.”
We’ve all heard the saying. And while it’s easy to brush off as a cliché, it holds more truth than we often give it credit for.
Over the past few months, this theme has come up time and time again in my coaching sessions, and conversations, not just with emerging leaders, but with experienced ones too. I’ll ask about what’s ahead, what success looks like, and the next steps. The response? Often something along the lines of:
“Oh I’ve got a plan… it’s just in my head.” Usually said with a laugh, like it’s no big deal.
But here’s the reality – if it’s only in your head, it’s not a plan, it’s an idea. Ideas are important, of course. But ideas without structure and visibility are dangerous. They shift under pressure, get lost in the noise, and are almost impossible to execute individually and as a team. If you’ve ever felt like you’re busy all the time but still not making progress where it matters most, this might be why.
Planning well is one of the most powerful and underrated productivity tools we have. And yet, it’s often avoided. Not intentionally, but because it feels like something we’ll get to “once we’ve got some time”. Once our inbox is under control. Once the noise dies down. The problem is that moment rarely comes. There’s always something urgent, something reactive. So, we push planning to the side, hoping clarity will appear on its own.
But it doesn’t work like that.
Here’s the paradox – time spent planning is time that creates more time. It gives shape to our work. It reduces the back and forth. It saves our teams from spinning wheels. It creates focus, reduces duplication, and lets us make better trade-offs between effort and impact. It also helps us identify what not to do, something that’s just as valuable as knowing what to prioritise. “If I say yes to this, what am I saying no to?”
The mistake I see in organisations isn’t just a lack of planning; it’s a lack of planning capability. We assume people know how to plan. But very few of us were ever taught how to do it well. Not just writing a to-do list but building a plan that connects the dots between a big goal and the series of decisions, dependencies, priorities, and milestones that will get us there.
I often ask: Does your team know how to plan?
Do they know how to break big ideas into actionable work?
Do they know what the very next step is, and have this documented?
Do they know how to map dependencies, identify risks, and flex when the unexpected hits?
Great planning isn’t about rigid control; it’s about shared clarity. It’s what enables agility. When everyone understands what success looks like and how their part contributes to it, they can adjust with confidence. They can collaborate better. They waste less time second-guessing or duplicating effort.
And here’s where leadership comes in. It’s not enough to have your own plan. If you’re the only one who can see it, then your team is operating in the dark. Effective planning is visible. It’s shared. It’s reviewed. It evolves. When your team can see the plan (and contribute to it) you create shared ownership. That’s when momentum builds.
The research backs this up. Teresa Amabile’s work at Harvard found that the single biggest motivator for employees is making meaningful progress. It’s not perks or praise, it’s forward momentum in meaningful work. Progress requires clarity. In the field of neuroleadership, David Rock’s SCARF model highlights the importance of reducing uncertainty. Good planning does all of that. It helps people feel confident in what they’re doing and why.
When planning is done well, it’s not a document that gathers dust or lies buried in the depths of a sharepoint. It’s a living, breathing tool that guides decision-making, protects focus, and helps people stay connected to purpose. It’s also a reflection of culture. A team that plans together, reflects together. A team that reviews and adjusts openly builds psychological safety, and better outcomes.
If your calendar feels full but directionless…
If your team is constantly busy but rarely aligned…
If projects are dragging or energy feels scattered…
Take a moment to pause and ask:
Is the plan visible?
Is it shared?
Is it alive?
Because if it’s still just in your head, that’s not a plan. Your team deserves more than that.
Let’s stop treating planning as a luxury.
It’s one of the most human, high-impact leadership disciplines we can model and teach. It might just be the difference between surviving the week — and actually making progress on the work that matters.