Why Most Business Plans Don’t Work
And how to build an environment where they do
This is one of my fav episodes from Friends - it lands because it’s also kind of true. Most of us start with big goals and intentions, but then life / reality gets in the way. Some of us (unlike Phoebe here) even write detailed plans. But turning those plans into real progress? That’s the hard part.
It’s no different in the business world. “We just need a better plan.” I’ve heard that line in nearly every strategy meeting I’ve been part of as a business consultant.
But often, it’s not the planning that’s the problem. It’s the conditions we expect those plans to survive in. Plans can be deceivingly beautiful on paper - trust me, I’ve spent a lot of time in PowerPoint! When you present it, people offer you feedback on how to make the plan even more perfect - more milestones, more activities, …
Yet a few weeks in, it’s very possible that nothing translates into real results. And people feel stuck, afraid to pull the plug without going back to the drawing board and building a whole new plan.
The patterns behind ‘bad’ plans
What I often see when I’m brought in to support a team mid-implementation are ‘conditions for execution’ problems
Teams say yes to bold ideas, but nothing gets taken off their plates. This results in burnout, bandwidth bottlenecks, and frustrated follow-through “Everyone was excited - until they realised they still had 5 other priorities”
People leave planning sessions unclear on who’s driving what. What gets done depends on who remembers, or who gets tired of waiting.
Plans that don’t change with the times and become irrelevant
Junior staff see issues early, but don’t feel safe flagging them.
What actually makes a plan work?
The best plans I’ve seen share four things in common:
Air cover for execution:
Plans need space. The best leaders ask:
What are we pausing, reassigning, or stopping to make this plan real?
Where are we investing, not just money, but people, time, and trust?
Clear roles and decision makers
Every priority needs a clear owner (single owners tend to do better than shared ownership where shirking is harder to identify). However, ownership, does not mean “do it all alone”. The owner is responsible for driving the initiative forward, making decisions, and pulling in resources to make things happen.
Visible check-ins & Data collection
Great teams revisit their priorities regularly. Not to report, but to adjust.
No plan is set as set in stone, but merely a starting point to learn from reality, not just assumptions. Smart teams treat their plan like a living system: constantly shaped by what they’re hearing, learning, and seeing on the ground. The goal isn’t to stick to the plan, it’s to stick to the purpose, even if the path shifts.Psychological Safety + Feedback Loops
Plans work when teams feel safe to surface what’s hard. If something fails, it is not seen as a failure for the initiative lead, instead an opportunity for the full team to learn and improve.
What this looks like in practice
Here’s what I’ve helped teams do instead of rewriting the plan again:
Run “priority pressure tests.” Lay out every major initiative, then ask: If we only had 60% of our capacity, what survives?
Define one-page execution maps. Who’s leading, who’s supporting, and how will we know if it’s working?
Set up short-cycle check-ins. Monthly syncs where the question isn’t “What’s the update?” but “What needs to shift?”
Invite honest reflection. Create space for anonymous input, skip-level conversations, or peer reviews that ask: What’s helping? What’s holding us back?
Try this if you’re in charge of setting and driving strategy —> Pick one plan you’re currently leading. Ask your team these four questions:
Where do we need to make space for this to actually happen?
Who owns what — and do they have what they need?
How will we know if we’re off track — and what will we do then?
Where might people be holding back honest feedback?
The answers will show you where your real plan lives.
And where it might be quietly breaking.
In a nutshell
Bold strategies are easy to write, the hard part is making them real. Not by pushing harder, but by designing the conditions that make follow-through possible: clarity on what matters most, shared ownership across the team, space to adapt when the terrain shifts, and room for honest conversations along the way. Plans need to breathe. That’s what makes them work.
Best,
Nareen
P.S. If this resonates, I write about strategy, execution, and leadership every Friday - subscribe for free, to get weekly insights right into your inbox