The Planning Paradox: Why your plans are useless, but planning isn't.
How the act of planning drives teams to launch while the plan itself becomes obsolete.
Hello Product Party-ers! I’m going to take a 2-week break after this post to lean into the holiday spirit, put together my year-end posts, and come up with a content strategy and 2026 goals.
I’m excited to round out 2025 with you all and look forward to building more in public and sharing along the way. If you want to consider a collaboration (building, writing), please feel free to reach out to me - mike@productparty.us
On to the good stuff…
Your carefully crafted roadmap is probably fiction within weeks of creating it. Priorities shift. Leadership changes direction. That feature everyone agreed on in Q1 planning feels irrelevant by April.
I learned this while launching a massive CRM overhaul at one of my previous employers. It wasn’t the plan that saved us. It was the planning.
We needed to replace our aging Oracle CRM, but getting any change approved meant navigating multiple levels of sign-off. So we built what I came to think of as “the plan behind the plan” - not just development milestones, but our organizational strategy for getting clearance and building credibility.
We created pilot groups of actual salespeople who tested and provided real-time feedback. By the time we asked for full rollout approval, leadership had been watching it work for months. Regional releases went live within three months with strong adoption.
The original plan changed constantly. We reprioritized features, adjusted timelines, and shifted our rollout sequence. But we shipped successfully because everyone shared the same mental model of what we were trying to accomplish.
That’s the paradox: the plan became obsolete, but the act of planning together made us capable of executing even as everything changed.
What planning actually does (that plans don’t).
I learned this lesson the hard way on one of my first projects with that same CRM system.
Leadership wanted better data collection, so we built two dropdown fields on the customer profile. Simple enough, right? Except those dropdowns became the center of three full senior sales leader meetings (plus countless pre-calls) just to decide what options should appear in each dropdown.
We debated categories. We argued about terminology. We revised the options multiple times based on who had spoken to leadership most recently. And you know what happened when we finally launched it?
No one used them.
The salespeople didn’t want to fill out more fields. The data we collected wasn’t actionable. The whole feature became a monument to wasted effort, and I couldn’t understand why we’d spent so much time on something that delivered so little value.
The problem wasn’t the dropdown design. We never planned the fundamentals. We skipped straight to implementation details without establishing a shared understanding of what problem we were solving, whether users actually wanted this, or how success would be measured.
Planning creates three things that individual plans can’t capture.
1. Shared vocabulary
When teams plan together, they build a common language. The CRM project team could say “like we discussed in our pilot testing strategy” and everyone immediately understood the trade-offs we’d already considered.
With the dropdown project, we had no shared foundation. Every meeting started from scratch, rehashing the same debates because we’d never established what we were collectively trying to achieve.
2. Decision scaffolding
Good planning names your assumptions explicitly. For the CRM rollout, we knew our plan depended on getting regional leadership buy-in early and maintaining pilot group enthusiasm. When technical delays threatened our timeline, we knew exactly which assumption was at risk and could adjust our approach accordingly.
The dropdown project had no scaffolding. When adoption tanked, we had no framework for understanding why or what to do differently. We’d never articulated what had to be true for this to succeed, so failure just felt like generic disappointment rather than a specific lesson.
3. Forcing functions for hard conversations
This is the one people underestimate most. Planning surfaces conflicts before you’re mid-sprint with no time to resolve them. The CRM project forced us to have uncomfortable conversations about organizational politics, user resistance, and technical constraints before we were too deep to pivot.
With the dropdowns, we avoided the hard conversation (”Will salespeople actually use this?”) and instead debated the easy one: “What should the dropdown options be?” We spent meeting after meeting on implementation details because we’d never done the planning work to question the premise.
So…the kicker? Both projects were within the same organization, using the same product, and faced similar bureaucratic challenges. The difference wasn’t the plan’s accuracy. Both plans changed constantly.
The difference was that one team did the hard work of planning together, while the other team just scheduled meetings to argue about details.
Planning for obsolescence.
If plans become obsolete but planning matters, what kind of planning actually works?
I’ve developed what I call the “Plan to Pivot” approach. It’s not about predicting the future better. It’s about building the foundation that lets you respond quickly when the future inevitably surprises you.
Name your assumptions explicitly.
This is the practice that saved us most often with the CRM rollout. We wrote down what had to be true for our plan to work: Regional leaders needed to see value in the pilots. IT security would approve our Oracle implementation. Salespeople would engage with testing groups rather than treating it like extra work.
When technical delays threatened our timeline, we didn’t panic about the schedule. We asked, “Which assumption is this threatening?” It turned out the delay risked pilot group enthusiasm (our third assumption), so we focused our energy there.
We kept the testing groups engaged with regular updates and made sure they felt heard even when we couldn’t deliver new features immediately.
Without those named assumptions, that delay would’ve just felt like generic project stress. With them, we knew exactly where to focus.
Try this Monday: Take your current project and write down three things that have to be true for it to succeed. Not hopeful things, but actual dependencies. When something changes, you’ll know which domino fell.
Set decision points, not deadlines.
The dropdown project failed partly because we had a deadline (ship by end of quarter) but no decision points (when do we validate whether salespeople actually want this?).
The CRM project worked because we built in specific moments to reassess: after the first pilot group feedback, after regional leadership reviews, after the initial security audit. These weren’t gates that slowed us down. They were checkpoints that told us whether our assumptions still held.
“We’ll reassess after the first 50 users have tested this for two weeks” is more valuable than “Launch by Q3.” One gives you information. The other gives you pressure.
Plan in chunks, not marathons.
The biggest shift in my planning approach came from realizing I don’t need the same level of detail for everything. I need specificity for the next hill I’m climbing, and direction for the mountain range beyond it.
For the CRM rollout, we planned the first pilot group in detail. Which departments? Which regions? What feedback mechanisms? How would we incorporate their input? That planning was concrete and specific.
But we kept the full rollout plan deliberately fuzzy. We knew roughly which regions would go next, but we didn’t lock in the sequence until we’d learned from the pilots. That flexibility let us adjust based on what we discovered rather than forcing us to stick to assumptions we’d made months earlier.
Planning everything in equal detail is a trap. It creates the illusion of control while actually making you less adaptable.
Final thoughts.
Your plan will be wrong. The market will shift, priorities will change. That’s not pessimism - it’s just product work.
But planning gives you a team that can pivot quickly because they’ve already wrestled with the hard questions together. Both the dropdown project and CRM rollout faced unexpected challenges. One team adapted. The other scheduled more meetings.
The plan is your map, but planning is learning to navigate. The map becomes outdated. The navigation skills stick around - and they’re what separate teams that ship from teams that schedule three senior leader meetings to debate what goes in a dropdown.
Until next week,
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