Why Your Best Hires Stop Sharing Opinions
(And How Decision Memos Fix It)
Remember when you were being recruited for your current role?
Every conversation felt like your opinion mattered. The VP who interviewed you wanted to know your take on the tech stack. The CMO asked how you’d approach demand gen differently. They hung on every word about your framework for market segmentation.
Then you got hired.
Suddenly, decisions happen in closed-door meetings you’re not invited to. Strategy gets set by people three levels above you. That brilliant take you had on the MarTech stack during your interview? Cool, but we’re already committed to this vendor because someone with a VP title signed off.
I watched this pattern play out at every company I worked at before Chili Piper (and low key most companies I’ve worked at since 😬). Smart people got hired for their thinking, then immediately stopped being asked to think.
At Chili Piper, we did something different. We used decision memos for everything from ditching MQLs as a core KPI (wild in 2020, boring today) to choosing whether to launch a podcast, or invest in a certain piece of tech, or even to go solve certain market problems or to avoid them and stay the course. And what made it work wasn’t just the process. It was the cultural belief that if you hired someone good enough to join your team, their opinion deserves to be heard on decisions that matter.
And one more thing. After I’d been there a while, the company had gotten used to going along with decision memos so they introduced this concept of incentivizing you if you provided a “contrarian take” that ended up being the route the company took. They’d pay you $1,000 if your contrarian take won.
👋 Hi, it’s Kaylee Edmondson and welcome to Looped In, my newsletter covering demand gen and growth in B2B SaaS. Subscribe to join 2k+ readers who get Looped In delivered to their inbox every Sunday.
How Most Companies Make Decisions
What usually happens:
Decisions get made in silos. Marketing picks a new automation platform without talking to sales ops. Product chooses an AI tool that doesn’t integrate with the rest of the stack. Nobody knows a decision is even being discussed until it’s announced.
Or they’re purely top-down. Only VPs and above get invited to strategic conversations. If you’re an IC or manager, you find out about major shifts when they’re already locked in. Your expertise doesn’t matter if your title isn’t senior enough.
Or they happen in chaos. Endless Slack threads where whoever posts last wins. Meetings that go nowhere because there’s no clear framework. The loudest voice or the HiPPO (highest paid person’s opinion) carries the day.
All of this leads to the same outcome: You worked hard to hire talented people, then you ignore their expertise when it matters most.
What Decision Memos Are
A decision memo is a structured document that lays out a business decision before it gets made.
Here’s the basic structure:
Stakeholders: Who wrote this, who contributed, who makes the final call
Context: What’s the background? What changed? What’s the problem or opportunity?
Business Case: Why does this matter? What’s the impact on time, revenue, or decision-quality?
Options: Always include “do nothing” as Option 1, then lay out alternatives with pros, cons, and resources needed
Recommendation: What you think should happen, plus space for contributors to weigh in
Decision: What actually got decided and when
The person proposing the idea writes the memo. Everywhere with relevant knowledge can, and is encouraged to, contribute. One person makes the final call. But everyone gets to see the thinking.
I’ve included a template you can copy here: Decision Memo Template
Why This Actually Works
Decision memos solve three problems at once.
They democratize access to decisions. When I was at Chili Piper, I could read decision memos for projects way outside my direct scope. That visibility made me smarter about how the business worked. It also meant I could contribute if I had relevant experience, even if it wasn’t technically my domain.
They create accountability. Everything is documented. You can see who recommended what and why. If a decision goes sideways six months later, you can trace back the thinking instead of playing blame games.
They reward good thinking over hierarchy. Your opinion carries weight based on the quality of your argument, not your title. I saw individual contributors write memos that changed company strategy because their reasoning was sound.
But I really think what makes them work is the contrarian incentive.
At CP, the co-CEOs announced at an all-hands that if you wrote a decision memo with a contrarian take and the company went with your recommendation, you’d get $1,000.
Think about what that signals. We don’t just tolerate disagreement. We actively want you to challenge our assumptions. We’ll pay you to think differently than the default path.
That’s the cultural piece that makes decision memos more than just another doc template. You have to actually want to hear from your team. (Imagine me clapping as I’m saying all of this. It’s powerful. I’ve literally never seen another company stand on the shoulders of their employees, all employees, in this way.)
Implement Decision Memos (Tomorrow)
You don’t need to roll this out company-wide on day one. Start small.
Option 1: Just your team. If you’re a marketing leader, use decision memos for your next tool purchase or campaign strategy shift. Get your team used to the format before evangelizing it wider.
Option 2: Pilot with one major decision. Pick something coming up that matters. MarTech consolidation. AI implementation. Team restructuring. Use the decision memo format and see how it changes the conversation.
Option 3: Make it lightweight. The template can feel formal. Start with just Context, Options, and Recommendation if that’s less intimidating. Add structure as people get comfortable.
The key implementation steps:
1. Set clear stakeholder roles. Who writes the memo (person proposing), who contributes (anyone with relevant knowledge), who decides (one person with final call). Don’t let this turn into design by committee.
2. Make memos visible. If only five people can see the doc, you’re not democratizing decisions. Share broadly. Even if someone can’t contribute, they can learn.
3. Actually read and respond. If you ask for contributors and then ignore their input, you’ve killed trust. Even if you don’t go with their recommendation, acknowledge their thinking.
4. Document the decision. Don’t let memos sit in limbo forever. Set a deadline, make a call, record what was decided and why.
5. Review outcomes. Six months later, was the decision right? What did we learn? This closes the loop and makes everyone smarter for next time.
The biggest mistake I see is treating this like a bureaucratic checkbox. Decision memos only work if you actually want to hear from your team. If you’re just going through the motions to look collaborative, don’t bother.
This Probably Matters More Than Ever
We’re making more decisions faster than at any point I can remember.
AI is moving so fast that tool decisions you make today might be obsolete in six months. The cost of steering your entire GTM motion down the wrong path is massive.
Let me give you some examples of expensive mistakes I’m seeing right now:
AI stack sprawl. A company invests in five different AI tools because each team picked their favorite. None of them integrate. Now you’ve got data silos, duplicated workflows, and a $50K annual bill for tools that don’t talk to each other. A decision memo would have forced the conversation about integration and cross-functional impact before anyone signed contracts.
Premature AI commitment. A marketing team goes all-in on an AI content platform before they’ve cleaned their data or defined their content strategy. Six months later, they realize the AI is amplifying their existing problems, not solving them. They want to switch platforms but they’re locked into a year-long contract. A decision memo would have surfaced the dependency on clean data and clear strategy up front.
Shiny object pivot. A CEO reads about AI agents and decides to rebuild the entire GTM motion around this new approach. Marketing scrambles to execute without the foundational systems in place. Three months in, it’s clear this was premature. But now you’ve blown budget and momentum. A decision memo would have let the team pressure-test assumptions before the pivot.
These aren’t hypothetical. I’m watching variations of all three happen right now with clients and peers.
When decisions were slower and stakes were lower, maybe you could wing it. But in an environment where you’re choosing between AI platforms that will shape your entire go-to-market motion for the next two years? The cost of a bad decision is too high to leave it to whoever posts last in Slack.
So, tomorrow?
If you’re a leader, pick one upcoming decision and try the decision memo format. Use the template I linked above or simplify it to fit your culture.
If you’re an IC or manager, propose writing a decision memo for something on your roadmap. Frame it as an experiment. Most leaders will say yes if you’re doing the work to structure the thinking.
If you’re building culture from scratch, steal Chili Piper’s contrarian incentive idea. Put real money behind the message that you want people to challenge assumptions.
The goal is to close the gap between how you hired people (valuing their opinion) and how you operate (asking for their opinion on decisions that matter).
Your team already has the answers to most of your hard problems. You just need a system that lets you hear them.
Here’s the template again: Decision Memo Template
See ya next week,
Kaylee ✌