"But Did You Ask?"

"We can't implement this solution because Marketing will never approve it."

"Engineering is going to push back hard on this timeline."

"Our VP would never go for that kind of approach."

Sound familiar? In nearly every organization, these predictions about how others will respond to our ideas have become a peculiar form of corporate fortune-telling. We devote countless hours to anticipating objections, preparing counterarguments, and sometimes even shelving promising initiatives based entirely on assumptions about what someone else might think.

But when we pause and ask, "What did they say when you actually asked them?" the answer is often: "Well, I haven't asked them yet."

This “Assumption Paralysis” costs us more than just time; it stifles innovation, breeds unnecessary politics, and creates artificial barriers to progress. And it often thrives in cultures where work happens behind closed doors until it's "ready to share."

The High Cost of Assumption and Hidden Work

When we combine this tendency to assume others' reactions with a culture of keeping work to ourselves until it's "perfect," several potentially damaging patterns emerge:

• Ideas sit in limbo while we prepare for objections that may never materialize. By the time we finally act, the opportunity may have passed, or the problem may have grown substantially.
• We approach conversations defensively, often creating the very resistance we feared through our presentation style.
• Promising ideas and innovations get watered down or abandoned before they're even shared, because we self-censor based on imagined reactions.
• We begin viewing colleagues and distorting relationships through the lens of our assumptions rather than their actual responses, degrading trust over time.
• When we finally do have the conversation, we're primed for confirmation bias as we interpret any hesitation or question as validation of our fears.
• When feedback finally comes — often too late in the process — the cost of changing direction is much higher than if we'd invited other perspectives earlier.
• Without visibility into what others are doing, teams often solve the same problems in parallel, wasting time and resources and creating integration headaches later.

Why We Do This

Our tendency to avoid direct conversations isn’t irrational — it’s human. We create these elaborate stories in our heads about how people will react because it feels safer than just asking the question. Think about the last time you hesitated to bring up an idea in a meeting. You probably weren't worried about the idea itself; you were worried about how others might respond. Maybe you thought your manager would shoot it down, or a teammate would see it as stepping on their toes, or stakeholders would raise objections you couldn't address. So instead of speaking up, you kept quiet. Or maybe you spent weeks refining your approach before sharing it. In organizations where relationships matter and reputation is currency, this caution makes sense. The problem is that our imagined scenarios rarely match reality. The boss who we think will be overly critical of our idea might actually champion it. The teammate we think will feel threatened might become our biggest ally. But the longer we sit with our assumptions, the more "real" they feel, until the story we've created becomes a bigger obstacle than any actual resistance we might face.

The Simple Power of "Let's Just Ask"

I once worked with a product manager who was hesitant to propose a pivot in strategy because she was convinced the engineering lead would push back due to timeline concerns. For two weeks, she refined her proposal, adding contingency plans and workarounds for objections that hadn't even been raised. When she finally brought it up in our one-on-one, I asked: "What did the engineer say when you ran this by him?" Her answer: "Well, I haven't actually discussed it with him yet." We walked over to his desk together, had a 10-minute conversation, and discovered he was not only supportive but had some ideas that actually improved the approach. Those two weeks of worry and over-preparation? Completely unnecessary.

This experience illustrates the power of a simple question: "Have you asked them directly?" When we bypass our elaborate mental simulations and just have the conversation, we immediately test reality against our assumptions. Issues that might have festered for weeks get addressed in minutes. These direct conversations rarely kill good ideas; instead, they typically improve them by adding perspectives we couldn't have generated on our own. Perhaps most surprisingly, addressing potential concerns directly often strengthens relationships rather than damaging them, as it demonstrates respect for others' expertise and creates allies in implementation.

Consider how differently these scenarios play out:

With Assumption Paralysis:

Alex spends three weeks refining a proposal, anticipating all possible objections from the leadership team. The presentation grows increasingly complex as Alex tries to preemptively address concerns that may never arise. By the time Alex finally presents, the original elegance of the idea has been lost in a tangle of qualifications and contingencies.

With the "But Did You Ask?" Principle:

Alex schedules a 15-minute conversation with key stakeholders early in the process: "I'm exploring this approach and would value your initial thoughts." Alex discovers that the anticipated objections don't exist; in fact, leadership has been looking for exactly this kind of solution. The implementation begins three weeks earlier, with more stakeholder buy-in.

Creating a Culture of Early Sharing and Direct Questions

Teams that excel at direct communication also tend to be the ones that share work early and often. These two practices reinforce each other symbiotically. When people get comfortable showing unfinished work, they naturally invite input before assumptions can take root. And when direct questions are welcomed, sharing early work feels less risky.

As leaders, we can nurture this environment through some simple but powerful approaches:

When someone tells you what another team or person "will think" about an idea, gently ask: "What did they say when you asked them?" This simple question can short-circuit days or weeks of unnecessary worry and preparation.

Share your own thinking and works-in-progress before they're polished. When you demonstrate comfort with imperfection, your team will follow suit. Some of the best ideas emerge when concepts are still malleable enough to be shaped by diverse perspectives.

Create informal channels for sharing half-baked ideas, whether it's dedicated Slack channels, coffee chats, or regular show-and-tell sessions with a "no criticism, only questions" rule. These low-stakes environments make it safer to test assumptions early.

Celebrate the positive outcomes that come from direct communication and early sharing. When someone's courageous question leads to a breakthrough, or when early feedback prevents a costly misstep, highlight these wins to reinforce the value of these practices.

Help your team recognize the difference between thoughtful preparation and hiding work out of fear. The former improves ideas; the latter usually means assumptions are controlling the process.

Starting Small

The beauty of this approach is that it can start small. You don't need to transform your entire communication style overnight. Begin with low-stakes situations where you'd normally make assumptions:

• When you think a colleague might be too busy to help, ask anyway.
• When you believe someone will object to your idea, test that belief with a simple inquiry.
• When you're certain you know how someone will respond, check your assumption.

Each time you replace an assumption with a direct question, you're strengthening your "assumption-breaking muscle" and modeling this behavior for others.

When teams begin having direct conversations and sharing work earlier, the benefits compound quickly. Projects move faster because issues surface and get resolved sooner. Teams build trust because assumptions get tested before they create false narratives. Innovation thrives because ideas get improved by diverse perspectives while they're still flexible enough to change.

I've seen this play out countless times. What seemed like an insurmountable objection based on assumption often turns out to be a minor concern in reality. The Marketing team that would "never approve" actually sees potential in your idea once they understand the context. The Engineering lead you worried would push back about timelines actually has a simpler implementation approach you hadn't considered. The executive you thought would reject your proposal becomes your champion after having the opportunity to shape it early.

Even when your assumptions turn out to be partially correct, the conversation usually produces valuable insights that help you navigate the situation more effectively. And by addressing concerns directly rather than through layers of interpretation, you demonstrate a level of respect that strengthens relationships rather than straining them.

Open Work, Direct Questions

When teams combine early sharing with direct communication, something remarkable happens: work moves faster, relationships strengthen, and the best ideas emerge sooner.

The next time you find yourself crafting elaborate theories about how someone might respond to your work, pause and consider: Is this helping you improve your work, or are you simply building a mental fortress around an untested assumption?

Or, the next time you're tempted to keep a project or proposal to yourself until it's "perfect," ask yourself: What valuable perspective might I be missing by not inviting others into this conversation earlier?

The most successful organizations I've been part of weren't characterized by perfect execution or absence of conflict. They were defined by people's willingness to show work early and ask direct questions — creating environments where assumptions rarely survived long enough to become barriers.