How to Develop Insights Executives Care About

Executives love receiving insight from employees, something they didn’t already know, and something that changes what they do or how they think about what’s next. 

So, Where Does Insight Come From?

Insight comes from contradiction. It might be a pattern in the data that shouldn’t be there. Chris Argyris and Donald Schön famously described how detecting a mismatch between expected and actual results forces a deeper kind of learning called double-loop learning that challenges the underlying assumptions about what is known. In other words, when things don’t go as expected, zoom in. 

In cognitive psychology, the classic aha moment occurs when a person hits an impasse and suddenly restructures their approach. Asking yourself questions like, What story is this data telling me? What is the meaning behind these numbers? And brainstorming recommended actions will help you to generate insight.

Being curious about your organization's priorities also helps. Listen closely in meetings and be sure you understand the strategic direction. Then, see how the numbers support or do not support that direction. Gather information from customer interactions, team interactions, and available data to come up with new thinking.

At times, you may have to be brave and point out what the data implies before someone else does. Sometimes, that means having the courage to voice an uncomfortable truth drawn from the facts. If you are in this situation, be sure to bring your fact-based evidence along and support your point of view with data.

Insight = Business Relevance + Surprise

Not every interesting finding qualifies as an executive insight. Two criteria must collide: business relevance and novelty. If an observation doesn’t relate to revenue, cost, risk, or strategy, it won’t appear on an executive’s list of concerns. And if they already know it, it’s just a recap, not an insight. 

A helpful definition from industry experts is that an insight is “new information that challenges our existing understanding”. It provides a revelation that upends assumptions, and it matters for the business. Research on actionable knowledge in organizations echoes this. Compelling insights have purpose, are tied to a business need, disturb the status quo, and present an unexpected reality. In short, an insight should be both relevant and strategic.

If what you’re sharing is buried in fluff or unconnected to a key business outcome, it’s noise in the executives' minds. If it lacks context, the executive may not follow. A true insight might sound like: “Our top customers are using less of the feature that best predicts renewal, this is a churn risk.” Or, “The team saw a 10% drop in product adoption, even though no one has raised a flag yet.” These statements get attention because they marry a surprise finding with business relevance. They don’t have to be earth-shattering to be valuable; they just have to relate to something that leaders care about, like customer behavior, growth, efficiency, or risk.

How to Build Insights Executives Want

Crafting an insight that executives care about is a skill you can cultivate. It requires shifting your approach from reporting what’s easy to see to digging for what truly matters. Here are five practices to guide you:

Start with Their Scorecard. Begin where the executive’s priorities lie. What do they wake up worrying about? Revenue? Market share? Operational risk? Customer success? If you can’t map your finding to one of the leadership’s core objectives or KPIs, it’s not ready to be an executive insight. Tie every insight to the P&L or strategic plan. This focus not only ensures relevance but also mirrors how high-performing organizations use analytics. 

In practice, this means ditch the vanity metrics and nice-to-know trivia. Executives don’t ask how many clicks a campaign got; they ask how it impacted pipeline or closed-won business. As one analytics expert puts it, “Metrics only matter if they inform decisions. If you’re unsure whether a number belongs, ask: "What would someone do differently if this changed?" If the answer is nothing, it doesn’t belong.” In short, frame your analysis around the levers that leadership actually wants to pull.

Look for the Anomaly. Don’t start with the averages and the green lights. Start with the friction. What’s harder than it should be? What isn’t improving, or what suddenly changed for the worse? Executives, by nature, are problem-solvers; they want to know what’s getting in the way. In fact, they often crave the truth, especially when it’s uncomfortable. Yet in many organizations, there’s a tendency to gloss over bad news. Psychologists call it the MUM effect, people’s natural aversion to delivering unpleasant information. But great leaders do not want a sugar-coated view; they need to know about brewing issues. That point of tension is your doorway to insight. Executives will appreciate the candor when you can clearly show, “Here’s something you might not realize, and it’s affecting our business.”

Build the Bridge. A good insight is not just what’s happening, it’s what it means. Most teams stop at observation (“X is down 10%” or “Y increased this quarter”). You have to go further, from analysis to interpretation, and interpretation to implication. What’s the risk if nothing changes? What decision needs to be made, or what part of the strategy is impacted by this finding? In other words, answer the So what?. An insight is only as valuable as the action or decision it informs. Don’t make senior leaders connect the dots. For example, instead of saying “Customer satisfaction is 85,” you might say, “Customer satisfaction fell 5 points this quarter, which we predict will lower renewal rates next quarter by about 10% unless we address issue A or B.” Wrap the observation in context and consequences. Executives don’t just want to know what’s happening; they want to know what to do about it.

Add Contrast. Insight loves contrast. Saying what changed and by how much is far more compelling than stating a static fact. Always show from what to what, over what period, or compared to which benchmark. Humans understand change; we notice when a line in a chart breaks the pattern. Trends, breaks, acceleration, and deceleration all give meaning to the numbers. For example, instead of a single snapshot of 40% adoption, you say “adoption fell from 65% to 40% over six months among enterprise clients, reversing last year’s growth.” Now the data is telling a story. Executives are attuned to patterns: something fragile or off-trend will immediately get their attention. Always give that context. Show the before-and-after, the here vs. there. It makes the insight tangible and easy to understand.

Say It Plain. If it takes four slides to explain, it’s not an insight, at least not one ready for an executive audience. Clarity and simplicity are essential. Strip away jargon and technical complexity in your messaging. The aim is to convey the core insight in one or two sentences. A good litmus test is whether a non-expert could understand why this insight matters. If not, refine it. By speaking plainly, you not only make the insight digestible but you also project confidence in your analysis. Executives appreciate straight talk. As the proverb goes, less is more.

Insight Is a Skill, Not Luck

Too many teams act as if insight is a magical talent that some people just have. The star account manager just has great intuition; the sharp product analyst sees the pattern. But insight is not magic. It’s a skill, one that can be learned, practiced, and honed. In fact, research in cognitive psychology indicates that what feels like an intuitive Eureka! stems from the same mental processes that any of us can develop. 

In plain terms, insightful problem-solvers aren’t relying on mystical inspiration; they’re applying techniques that can be practiced, like looking for parallels, re-framing the problem, and questioning initial assumptions. Train your team to ask the extra why? and what now? questions. Make it safe to point out inconvenient truths. Over time, the collective ability to spot meaningful patterns and implications will grow. 

Great operators create direction. And insight is how they do it. The best leaders and teams use insight as their compass, steering conversations and strategies with evidence-backed surprises that reveal where to go next. Developing insight is a skill you can cultivate with deliberate effort. Start by asking better questions, getting comfortable with uncomfortable answers, and insisting on meaning. The more you do this, the more aha moments you’ll experience.

Executives Don’t Ghost Insight

Think about the meetings that senior executives blow off or delegate; they’re usually the status updates, the lengthy reviews that anyone could read in a report later. Executives do ghost those routine check-ins and verbose slide decks. But they don’t ghost insight. If you consistently show up with something they haven’t seen before and it affects something they care about, you’ll capture their attention every time. 

Top executives are perpetually scanning for signals that require action: an emerging risk, a new growth opportunity, an inefficiency to fix. When you hand them that signal on a silver platter, backed by data, they lean in. They ask questions. They want to know what happens next. On the flip side, if all you bring is a summary they’ve heard before or a generic just checking in, they’ll find an excuse to cut it short.

In practical terms, earning the room means bringing concise, relevant information that is surprising enough to prompt a decision or a change in strategy. Everything else is background noise. Before you schedule a meeting, ask yourself if you have an insight that bears on a decision, illuminates a risk or opportunity in the business, or changes perspective. If yes, you have an executive insight; if not, it might not be worth the meeting.

Most executives want to be challenged with new perspectives, as long as those perspectives are grounded in evidence and tied to business outcomes. They want their thinking provoked. Lead with what matters most: the trend or contradiction that changes how they see the business. By doing so, you demonstrate respect for their time and a shared commitment to advancing the company. And you’ll find that even the busiest leaders make time for you, because you’re helping them see what they otherwise would have missed.

The executive’s world moves fast; bring the signal. Deliver accurate insights, those characterized by business relevance and surprise, and you’ll not only earn your seat in the room, but you’ll also eventually help lead it. 

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