Think Deeper Before You’re at the Executive Table
Prepare your perspective so executives see your value.
Executives don’t buy features. They buy outcomes, consequences, and clarity. If you can’t frame what’s broken and what’s possible better than they can, you don’t belong in the room. Deep thinking gives you pricing power, confidence, and differentiation.
This is where most sellers fall short, not because they lack a good offer, but because they’ve only trained themselves to talk about what’s immediately visible. They show up with a service, or even a great product, but no perspective. No clarity. No edge.
If consultative selling is the vehicle, insight is the engine. And insight doesn’t just help you win the meeting, it helps you understand what your offer is worth.
At the executive level, the conversation isn’t about features or deliverables. It’s about consequences. It’s about understanding what happens across the business when your offer takes root, how it affects workflows, budgets, power dynamics, reputational risk, and executive credibility. If you can’t see those ripple effects, you’re not just underprepared, you’re underpriced. Because the truth is, your client doesn’t need a better tool. They need someone who can help them reimagine the way forward. That’s why thinking deeper isn’t just a mindset upgrade, it’s a sales strategy.
Most sellers show up with surface-level value props: “We’ll save you money,” “We’ll improve efficiency.” But executives have heard that line a hundred times. What they haven’t heard is a point of view that cuts through the noise with clarity. One that names what’s truly broken. One that frames the problem in a way they haven’t considered, but can’t ignore once they see it.
This is where most of the industry gets stuck. They’re trapped in what I call maze-thinking, a narrow loop of small promises and tactical feature wars. Everyone in the maze is fighting for 10% better. But executives aren’t in the maze. They’re above it, trying to decide whether the maze even matters anymore.
Thinking deeper means you stop trying to prove that your offer is slightly better. You start showing them that their frame is outdated. That the system they’re optimizing is the very thing holding them back. You stop saying “Here’s how we help” and start asking “What if you didn’t need that system at all?” That’s when the real conversation starts.
To earn that level of clarity, you need more than industry knowledge. You need proximity.
This is one of the most important, and most overlooked, principles in high-value consulting: stay close to the work. Not just the meetings. Not the strategy decks. The actual work, what’s happening in the team, in the tools, in the decision loops.
When I was running a consulting firm, I stayed close to the client’s work, not just to deliver results, but to witness what happened when the work landed. Because from a distance, everything looks clean. The process maps make sense. The slide decks are persuasive. But proximity tells a different story. When you’re embedded enough to see how a recommendation lives inside the day-to-day, you start noticing everything that doesn’t show up in the plan.
I saw workflows that sounded efficient on paper but created bottlenecks in practice. I saw “timesaving” tools that drained morale. I saw leadership assumptions that made perfect sense in theory, but collapsed under operational reality. And in almost every case, the real value wasn’t in what we built. It was in what we removed. The drag we eliminated. The decisions we made were easier. The clarity we restored.
That’s what proximity gives you: not just insight, but accuracy. It sharpens your intuition. It helps you predict friction before it hits. And most importantly, it builds trust, because clients can feel when you’re solving the real problem, not just the one they described in the RFP.
A lot of people think that to scale, you need distance. I think the opposite. The more embedded you are, the more undeniable your value becomes. That’s what gives you pricing power. That’s what creates internal champions. That’s what makes your presence feel less like a cost, and more like an advantage they can’t afford to lose.
You start to notice what’s outdated. What’s duplicative. What’s slowing everything down. And instead of tweaking the current setup, you start designing solutions that leap past it. That’s where pricing confidence comes from. That’s where differentiation lives. When you understand the second- and third-order consequences of your solution, not just what it is, but what it unlocks, you start to see the full size of what you’re selling. And so does the client.
That’s when your pitch gets sharper. Your proposals stop sounding like persuasion and start reading like strategy. Because you’re not just describing a better tool. You’re offering a smarter future. And you’ve thought about it more deeply than anyone else.
Before you walk into your next executive conversation, ask yourself: Do you know what’s broken, not just what’s inconvenient? Can you speak to the cost of that problem, not just in dollars, but in operational drag, team behavior, decision bottlenecks, and missed opportunities? Have you developed a perspective they haven’t heard before, but can’t unsee once they hear it?
Because if you can do that, you’re not there to sell a product. You’re there to architect a new possibility. You’re not offering improvement. You’re offering elevation. And when you show up with that kind of insight, pricing becomes easy. Differentiation becomes obvious. And the close? It happens long before the proposal hits the table.
You don’t just win because your solution works. You win because your thinking makes everything else feel obsolete.
Carve Out Thinking Space
Thinking time isn’t some fluffy CEO habit, it’s a lifeline. I started scheduling it after hearing a story that stuck with me. Keith Cunningham once shared a story about pitching to an investor, and after the meeting, the investor just said, “My next thinking time is Thursday at 4 a.m. I’ll decide after that.” That was it. No follow-up. No spreadsheet. Just... thinking time. That hit me.
So, I made it non-negotiable. Once a week, I sit down with nothing but a pen, a question, and zero distractions. Sometimes it’s: What do my best clients wish someone would solve for them? Other times, it’s: What assumptions are they trapped in? What breakthrough am I sitting on that I haven’t given the space to surface? It doesn’t always lead somewhere obvious, but it always sharpens me.
In fact, one of the most significant breakthroughs I’ve ever had, the kind that shifted the valuation of my company and redefined how clients perceived our value, started during one of these quiet sessions.
Reach Out (Without the Pitch)
I’ve learned that the best way to stay top of mind with senior executives isn’t by pitching them, it’s by thinking about them. Literally. Taking the time to sit with their business in my mind, turning it over, asking: What haven’t they seen yet? What’s sitting right in front of them that no one has dared to say?
One of my favorite stories came from a major consulting firm that, honestly, no one even liked working with. My friend asked the client why they kept renewing, and the answer was simple: “They bring us big ideas every quarter.” That’s it. Not results. Not amazing delivery. Just perspective. They made themselves useful by thinking.
That stuck with me. Every so often, I’ll reach out to a client, no agenda, no deck, no proposal, and say something like: “I’ve been thinking about your business. I noticed a few things I think are worth unpacking. Not selling you anything, just thought it might be worth a quick chat.” And they always say yes. Always. Because everyone’s hungry for real perspective, especially when it’s offered with no strings attached.
You don’t need to be selling to create momentum. Sometimes the most powerful move is to show someone that you’re still thinking about them, even when there’s nothing on the table. That’s what builds trust. That’s what gets remembered. That’s what leads to deals.
If you’d like to see how I implement this inside commercial teams, I run an immersive “Selling to the C-Suite” program that includes assessment, strategy building, workshop, and in-field reinforcement.
Email me at lisa@lisatmiller.com to learn more or schedule through my calendar: https://tidycal.com/lisamiller/30-minute-meeting