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    Use The Difficulty To Make More Sales

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    I’ve been thinking about the idea of “using the difficulty” lately, in the context of complex sales. I encountered the concept in a post by Sahil Bloom on LinkedIn, where he describes a lesson Michael Caine learned as a young actor rehearsing a scene.

    There was a chair blocking the doorway onto the stage, and Caine stopped the scene to let his fellow actor know that he couldn’t get by. The other actor said something that changed Caine’s life: “Use the difficulty.”

    The idea: If your scene is supposed to make people laugh, you can trip over the chair in a funny way. If your character is angry, you can pick the chair up and throw it. Instead of treating the obstacle like a scene-breaker, use it as an opportunity to progress the scene.

    In complex sales, we often encounter visible and invisible obstacles that can be deal breakers. But when we learn to turn those difficulties into advantages, the deal breakers become the deal makers. Too many stakeholders, risk-averse customers, stiff competition, industry challenges, and more, can tank a deal… but here’s how to turn them to your advantage.

    One: Too Many Stakeholders

    In complex sales, there is always more than one person involved in the decision-making process. Often, these other stakeholders are in the background while one person performs research and engages with salespeople to choose a solution.

    These “hidden” stakeholders represent a significant difficulty for salespeople. While the person you are engaging with might be excited and understand exactly how you can help, hidden stakeholders can nix the deal, and you may never know why you lost. Uncovering hidden stakeholders and engaging them in the process changes the game.

    Our research has shown that salespeople who reach the right number of stakeholders are more likely to close the deal successfully. By understanding who the stakeholders are, their perspectives on the matter, and developing a shared mental model, the winning team becomes a decision-making catalyst that turns that stage chair into a solid place to sit.

    Two: Risk-Averse Customers

    Another hidden danger in complex sales is your prospect’s natural aversion to risk. In many cases, the biggest competitor to your solution is not another company, but the status quo. That’s because change is risky, and your prospects are keenly aware of that.

    It is tempting in sales to try to ignore the risks to the customer in hopes that they will also ignore them. This is a little like trying to barge through the stage door despite the chair and then being surprised when it throws you sprawling across the floor.

    But you can turn these risks to your advantage by choosing the counter-intuitive option of asking about them. By bringing them into the light and acknowledging them with the customer, you differentiate yourself from the competition. Then, you can position yourself to help the customer resolve those concerns and relieve their pressure so they can complete the deal.

    Three: Stiff Competition

    Who wouldn’t love to be in a field where your solution is the only viable option? Fortunately for customers and unfortunately for sellers, there is always competition. Other companies with similar solutions, other companies with alternate solutions, other internal priorities and… inertia.

    It might seem smart to face this difficulty by bad-mouthing the competition, but there’s a better way to turn it to your advantage. Make how you sell why you win. To do that, you have to become a partner to your prospects in developing the solution that resolves their concerns and demonstrates to all relevant stakeholders that you are the right choice.

    To do this, your salespeople must know your competition, ask prospects what other solutions they’re considering, uncover their hidden stakeholders, understand their perspectives on the problem, and build a shared mental model that everyone can get on board with.

    Do that, and you’re positioned not just to handle one chair blocking the doorway–you can handle an entire army of them.

    Four: Industry Challenges

    Changes in your market’s industry can pose a significant risk to your sales team. When their industry is experiencing a slump or a significant transformation or uncertainty, purchasing is often the first thing that grinds to a halt. Fear can paralyze a company into choosing the “no choice” option until more certainty returns.

    Again, the advantage lies in knowing enough to have the difficult conversations with your prospects. The salesperson who knows the customer’s industry and can talk intelligently about the challenges they’re facing is a salesperson who can help that prospect find their own advantage in the difficulty. And when your salespeople help prospects turn the difficulty to their advantage… then they also have turned the difficulty to their advantage.

    If your salespeople are stopping the scene because there’s a chair in front of the door, they are missing out on a world of rich opportunities to advance the plot. But when they acknowledge the chair, they have the opportunity to turn it into a winning advantage.

    Tell me, when have you encountered a “chair in the doorway” in your sales journey, and what did you do to turn it to your advantage?

     

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    George Brontén
    Published July 22, 2026
    By George Brontén

    George is the founder & CEO of Membrain, the Sales Enablement CRM that makes it easy to execute your sales strategy. A life-long entrepreneur with 20 years of experience in the software space and a passion for sales and marketing. With the life motto "Don't settle for mainstream", he is always looking for new ways to achieve improved business results using innovative software, skills, and processes. George is also the author of the book Stop Killing Deals and the host of the Stop Killing Deals webinar and podcast series.

    Find out more about George Brontén on LinkedIn