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    You Have to Get Vulnerable and Push Back

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    We are firmly in the age of AI now, with all its exciting sales tools and supports. At Membrain, we’ve got our own take on it that we’re excited to be unfolding for you. And here I am, as I often am, reminding us that yes, we need the technologies to support complex sales. But we also need our humanity.

    In simple, transactional sales, many functions of the salesperson can be completely replaced with AI. AI chats, AI-generated emails, AI answers, automated and AI-assisted fulfillment. You often don’t need a human touching a thing, unless there’s a problem.

    In complex sales, AI can also replace and augment many formerly human functions. It can help salespeople craft on-brand emails, suggest cadences, unearth valuable research, and complete routine tasks faster and, sometimes, better.

    But if you’ve followed my writing, you know I have been preaching for a long time that efficiency is not the same as effectiveness. In complex sales, effectiveness is what matters, and effectiveness requires not less humanity, but more.

    Salespeople in complex environments need to be able to think for themselves.

    Listening to a Guy Kawasaki podcast Remarkable People recently, I heard Harvard Business School professor Alison Wood Brooks point out something I found interesting: AI conversations can be validating, useful, and affirming. But what AI conversations don’t do (yet) is get vulnerable, or push back. This got me thinking about what salespeople need to bring to the table in the era of AI. And in my opinion? Exactly that: Vulnerability, and push-back.

    Emails Get the Door Open

    Relevant, well-written, and well-targeted email conversations are within the realm of possible for AI (and our new AI tools show you how). But in complex sales, the goal of the emails is not to generate more emails: It’s to open the door to meaningful dialog and discovery.
    Complex sales deals don’t happen because one person feels good about a purchase. They happen because somebody applied their skills to dig deep, find the relevant stakeholders, have the critical conversations, and facilitate alignment with a course of action.

    It’s not just about exchanging information. It’s about understanding problems, analyzing opportunities, and designing solutions that overcome the former and maximize the latter.

    Two Skills Your Salespeople Need for After the AI-Handoff

    A salesperson who is using their AI tools effectively will have more prospects and conversations in their pipeline than one who isn’t. But once the AI-assisted emails have landed a prospect on the phone, it’s up to the salesperson to utilize skills that their AI tools can’t give them. Namely:

    1. Vulnerability
      Alison Wood Brooks said that one reason conversations with AI feel a little hollow is that the AI engine can’t get vulnerable and share personal experiences. In human interactions, one of the ways we build trust is by sharing common experiences.

      I tell you a story about a time I hired and fired salespeople thinking it was their fault, only to find out it was a lack of leadership on my part. Then I tell you how I gained the skills and knowledge, and built the tools that enabled me to build an effective sales team.

      My vulnerability at the start builds trust: I am fully human to you, I share a struggle you also may struggle with, and I am honest about my shortcomings.

      Regardless of whether it is sentient or not, an AI bot has no personal humanizing stories of their own to share, because they are not human. They can fake it, but we know it’s not real, so it doesn’t build trust, it erodes it.

      Your salespeople need to develop the skill of knowing when to tell a personal story to empathize and connect with buyers and guide them into deeper conversation. This builds trust in a way that sets them apart from competitors who may be leaning on more generic tactics and tools.
    2. Push-Back
      It’s never been a good look for salespeople to be pushovers. And yet, it’s always been a common problem. You want buyers to like you, you feel like being amiable builds trust, and you don’t want to piss them off. All that is good and well, and that’s probably why vanillla AI chat engines (so far) are trained not to push back. It keeps you engaged and coming back for more.

      But being a pushover doesn’t actually win trust. Humans are wired to be suspicious of anyone who is always only agreeable. And even if they think you’re telling the truth, they won’t believe that you know what you’re talking about if all you ever do is reflect back what they’ve already told you. And in complex sales environments? Always agreeing with the client won’t help them find the best solution to their problems.

      Salespeople in our complex environments need to be able to think for themselves, to analyze the situation, and then to push back on prospects when they know the prospect is wrong or would be served to see the situation from a different perspective.
      AI can support all of this, by coaching salespeople in skills, and in pointing out opportunities to offer a personal story or push back on a client. But at present, it can’t replace it.

      At Membrain, as we continue to ramp up our AI Insight Engine, we’ve got our eye continually on the goal of helping salespeople have better conversations that lead to better sales. Because the future of sales is not just more automation: It’s more relevance, curiosity, and trust. And that means using AI to support us in being more human, not less.

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    George Brontén
    Published September 17, 2025
    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