The sales landscape has fundamentally shifted. I keep reading posts and stories about AI replacing sales teams, and it may be for more commodity-type sales, but it will be some time before it replaces Enterprise sales teams. Building relationships and trust is the foundation for an executive to take a risk on your product, especially when it is critical to their success. AI is currently not at that level, and with behavior changing with every key release, building trust with an AI will be challenging for many years to come. But today, AI can be a powerful enablement tool for your team when leveraged correctly.
Your prospects no longer need salespeople for information; they need us for Insight. They have done their research. They expect their time to be an investment, not a discovery exercise. Does your presence and knowledge project confidence and inspire trust? Does the prospect view you as someone interested in helping their business, or just someone trying to close a deal? Impress them, and you could earn the opportunity to dig deeper. Disappoint them, and good luck trying to recover.
Two years ago, I was selling to a Fortune 100 Financial Services company. I understood their business needs, which we easily achieved. We demonstrated that we could take a key manual process that typically took 7 weeks to complete, automate it and maintain full compliance, and complete the task within 10 minutes. The SVP told me his priorities for selecting any new vendor were: 1 – Company Stability; 2 – Relationship with the Vendor; 3 – Product Quality; 4 – Product Value to their business; and 5 – Total Solution cost. Prior to selling their IP, the company fired the sales team, and the remaining execs went in and offered the deal at an even greater discount. It never sold because the executive team did not understand what was important to this buyer. The company had a high-level relationship with the stakeholders, but lacked the trust and credibility that I had built over several months. This is one of the main reasons why I believe AI won’t take over Enterprise Sales anytime soon.
So, how do you get it right?
The question for every CRO or VP of Sales isn’t whether their team is busy, but whether their activity is revenue-focused and leads to predictable and scalable results. There is much money to be made by everyone, but following the same old tired formulas seldom works.
For leaders aiming to build next-generation teams that deliver zero surprises in the forecast, the approach must be recalibrated around three core pillars: Strategic Preparation, High-Agency Coaching, and Outcome Focused Messaging (“context.”) It is much more than cold calling for two hours a day or having 5-10 meetings per week. Things like that are important, but they are just activities if you are not targeting the right companies and people, or if your team blows it once you have found those people. This will be a significant cultural shift for many companies.
Strategic Preparation: From “Discovery” to “Insight”
When a prospect books a meeting, they are giving us one of their most precious assets: time. If we treat that time as a standard discovery call, we set negative expectations, which signals the lack of perspective (the ‘P’ in PIE) and perceived value. This isn’t theory—it’s the PIE framework (Perspective, Insight, Experience)I’ve used to sell large deals, turn around at-risk customers, and scale teams for many years.
The C-Suite Mandate: Accelerate deal velocityby focusing on specific quantifiable impact for your prospects, and increase win rates by targeting identifiable business pain.
Come with an Understanding of their Market, Changes, and Competition. Before the first call, we must demonstrate that we’ve already invested time in understanding their operational constraints, their competitive pressures, and their budget priorities. The goal is to move the conversation immediately from the tired, “What keeps you up at night?” to “We have seen [problem] with companies in your industry. Is that something you have experienced or have concerns about?”
Long Discovery Calls or Presentations Typically Won’t Work. Customers are fatigued by generic questions. Every interaction must be purpose-driven and meaningful. If the call runs longer than planned, it must be because the conversation has become mutually valuable, not because we were ill-prepared and just keep talking.
Discussions Must Be Targeted to the Problems They Are Most Likely Experiencing. This is where we leverage Insight (the ‘I’ in PIE). Use your background and AI to hypothesize the top three pain points before you dial. Our role is to validate these points, quantify the impact, and then introduce a Shared Vision of Success (our solution) anchored by measurable business outcomes.
Player-Coach: Enhancing Team Capabilities, Not Just Motivating Activity
If you are a sales leader who only focuses on closing your team’s most challenging deals, you are creating a dependency, not a capability. A Player-Coach must be accountable for the team’s numbers and its health.
The C-Suite Mandate:Drive organic growth by building repeatable processes and cultivating high-agency talent.
Not a One Size Fits All Proposition. True coaching is not a template. It requires a methodical but human approach to diagnostics. That takes time, effort, and a genuine desire to help people grow.
Identify Skills Gaps and Tailor Efforts. Test skills, identify gaps, and then create targeted efforts around building skills that address someone’s specific deficiencies. This personalized attention is how we build the high-performance culture and accountability required to sustain long-term success.
Leverage the Team – Role Playing and Team Reviews. We must create a culture where knowledge sharing and feedback loops are the norm. Leverage team reviews and structured role-playing to sharpen execution. This is how we transform luck into a predictable process.
Give teams the latitude to adjust their messaging and test approaches. Adapt messaging to business trends, changes in the competitive landscape, and changing terminology. Then, have your team share their experiences and findings (good and bad) with the team to review, provide feedback, and refine. Structured agility helps your team maintain its competitive edge.
The Leadership Mandate: Context Over Content
We are past the hype cycle of AI. The C-Suite doesn’t care about the tool; they care about the ROI and the risk of poor execution. As leaders, we cannot just hand our teams a login and say, “Go use AI.” That’s a recipe for chaos and a quick erosion of professional credibility. We must lead by example.
We need to teach our teams that AI generates content, but humans generate context.
Do use AI to deepen your understanding of the prospect’s industry so you can become a true consultant. Use the technology to gain understanding and market intelligence and tie it to your Experience (the ‘E’ in PIE) as preparation before any call.
Don’t use AI to automate a thousand bad emails. Mass communication is cheap; individualized insight is priceless.
Do use AI to research the one hundred prospects that actually matter. Focused efforts yield significantly better results.
Don’t use AI to fake expertise. This leads to the quick death of credibility, as any good consultant will tell you.
The “Million Dollar Deal“ isn’t won by a bot. It’s won by a human who understands the nuances of the prospect’s business, builds trust, and navigates the internal structure and politics. AI is simply the tool that clears the path so you can do that work faster and with better data. AI is leverage, not a crutch.
Call to Action: Are You Building a Team or a Capability?
The next-generation sales leader understands that customer success is at the heart of everything we do. We win when they succeed. Your most valuable asset isn’t your pipeline—it’s the predictable capability of the individuals on your team. Consistently doing the right things is critical to success.
The challenge for every business leader today is this:Are you enabling your teams to sell like consultants, or are you still measuring them (and driving their behavior) on activity-based metrics? Focus on building intelligent and creative teams that deliver consistent results with zero surprises. It doesn’t happen overnight, but it is an investment in your future success.
Let’s discuss how we can implement the PIE framework and position your team to deliver scalable, organic growth in your organization.
For the past two years, I have performed part-time, contract go-to-market consulting. My wife had a surgery that had gone wrong 18 months ago, so I needed something that would allow me to take care of her, stay sharp, earn money, and help companies grow.
Most of the work was with small to midsize companies, but the problems and needs mirrored what I have encountered at larger companies. The main difference is that large companies tend to look to software to address problems. In contrast, smaller companies lack the budget for what they view as an unproven solution that increases complexity.
Here are my Top 5 findings:
GTM plans are often developed at the highest levels, often in isolation, without market testing and validation.
Sales teams are pitted against one another, rather than working together to help everyone achieve more (i.e., “A rising tide lifts all boats.”)
Sales teams are focused on selling features rather than solving business problems.
CRMs are not consistently used and often reflect idealized fiction rather than reality.
Sales management and teams are not leveraging AI to help focus their efforts.
Here are the related Lessons Learned:
Identifying common business problems and describing how your product or service solves them should be the foundation of the plan. Perform market analysis. How do companies describe those problems? Their terminology, often found in job ads, can help create effective messaging that resonates. Work to become the natural fit for what your prospects are seeking.
Individual contributors get paid to win, but sales management needs to create incentives for collaborative efforts that lead to wins.
For one company, I convinced them to implement a 2% SPIV (like a SPIFF, but team-focused) for every team member who actively contributed to team improvement. SPIV payments were quarterly, and there was a running total so the team could see the fund growth. Initial indications of a positive impact are good.
Another benefit of collaboration is that it helps teams focus on approaches that work due to ongoing testing and refinement. Collaboration also helps teams focus on a more accurate ICP (ideal customer profile). Sales management can then feed their findings back to Marketing to improve and tailor their efforts.
Selling is a byproduct of problem-solving. You can’t solve problems if you don’t know what they are. Every interaction with a prospect should focus on gathering information, building trust and relationships, and leveraging prior interactions to demonstrate that your solution will solve their problem and ease their pain.
CRMs often either lack information or are full of wishful thinking. They focus on activities, and not progress and next steps. Using MEDDIC/MEDPICC as a foundation for reporting is a much better start. Sales managers need to independently validate the information to ensure their teams are being upfront and honest. Trust, coaching, and collaboration work together for the win.
AI is not a panacea, but it is very effective for research, market validation, prospecting, and meeting preparation. Going in prepared builds respect and credibility, saves time, and lets you quickly qualify prospects in or out. There may be a nurturing program for some of the prospects qualified out for immediate deals, but your time is valuable, and you will go hungry chasing deals you can’t close.
So, what are your thoughts? Have you seen some of these problems yourself? How did you handle them? Let me know in the comments below.
And if you are looking for a Consultant to help your business grow or someone who can add immediate value to your team, then contact me.