Managing in the Age of Uncertainty

Salespeople are helpers first and sellers second

Lessons from the Best: the most human of skills is what defines a winning salesperson in the age of AI

I’ve been lucky in my career to know people who can only be defined as “sales champions”— those people who have finished not in the top 10 percent, but in the top 1 percent.

I reached out to a number of these champions to weigh in on how the sales profession has changed because of AI, and what advice they would give current and prospective sellers about charting a successful career in sales.

Readers of this newsletter know I believe AI has forever changed career-pathing — and soon concepts like the corporate ladder will be a distant memory, or not even a memory at all, to millennials, gen-z and the generations that follow.

The ladder in sales was a path forward over many decades in the same company: account manager, territory manager, region manager, area manager, national manager, global manager.

Of all the functions in a company, sales remains the one most rooted in our humanity. While the corporate ladder may be dying because of AI, what isn’t changing about the sales profession is the unique way our human-ness drives success at the highest level. The champions I talked to stressed what only humans can truly do: empathy, trust, lived experiences, curiosity.

I write this newsletter for managers of teams and want to provide perspectives on how to build a great team. Here are four perspectives from sales gurus on how to prosper in the age of AI.

1. A salesperson is a “helper.”

My good friend and former Cisco colleague Mohammad Abdel-Khaliq — “Mo” — was born with warmth and charity, and it’s not surprising that he would focus on the most human of all traits as a differentiator for sellers: helping others.

“Selling isn’t about explaining,” he tells me. “It’s about helping someone with 100 percent authenticity.”

I asked him what authenticity means in a sales context, and this is what he says: “You have to organize your thoughts in order to internalize what you have to say based on empathy for the customer — not what product you are selling.”

I love Mo’s concept of “internalizing” empathy as a way to ensure a seller’s authenticity with the customer. Internalizing means your really believe something, the key to being true to yourself.

How do you know you’ve internalized your thought process? “You message is simplified,” Mo says. “If you can’t simplify you message around how you can help someone you haven’t internalized your empathy for the customer.”

As you think about yourself or the people you manage, how hard is it for you to simplify your message? Do you have an internal approach to empathy?

2. Your Digital Footprint is the New Reference Check

I’ve always found Lou Viveros — one of the sellers who invented the video game industry — to be one of the most creative thinkers I know. His view of selling in the age of AI is grounded in how sellers build trust with their customers.

“It used to be that we could point to the feature/benefit stack to validate why we have the right solution,” Lou tells me. “That’s just not true any more because customers today are the most informed in history, and they don’t need anything explained to them.”

Instead, Lou tells me, customers are looking for sellers who can be trusted to understand and believe in the mission of their companies — in other words, the seller has the customer’s best interests in mind, not the “transaction.” “The bigger the buy, the higher the need for trust,” Lou says.

I ask Lou how customers can validate that a seller can be trusted to have their best interests in mind? “Your history as a seller is reflected in your digital footprint — your reviews on LinkedIn, your posts, your connections, your followers — it’s all right there in your feed.”

I’ve talked a lot about the idea of “building in public,” and Lou is hammering it home: “Your digital footprint is the new reference check and the greatest indicator of whether you can be trusted.”

Then Lou tells me this: “The gatekeeper used to be your customer’s admin. Today, the algorithm is the new gatekeeper.” Wow. Your social communication is more than a feed, it’s your reputation, Lou tells me.

Like empathy, trust can’t be replaced by AI. Think about yourself and the people you manage. How are your building “trust in public”?

3. Relevancy means you’ve worked “in the trenches.”

It’s easy to use AI to find out and examine the challenges or problems of any industry, a vertical or even a specific customer.

My friend, former Cisco colleague and weekly zoom buddy Mark Poreman is adamant that the “human touch” comes not from regurgitating facts from AI but from showing the customer that you’ve walked in their shoes — that you as a seller know what it means to work “in the same trenches” as them.

I love this idea of differentiating yourself as a seller by your depth of experience actually solving the real-world problems customers have. It’s such a great analogy: “in the trenches” with customers.

In many ways, Mark tells me, the phrase “walking in the shoes of a customer” is only as credible as your lived experience with what the customer cares about.

“It’s all about how to be truly relevant to what matters most to a customer,” Mark tells me. “The more technical the sale, the more hands-on you need to be.”

It’s similar in concept to what Lou told me about the benefit feature stack: As helpful as AI can be, “you can’t come in with a theory anymore,” Mark says.

It’s a great exercise for sellers building their career stories: how you prove and validate that your lived experiences in the customer’s world. How would you tell your story or help members of your team tell better stories of life “in the trenches”?

4. Personalized analogies can “arrest the attention” of a customer.

Some people have special talents and Brian Panosian is one of them. My friend and former Cisco colleague has an aptitude for using analogies as a way to capture the attention of a customer.

But Brian’s not talking about a casual use of analogies; he’s saying an analogy only works if it is deeply meaningful to the customer. “You have to be super-curious about the people you’re selling to and what they really care about,” Brian shares. “That’s not something AI can do.”

I ask Brian to share an example. “You can’t tell a customer that solving the problem is ‘like a tap-in birdie putt’” if the customer doesn’t care about golf,” Brian says.

What I love about what Brian is saying is the idea that every person is a unique individual — and if you can identify with them on an individual level, you can connect with them in a personalized way through analogies. Talk about opposite of AI.

What’s secret sauce to personalized analogies? “Ask a lot of relevant questions,” Brian says. “Selling is a craft; it has to be nurtured.”

Think about yourself. Do you have a special skill in communicating? I was always good at summarizing the key message. Brian’s all about the analogy. What about you?

Career Story Builder Review: Mohammad Abdel-Khaliq

My good friend and former Cisco colleague Mohammad Abdel-Khaliq mentioned on LinkedIn that he had tried the tool.

I asked Mo for his thoughts on Career Story Builder: “It’s thought-provoking. I found the questions a great starting point to help me open up about myself that I haven’t thought of. You have to honest and genuine but it really brings out a meaningful story about yourself.”

I asked Mo if I could share what Career Story Builder created for him.

Here is the “Act One” summary of his career story (I’ve known Mo 25 years and this is SPOT ON):

Act I — Strengths

I’m a partnerships and relationship builder who thrives on creating connections and unifying diverse teams around shared outcomes. I excel at architecting ecosystems that deliver innovative business and personal results, starting with deep listening—understanding regional cultures, concerns, requirements, and pain points—and then orchestrating the right mix of local teams, solutions, financials, partners, and goals. This approach has powered programs and field campaigns that generated billions of dollars in revenue for my organization and its partners, while building long-lasting, trust-based relationships.

Try Career Story Builder

Give the Career Story Builder a try. It’s free and unlimited. I’d also love to hear your feedback about how to make it better. It’s new and I’m sure it can be improved. Send me a DM with any thoughts.

In Summary: Principles of Managing in the Age of Uncertainty

• I left Cisco to answer this question with research and evidence: What does the manager of the future look like? What are millennials and gen-z seeking in a manager? Which behaviors, tactics, skills or processes matter? What’s it going to take to attract and keep the best people over the next decade? In short, how to be a great manager.

• Based on this research, the core philosophy of this newsletter is rooted in one idea: successful managers in this moment in time, for this generation of talent, need to be “career dot-connectors.” The next-gen doesn’t expect to spend their entire career on your team — that’s an idea boomers grew up with. A job on your team is like a chapter in a career story to the current generation. If you want the best people on your team, you have to connect the dots between roles on the team and the career opportunities of the people working on the team.

• What is the“Age of Uncertainty”? If the industrial age was about taking predictable steps up the ladder, the age of uncertainty is about finding or discovering the path of a career without any predictable steps, without an obvious ladder — it’s why being a career dot-connector will differentiate you as a manager.

• How to be a Great Manager in the Age of Uncertainty: Be a Career Dot Connector is available on Amazon.

• What kind of manager are you? Take my free self-assessment and learn about yourself.