A huge trend I am seeing in conversations with clients and prospects about leadership development, business acumen, and AI is the need for stronger critical thinking skills. People want their teams to ask better questions, look beyond the obvious, and think through a situation before jumping to a recommendation.

AI is adding another layer to these conversations. We can get information, analysis, and recommendations faster than ever with AI. But how do we make sure people are thinking through what they get back? And how do we help them use AI to expand their thinking without getting into the habit of accepting whatever it gives them?

It has me thinking about what we really mean when we say someone needs to develop their critical thinking. Is it a set of skills we can teach? A mindset we need to encourage? Or both?

I think it is both. We can teach people how to evaluate information and question assumptions. But they also have to be willing to do it, especially when the answer in front of them supports what they already believe.

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 How everyday decisions keep a business moving, and why understanding their impact matters. 

A business never really sleeps.

The office may be quiet, but orders are still moving through the supply chain. Marketing’s latest ChatGPT-assisted masterpiece is reaching customers through automated workflows and email sequences. Sales teams are having conversations and making commitments. Somewhere, someone is figuring out how to deliver on those commitments by Friday.

We spend a lot of time developing plans, choosing strategies, building budgets, and getting everyone aligned. All important work. But the business does not pause while we figure things out. Customers continue to buy, costs change, and people make decisions based on the information they have at that moment.

By the time we finish the planning meeting, the business has already moved forward.

That is one of the challenges of managing a business. We need a clear direction, but we also need to understand what is happening as the work gets done. And it is easy to miss some of that when we are focused on our own responsibilities.

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Every experienced Sales Professional has that horrible story of winning a big deal, “ringing the bell,” starting implementation while the contract was still being signed, and feeling great about life…

Until the bottom fell out when a different vendor “stole the deal.”

I was working with a client in the specialty chemical industry to design a new strategic selling program. During a subject-matter-expert interview, I heard a story about a salesperson who won a brand-new logo from an incumbent vendor. The incumbent, who had been living in the account for more than a decade, apparently became complacent, got expensive, and saw quality decline. So, the customer decided to shake things up and issue an RFP.

My client’s organization responded quickly, demonstrated credibility, and offered a higher-quality product at a lower price, winning the business.

But something nefarious happened on the way to happiness. The former vendor, who had built up numerous high-level relationships within the account, went crazy and started pulling in executive-level contacts to save themselves and override the decision.

And painfully, they were successful.

Think about that. The challenger had a better product, a better price, and the customer's decision. Yet somehow, the incumbent walked away with the business.

That story got me thinking about the strategic selling skills and tools that could have prevented this disaster. Based on experience and some painful lessons from the real world of selling, I'd like to share five insights.

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The temptation now exists for anyone in talent development to make training so rigorous, structured, and scripted with AI tools that it leaves no room for spontaneity, discovery learning, or exploration.

As someone who has designed and delivered sophisticated business simulations for decades, I'm wired to encourage learners to explore, try different approaches, fail, learn, and try again. Some of the greatest learning moments I've witnessed have occurred when something completely unexpected happened during a learning experience.

But over the past several months, as everyone has started using AI assistants to do their work, I've noticed a concerning trend. Training programs are becoming bloated with AI slop, too many PowerPoint slides, and a rigid focus on cramming more information into less time.

Apparently, if AI can create 100 PowerPoint slides in 30 seconds, we're now obligated to show all 100 to learners. And just to make sure we're getting our money's worth, we should probably add a 40-question knowledge check at the end.

This approach risks starving learners of opportunities to think, explore, and discover. Ultimately, it also starves companies of the talent they need to make decisions that drive business success.

The people designing these programs probably think they're being efficient. But in practice, this approach can be lazy, ineffective, and potentially very expensive.

The goal of training isn't to get through the content. The goal is to develop people who can think and perform when the content doesn't have the answer.

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Any sales professional who's been selling for more than three years knows what I am talking about. It's that moment in the sales process when someone on your own team starts to go negative and suddenly becomes the unofficial head of the "anti-sales department."

I recently interviewed a senior sales professional at a specialty chemical company who told me how brutal it is out there right now. She shared a story about conducting a quarterly account review with an important customer. She prepared especially well, researching the customer's business strategy, their customers' needs, their financial goals, and more. Based on this research and her institutional knowledge of the account, she developed an agenda filled with ideas and potential solutions to help the customer improve their business.

But instead of being gracious and thankful, the customer exploded.

"I have to be very open with you. I am taken aback that you would come in here and try to upsell me on new products and services. I thought in all of your research you would realize we are struggling with cash, margins, and budgets. The last thing I am thinking about is spending more money."

And then it happened. Five minutes after the meeting, the Technical Service Manager, who was there to support the sales professional and demonstrate some of the company's new technologies, turned to her and said the fateful words: "See, I knew this was a bad customer. I don't know why we waste our time."

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