Flexible Planning, Strategic Execution Turns Negotiation into a High-Stakes Masterclass
I wear two hats. Dr. James A. Tompkins analyzes supply chains, while Jim Tompkins studies leadership.
For many nights, I have not been able to sleep as “Jim.” Like many people, my mind keeps trying to figure out an important question: What exactly is President Trump doing?
Watching his presidency unfold for the past month has been like watching a masterclass in successful negotiation and leadership. And I suspect that few people fully understand this method of closing deals.
So, I’m setting aside my supply chain hat for a moment. In understanding Trump’s negotiation strategies, I really need to concentrate with my leadership hat.
Trump’s Approach Plans but Does Not Predict
Anyone trying to predict what Trump will do next is setting themselves up for failure. Why? Because Trump doesn’t know what he’s going to do next – not in the way traditional politicians might.
Instead, he operates within a structured framework. However, this structure includes optionality. Therefore, Trump can handle flexibility and make rapid decisions based on real-time feedback.
Over the past four years, while out of office, Trump wasn’t just campaigning – he was preparing.
He created a list of objectives. Some were short-term (e.g., “drain the swamp,” “secure the border,” “end the Russia-Ukraine war”). Others were long-term (e.g., “balance the budget,” “achieve energy dominance”). He didn’t just jot these down as talking points; he built detailed action plans for each one.
For each objective, he developed a range of options – different paths he could take to reach his goals. Then, he assigned responsibilities to various team members. Charlie owns Objective 1, Mike owns Objective 2, Susan owns Objective 3.
And rather than making rigid decisions upfront, he plays his options like a grandmaster plays chess. His teams bring him alternatives to a negotiated settlement. Or he gets feedback from the news cycle. Or he sees how an adversary reacts.
With optionality, now Trump can move pieces based on what happens, not some rigid political theory,
The Art of the Deal, AKA Leadership in Action
Let’s take rare earth minerals, a critical factor in U.S.-China relations. China dominates the global supply, meaning they hold a key economic weapon. Trump’s plan? Secure rare earth minerals from alternate sources.
That ties into another objective: ending the Russia-Ukraine war. Let’s say the U.S. strikes a deal with Ukraine to develop their rare earth resources. That move weakens China’s leverage and strengthens Ukraine economically.
However, Trump’s leadership here isn’t about forcing a singular outcome. His negotiation skills include maneuvering the board to create multiple pathways to success.
So yes, Trump tells us Mike and Susan to get together. You two figure out how the U.S. can gain access to Ukraine’s rare earth minerals to eliminate the upper hand China has when we start negotiating on tariffs.
But he also throws in optionality. Which is why he is making noise about Canada and Greenland. Canada and Greenland both have a wealth of resources.
No, I do not think Canada will become the 51st state. I do not believe the U.S. will invade Greenland to secure resources. But the U.S. does have a 1951 treaty to defend Greenland.
So, when the U.S. negotiates with China, and China threatens to cut off the U.S. supply of rare earth minerals, Trump says OK. We’ll just get them from Greenland, Canada and Ukraine.
This is all in The Art of the Deal, Trump’s book.
And yes, I know Trump and Ukrainian President Volodymyr Zelenskyy had that dust up last week in Washington. But I still haven’t closed off the possibility that Ukraine will be some part of a deal that offers them security and the U.S. rare earth minerals.
But that’s also why Trump is including the options of Canada and Greenland. He knows that negotiating an agreement does not guarantee reaching an agreement.
Decisions in Real Time, from Tariffs to ‘Common Sense’
In fact, Trump knows there are no guarantees. Take the question everyone is asking: Will Trump impose tariffs on Mexico and Canada today?
At this moment, I don’t know. You don’t know. Trump doesn’t know.
And that’s exactly the point. It depends on what happens between now and then. It depends on how Mexico and Canada respond, how negotiations evolve and whether other pieces of Trump’s plan come into play.
By the time I publish this blog on Tuesday, we may know that Trump has enacted those tariffs.
However, Trump has an adaptive leadership style that reacts in real time. If things are going his way, he might delay the tariffs. If he needs to apply pressure, he’ll enforce them, but perhaps with selective carve-outs to maintain balance.
He might adjust tariffs strategically to minimize economic harm. For example, he could impose tariffs on Canada but exclude the automotive sector to maintain strong industry ties. He might also exclude tariffs on Canadian energy resources.
With Mexico, he might recognize the challenges but remove tariffs on agricultural goods.
These adjustments create uncertainty, making businesses rethink their strategies. A Mexican company, for instance, might shift manufacturing to Texas to avoid tariffs. Trump would likely see such shifts as a win.
And if he doesn’t like what’s happening in the news cycle, Trump will go beyond his major objectives to maintain momentum. I think keeps a list of common-sense issues – hot-button topics with 90% public support. When he needs to, he pulls one out.
He might roll out a position like, “Boys shouldn’t compete in girls’ sports.” Or maybe “We’re spending too much money teaching people in the jungle how to draw pictures.” These aren’t distractions. Instead, they are strategic plays to control the narrative and reinforce his brand of leadership.
Trump’s Master Class in Leadership and Negotiation
This isn’t Leadership 101. This isn’t even the senior-level course. This is a master class in real-time leadership and negotiation.
Trump defines clear objectives, developing multiple strategic options for each one.
Trump then assigns responsibility for managing these objectives, releasing news, getting feedback.
Then, Trump makes real-time decisions based on feedback. And he pivots when necessary.
It’s an approach that moves at the speed of business, not the sluggish pace of government bureaucracy. That’s why, in just over a month, Trump has accomplished what would take most administrations years to push through.
Where Does Trump’s Leadership Go from Here?
I don’t know what Trump will do next, but I do know why he operates this way. He is not a conventional politician. He’s a CEO at heart, running America like a business – prioritizing results over process, negotiations over bureaucracy and momentum over political stagnation.
Some people will love his approach. Others will hate it. But one thing is undeniable: There is a method to what many mistake for madness.
As someone who’s spent a lifetime studying leadership, I see a system at work. Trump has built a machine for rapid execution, and it’s running at full speed. The question now isn’t what he’ll do next. It’s how the world will react to his next move.
Related Reading
- Dynamic Optionality Beats Expanding Your Supply Chain House
- ReGlobalization: Supply Chains in a Trump Disrupted World
- 6 Strategies to Surf Through the Trump Tariff Tsunami
Jim Tompkins, Chairman of Tompkins Ventures, is an international authority on designing and implementing end-to-end supply chains. Over five decades, he has designed countless industrial facilities and supply chain solutions, enhancing the growth of numerous companies. He previously built Tompkins International from a backyard startup into an international consulting and implementation firm. Jim earned his B.S., M.S. and Ph.D. in Industrial Engineering from Purdue University.
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