When I was in law school, negotiation was not a required class (it now is). Still, the reputation of our negotiation program and negotiation faculty convinced me negotiation would be more than worthwhile to take as an elective.<\/p>\n
I learned a lot in that course, and further honed my negotiation skills during a decade and a half of civil litigation. I wouldn\u2019t claim to be a negotiation expert \u2014 I could mention a couple other attorneys out there who really are \u2014 though I held my own in settling a lot of cases.<\/p>\n
We are not going to cover every nuance of negotiating successfully here in a few hundred words. Even so, some basic principles are critical to any type of negotiation.<\/p>\n
You want to go into a negotiation knowing a lot. You need to know your strengths, and even more importantly, your weaknesses. But a negotiation, by definition, is not only about you. Sun Tzu had this figured out<\/a> some 2,500 years ago:<\/p>\n If you know the enemy and know yourself, you need not fear the result of a hundred battles. If you know yourself but not the enemy, for every victory gained you will also suffer a defeat. If you know neither the enemy nor yourself, you will succumb in every battle.<\/p>\n<\/blockquote>\n Every once in a while, especially if one or both sides are bluffing, you can resolve a case through early mediation. This is exceptionally rare, however, because in the absence of robust discovery both sides go into it essentially knowing nothing beyond their own exceptionally biased viewpoints.<\/p>\n In a lawsuit, you need to know the other lawyer\u2019s skills, their appetite for trial (and appeal), and their ability to accurately assess the strength of their case. You need to be introspective enough to have an equally good look at yourself about these things. You need to know the judge: how he or she has ruled in similar cases in the past, how his or her decisions tend to hold up on appeal. You need to know the clients, on both sides. How much are they willing to spend? Are they mostly rational in terms of the results they seek, or is it all about something other than money to them? Do they have some sense of honor in adhering to what they\u2019ve agreed to, or will they try to weasel out of any deal that isn\u2019t locked down as tightly as possible?<\/p>\n There is also a lot of material out there about what I would somewhat derisively call gamesmanship during the actual negotiation itself, like anchoring the other side\u2019s perception of value. Knowing about that stuff isn\u2019t going to necessarily hurt you, in that at the very least you can avoid succumbing to the other side\u2019s psychological tricks. Yet, it\u2019s not going to win you anything you weren\u2019t otherwise already going to get when faced with a well-prepared opponent either. Like many things, a successful negotiation is mostly about preparation and knowledge.<\/p>\n Meanwhile, President Donald Trump, the self-styled \u201cdealmaker\u201d president, is just about the worst person I have ever seen anywhere at negotiation. It\u2019s all gamesmanship, and not even cogent gamesmanship. Rather than developing an intimate understanding of both sides of a complex issue so he knows where he can strategically apply leverage to achieve the best result possible within the range of realistic outcomes, it\u2019s more like he barrels in, knowing nothing, with a laundry list of irrational demands that often don\u2019t even benefit him and almost never actually benefit the United States of America. He refuses to budge, he makes threats, he insults everyone on both sides, he talks to someone on the other side then completely switches sides before switching back again, he throws a tantrum like a small child, and eventually, whatever the actual outcome, he announces victory with no mechanisms in place to enforce the supposed agreement. A few weeks later he\u2019s typically forgotten all about the whole thing and moved on to something else.<\/p>\n There are far too many examples of this \u201cdotard asshole negotiation\u201d approach to go into each in detail. But what has been consistent, from Trump\u2019s many trade negotiations ([insert untrustworthy country here] promised to invest a gajillion, kajillion dollars in the U.S.!) to the \u201cpeace\u201d he \u201chelped\u201d broker in the Middle East (which amounts to Israel simply having been allowed to level Gaza with U.S. taxpayer support), his direct involvement in any negotiation results in a worse result for the American people.<\/p>\n The only time Trump\u2019s negotiation style worked was when he used it against several large law firms and a handful of big corporations because they are gigantic cowards who somehow managed to know even less than he did. His signature bombardment of nonsense will not do anything to help end the unjustified Russian invasion of Ukraine, the latest example of Trump trying to apply his nonskills as a dealmaker by pressuring Ukraine to simply accept all of Russia\u2019s demands<\/a> and thereby invite their adversary back to finish the job in a couple years.<\/p>\n In refusing an offer to be evacuated<\/a> during the early days of the war, when everyone though Russia would trample its much-smaller opponent in a matter of days, Ukraine\u2019s President Volodymyr Zelensky said, \u201cI need ammunition, not a ride.\u201d I was just in Ukraine last month, and the Ukrainian people\u2019s will to fight on has not waned. They are not going to surrender their country, especially not because of Trump\u2019s ineffectual flailing about.<\/p>\n Trump can\u2019t negotiate his way out of a paper bag. He\u2019d do better, and come off better, if he focused instead on helping Ukraine get Russia out of their country militarily.<\/p>\n Jonathan Wolf is a civil litigator and author of\u00a0<\/em><\/strong>Your Debt-Free JD<\/em><\/strong><\/a>\u00a0(affiliate link). He has taught legal writing, written for a wide variety of publications, and made it both his business and his pleasure to be financially and scientifically literate. Any views he expresses are probably pure gold, but are nonetheless solely his own and should not be attributed to any organization with which he is affiliated. He wouldn\u2019t want to share the credit anyway. He can be reached at\u00a0<\/em><\/strong>jon_wolf@hotmail.com<\/em><\/strong><\/a>.<\/em><\/strong><\/p>\n The post The \u2018Dealmaker\u2019 President Has The Worst Negotiation Skills I\u2019ve Ever Seen In Person, In Public, Or Professionally<\/a> appeared first on Above the Law<\/a>.<\/p>\n When I was in law school, negotiation was not a required class (it now is). Still, the reputation of our negotiation program and negotiation faculty convinced me negotiation would be more than worthwhile to take as an elective.<\/p>\n I learned a lot in that course, and further honed my negotiation skills during a decade and a half of civil litigation. I wouldn\u2019t claim to be a negotiation expert \u2014 I could mention a couple other attorneys out there who really are \u2014 though I held my own in settling a lot of cases.<\/p>\n We are not going to cover every nuance of negotiating successfully here in a few hundred words. Even so, some basic principles are critical to any type of negotiation.<\/p>\n You want to go into a negotiation knowing a lot. You need to know your strengths, and even more importantly, your weaknesses. But a negotiation, by definition, is not only about you. Sun Tzu had this figured out<\/a> some 2,500 years ago:<\/p>\n If you know the enemy and know yourself, you need not fear the result of a hundred battles. If you know yourself but not the enemy, for every victory gained you will also suffer a defeat. If you know neither the enemy nor yourself, you will succumb in every battle.<\/p>\n<\/blockquote>\n Every once in a while, especially if one or both sides are bluffing, you can resolve a case through early mediation. This is exceptionally rare, however, because in the absence of robust discovery both sides go into it essentially knowing nothing beyond their own exceptionally biased viewpoints.<\/p>\n In a lawsuit, you need to know the other lawyer\u2019s skills, their appetite for trial (and appeal), and their ability to accurately assess the strength of their case. You need to be introspective enough to have an equally good look at yourself about these things. You need to know the judge: how he or she has ruled in similar cases in the past, how his or her decisions tend to hold up on appeal. You need to know the clients, on both sides. How much are they willing to spend? Are they mostly rational in terms of the results they seek, or is it all about something other than money to them? Do they have some sense of honor in adhering to what they\u2019ve agreed to, or will they try to weasel out of any deal that isn\u2019t locked down as tightly as possible?<\/p>\n There is also a lot of material out there about what I would somewhat derisively call gamesmanship during the actual negotiation itself, like anchoring the other side\u2019s perception of value. Knowing about that stuff isn\u2019t going to necessarily hurt you, in that at the very least you can avoid succumbing to the other side\u2019s psychological tricks. Yet, it\u2019s not going to win you anything you weren\u2019t otherwise already going to get when faced with a well-prepared opponent either. Like many things, a successful negotiation is mostly about preparation and knowledge.<\/p>\n Meanwhile, President Donald Trump, the self-styled \u201cdealmaker\u201d president, is just about the worst person I have ever seen anywhere at negotiation. It\u2019s all gamesmanship, and not even cogent gamesmanship. Rather than developing an intimate understanding of both sides of a complex issue so he knows where he can strategically apply leverage to achieve the best result possible within the range of realistic outcomes, it\u2019s more like he barrels in, knowing nothing, with a laundry list of irrational demands that often don\u2019t even benefit him and almost never actually benefit the United States of America. He refuses to budge, he makes threats, he insults everyone on both sides, he talks to someone on the other side then completely switches sides before switching back again, he throws a tantrum like a small child, and eventually, whatever the actual outcome, he announces victory with no mechanisms in place to enforce the supposed agreement. A few weeks later he\u2019s typically forgotten all about the whole thing and moved on to something else.<\/p>\n There are far too many examples of this \u201cdotard asshole negotiation\u201d approach to go into each in detail. But what has been consistent, from Trump\u2019s many trade negotiations ([insert untrustworthy country here] promised to invest a gajillion, kajillion dollars in the U.S.!) to the \u201cpeace\u201d he \u201chelped\u201d broker in the Middle East (which amounts to Israel simply having been allowed to level Gaza with U.S. taxpayer support), his direct involvement in any negotiation results in a worse result for the American people.<\/p>\n The only time Trump\u2019s negotiation style worked was when he used it against several large law firms and a handful of big corporations because they are gigantic cowards who somehow managed to know even less than he did. His signature bombardment of nonsense will not do anything to help end the unjustified Russian invasion of Ukraine, the latest example of Trump trying to apply his nonskills as a dealmaker by pressuring Ukraine to simply accept all of Russia\u2019s demands<\/a> and thereby invite their adversary back to finish the job in a couple years.<\/p>\n In refusing an offer to be evacuated<\/a> during the early days of the war, when everyone though Russia would trample its much-smaller opponent in a matter of days, Ukraine\u2019s President Volodymyr Zelensky said, \u201cI need ammunition, not a ride.\u201d I was just in Ukraine last month, and the Ukrainian people\u2019s will to fight on has not waned. They are not going to surrender their country, especially not because of Trump\u2019s ineffectual flailing about.<\/p>\n Trump can\u2019t negotiate his way out of a paper bag. He\u2019d do better, and come off better, if he focused instead on helping Ukraine get Russia out of their country militarily.<\/p>\n Jonathan Wolf is a civil litigator and author of\u00a0<\/em><\/strong>Your Debt-Free JD<\/em><\/strong><\/a>\u00a0(affiliate link). He has taught legal writing, written for a wide variety of publications, and made it both his business and his pleasure to be financially and scientifically literate. Any views he expresses are probably pure gold, but are nonetheless solely his own and should not be attributed to any organization with which he is affiliated. He wouldn\u2019t want to share the credit anyway. He can be reached at\u00a0<\/em><\/strong>[email\u00a0protected]<\/em><\/strong><\/a>.<\/em><\/strong><\/p>\n","protected":false},"excerpt":{"rendered":" When I was in law school, negotiation was not a required class (it now is). Still, the reputation of our negotiation program and negotiation faculty convinced me negotiation would be more than worthwhile to take as an elective. I learned a lot in that course, and further honed my negotiation skills during a decade and […]<\/p>\n","protected":false},"author":3,"featured_media":137667,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"_et_pb_use_builder":"","_et_pb_old_content":"","_et_gb_content_width":"","_jetpack_memberships_contains_paid_content":false,"footnotes":""},"categories":[16],"tags":[],"class_list":["post-137666","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-above_the_law"],"jetpack_featured_media_url":"https:\/\/i0.wp.com\/xira.com\/p\/wp-content\/uploads\/2025\/11\/donald-trump-GettyImages-1152627372-zv1ial.jpg?fit=1024%2C683&ssl=1","jetpack_sharing_enabled":true,"_links":{"self":[{"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/posts\/137666","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/users\/3"}],"replies":[{"embeddable":true,"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/comments?post=137666"}],"version-history":[{"count":0,"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/posts\/137666\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/media\/137667"}],"wp:attachment":[{"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/media?parent=137666"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/categories?post=137666"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/xira.com\/p\/wp-json\/wp\/v2\/tags?post=137666"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}\n
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