Trump and Zelensky in the Oval Office: The Sequel

Aug 28, 2025 | Leadership, Narcissism, Thought leadership

By Paul Vanderbroeck

Crucial conversation lessons

Following the Oval Office meeting on 28 February between Presidents Donald Trump and Volodymyr Zelensky that had a disastrous outcome for Mr Zelensky, I identified seven lessons for leaders entering a high-stakes discussion. A little less than six months later, the two leaders met again on 18 August for another crucial conversation. Given what we are able to observe, the consensus in the world press thus far is that the new meeting went a lot better than the previous one. Apparently, President Zelensky took these lessons to heart.

So how did Zelensky perform this time round and what did he learn?

1. Increase your self awareness

Investing in self-awareness creates the conditions for targeted and just-in-time skill development to meet important and unexpected challenges.

Zelensky showed up smartly dressed, rather than in his usual military attire. The latter does well in Ukraine to show that the president is part of the war effort. For the Oval Office this time, Zelensky’s dress showed that he is part of the peace effort, preventing being labelled as an uncooperative war monger. Trump positively remarked on it. Clearly, Zelensky was more aware of how others may react to his behaviour and how he could influence others’ perception.

2. Consider the context

Before engaging in a challenging conversation, it’s crucial to analyse the context of your counterparts thoroughly. It includes understanding how the context could influence their behaviour and their stake in the discussion. Such understanding can help you anticipate their reactions and prepare accordingly.

Zelensky met his counterpart in a similar context to previous meetings, where Donald Trump needed to show the world and his followers that he is making progress towards bringing peace and that the efforts he makes are not a one-way street, but serve the interests of the American people. This time around, Zelensky did well in not emphasising obstacles and what was not going well. Zelensky focused on the positive, thereby assisting Trump in his message of progress. The Ukrainian president expressed his gratitude to the US several times, including personal thanks to President Trump. In addition, he announced that Ukraine would spend a significant amount of money to import military equipment from the US. He also emphasised that this weaponry was mainly for protection and defence, hence to sustain any peace agreement.

3. Beware of labels

When faced with negative labels from your professional relationships, it’s important to counteract them effectively. Show empathy, ask for clarification to address any concerns, and most importantly, state verifiable facts to diffuse the label. This approach can help you maintain control of the conversation and steer it in the right direction.

Zelensky has suffered from being perceived as illegitimate and as stalling the democratic process for new elections. A journalist again brought this question up in the meeting. This time, Zelensky factually explained the constitutional boundaries of such elections in wartime and described how an election would take place once there is a ceasefire.

4. Level the playing field where you can

Think of ways, even small ones, that allow you to reduce an unfavourable power balance and remind your counterparts that they need you too.

In this regard, Zelensky did very well. He managed – whether or not at his initiative – to have seven senior European and Nato leaders present to back him up. It significantly evened out the power balance.

5. Prepare and practice

If it is imperative and if you expect a challenging conversation, take the time to prepare and mobilise the support you need for your preparation.

As with self-awareness, the observable, more constructive behaviour indicates that there has been good preparation this time around. Bringing a letter and a gift shows that the Ukrainian (and European) team had a strategy thought out in advance.

6. Learn to de-escalate

Be prepared for eventualities and have some ruses up your sleeve to de-escalate.

In the available video material, no escalation can be observed. There has been no report of an escalation happening behind closed doors. One reason is that Zelensky took active steps to prevent escalation by making a personal connection with his counterpart: Zelensky handed Trump a personal letter from his wife to Mrs Trump. In addition, Trump received a golf club from a Ukrainian officer, who uses golf to recover from his war injuries. A smart way to establish an emotional connection between Trump and the war in Ukraine through his favourite sport. Preventing escalation was clearly Zelensky’s strongest behaviour. He used humour effectively when a journalist complimented him on his different suit. Getting everyone to laugh is a great way to create a positive and cooperative atmosphere that prevents escalation.

7. Stay with the facts and yourself

Stay with the facts and talk about yourself and your interests, even if the other party throw opinions, assumptions and accusations at you.

Zelensky did this by staying in his role as president and being respectful towards others and their responsibilities. He remained with the facts (e.g. working towards a meeting with Putin). He refrained from answering speculative questions (e.g. land concessions). He emphasised several times the common ground of the two parties.

In summary

In high-stakes conversations, preparation, strategic positioning, awareness of power dynamics, and emotional intelligence make the difference between influence and frustration. Zelensky’s first experience in the Oval Office serves as a stark reminder that even the most capable leaders must continuously adapt to shifting dynamics. The ability to anticipate, counteract, and de-escalate is fundamental. Zelensky’s second experience in the Oval Office, therefore, holds up a clear example of the benefits to this approach. At least for this crucial conversation, President Zelensky has shown an exemplary capability and willingness to learn. How it exactly happened, we do not know for sure. However, most likely he received feedback and coaching from his team and his peers in Europe.

To be continued…

Oriane Kets de Vries:

Oriane Kets de Vries is CEO and owner of the Kets de Vries Institute. She leads a global team of coaches, consultants and educators dedicated to developing reflective, emotionally intelligent leaders and cultivating workplaces where people can thrive. In her faculty role, she draws on extensive experience designing and directing leadership programmes for senior executives, contributing her expertise in psychodynamic coaching, organisational culture, and transformational leadership development.

Oriane has served as consultant, coach, and programme director for clients including Pictet, Deutsche Bank, Merck, UBS, Mishcon de Reya, and Engie, and she has taught on open-enrolment programmes with leading institutions such as Cambridge Judge Business School, Oxford Saïd, INSEAD, ESCP, ESMT and CEDEP. Her interests centre on the human side of leadership, particularly identity, creativity, entrepreneurship and gender dynamics. She holds an MBA and Executive MA in Coaching and Consulting for Change from INSEAD, has trained at the Harvard Kennedy School, and brings more than a decade of professional experience in creative and entrepreneurial industries into her work with leaders.

Manfred Kets de Vries:

Manfred Kets de Vries is a pioneering authority in leadership development, coaching, and organisational change. He is a founder and director of the Kets de Vries Institute (KDVI) and served as Distinguished Clinical Professor of Leadership Development and Organisational Change at INSEAD. With academic credentials in economics (University of Amsterdam), management (MBA and DBA, Harvard Business School), and psychoanalysis (trained in Canada), he brings a uniquely interdisciplinary perspective to leadership. His work bridges management theory and clinical insight, establishing him as a global thought leader in executive coaching and transformation. At INSEAD, he founded the Global Leadership Centre and led the flagship programme The Challenge of Leadership for 31 years. He also served as scientific director of Coaching and Consulting for Change, an 18-month Executive Master’s programme that has shaped over 3,000 senior leaders and executive coaches worldwide. He has advised and coached senior executives at global firms including Goldman Sachs, BP, Shell, Unilever, McKinsey, and Volvo. A prolific author of over 60 books and 400 articles, his work appears regularly in The Financial Times, The Economist, and Harvard Business Review. Recognised by Le Capital, Wirtschaftswoche, and The Financial Times as one of the world’s top 50 management thinkers, he is widely regarded for advancing more human-centred approaches to leadership.

Yulia Chupina:

Senior Adviser (Luminary) at Accenture and executive coach with over 12 years of board experience. Formerly a banker and McKinsey consultant, Yulia has led banking transformations in digital, agile, organisational change, and talent development. Her coaching spans the finance, tech, and consumer goods sectors, blending technological insight with emotional intelligence to guide leaders through transformation. Recently, she advised BBVA on agile methodologies and senior talent development. Influenced by thought leaders such as Manfred Kets de Vries and Gabor Maté, Yulia brings an analytical, reflective approach to leadership. She has lived and worked across the UK, Spain, the US, and Russia.

Elizabeth Florent:

Elizabeth has worked closely with Manfred Kets de Vries for many years and has served as a Senior Lecturer and Research Fellow at INSEAD. Her extensive background in leadership development spans organisational consulting, executive coaching, and academic research. She holds advanced degrees in Organisational Development and Clinical Organisational Psychology and is a certified Coaching Supervisor through the Tavistock Institute. Her doctoral research explored experiential domains in executive education, and she has authored or co-authored numerous academic articles, case studies, and books on leadership and organisational dynamics. Elizabeth led the development teams behind KDVI’s diagnostic instruments, including the GELM, OCA™, and ITI. Drawing on her diverse training and global experience, she brings deep cross-cultural insight to her work with leaders worldwide. Originally from California, Elizabeth has made France her home for over 30 years.