Hard talks: navigating difficult conversations in public, corporate and family arenas

At a recent Withers KhattarWong seminar held in collaboration with The Obama Foundation, the speakers explored how difficult conversations could be approached with greater clarity, confidence, and contextual understanding.

Difficult conversations are an unavoidable part of leadership, decision-making, and relationships. Moments of tension test how we communicate with others when the stakes are high. How do we navigate situations when alignment breaks down, expectations diverge, and trust is tested in unavoidably difficult conversations? 

The conversation drew upon the rich experiences of our panelists in the government, corporate, philanthropic and family contexts, and sought to answer the central question – are there conversational techniques that can be used across all these scenarios? 

Overcoming conflict aversion

Conflict aversion is a common human tendency, with choosing to remain silent as an equally common response. This is often followed by attempts to break the awkward silence, usually by diverting everyone's attention away from the conflict. 

Yet, doing so may be counterproductive as issues fester and are swept under the rug. Maya Soetoro, Faculty Specialist with the University of Hawai'i at Mānoa, who serves as the university's liaison with The Obama Foundation said, "Instead, it is in these moments of silence and pauses that we digest the discomfort of the conflict. Reflection often comes after this period of generative stillness".

This issue is accentuated in Asian family businesses. Stacy Choong, Partner at Withers KhattarWong said, "In Asia, the story of the business is often inseparable from the story of the family. There is no clean line between work and home – only a constant overlap. This makes conflict harder to confront, because disagreements do not end when the meeting does; they linger, echoing through family life." She observed that many families often grapple with the question of who should make the first move, ultimately choosing silence as the easiest response. Appointing a family governance advisor to identify communication driven tension points can give families the necessary push to break through inertia.

Conditioning ourselves to the discomfort of silence may instead be the most effective. Elaine Yew, an advisor on leadership, succession planning and executive development, observed how silence is often the most productive moment in difficult conversations. Rather, the instinct to fill awkward silence or smoothing over it, only results in superficial agreements. This in the long run is precisely what prevents meaningful organisational change. 

Tina Tchen, Executive Vice President of Programs at The Obama Foundation echoed these sentiments, emphasizing the importance of leadership in managing difficult conversations and conflicting voices. "Intellectual friction is how people learn to speak and listen to one another. The importance of leadership cannot be understated, because leadership sets the tone for what follows," she said. Drawing upon her experience working in the Obama administration, Tina spoke about how leaders could create formal structures and safe spaces with clearly defined rules that allow for voices to be heard. 

The discussion also touched on how leaders could increase their comfort with conflict by viewing each difficult conversation as an opportunity for growth. "We need to rethink how we look at conflict. Not all conflict requires conflict resolution at this point. Instead, we should be moving towards a lens of conflict transformation," said Maya.

Navigating emotions

Emotions invariably enter the arena as tensions rise during difficult conversations. Letting emotions run high in the course of conflict, however, does not mean that the conversation would be unconstructive. "Emotions are a double-edged sword. Emotions are important in humanizing the situation, but raw emotion is almost always unhelpful," said Elaine. Echoing this, Stacy noted how in any heated discussion when emotions are running high, the advisors should seek to engage parties separately to diffuse tension and distil their core concerns. "When emotions run high, people may say things they later regret. Giving parties time and space to calm down helps them clarify what they truly want to communicate, before bringing them together in a safe space for a more constructive dialogue", she said. 

Yet, such safe spaces do not exist by default and must be created. Leadership must empower people to bring their voices into the conversation by setting clear permission structures, ground rules that facilitate discussion, and engendering conducive environments where different perspectives are valued and heard.  

The crux therefore lies in the role of leaders in managing these emotions and creating such safe spaces. "Leaders have to show that they are listening – deep and genuine listening – and that they are moving with trust with the community," said Maya. "People will know and feel the authenticity in the room, and that is when they open up in a safe space". 

Leaders must also be aware that the avenue of the conversation, whether public or private, matters greatly. Elaine noted that effective Chairs of boards manage the group discussion actively, including having one on one conversations to tee up for a productive conversation as a group subsequently. Leaders also have a crucial role to play in diffusing tensions as they arise, which could be achieved by emphasizing shared values of the parties, letting the other person know that they are being heard, or even using humour. 

Key points to note for managing difficult conversations in the family context 

Overall, the seminar touched on the following broad themes that the panel invited participants to sit with and return to in their own organisational and family contexts: 

1. Learning to work through disagreement is essential for deeper understanding and growth. But when conflict avoidance is mistaken for harmony, it does not protect relationships – it quietly hardens tension.
2. When Family and Business Collide. In Asian family enterprises, the close interweaving of work and family makes difficult conversations both more sensitive and more consequential. That reality demands greater care in engagement, not silence.
3. Silence, when held intentionally, can actually be constructive. It creates space for reflection, discomfort, and the deeper conversations that rushed dialogue often suppresses.
4. Emotions must be managed, not buried. Productive dialogue requires safe spaces, separation where needed, and deliberate pacing – especially when emotions are highly charged.
5. Despite their importance, the so called “soft” dimensions of leadership – emotional intelligence, relationships, and cultural nuance – remain consistently underinvested in. Yet these capabilities are deeply human, critical to long term success, and not easily replicable by artificial intelligence. Family leaders must therefore recognise, nurture, and actively value this essential skill set.
6. In moments when families find themselves stuck, a trusted and independent advisor can be pivotal. Progress often requires an external catalyst. A trusted and independent advisor provides the neutrality, structure, and emotional containment families need to address unspoken tensions and move forward when internal momentum has stalled. Such an advisor can help steer discussions constructively, surface issues before they escalate, and importantly, have the courage to ask the difficult questions that others shy away from. A good advisor can help families and organisations identify blind spots and create the space for more meaningful conversations.

If you would like advice on how we help families with multi-generational planning considerations or other more complex family governance requirements, we would be pleased to assist.