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Empathetic assertiveness: piloting tough negotiations 

Leadership

Empathetic assertiveness: piloting tough negotiations 

Published August 14, 2025 in Leadership • 9 min read • Audio availableAudio available

Negotiating in conflict zones or during a hostage crisis demands skill, courage, and emotional intelligence, all of which can transfer to the business world. Here are lessons from the frontline.

Even seasoned negotiators can hesitate when addressing sensitive issues in difficult situations. Take the following simulation exercise: participants were tasked with confronting a military commander about serious allegations of sexual violence committed by soldiers under his command at a displaced persons’ site. Despite the gravity of the situation, the negotiator – fearing that a direct confrontation could jeopardize humanitarian access for critical services like food deliveries – softened the message, saying something along the lines of: “Commander, I just want to raise a small issue about a few violations that we heard about.”

In doing so, they unintentionally diminished the severity of the crimes, jeopardizing not only justice for the victims but also undermining their credibility during the negotiation. The military commander likely interpreted the message as referencing unconfirmed rumors of misconduct, rather than serious, substantiated allegations. As a result, the chances that he would take meaningful action became minimal, and he was likely unimpressed that such vague and seemingly minor concerns were even raised to his level of authority.

This raises crucial questions: What went wrong? How could such a sensitive and serious concern have been communicated in a way that maintained both access and integrity?

Effective communication is shaped by a combination of skills, cultural influences, personality traits, and individual confidence. While some people are naturally direct in addressing issues, others may avoid making a clear point. Directness can sometimes come across as harsh or confrontational, while hesitating to speak up can lead to confusion and make you appear weak or indecisive in the eyes of the other party. How can we address sensitive topics openly and honestly without antagonizing the other party and, instead, foster a conversation that leads to a mutually beneficial solution?

In this article, we explore our concept of empathetic assertiveness, which provides guidance on how to communicate effectively in difficult situations at work while maintaining positive, productive relationships.

Assertive vs. submissive communication

Avoiding conflict often leads to submissive communication, which may prevent confrontation in the short term. However, submission comes at a cost: you risk losing your self-respect and the respect of others. People who fear conflict may convince themselves they are simply being patient, but this avoidance can lead to growing frustration over time.

When conflict is acknowledged, it creates an opportunity for productive confrontation. With the right balance of assertiveness, this confrontation can evolve into a negotiation that benefits all parties. However, too much assertiveness can quickly shift the dynamic. If a negotiator becomes overly aggressive or defensive, the conversation can escalate into a standoff, effectively ending the discussion without resolution. The key lies in striking the right balance between assertiveness and empathy: navigating conflict with respect and purpose, asserting your position while simultaneously demonstrating genuine respect for the perspectives of others.

We recognize that the strongest place in any relationship is the combination of empathy and assertiveness, but that is not the same as merely stating your demand and then respectfully holding that position, which is known as “anchoring”.

In our experience, it is often more advantageous to delay asserting your position until you fully understand the other side’s perspective. It may initially feel submissive, but it is actually a strength. By choosing the right moment to present your position, you can shape it in a way that resonates more deeply with the other side.

Applying the “Empathy First, Assertiveness Later” approach asserts your position at the optimum time – when the other party feels heard, understood, and more open to considering perspectives beyond their own, including yours.

Mere assertiveness is not enough in a negotiation

Assertiveness can take many forms, and people often believe that to be perceived as strong, they must make forceful points and assert themselves, sometimes at the expense of acknowledging the other side’s needs. However, assertiveness alone is not enough to navigate complex negotiations; it must be accompanied by an awareness of your own and the other party’s emotional dynamics.

Four emotional states can accompany assertiveness in negotiations:

  1. Empathy is the ability to perceive and understand the emotions that others may be feeling. It involves recognising and articulating what you see, hear, and understand, while also considering the surrounding context, which adds depth and value to the connection. Think of it as having an insider’s view into their situation and feelings, without passing judgment.
  2. Sympathy occurs when you feel the emotions that the other party is experiencing. You internalize their feelings, often creating a deeper emotional bond, which can naturally lead to offering support or assistance.
  3. Antipathy is when you recognize the emotions of others but consciously choose to disregard or ignore them, often as a form of self-protection. This response can arise when you feel overwhelmed by negative emotions or intentionally create emotional distance to maintain objectivity or resilience.
  4. Impassivity is when you do not feel any emotional response at all. You may appear indifferent or emotionally detached from others, which can be a sign of emotional disengagement. In extreme cases, this can resemble psychopathy, where emotional connections are absent.

Understanding these emotional stages is crucial in a negotiation, as the way you engage with the other party’s emotions can significantly shape the outcome. Skilled negotiators balance assertiveness with emotional intelligence and empathy to foster productive, mutually beneficial discussions.

The ability to recognize others’ emotions within their specific context is vital in negotiation. When both parties genuinely share an emotion, such as sadness or happiness, the connection formed is often deeper and more meaningful than a simple demonstration of understanding.

The sweet spot: empathetic assertiveness

The strength of any negotiator and leader lies in mastering empathetic assertiveness. This involves acknowledging the other party’s emotions with empathy while asserting yourself without aggression or defensiveness. It’s a way to establish an effective relationship where the other party respects you, yet you remain neither hurtful nor confrontational – hard on the point, soft on the person. For senior leaders, mastering empathetic assertiveness is a strategic leadership asset. The ability to address complex issues with clarity and empathy enhances your credibility and shapes the culture of communication across your organization. When leaders model assertiveness grounded in respect, they empower their teams to tackle challenges head-on, speak up without fear, and collaborate more effectively even under pressure.

In high-stakes environments, the instinct may be to prioritize results over relationships or to soften critical messages for fear of backlash. However, the most effective leaders can do both: drive performance while fostering trust. Empathetic assertiveness offers a way to achieve that balance. It enables you to hold others accountable, communicate with integrity, and build alignment without sacrificing humanity.

Ultimately, senior leadership isn’t just about making the right decisions; it’s about creating the conditions for others to do the same. By practicing and championing empathetic assertiveness, you set the foundation for a culture where difficult conversations become opportunities for growth, connection, and meaningful progress.

Learn how to use the five steps to empathetic assertiveness

Exercise 1

Think of a recent situation where you avoided a difficult conversation or entered it too forcefully. Ask yourself:

  • What was I trying to protect: myself, the relationship, or an outcome?
  • How did I feel before, during, and after the conversation?
  • What did I lose or gain by approaching it the way I did?
  • If I had to do it again, what would I do differently?

Write down your reflections and look for patterns across multiple situations. This awareness is the first step in knowing and shifting your default response.

Tip: Before your next negotiation or difficult conversation, reflect on the questions above. Carefully consider who you’ll be speaking to, how they will likely respond, and how your message might be received based on how it is delivered. Thoughtful preparation, especially with the other person’s perspective in mind, can make all the difference in achieving a constructive outcome.

Others can often interpret how we phrase our requests in ways we never intended. As the message sender, we are responsible for anticipating how the other party may read between the lines. They might perceive that we are appealing for their action, that there is an imbalance of power in the relationship, or that we have revealed deeper opinions or values through the way we framed our request.

It’s not enough to claim they “took it the wrong way.” Communication breakdowns usually occur because we fail to craft our message with sufficient sensitivity.

Exercise 2

Think back to a recent negotiation or emotionally charged conversation. Ask yourself:

  • Which emotional stage was I operating from: empathy, compassion, antipathy, or impassivity?
  • How did my emotional state influence my tone, body language, and ability to listen?
  • How did I respond to the emotions of the other party? Did I acknowledge them, ignore them, or feel overwhelmed by them?
  • What impact did that emotional dynamic have on the outcome of the conversation?

Consider how the conversation might have unfolded differently if you had engaged from a different emotional stage.

Tip: Before entering a negotiation, pause to assess your emotional state. Ask yourself: Am I open and connected? Am I emotionally guarded or disengaged? Then consider the likely emotional state of the other party. Preparing this way allows you to show up with greater empathy and emotional agility, essential ingredients for navigating complexity without losing clarity or composure.

Exercise 3

Imagine you’re managing a team of 40 people who have grown comfortable working from home since the COVID-19 pandemic. However, you’ve noticed communication gaps, and client complaints have begun to surface. As a result, you need some of your executives to return to the office more regularly. There is clear resistance to this change, and now you must address this delicate issue by calling them into your office for a conversation.

Your task: Record a voice note where you deliver this message with empathetic assertion. When you are done, replay the recording and listen as if it were directed at you.

  • How does it feel?
  • Do you feel supported and understood?
  • Is the message clear, and do you know the next steps?

If you’re nodding along, congratulations! You’ve nailed compassionate assertiveness.

  • Are you not sure what you were told?
  • Do you feel that many issues were raised before you were told why you ended up in your supervisor’s office?

If so, you should practice your empathetic assertiveness. When delivering a difficult message or raising a critical point, get to the point quickly and aim to be hard on the point, soft on the person. This helps maintain trust and dignity while addressing what matters most.

In Exercise 3, the message could have been delivered as follows:

1. Prepare yourself first. Understand the business reasons why the person needs to return onsite (e.g., team collaboration, service delivery, client needs). Be ready with clear facts, not opinions.

2. Start with empathy. “I really appreciate the way you’ve adapted to working from home, and I understand it’s brought benefits for your work-life balance and focus.”

3. Be clear and honest about the business needs/issue at hand. “At the same time, we’re at a point where the clients’ needs require more in-person presence. We’re seeing gaps in communication and team support that we can’t fully address remotely.”

4. Stay firm on the issue, but kind to the person. “I know this might not be what you were hoping for, and I acknowledge this is a big change. I’m here to discuss how we can make this transition work for you, while meeting the team’s and the clients’ needs.”

5. Invite collaboration without compromising the non-negotiables. “Let’s explore what support or adjustments would help you feel more comfortable returning. While we do need more in-person presence, I’m open to talking about how that might look in practice.”

Authors

Fiorella Erni

Professional negotiator

Fiorella Larissa Erni is a professional negotiator at Negotiated Resolutions, a former frontline humanitarian worker, and the founder and CEO of Cheetah Stories, an innovative sustainable footwear company. 

Kirk Kinnell

Founder and CEO of Negotiated Resolution

Kirk Kinnell is the founder and CEO of Negotiated Resolution, and a former senior police officer with over 30 years of experience in high-stakes negotiation and law enforcement. He was the Head of Hostage Negotiation and Armed Policing for Police Scotland.

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