Difficult conversations sit at the core of every leadership role, and hardly anyone has been taught how to have them. The dismissal, the feedback after a failed project, the stakeholder who feels bypassed: Such conversations can be postponed, rarely avoided. Postpone them, and you have them later, under worse conditions.
In September 2021, Forbes asked 15 members of the Coaches Council how leaders handle a difficult conversation so that a usable outcome stands at the end. I was one of them. Here are the 15 ways as I read them today, after a good 20 years of working with executive boards.
One observation up front: Half of the answers are about preparation. Most difficult conversations are lost in the five minutes before they start, when someone walks into the room without a plan.
Xavier Preterit sees difficult conversations as the instrument leaders use to readjust course: On value, strategy and results. Make these conversations routine, explain their purpose to the team, and they lose their weight. The exception becomes a working format.
Kirsten Meneghello suggests pausing for a minute before the conversation: What should stand at the end for the relationship with this person? The answer usually leads to one clear, direct sentence about your intention. Put it first, and the other person stops guessing your motives for ten minutes.
Amie Devero frames every conversation to fit the person across the table: For an employee, the commitment to good performance; for the management team, the determination to perform as a team; for a stakeholder, their own goals. With the right context, criticism becomes a contribution. Without context, every piece of feedback sounds like an attack.
Difficult conversations almost always grow out of expectations someone has not met, says Emily Letran. Make sure the other person feels heard first, then put the facts on the table and ask for solutions, and you get a partner rather than a defendant. Done right, these conversations are where breakthroughs happen.
It is comfortable to stay with the problem and work out who caused it. Lori A. Manns asks leaders for the opposite: Bring proposals, and stay open to the proposals of others. Where everyone may contribute, the odds of a solution that holds go up.
When difficult conversations escalate, it is usually down to one mistake that happens early: Someone switches into battle mode. From then on the conversation is a zero-sum game with a winner and a loser, and in the end both look bad. My contribution to the panel was therefore simple: The opponent is battle mode, and you notice it in your own pulse before you hear it in your sentences. Notice it, and you can switch. With preparation and some practice this works under pressure too.
Jill Hauwiller keeps it simple: Listen, take a few deep breaths, then answer. Listening shows the leader what the other person is really after and allows an answer that starts there. Breathing keeps the pulse down, and a perceived conflict loses temperature before it becomes one.
Amy Nguyen prepares such conversations with the SCARF model from the NeuroLeadership Institute. The five letters stand for status (the other party is respected and heard), certainty (clear intention, duration and goal), autonomy (create options and allow theirs), relatedness (connect at a human level) and fairness (a solution where both sides win). Walk through the five fields beforehand and you usually find the point where the conversation could tip.
Pernille Hippe Brun asks herself five questions before the conversation: What is my main message? How will I deliver it? What will I do if the reaction is negative? How do I stay calm and open? And what will we have achieved if it goes well? Then she walks in curious, ready to learn something herself.
Shelley Hammell answers four questions in the conversation, in this order. Why are we having it, which factors caused the problem? What do we already know, which facts are on the table? Who is affected or needs to be involved? And how do we proceed, who takes on what? The order takes the arbitrariness out of the conversation.
Darcy Eikenberg enters every conversation assuming that each side has a reason for its position and that its intention is as valid as her own. Respect and trust at the start almost always lead to a better place, and they cost nothing in clarity.
Arthi Rabikrisson reminds us that language can build up or take apart. A good message is specific and easy to understand. Then there is the body: Posture, tone of voice and facial expression create calm, confidence or stress long before the content lands. Together they decide whether the message arrives as it was meant.
Christine Allen offers three guardrails. First, speak in a way that keeps your own integrity intact, which means without derailing. Second, speak in a way that preserves the relationship as far as possible, even when dismissing an employee or parting with a stakeholder. Third, stay with the outcome and look for a solution both can live with.
A conversation is a conversation, says Angela Cusack. It becomes difficult through our practice in having it, or the lack of it. See a conversation as relevant to the growth of a person or the company, and you have the choice to call it something other than difficult. It is then the conversation that helps us take care of what matters to us.
Loren Margolis observes that leaders plan difficult conversations chronologically and then get lost in the individual steps. Her question instead: What should each person know, feel and do at the end of this conversation? Once the goal is clear, planning the steps pays off.
Little has changed about the 15 ways since 2021. What has changed is what I observe in coaching: Most leaders are able to handle difficult conversations. What they lack is timing. The feedback after the failed project comes weeks later, the dismissal after the third attempt, the conversation with the stakeholder only once he has already complained. Each of these delays makes the conversation harder than it needed to be.
Two things have proven useful with my clients. First, a fixed date for the conversation before the courage for it exists; the date creates the courage, rarely the other way round. Second, one sentence written down in advance: What should stand at the end. The rest follows from way 6. As soon as the pulse rises, I am in battle mode, and then listening is the only move that still leads toward the goal. What this looks like in leadership teams is in the article on conflict management; the foundations belong in leadership coaching and Executive Coaching Zurich.
Further reading on hofmann.coach: Conflict management: What leads to a constructive conflict culture · 16 leadership behaviors that set a bad example for the team · Leadership excellence: 14 lessons for new leaders
Note: This page goes back to the Forbes Coaches Council expert panel “15 Ways Business Leaders Can Ensure The Best Outcomes From Difficult Conversations”, published 10 September 2021. The 15 ways come from the members named; way 6 is my own contribution. The framing is mine.
Cristian Hofmann is an executive coach in Zurich and Schaffhausen (MAS Coaching & Supervision BSO, Forbes contributor). Over more than 20 years he has coached more than 1,500 leaders: CEOs, executive boards and leadership teams in Switzerland, with measurably agreed goals and, on request, pay-for-results. More about Cristian Hofmann.
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