CEO Insider

The Five Steps for Having Tough Conversations

Gerard Penna

Many leaders avoid tough conversations.  As a result they contribute to mediocrity, and perpetuate an unsatisfactory status quo. They leave other people unaware of the problems and challenges that are theirs to solve and make progress with.  My work has focused on revealing the differences between more extraordinary leaders, and the average, typical, ho-hum leadership we tolerate in our daily lives.  

One key I’ve discovered is how they use tough conversations to transform relationships and outcomes.  How do more remarkable leaders torque the odds in their favour that a tough conversation will be an effective one?  Here’s five steps that I’ve learned from observing, coaching and teaching leaders for more than three decades in countless board rooms, back offices and break rooms.

  1. Check for competing intentions:
    Have you ever approached a conversation with an intention to show up a particular way, but actually behaved in a way that was not as you intended?  Maybe your intended assertiveness morphed into submission, or deliberate calm turned to anger? If so, it’s likely the deliberate intention held by your thoughtful modern forebrain was blocked by a powerful non-conscious survival intention originating out of your instinctive reptilian brain.  You can avoid being caught unaware by these instinctual urges by asking beforehand, “What competing non-conscious intention might show up, and how could I minimise its effects?”
  2. Avoid triggering a fight-flight-freeze response:
    Just as your brain will be trying to keep you safe, so too will the other persons.  Their survival brain will be evaluating what you say and do to decide if this is an unsafe conversation.  If their powerful
    fight-flight-freeze response is triggered, it can render them unable to engage productively.  To avoid triggering this survival reflex, think carefully about the words you will use in the first ten seconds to convey the purpose of the meeting.  For example, “I’d like to discuss how we can get your best contributions in our team meetings” is a much less threatening statement than “We’re here to fix your poor behaviour in team meetings.” 
  3. Give them a reason to engage:
    It’s a conversation you’re not looking forward to, and neither are they.  How do you keep them engaged in a discussion that might be quite uncomfortable?  The answer is to reveal for them how having this conversation will produce something that they desire and care about – something they will benefit from.  This requires you to have some insight into their needs and motivations.  You then translate that motivational insight into a statement that highlights the payoff of engaging.  For example, if this person cares about delivering outcomes you might say “By talking about it, you can avoid some real risks to completing this project on time and on budget.” 
  4. Ask before advocating:
    I’ve observed that most leaders tell before asking.  They also spend more time advocating their point of view than they do inquiring into other peoples.  This has the unfortunate effect of limiting the other person’s involvement and engagement, producing resistance and reluctance.  This simply makes a tough conversation even more difficult.   If instead you ask before advocating, you activate the psychological
    Law of Reciprocity reported by Robert Cialdini PhD. This states that by listening first to the other person’s point of view, they will then be more willing to listen to yours.  When coaching executives to prepare for tough but important conversations, I encourage them to spend as much time thinking about the questions they could ask, as they do thinking about the points that they want to make. 
  5. Welcome the heat:
    Conflict between perspectives and points of view can create friction, which in turn produces heat as people and their emotions become activated. That heat is unavoidable if you are getting close to revealing the real issues and perspectives, yet many leaders are afraid that the heat will quickly escalate and go nuclear, damaging themselves and their relationships in the process.  This can cause them to withdraw too quickly, submit, and otherwise fail to stand up for themselves. 
    Learning to expect and embrace heat as a necessary condition is a key growth area for leaders who wish to use tough conversations to transform the status quo.  

Whilst there’s no way of guaranteeing a tough conversation will produce only positive outcomes or feelings, you can increase the likelihood of success by thinking carefully about your approach beforehand, and then executing consciously, considerately and courageously.  


Written by Gerard Penna.
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Gerard Penna
Gerard Penna is a leadership advisor and coach to CEOs, boards, billionaires, and senior leaders. He teaches in diverse settings from desert mining camps to hi tech start ups and sky-scraping boardrooms. He is the author of Xtraordinary: The Art and Science of Remarkable Leadership, host of the Xtraordinary Leaders Podcast, and CEO and Founder of Xtraordinary Leaders; a training company deeply committed to lifting the bar on leadership and leadership development.


Gerard Penna is an opinion columnist for the CEOWORLD magazine. Connect with him through LinkedIn. For more information, visit the author’s website.