Crucial conversations — about an employee’s performance, professional development or career path — have the potential to become emotional. This is terrain that many executives would prefer to avoid at all costs. After all, feelings can get messy. While many leaders are perfectly comfortable managing multi-million dollar budgets, the thought of handling an employee’s unpleasant emotional reaction can produce enough anxiety to keep such dialogue at bay. But not having these conversations, however difficult, creates a gap in leadership and can significantly impact employee morale, retention and the company’s bottom line.

Avoiding crucial conversations: the ripple effect

The inclination to avoid difficult conversations is a two-way street. Employees and leaders are equally prone to wearing blinders, hoping that the status quo will suffice. And it often does — but at the cost of missed opportunities. Without addressing what’s wrong, what’s missing or what could be better, there is no room for growth. Consider the following examples, illustrating the potential impact of avoiding crucial conversations:

Loss of a Valuable Employee — and Potential Revenue

Imagine firing an employee for showing too much potential. It happens. Probably more often than you think — simply because someone at a high level of leadership wanted to avoid a difficult conversation.

Case in point: Meghan, a bright, ambitious, young professional was hired into a management role at an educational software company on the West Coast. She was brought in to revolutionize a new area, reporting directly to the Chief Operating Officer (COO). A thought leader in her industry, Meghan was exactly what the Chief Executive Officer (CEO) wanted in a new hire. Her job performance was impeccable. Meghan was a model employee, bringing innovative ideas to the table and working hard to make sure her team met — and often exceeded — its goals.

When the COO became threatened by her potential, Meghan found herself out of a job. Rather than engage in a crucial conversation with the COO or create a new vertical for Meghan to manage, the CEO found it easier not to make waves. As a result, the company lost millions of dollars in potential revenue. The good news: Meghan landed on her feet. Within two weeks, she accepted a position with a company that acknowledged her tremendous talents. Her new employer offered her a far more generous salary, a great benefits package, a signing bonus — and equity ownership in the company.

Ineffective Performance Feedback

When an employee has been put on a Performance Improvement Plan (PIP), the goal is to rectify specific job-related performance issues. In many cases, however, the employee’s manager is so averse to having a crucial conversation that the PIP lacks meaning.

Take the case of Kevin. The Human Resources Director placed Kevin on a PIP for his brash treatment of his direct reports. While he was an industry leader, highly respected for his cutting-edge research in the field of green energy innovation, Kevin instilled fear among his team members. Turnover rate in his department was high, and several employees had filed formal complaints against him.

Rather than having the crucial conversation with Kevin about his behavior and what needed to change, the CEO and Human Resources Director handed him a PIP to read through. It contained no clear expectations for his behavior, no measurable goals and no steps to achieve them. Kevin wondered about its sincerity as an “improvement” plan — was it really just a set-up on the way to being fired? Fortunately, as part of his PIP, Kevin was referred for executive coaching services, where we had the crucial conversation his superiors had avoided. By the end of our six-month executive coaching engagement, Kevin was able to achieve remarkable progress, improving communication with his team members and becoming much more effective in his role.

Obstruction of Professional Development

Jill, a copywriter in the marketing department of a large retail chain, didn’t understand why her boss appeared to be avoiding her. It had been over a month since she had approached her boss about a promotion to manager that she was confident she had earned. Behind the scenes, Jill’s boss was withholding valuable information from her. There were no plans to promote her to a management-level position any time soon.

Regardless of Jill’s seniority, other candidates were simply more qualified for the job. While Jill was a good copywriter and loyal employee, her lack of interpersonal skills hindered her management potential. Not wanting to offend or disappoint Jill, her boss found it easier to avoid the discussion altogether. By sidestepping a meaningful conversation, Jill didn’t just miss out on a prospect for career advancement, she also lost an opportunity for professional development. Had her boss initiated an honest conversation with Jill about interpersonal skills, she could have taken steps to improve them. Perhaps her boss could have recommended executive coaching services or suggested books that Jill could have read. Instead, Jill continued blindly in the same position, and her level of trust in her boss faltered. Over time, her frustration grew to the point where it impacted her job performance and she eventually quit. It was a situation in which everyone lost.

Small steps to tackling crucial conversations

In learning how to proficiently handle crucial conversations, it helps to take small steps along the way. The following strategies can point you in the right direction.

  • When you are the one initiating a crucial conversation, take a few moments before you meet with the other person to imagine their thoughts and feelings. Construct a sentence or two that you can use to introduce the conversation in a way that will help them feel recognized and understood. Your empathy will lower the likelihood of a defensive response from the other person. It will also allow them to be more open to hearing and digesting the content of your conversation.
  • During one-on-one meetings with your direct reports, choose one item, no matter how small, to address that will help them improve their performance.
  • Understand how to deliver effective feedback.
  • Breathe throughout the conversation, particularly if you feel yourself being triggered. Watch for signs of stress — e.g., changes in your breathing, tension in your muscles or the need to defend your position — and bring yourself back to a calmer state by taking a deep breath. If you feel like you’ve lost your composure or judgment, thank the other person for their opinion and let them know you’d like some time to reflect on their comments. Before they leave the room, schedule the next time to meet in order to continue the discussion. This ensures that you will not avoid the conversation or disassociate.
  • Stay curious. If you agree or see a point from the other person’s perspective, keep asking questions to understand their point of view more thoroughly. Avoid arguing, defending your position or attacking — even if you feel the impulse to engage.


Executive strategies for addressing crucial conversations

Perhaps the most common reason executives dodge crucial conversations is that they lack the skill set to engage in meaningful discussions about potentially thorny issues. Many factors can lead to your potential discomfort with crucial conversations, including knee-jerk reactions that trace back to childhood. What were your parents’ templates for handling difficult issues — did they avoid or confront them? Working with an executive coach, you can learn to address and overcome the underlying dynamics that make it difficult for you to have these conversations.

Regardless of your past, you have the capacity to hone that skill set by following these steps:

1. Develop an awareness — Own whatever feelings of discomfort you might experience relative to crucial conversations. Face your own emotions. For example, do you fear rejection if you offend someone or offer an opposing viewpoint? Or do you worry that you’ll say the wrong thing and risk looking bad in front of your direct report?

2. Practice — Allow yourself to experience these feelings by moving toward — not away from — the emotions that surface. Instead of holding on to “stories” you may be telling yourself or others (e.g., “It would be in the company’s best interests to terminate this employee” or “If I ignore this problem, it will work itself out in time”), practice being vulnerable by choosing honest, open communication. Take small, manageable steps (see “Small Steps to Tackling Crucial Conversations,” below).

3. Make effective requests — Oftentimes, when discussing an employee’s performance or development opportunities, you make a request of them — to alter their behavior, to complete a task, to enroll in a class. How successfully that request is met depends in large part on how effectively the request was made.


Effective requests are the foundation for working well together because they ensure that both parties understand one another. The 6 elements of an effective request include:
  1. A committed speaker — engaged and specific in their request
  2. A committed listener — attentive and clear in their understanding of the request
  3. Future action/conditions of satisfaction — specific parameters of request
  4. Time frame — expectation of completion/deadline
  5. Mood/tenor — tone
  6. Context — explanation of how the request fits into the big picture

Excerpted from the JMA Accountability Mirror Workshop, a one-day interactive program that teaches individuals, teams and leaders strategies to immediately reach a higher level of performance.

Crucial conversations

4. Encourage — To truly engage in open, honest communication, it must go both ways. Encourage your direct reports to initiate crucial conversations with you. Be amenable to the fact that, at times, they may bring up topics that you might prefer not to discuss, including your performance as a leader.

Crucial conversations don’t have to turn into uncomfortable confrontations. Rather, they should be recognized as a powerful means of aligning perspectives and achieving results.

For more strategies to help you master crucial conversations, we also recommend the book Crucial Conversations: Tools for Talking When Stakes Are High by Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler, highlighted in our article Master Crucial Conversations.

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