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How To: Host Difficult Conversations With Success

Difficult discussions are an essential part of life and leadership. They have the power to change behavior, better businesses, and develop leaders. However, difficult discussions are often avoided, and executive coaches can fall into discussion avoidance if they are not careful. How can you harness the power of difficult discussions in your coaching practice? Read on to find out.

The role of an executive coach is to support business leaders in their career goals, business ventures, and leadership development. To do this, business leaders need executive coaches who will help them correct or redirect. As such, executive coaches must be skilled in having difficult discussions because they are the catalyst for change itself.

“When we avoid difficult conversations, we trade short-term discomfort for long-term dysfunction.” - Peter Bromberg

Why we avoid difficult discussions

Fear of conflict

The opportunity for growth that difficult discussions provide is often lost due to a fear of conflict. Executive coaches who are afraid of offending or upsetting their clients are likely to avoid the necessary but difficult discussion (Montilla, 2020). When difficult discussions are not handled with skill, CEOs and business leaders can be offended which leads to unnecessary conflict. Because of this, executive coaches sometimes choose to avoid the potential conflict and avoid the discussion altogether.

Image preservation

Along with a fear of conflict, executive coaches can avoid difficult discussions because they want to ensure they remain “liked and supported” by their clients (Montilla, 2020). When executive coaches bring up difficult conversations with improper techniques, they can potentially damage the image that their clients have of them. For example, if an executive coach asks a question that addresses a current challenge faced by a CEO, but the CEO takes it as an offense, the CEO can lose respect or start to dislike the executive coach. Because of this, executive coaches can refrain from difficult or challenging questions out of a desire to maintain their image.

“You cannot change what you refuse to confront.” - John Spence

Consequences of avoided conversations

Problems grow

When executive coaches avoid difficult conversations, they ignore the challenges faced by their clients. As these challenges and difficulties are ignored, their repercussions grow. For example, consider a CEO with declining profits who has not yet recognized their need to develop a marketing team. If an executive coach does not have the boldness to ask questions such as “what areas in your business do you think could be improved to increase your profit?”, the CEO will likely continue losing profit because they did not realize their need for marketing. The avoidance of difficult discussions can be “detrimental to the overall success” of a client’s company and “professional growth.” (Burke, n.d.).

Loss of professional growth

With every challenging or difficult question, comes an opportunity for understanding and growth. If these questions and conversations are avoided, CEOs and business leaders lose the opportunity to grow in their understanding of their business practice, leadership skills, and career goals. This loss of growth can have a “negative impact” on the business leader and their “business as a whole” (Leader’s Edge, 2019). One of the primary goals of executive coaching is to promote the growth of the business leaders involved. By avoiding difficult conversations, the efforts of executive coaching can ultimately be minimized due to a lack of professional growth.

“We all need people who give us feedback. That’s how we improve.” - Bill Gates

Benefits of difficult discussions

Difficult discussions develop leaders

Feedback can often be the topic of difficult discussions. Unfortunately, it is avoided at times by executive coaches. In the words of Ken Blanchard, “Feedback is the breakfast of champions.” Without difficult discussions that give feedback and support, business leaders and CEOs can “be starved of improvement because” they aren’t given the opportunity to learn through these difficult discussions (Burke, n.d.). Difficult conversations can reveal “blind spots” that executive coaches and their clients can work together to resolve, making business leaders stronger and more successful (Burke, n.d.).

Difficult discussions foster communication skills

When executive coaches lead their clients through difficult discussions they set an example for their clients. Their clients are also given the opportunity to practice having difficult discussions. Having constructive but difficult discussions can help build “empathy,” “perspective-taking,” “insight,” “decision-making skills,” and communications skills for both the client and executive coach (Rothaizer, 2021). As the old saying goes, “practice makes perfect,” and giving business leaders and CEOs the opportunity to engage in difficult conversation can perfect their own ability to communicate through difficult situations.

“Engaging well in difficult conversations is a sign of health in a relationship.” - Douglas Stone

Difficult discussions build trust

Difficult discussions, when done correctly, can build trust between an executive coach and their client (Glaser, 2016). When executive coaches ask questions that can be challenging, from a place of genuine concern and curiosity, their clients learn that their coaches genuinely care about them and aren’t afraid to ask the right questions that push them towards success. The questions that executives ask their clients display their belief in their clients’ ability to have these discussions and develop their businesses further. This development of trust has a ripple effect of positivity across the executive coaching journey.

“Fearing our confrontations is one thing… facing them unarmed is a completely different matter.” - Mark W. Boyer

Facing difficult discussions with success

The benefits of difficult discussions are contingent upon how they are executed by an executive coach. Without the right toolset, these challenging questions and discussions can fall short of developing trust and inspiring growth. Consider the following tips on how to host difficult conversations in a constructive and beneficial manner in your executive coaching sessions.

Face your fears

Before having a difficult discussion, it is important to face your own fears that hold you back from having that conversation (Leader’s Edge, 2019). Acknowledge this fear and “reframe your thinking about difficult conversations” (Montilla, 2020). If you are afraid of conflict, ask yourself why. Do you avoid conflict out of habit, or are you afraid of offending your client? What steps can you take to ensure that offense isn’t taken? By addressing your fears head-on, you can change the way you see difficult discussions and begin to see the benefits of these conversations.

Stay curious

Curiosity is a central characteristic of a skillful executive coach, in fact, it is included in the ICF Core Competencies. Before engaging in a difficult discussion, it is vital that you ensure you are coming from a “place of respect and genuine curiosity” (Montilla, 2020). Difficult discussions are not productive if they are rooted in a desire to be right. Curiosity allows executive coaches to learn more and make even better decisions in how they will guide and coach their clients to success. Curiosity helps coaches get to the root of their clients’ challenges. Curiosity is essential to a successful discussion.

“Be open to every uncomfortable, awkward, difficult conversation you will engage. Disturb the ground to grow. Then adjust the margin of grace.” - Dr. Octavious Bishop

Be kind and compassionate

Because difficult conversations can bring up emotions, it is important for executive coaches to make it a priority to maintain a “positive attitude and a genuine desire” to help their clients and “learn something new” (Montilla, 2020). When executive coaches intentionally set a tone of kindness and compassion, their clients are more likely to trust them and inform them about the challenges they face in their careers and businesses (Schneider, n.d.). This further develops the coaching relationship even beyond the challenging questions and discussions.

Have a plan

Before asking a difficult question or starting a challenging discussion, ask yourself “What are the main topics that need to be addressed?” By doing this, you can plan the “major themes and goals for the conversation” (Schneider, n.d.). You can plan your conversation according to how your client has responded to previous conversations and challenges, further tailoring their coaching experience to their needs (Rothaizer, 2021). Having a basic plan for your discussion can help you guide the conversation in the right direction and reduce your chance of being caught off guard. It can also increase your confidence when entering the conversation.

Be clear

Clarity is essential to the success of a difficult discussion (Glaser, 2016). Clarity eases the conversation by clarifying the purpose and identifying the tone of the conversation. Clarity can be achieved by letting your clients know that although the questions and discussions may be challenging, that “you care about them” and are invested in their career development (Glaser, 2016). Many CEOs and business leaders are likely to feel “shame and embarrassment” when confronted about how they run their business or the decisions that they have made. Being clear about your goals and the tone of the conversation decreases these feelings and allows the client to focus with you on “what can be done to improve their development” (Glaser, 2016). Clarity reduces conflict, enhances conversation, and supports development.

“Sometimes the most important conversations are the most difficult to engage in.” - Jeanne Phillips

Main Takeaway

Difficult discussions and questions, when executed correctly, can have a massive positive impact on the executive coaching process. Unfortunately, many executive coaches avoid these questions and discussions because they wish to avoid conflict and upsetting clients. However, these fears pale in comparison to the massive benefits that clients gain from these conversations. Difficult discussions can help business leaders develop their leadership and communication skills. They can also build trust between the executive coach and client. With the proper tools, executive coaches can ask the necessary but difficult questions and reap the benefits of difficult conversations.

“A person's success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.” - Timothy Ferriss


Burke, K. (n.d.). Why the Tough Conversations Are Always the Best Conversations. Retrieved from

Glaser, J. E. (2016, July 27). 6 ways to manage difficult conversations. Retrieved from

Leader's Edge. (2019, November 26). How Leaders Abdicate Responsibility - Avoiding Difficult Conversations. Retrieved from

Montilla, E. (2020, June 06). Difficult Conversations: Why We Should Stop Avoiding Them? Retrieved from

Rothaizer, J. M. (2021, April 20). Council Post: Dreading A Difficult Conversation? Ask Yourself This Transformational Question. Retrieved from

Schneider, M. (n.d.). Most People Handle Difficult Situations by Ignoring Them -- and the Fallout Isn't Pretty. Retrieved from

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