Any relationship, personal or professional, requires a means to address and resolve difficult or distressing issues. In fact, the ability to address and resolve issues is a good barometer to measure a relationship’s health. An inability to confront issues that are disturbing or hurting anyone in the relationship allows counterproductive patterns to persist, making the issues more pronounced over time.

Difficult conversation

Although we can never make someone change or force them agree with us, we can help to foster positive change in others and ourselves by engaging in constructive dialog. Speaking truth in a non-combative, loving, and kind way fosters growth emotionally, spiritually, intellectually, and relationally. And even if the other person does not respond favorably to our attempt, at least we can rest in the knowledge that we tried and did not merely sit by and wait for change that would probably never otherwise occur.

The key to navigating a difficult conversation is the ability to confront the other person without appearing confrontational. In this post, I offer guidance on how to do just that.

Establish a constructive mind-set for confrontation

Before you approach anyone about an issue that is troubling you, establish a constructive mind-set. I suggest the following:

  • Adopt a positive motivation (a “for” stance); for example, improving the relationship, helping the other person become more successful, optimizing the team’s productivity, or helping yourself do a better job. Be careful of negative motives such as punishment, revenge, or a desire to fix or change the other person.
  • Conduct a self-check by asking yourself the following questions:
    • Is my attitude pure in calling this conversation?
    • Do I have an ulterior motive? Am I secretly blaming and masking it by calling for this conversation?
    • Do I have an inherent desire to be right?
  • Be clear about your objective — the desired outcome.
  • Be present, not distracted, and in tune with the state of the other person’s “present” as well. Be sensitive to cues regarding the other person’s “present” and state of attention as reflected in the person’s eyes, facial expression, nervousness, etc.
  • Be clear on “you” and “I”:
    • Place yourself in a state of empathy, thinking how the person is likely to feel.
    • Speak from your need, not the other person’s; for example, “I need the workplace gossip to stop,” versus, “I need you to stop gossiping.”
    • Be humble, not looking to be “right.”
    • Be clear about the problem you are trying to solve or the issue that is troubling you.
  • Select one issue. Confrontation is not a clearinghouse for multiple issues. The conversation should be short. Remember to put yourself in the shoes of the other party; if too many issues are presented at once, the other party will be overwhelmed, and the key issue will be lost or diluted. For example, a direct report could have many issues: tardiness, slovenly dress, lack of contribution in team meetings. Start with the most disturbing issue and see how the person responds after the conversation.
  • Keep in mind that you can control only yourself and your choices; you cannot control anyone else, what they choose to say, or how they choose to behave. Perhaps more importantly, know that nobody can control you, either.

Take the 9 steps to navigating a difficult conversation

As a certified role-play coach, I have the unique privilege of rehearsing challenging conversations with executives before they happen with their direct reports, members of their board, colleagues and peers, or a family member.

This role-play allows an opportunity to role reverse with the executive. I take the role of the executive, while the executive plays the employee, board member, friend, or family member. During this role-play exercise, I model the following nine-step approach to navigating a difficult conversation, steps that I use in both my personal and professional life:

  1. Express your need to talk or meet with the other person; for example, you might say something like “Charles, I want to talk about something that will help me do a better job.” Avoid initiating the conversation with “We need to talk,” which often induces fear; it’s the equivalent of being called down to the principal’s office.
  2. Soften the conversation by expressing your “for” stance. For example, in a personal encounter, you may say something like “I just want you to know that I believe in us.” I call this “sandwiching the conversation with praise” which is repeated in Step 8. The “for” stance prevents the other person from flipping into panic mode. If you immediately state the problem or begin with negative feedback (criticism), the other person is more likely to take a defensive position and be less receptive to what you have to say.
  3. State the problem in terms of performance, attitude, or relationship, as the problem is bound to fit into one of these three categories.
  4. Express ownership of anything you have done that may have contributed to the problem, situation, or circumstances. If you are at fault in any way, admit it.
  5. Listen to and hear the other person’s side of the story, without letting the other party hijack the conversation. If this should occur, let the person speak for a minute, express empathy, and then redirect the person back to the issue at hand. For example, you may say, “Let’s address your other concern at a different time,” then point out the specific purpose for which you called this meeting.
  6. State your request, being specific about what you need — the desired outcome.
  7. If necessary, describe the consequences that will result if the desired outcome is not achieved.
  8. Reiterate your “for” stance. (This is the other half of the praise sandwich.)
  9. Check back within a day, depending on the party involved and the situation. (For example, when my sons were younger, it was always best if I did not wait too long to glean their reflections on our conversation and to remind them of the consequences should I not see change.)

Lead with grace and follow with truth

Grace neutralizes the conversation. When I lead with grace, I can see the change in the other person; as the fear and defensiveness dissipate, the person’s facial expression and body stance relax.

I once began a difficult conversation with a business partner of mine and though I was cognizant of giving the person grace and praise at the onset of the conversation, I jumped into the truth of the issue too rapidly and lost all grace. It then felt like two entirely different conversations.

Difficult Discussion

More importantly, the person began to cry about a totally unrelated set of serious issues in their life; I put the entire conversation on the back burner so that we could focus on their more pressing matters.

Later, after the person had addressed the more pressing issues in their life, we were able to converse more openly about the issue that needed to be resolved.

Pro Tip: When I coach executives, my first question to them in any session (after an informal greeting) is one in which I offer them grace — “Do you have any 911’s today?” Emergency, all-encompassing distractions disable a client from focusing on what we need to accomplish, and client “agendas” always take precedence over mine. A pattern of 911’s on a regular basis, of course, needs to be addressed.

Tips for navigating a difficult conversation

The nine steps as outlined above provide an effective structure for navigating a difficult conversation — but during the conversation itself, knowing what to say and how to say it improves the outcome significantly. The following tips can help you keep the conversation on track while making the other person more receptive to what you have to say:

  • Be ready for a difficult conversation by dealing with your own “stuff” first. Taking ownership for your contribution helps to alleviate any fear and reluctance you may be feeling to confronting the other party. Alwaysapologize first if you are a part of the issue.
  • State your feelings and encourage the other person to state how he or she feels. For example, you may say something like, “When you do X, I feel Y.”
  • If the discussion ventures off course, empathize-and-return to get it back on track. If the other person attempts to change the topic, say something like, “It seems every time I bring up XYZ, you divert or blame,” and then ask, “Why?”
  • Don’t use phrases like “you should” or “you must” — no one likes to be “should” on. Instead, try saying something like, “From my experience . . . .” or “I’ve learned that . . . .”
  • Listen proactively, so that you hear and understand what the other person is saying. Ask questions until you fully understand.
  • Preserve the other person’s dignity, choice, and freedom.
  • Remember that the past, present, and future are unique:
    • The past focuses on forgiveness.
    • The present focuses on reconciliation.
    • The future focuses on trust.
  • Call attention to the effects of the other person’s choices to make them aware of these effects. Any buy-in the other person has to change is proportionate to the extent that person is aware of the effects of his or her choices.
  • In very difficult conversations (for example, infidelity, addiction, abuse), agree with the other person upon a course of action, which is essential in these situations.
  • Anticipate a “no” and be clear about any consequences, if necessary.
  • Stay in control of yourself at all cost; never let your emotions get the better of you. When you lose control of the conversation, the other person wins, and nothing is accomplished. If the other person knows, from past encounters, how to “push your buttons,” be especially careful to control your emotions.
  • For certain conversations, such as sensitive conversations with an employee of a different gender, consider including a third party, either as another participant in the conversation or as an observer.

Tips for handling workplace confrontations, specifically

Leadership research, management theory, and everything that has ever been studied about how good work environments operate highlight two key areas: tasks and relationships. Work has to do with getting the job done (tasks), which requires getting along well with the people who are performing the tasks (relationships). Both areas depend on good confrontational skills. To get a job done, we have to “face” things; to get along well, we must “face” one another.

In the work environment, everyone is serving, sacrificing, trying to please, and establishing friendships among team members, so you can expect to experience emotionally trying times. On the best teams, when differences become problematic, team members confront each other and resolve their differences with little, if any drama or bad feelings. However, people are often afraid to confront others; regardless of whether the other person is a superior or subordinate, the resulting conflict-avoidance is usually more of a personal than a work issue.

To facilitate productive confrontation, consider one or more of the following tips:

  • Discover the truth (reality). Find out what policies, if any, are already in place for dealing with the current situation.
  • Conduct a meeting specifically to discuss how issues should be addressed within the organization or team. Ask members, “How do you want us to talk about things when an issue arises between us?” A good team addresses the process and the way they work together. They have a plan and they talk about it.
  • Encourage and reward positive and negative feedback, both of which are good.
  • Show appreciation for the way others take negative feedback.
  • When change is needed, sit down and focus when giving feedback to others. Don’t give feedback on the fly.
  • Address each problem in the most effective way possible — for example, through confrontation, training, or coaching.
  • With non-compliance situations, involve other managers and supervisors, including someone from your Human Resources or Talent Management Dept., if necessary.

Keep in mind that avoiding confrontation does nobody any good. Avoidance enables the problem to continue and contributes to the resulting guilt. Confrontation is not only beneficial but essential in both your professional and personal lives, assuming you handle it properly. My hope is that this brief primer will enable you to confront others in ways that lead to more positive outcomes.

Interested in diving deeper into the science and methodology behind having difficult conversations? While there are many fine books on the topic, I recommend How to Have That Difficult Conversation: Gaining the Skills for Honest and Meaningful Communication (2015) by Henry Cloud and John Townsend.


About the Author: Jan Moorad, a former Deloitte management consultant and Major League Baseball team partner, is a Newport Beach, Calif.-based executive coach who helps C-Suite executives and their spouses pursue and achieve personal and professional fulfillment.