Holding a tough conversation is arguably a leader’s most difficult and draining responsibility. Many leaders dread these talks … and understandably so. But strange as it may seem, a tough conversation can be the most helpful thing you do for someone.

Done correctly, tough talks are more about caring for someone than being the bearer of bad news. Difficult talks give followers growth, give organizations effectiveness and give leaders credibility.

What a Tough Conversation is Not

A good way to learn how to have a constructive conversation is to first recognize what it is not:

Emotional or a reaction

While emotions can run high in troublesome situations, a corrective meeting must never be held when you are in an emotional state. It should never be held as a knee-jerk reaction. You are the leader. It is your job to communicate in a reasoned and caring manner.

Winning and losing

A successful difficult conversation is not one where you win and the other person loses. It is your responsibility to skillfully communicate. You are there to help the other person win and to bring improved results to the organization.


A difficult talk is never about diminishing a person as a whole—it is only about improving a specific behavior/situation or conveying a bad piece of news.


Leaders who improperly handle situations create “scar tissue” … and cause long-lasting damage to relationships. A certain amount of discomfort will be involved when having a difficult conversation. However, any pain should have a constructive outcome and not create permanent relational scaring. Of course you cannot control a person’s reaction. You may present everything well and still get an unusually bad reaction that causes damage. Your role is to do the best job possible with your part of the conversation.

Steps to Holding a Constructive Difficult Conversation

Okay, now we know what a difficult conversation is not. Here’s how to have one that’s constructive:

1. Start with yourself.

A tough conversation is a dialog that includes two people. It’s tempting to focus only on the person you’re speaking with. However, the correct place to start is with you. Make sure that your thinking and approach is respectful and well intentioned. Have the best interest of the other person and your organization in mind.

Your ability to hold successful conversations literally starts years in advance. A leader sets the stage by caring and encouraging people from day one. People will listen to you if they trust you, view you as competent and know that you have their best interest at heart.

Every time we interact with someone, it changes the balance in our “relational account” with that person. When we have a positive interaction, we make a deposit. Conversely, a withdrawal is made when we have a negative interaction. Good leaders keep ongoing positive account balances. By their nature, tough conversations may require a withdrawal. Starting with a positive balance allows you and the other person to approach a situation with confidence. Tough conversations are more difficult when there is a negative account balance (I will explore this later).

Make sure you’re not part of the problem. Check to see if you have somehow set up the other person for part of their behavior (unclear direction, lack of deadlines, etc.) If this is the case, acknowledge your issues and fix your own deficiencies.

Be willing to do the difficult tasks yourself. In the Old West, neighbors would do almost anything for each other, except shoot someone else’s sick horse. The relationship between the owner and the animal was so special that only the owner could properly do the difficult task. The dynamic is the same for leaders and followers. Leaders should hold the difficult conversations themselves and not delegate this responsibility to others. Relationship demands it.

If you’ve gotten anything at all out of following Christ, if His love has made any difference in your life, if being in a community of the Spirit means anything to you, if you have a heart, if you care—then do me a favor. Agree with each other, love each other, be deep-spirited friends. Don’t push your way to the front; don’t sweet-talk your way to the top. Put yourself aside, and help others get ahead. Don’t be obsessed with getting your own advantage. Forget yourselves long enough to lend a helping hand. (Phil. 2:1-3 MSG)

2. Know what you are going to say.

Be confident that you know exactly what the problem is. Have your facts straight. There are always two sides to every story … make sure you know both. Investigate in advance and gather information from all those involved, including the person with whom you will be having the difficult conversation. Know specifically what information you will present. Be specific about the outcomes you are seeking (start with the end in mind). Anticipate objections/concerns in advance and be prepared with an answer. Show how what you are saying relates to the organization’s broader plan; point to examples from other organizations and other people.

Have supporting documents and facts to which you can refer. For instance, if someone is breaking a policy, reference the policy manual. If someone’s behavior is inappropriate, make sure you have talked to two or three people who witnessed it.

A person should always know that there is good reason for the conversation (and not just your own personal opinion or preference). Make sure you are reasonable and that there is logic to what you say. Difficult conversations don’t always end with the other person seeing things as they should, no matter how correct you may be. They may completely disagree. However, if your position is reasonable and logical, even people who disagree will acknowledge that they can see where you are coming from.

3. Know how you are going to say it.

While the facts you present won’t change, you have flexibility in how you present them. This is when it’s important for you to know the other person. People learn differently. Your mission is to speak to people in their own language. If a person values acceptance, show them how their behavior puts people off. If a person values efficiency, show them how what they are doing makes them less effective. Despite your best efforts, sometimes people may not truly hear what you are saying to them. In this case, be prepared to say it to them again but with a different tact. Practice the conversation in advance if it will make you more comfortable.

Be empathetic. A person on the receiving end of a difficult conversation is just that—a person. They have feelings, aspirations, insecurities, strengths, responsibilities, accomplishments and problems, just like we all do. If they are on your team, they have already proven themselves in many ways (even if they may be in need of serious behavior modification at this time.) If you are genuinely human and empathic, people sense it … and the conversation will be significantly more constructive.

Many times a constructive starting point is to ask, “What’s that all about?” State an observation and ask the question. For example, “You’re generally an even-tempered person, but today you got mad in the meeting. What’s that all about?” This allows a person not only to explain, but to confront themselves. It shows that you are willing to listen. You may also learn new facts or something about the person that will help you better handle the situation.

Leaders carry a big megaphone. People automatically give weight to what leaders have to say. Your tone should be soft but firm. Speak from a position of humility. You are instructing and coaching, not necessarily sending an edict from the top down. Think win-win.

Body language is important. Yours should be open and relaxed. If the other person gets tense and you’re not sure what to do, mirror their body language. For example, if they lean towards you, then you lean into them.

4. Know where you are going to say it.

Be intentional about the location where you will hold a difficult conversation. Sitting behind your desk in a formal office setting is appropriate for corrective human resources issues and terminations. After all it’s business … and business should be done in a business-like setting.

If what you have to say is more informal in nature (performance coaching, for example), you might choose to talk over a coffee or a meal. Depending on the relationship and the issue, you might choose to talk while on a drive, a walk or while fishing or golfing. However, think twice before choosing an informal setting. If people think they’ll get chewed out while golfing, they’ll be reluctant to golf with you in the future. Golfing could inappropriately become synonymous with correction when it should simply be recreation and informal relationship.

Whatever the location, make sure you are out of earshot and sight line of anyone who knows you or the other person. If the conversation might get emotional, make sure there is reasonable privacy for the other person and that you have a box of Kleenex at the ready. Choose a setting that is most conducive and gives the conversation the greatest chance of success.

5. Be direct, be honest.

If you take away any one point from this article, let it be this one—Be direct and be honest. Many times leaders beat around the bush. They subtly suggest that something might be wrong in the hopes of sparing someone’s feelings or because the leader is simply too afraid to be direct. This rarely works. People are smart. They know when there is trouble and when leadership is glossing over a problem. This frustrates everyone and costs you credibility. Remember, your team depends on you as the leader to speak to situations.

If you can’t solve a problem, be honest about it. Let people know that the organization may not have the time or resources to deal with it, but you recognize that there is a problem and you won’t let it go on forever.

People appreciate directness on the interpersonal level as well. While they need your humility and tact when presenting the problem, they also need you to be perfectly straight with them. People need to know clearly when there is a problem and specifically how to fix it. At the core, tough conversations are about you serving the other person and helping them improve. People get this.

Further, people need to honestly know the whole problem, even the parts that are most difficult. There is a temptation when having tough conversations to share some of your concerns, but to hold off on the hardest of topics. This can make everyone feel like a tough conversation was had, but in reality it was left unfinished and less meaningful. If you have four concerns, share all four (not just the easiest three).

In order to be most effective, be direct. The person to whom you are speaking should intuitively understand that you have their best interest at heart. They can use the straightforward information you give them to make better choices and ultimately improve their lives. I know leaders who, after many years, have received letters from people thanking them for their frankness. Difficult conversations are often the pivotal point for someone to turn away from a destructive behavior. They may also cause re-examination, which ultimately results in a person better aligning their gift mix with the right job.

When being direct, you need to have a calm, confident tone of voice and be sure of your facts. You may present information with appropriate prefaces such as “This is what I have seen … or “When I spoke with ______ they shared with me that … ” Prefacing information helps keep the conversation about facts and reduces emotion.

You may have heard “brutal honesty” discussed in leadership circles. In as much as being “brutally honest” allows you to directly communicate all of your concerns—great. However, it is easy to get carried away with the “brutal” part. Good leaders are never brutal to the point of being demeaning or mean spirited. Jesus was perhaps the most brutally honest leader in history (woman at the well, calling out the Pharisees), but his intentions in doing so were always unquestionably grounded in love.

If your situation deals with an extended group of people, make sure that you are equally honest with everyone. Do not omit facts from some or gloss over things for different people. Be consistent. Say the same things to all involved. No surprises.

6. Focus on positives and benefits—like a salesperson.

The best salespeople view their mission as connecting a useful product with a customer who will benefit from it. Salespeople allow others to see possibilities that they normally would not. There is a certain “sales” element to holding a difficult conversation. While the person you’re speaking with may not immediately understand the value of what you are presenting, they will benefit from it in the long run. Cast a vision. Be a sincere cheerleader. Help them see (“sell”) the positives, benefits and the possibilities that come with change.

7. The “Compliment Sandwich.”

The Apostle Paul gives us a good template for tough conversations. His letters were corrective and instructive … written to churches that he started and that had subsequently run into trouble. A typical letter from Paul is structured as follows:

  • Compliment/affirmation
  • Direct discussion of problems/expectations
  • Compliment/affirmation

This compliment-instruction-compliment model is sometimes called a “Compliment Sandwich.” Paul’s style offers us great wisdom. Tough conversations are about correcting behavior or breaking bad news. They are not about diminishing the value of the individual. Affirming people at the beginning and end demonstrates that it is not the person who is being faulted but the behavior. While “two compliments to one correction” worked well for Paul, marriage researcher John Gottman says what is really needed is five positives for every negative. A multi-layered “Dagwood or Club Compliment Sandwich” might be even more effective.

8. Wrapping up the conversation.

Many times people have selective hearing. They may give weight to the affirming aspects of your conversation and block out the difficult. Reemphasize any points you’re not sure the other person correctly heard. Ask if there are any questions (and answer them frankly). After the person leaves, make note of the date, time and details of the conversation for future reference.

You can consider providing a written summary of your major points. This is required when discussing a corrective human resources issue (a formal paper trail protects you and the organization). A written summary is an option when the conversation is less formal. Summaries can be a plus if the person wants to review exactly what you said to them. However, people can also become fixated and legalistic about what was written … so use good judgment. Remember, the goal is changed behavior, not to beat up the person.

Preparing for and holding tough conversations can be exhausting … especially if it’s not something you do regularly. If you feel drained, it’s normal. As with any difficult task, the more experience you have, the less draining such conversations will become.

9. Follow up.

Some leaders unwittingly practice the “leave alone, zap.” Perhaps you’ve worked for a person like this. The leader leaves you alone for long periods of time, and then suddenly “zaps” you with a major problem or concern. When you hear nothing, you assume everything is fine. Then when “zapped,” you are surprised by the size of a problem or how long it had been going on.

A tough conversation can feel like a “zap.” Don’t let too much time go by before following up on your conversation. This can be informal. Follow-ups let the person know you are watching, praising progress and providing additional guidance where necessary.

Overcoming Challenges

When you are new to an organization, sometimes difficult conversations must be held before you have established positive relational account balances with your staff. If this is the case, simply acknowledge the dynamic at the start of the conversation. For example you might say, “I know that I have only been around here a few weeks. I was hired to help the organization reach its goals of ______. Early on here, I sensed that there is a challenge that hasn’t been discussed. As you get to know me, you’ll see that I’m not one to let problems go on without talking about them up-front. That’s why I wanted to speak with you today … ” Don’t be afraid to tackle obvious problems just because you are new to a position. Solving problems early makes it easier for your staff and builds your reputation as a leader who gets things done.

Tough conversations get tougher when you have a negative relationship with the person with whom you are speaking. Perhaps you have worked together for years, but just never clicked. Perhaps you have had past disagreements. Regardless, as the leader you still have the responsibility to hold difficult conversations with this person. Again, the best way to handle this is to acknowledge the dynamic. For example you might say, “You know I respect what you do. Still, you and I may not always see eye-to-eye, but I don’t want that to stop us from having an honest conversation today.”

Another challenge may happen if you are coaching a “specialist.” A specialist is a person who is an expert in a field that you are not. This person may have a hard time accepting guidance from someone who is not equally expert in their field. Yet again the way to handle this is to acknowledge the dynamic. You can say that you are not an expert, but that you have made a legitimate effort to understand the problem. You have read, consulted other experts and have seen the best practices in the field. While you can never “out expert” a specialist, you can do your homework. You can seek out other experts and share their counsel with your specialist. In short, don’t pretend to be an expert when you’re not … but don’t back down from providing the necessary leadership.

In the most extreme circumstances (firing, termination for cause) it is best to sever the relationship quickly and cleanly. Call them into your office and sit behind your desk. This meeting is formal and businesslike. Explain how their actions have left the organization with no choice other than to sever ties. Explain any severance terms you are offering and expectations you have of them going forward. Answer questions they may have about severance procedures. Thank them for the contributions they have made. Respect them as an individual. Don’t get drawn into a heavy conversation. The decision has been made and it is time to move on. If feasible, give them a brief opportunity to say goodbye to coworkers. Be professional and human but stand your ground.

No matter how well you handle a difficult talk from your end, you can’t control how the other person responds. If you think someone is going to be belligerent or threatening, have another person with you (perhaps the human resources person, another department head or maybe your boss). In today’s litigious environment, make sure you have another person with you anytime you handle a termination.

If a brother or sister sins, go and point out the fault, just between the two of you. If they listen to you, you have won them over. But if they will not listen, take one or two others along, so that every matter may be established by the testimony of two or three witnesses. If they still refuse to listen, tell it to the church; and if they refuse to listen even to the church, treat them as you would a pagan or a tax collector. (Matt. 18:15-17 TNIV)

An Easier Way

The easiest tough conversation is the one that never happens. Many times you can avoid difficult talks by making sure people clearly understand what you expect of them. If they slip, you can correct the problem immediately when it’s not a big deal. Make it a practice to keep short accounts. Don’t let little issues pile up and turn into a big problem.

Think of problems as a “pay me now or pay me later” proposition. You can pay a small price now by addressing small problems as they appear. Alternately, you can pay a big price later when all of the small problems have compounded. It’s always better to “pay now.”

The Tough Job of Holding Tough Conversations

I’m not an expert on difficult conversations. Like most people I don’t seek them out. What I share here is simply the result of having held many such conversations because my position required it. Many of those conversations have gone well, with good things happening for the individual and the organization. Some conversations did not go as well as I would have liked, especially those held when I was new to leadership. If you are nervous about having a difficult conversation, that is normal. A lot of people give into fear and simply avoid tough talks. I give you a lot of credit for caring enough to have a constructive difficult conversation.

Give yourself a little room. The conversation may or may not go as you would like. If your heart is in the right place, people know. They may not like what you have to say, but they will appreciate that you said it to them. Everyone wants a caring coach.