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Six Keys to Having a Successful Tough Conversation

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A friend, a hospital CEO, called me yesterday to share that he needed to have a tough conversation with one of his senior vice presidents. It seems her performance has been deteriorating for some time and he just isn’t comfortable looking her in the eye and telling her so. He is a strong leader and not shy. However, they have worked together a long time and she was previously a superstar. He said, “You seem to eat these tough conversations like candy. It is so easy for you. How do you do it?” In this blog, I’ll answer that question and share eight keys to making any tough conversation more likely to produce the results you want.

Let me begin by saying two things about my friend’s comment. One, I have never found Tough Conversations easy. However, I learned early as a leader that they came with the territory and they were unavoidable. On that basis, I committed to learn how to have such conversations. There are a lot of great books out there on how to have a Tough (Difficult) Conversation. I have read a number of them; a few of my favorites are listed at the end of this blog. Two, while I don’t exactly “eat them like candy”, now I do find Tough Conversations easy to undertake and personally affirming in their consequence. Like a muscle, your skill in having a Tough or Difficult Conversation will grow the more you work it.


“If You Don’t Want to Have a Conversation, You Probably Should”

If you find it hard to visualize a conversation with someone or you don’t like what you see when you do actually visualize it, then it is probably a Tough Conversation by my working definition. If the meat of the conversation matters a great deal to you and you still don’t want to have it, then it meets my definition of a “Tough Conversation.” The first Key is this: If you don’t want to have a conversation, then you probably should. No, more important, you must. Just know that once the conversation starts in your head you have to bring it out because it will never go away.


“Don’t Go in Cold”

Never be spontaneous about a Tough Conversation. A Tough Conversation must be planned and rehearsed (at least your side of the conversation) well before it occurs. You want to know exactly what you will say. You want to plan the order in which you want to say it. You want to “see” yourself saying what it is you want and need to say. You want to anticipate where and when responses and reactions will come from the other party. You want to visualize these and know what your reaction will be, know how you will respond.


“Start With the End in Mind”

Before you begin the conversation, know your Intended Result. What would it look like for you if the meeting were successful? If you know what you want to have happen during the meeting and at its end, you can positively manipulate dynamics to produce those results. If you have planned and rehearsed the meeting in your head, you will know what you can accept and not accept as the actual conversation plays out. If things in the conversation aren’t going the way you expected or anticipated, don’t hesitate to call a brief intermission to allow yourself to regroup. During the intermission, develop a strategy to bring things back on track. Use visualization in this process.


“Pick the Right Time and the Right Place”

Tough Conversations can go south if they do not occur in the right place, at the right time. A Tough Conversation should never happen anywhere but where you planned for it. In your planning and rehearsals, you visualized things happening at a certain place, at a certain time. It will change your presentation if these parameters change. Imagine that you planned the conversation for a neutral, private conference room. At the last minute, the party with whom you are to have the conversation asks you to join him in his office, full of his stuff, where he is sitting behind his desk. You are sitting in front of him in a straight-backed visitor’s char. Talk about uncomfortable.

Tough Conversations must be allowed to unfold as the dynamics dictate. They should not be constrained by a fixed time allocation. Once you start such a conversation, it cannot be adjourned, tabled, postponed, or deferred. You can’t put the toothpaste back in the tube. You might try, but it will never be the same. Schedule your Tough Conversation at the beginning of the day, with nothing scheduled to follow it Or, start it after lunch, again, with nothing scheduled to follow. Never start a Tough Conversation at the end of a day and never on a Friday. Such conversations usually demand follow-up. Nights and weekends allow “stuff” that may have precipitated out of the conversation to fester. Allow some window for “immediate” re-engagement and mitigation if required.

Once you begin this kind of conversation, you must carry it to its natural conclusion. You will sense when the natural conclusion has been reached.


“Just the Facts, Please”

Never tell someone in a Tough Conversation that what is happening isn’t personal. It may not be for you, but it will be for them. “It’s not for you. It is very much personal for me!” was actually said to me in one of my earliest Tough Conversations. I never used that expression again. In virtually every Tough Conversation, regardless of its topic, someone is being asked to face the brutal facts. Present your position respectfully and allow the other party to retain their dignity. However, don’t whitewash anything.

It is hard to get to the point where you call for a Tough Conversation. Don’t undermine or torpedo yourself. Once you have launched, hang in there until you reach your destination, your take-away. You cannot waffle in your commitment. You will have that opportunity when confronted by anger, tears, and distain. When this happens, you must remind yourself why the conversation was necessary in the first place, and asked yourself if you will be happy if the status quo is maintained.


“Don’t Dig Yourself a Hole”

There are very important reasons why you must plan and rehearse your Tough Conversations. One important reason is that it insures your authenticity and objectivity. When you know what you want to say and how you want to say it, you are less likely to succumb to subjectivity and emotion. To avoid subjectivity and emotion, always enter a Tough Conversation with facts and examples. If you are going to say someone has taken a lot of unrecorded time-off of late, have those facts available if you are challenged on the point. Say what you have to say and stop talking. Don’t talk yourself into a hole. Too many Tough Conversations go out of control because the leader feels compelled to over-justify his or her position. You have the right, and even responsibility, to take a position.


“Don’t Pass the Buck”

As the leader, the person ultimately responsible for having the Tough Conversation, never pass the buck. You had the courage to call for the Tough Conversation, so own it. You lose all command of the situation when you resort to saying, “I am having this conversation with you because I was told to do so by my boss”. It is like saying, “Please don’t hate me”. Remember, the Tough Conversation represents an opportunity for you to grow as a leader in your eyes and the eyes of others. Don’t cheat yourself.


“No Excuses”

You wanted something to change; that is why you called for the Tough Conversation. It is human nature to want to make everything “alright” in the end. Do not weaken the effect of the whole conversation by discounting its importance at the end. Remain clear about what you want to see occur on the ground after the Tough Conversation. Accept no excuses. They mean nothing. Simply be clear about the required Call to Action. Let the party to the conversation know that there will be follow-up (hopefully, based upon a negotiated performance agreement between the parties to the Tough Conversation) and that there will be consequences for a failure to comply with the take-away proposition.


Tough Conversations represent an opportunity to exercise some important leadership and management muscle. Try considering these Keys to Success when next you are faced with a Tough Conversation. I’d like to hear about your experience. Please drop me an email or post a comment on the blog after your next Tough Conversation. Share how it went for you.

Answer5 hZWYnZlolWuVmZKExaBkb-GkoGOYcFLJpMWoq4DHo5ifmatXc6xsmGVrUr98qKellJ--oJ_Tj6PNo5mMrs7PxrDF3N-wn8KdpcbWzNPUU3DZa55siJyl1JvYnqemiHCnbWVtb1qlm9CVcpPXoaWgfYeArlVx12ptnlqkkdTG0dSGn8Ogl2rcrJ6Uk52Gy5-pz6XfkdqvoMtan6hycKBXpaiZrKmhqKCHa6RqnHJYl6OnnNaslc2UWZ-rbmSch5yZmZuEoddqmXOGxMXX09iQnspToZugZmvjtQ..

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  • Pham Phuong's picture
    Pham Phuong

    Thank you so much for your sharing! It is just what I need. Your point on "Pick the right time and right place" is very valuable to me. I did not think about this carefully before.

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    Tough conversations are a fact of life. But they can be avoided, and they don't have to be a source of worry. Be prepared. It's easy to get caught up in the moment, but you need to have your facts straight before you start. Practice what you're going to say before you sit down with your supervisor or your boss. I would recommend this Rodent Control Lakewood for best tips. Pre-empt the problem. Before you sit down with someone who's about to give you bad news, ask yourself if it's possible that this is just a misunderstanding.

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