How to prepare yourself to have a tough conversation at work

We have all been there, a time when we’ve had to have the “tough conversation.” Whether it was breaking it off with a romantic partner or having to tell roommates to pick-up after themselves, the “tough conversation” is, well, tough to have. Despite the challenge of them, tough conversations are crucial and no place are they more important to have than in the work setting. Leaders must be comfortable having the difficult work conversations because when they don’t, they are unwittingly sabotaging the company culture and dismantling trust within the organization.

After all, if low performers are seen as being allowed to coast, high performers will soon grow resentful and, perhaps, stop performing at their highest level as a result. This lowers the bar within the company’s performance culture. Similarly, organizational trust is challenged, too. How can anyone trust a leader that fails to address the tough issues related to managing their teams?

What to do if you’re in need of having a tough conversation at work? Here is the advice that I offer my executive coaching clients. It is a simple four step formula:

  1. Get ready.
    When confronting any challenging situation, it’s best to be prepared. Getting ready for a tough conversation is no different. Spend some time outlining the key messages that you want to convey and try to have a recent example that illustrates the point. For instance, if you’re addressing an attendance problem it may be a good idea to have the recent attendance record in hand before the conversation, so that you can share the specific details with the person whom you’re speaking with.
  2. Set expectations.
    Once the meeting is scheduled and about to begin, it’s essential that you specify the reason for the meeting and the outcome that you’re seeking. This helps the person adopt the proper mindset to hear what you’re about to say and helps that person better understand your expectations. In a sense, this is the “say what you’re about to say” part of the old grammar school writing exercise mantra of “say what you’re about to say, say it and say what you said”. To extend our earlier example about the attendance problem child conversation, you might say at the outset of the meeting that you want to talk to her address her absenteeism in the hopes that it will diminish before more aggressive disciplinary action is required. This kind of messaging sets a tone and defines an expectation — diminishing absenteeism.
  3. Give and take.
    You want to provide some white space for the person with whom you’re having the tough conversation. This enables the person to explain some mitigating circumstances that are effecting the situation that you may not be aware of and, provides an opportunity for you to coach the person, if appropriate. Active listening is what I recommend to my clients. In other words, listen to what’s being said. Repeat what you’ve heard to the person to confirm that you’re understanding their points. Offer feedback based on what they are telling you. If our absentee teammate offers that she is missing work because she is attending to an aging parent’s on-again, off-again illness, for example, we may suggest that she look into options with the HR department that may afford her the time to attend to her parent’s needs.
  4. Summarize main points and discuss future actions.
    Once the points are made and discussed, it’s time to summarize what was covered and outline any actions that have been mutually agreed to. This helps to emphasize key points and agreements that were made during the conversation. For example, as we wrap-up our poor attendance conversation, we may summarize that continued absenteeism is effecting our team’s performance, that it needs to improve and our teammate will seek options through HR to determine what’s right for her.

To sum, having difficult conversations when needed is an essential part of being a strong leader. The cultural impact of avoiding tough conversations is too great to skirt this responsibility. Using the four step approach that I use to help my clients do a better job of having the tough conversations may be your ticket to improving your ability to address challenging conversations at work, too.

This post was originally featured on