How to Manage Difficult Conversations at Work

A manager and worker are modeling appropriate behavior for having difficult conversations at work

Managing an administrative team is a rewarding job. But like anything worthwhile, it also comes with its share of challenges. Having difficult conversations at work is one of the job’s tougher tasks.

Whether an employee’s problem is repeatedly coming in late, missing deadlines, carelessly sending emails to the wrong recipients or even getting a client’s name wrong, managers face a wide variety of demanding situations that may require a difficult conversation. When discussing difficult issues with the employee in question, a good manager knows how to use soft skills such as tact, diplomacy and strong communication techniques.

The ABCs of having difficult conversations at work

The following tips can help make having difficult conversations with administrative professionals less stressful:

  • Clarify the purpose of the conversation. A lack of focus only makes having difficult conversations at work more difficult. Clearly and concisely tell the employee about the issues with his performance. Avoid jargon and confusing acronyms (for example, “Numerous late and defective GST forms and FFR reports”). And stay away from vague statements that could make it difficult for the employee to understand the precise problem (“Your performance undermined our productivity goals”). Be specific.
  • Avoid going off-topic. A clear framework regarding what needs to be discussed prevents a wide-ranging back-and-forth that may veer off-topic without ever adequately addressing the main reason for the meeting. While other issues may need to be discussed at some point, keeping attention on the problem at hand will increase the likelihood of resolving it when having difficult conversations at work.
  • Review your own communication skills. Knowing what you need to say is only half the battle when having difficult conversations. You also need to know how to say it effectively. Before launching the discussion, ask yourself how you intend to convey your main point. Mentally rehearse your words and, if necessary, practice using a tone of voice that comes across more as a straightforward discussion about the issue than a lecture. Watch your body language and look for nonverbal cues from the other side as well.
  • Don’t forget tact is your ally. You want to be clear and straightforward when having difficult conversations, but frame the problem in a diplomatic way rather than in an aggressive manner. This will ensure the meeting doesn’t start off on the wrong foot and lead to an even more difficult conversation.
  • Use active listening techniques. In all cases, don’t leave the employee with only an explanation of the problems with her performance. Provide an equally clear explanation of what it takes to correct the deficiencies. Try to involve the admin in this by asking if she can pinpoint factors contributing to the problem and if any possible remedies come to mind. Listening closely to what she says, process the response with the intention of discerning possible solutions that may not be directly articulated. Having difficult conversations at work will be less stressful when there is an emphasis placed on listening as well as talking.
  • Allot time for a follow-up conversation. It’s not easy for an admin to hear that an aspect of his job performance has become unsatisfactory. Before concluding the meeting, invite the admin to come to you with any additional questions or concerns as he works toward improvement. When appropriate, put an additional meeting on the schedule to review progress and conclude the discussion on an optimistic note.

For more advice on having difficult conversations, check out our primer for building your communication skills as a manager.

Difficult conversations you're likely to have

No matter how skilled a manager you are, you will be forced to have difficult conversations from time to time. It's simply the nature of the job. Here are three scenarios you are likely to face at some point and tips for navigating each conversation:

Difficult conversation #1

An employee has been making sloppy mistakes, such as getting a client’s name wrong or sending out emails to the wrong recipients. In your mind, these are inexcusable errors for someone in an administrative capacity.

Solution #1

Meet with the employee and name the specific mistake or mistakes that prompted your concern. If a client’s name was misspelled, suggest a protocol for checking the spelling of names. If the wrong email was sent, or the wrong people received an email meant for someone else, ask the employee why she thinks that happened.

Help identify steps and procedures to prevent similar errors in the future, such as reviewing the “To” line and the body of the email before hitting Send.

Difficult conversation #2

An administrative professional on your team has been consistently late to work.

Solution #2

After describing the problem, ask if there are specific reasons he is late so often. If he blames public transit, suggest catching an earlier bus or train. If traffic jams are causing delays, suggest leaving earlier or trying a new route. If oversleeping is the problem, ask if adjustments to the sleep schedule are possible.

If he begins drifting into other life issues that aren’t directly related to being late, politely interrupt and ask that the focus remain on the issue at hand. Explain that it is critical for all of your administrative professionals to perform professionally, and that includes punctuality.

Difficult conversation #3

An administrative professional has been missing deadlines on a regular basis.

Solution #3

Once again, name the problem at the outset of the discussion and emphasize the importance of making deadlines. Ask if there are specific issues getting in the way.

If the employee says she does not have adequate time to complete the work, ask yourself how other employees with the same duties are performing. If they are generally on time, tactfully point this out. If he doesn’t seem to know why making deadline is so difficult, suggest that he take notes over the next week or so to help identify where he’s getting bogged down.

In closing, reiterate the importance of making deadlines and schedule a follow-up meeting to gauge progress.

The approach a manager takes in addressing performance issues with an admin plays a critical role in eliminating the problem. Having the necessary soft skills to navigate difficult conversations at work will help everyone involved and contribute to efficient solutions.

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