An Easier Way to Have a Tough Conversation

September 28, 2018      By Kate Bischoff

managers tough conversationsFrom time to time, we invite guest contributors to provide their personal perspectives about trending HCM topics. The views, opinions, and comments expressed below are solely those of the author and do not represent Ultimate Software. This post was commissioned by Ultimate Software and the author has or will receive compensation for their work.

Managers are often in tough spots. They are required to complete projects while managing their people well. Because people are people, complete with mistakes, errors, and sometimes even naivety, employees can put managers in situations where difficult conversations have to occur. Whether it’s someone isn’t doing her job, creating problems for coworkers or customers, or not even showing up for work, these difficult conversations can cause our overworked managers anxiety. In fact, a recent Harvard Business Review article found that two-thirds of managers are uncomfortable with these conversations due to the anxiety of how the employee will react. We, in HR, can do something about that.

We can equip managers with both support and a checklist. The support means coaching them through prep work for the chat. Offer advice on what to say and how to say it. Tell them, “You’ve got this” and, “I’m here if you need me.” These words of comfort are important.

As for the checklist, here’s how to help managers prepare for those tough conversations:

  • Plan. Prepare a script. I recommend managers draft an email with some bullet points with the main message or a full script of what they need to convey to the employee. If a manager doesn’t plan, it’s possible that the conversation will veer into uncharted waters and the manager may miss the clear messaging she wanted to discuss.
  • Consult. Consult with HR, another manager, and/or the manager’s manager. Soliciting feedback about misconduct or poor performance can help improve the messaging or alter the manager’s wording to make the message even more clear, less emotional, or less harsh.
  • Take a beat. Yes, performance and discipline should be addressed as soon as possible, but a discussion should not happen in the heat of the moment or in anger. Managers need a beat to breathe, plan, and consult. It’s okay, and even preferred, when the manager’s own emotion could hinder the discussion. Just don’t let the beat last longer than one business day.
  • Schedule. This is a short, in-person meeting—usually less than 15 minutes. There should not be a long list of things the manager needs to cover. Bogging it down with other subjects reduces the importance of the poor performance or discipline part of the discussion, so these issues should be the only topic of conversation, from the manager’s perspective. Plus, if a manager adds other topics, the employee may not remember the most important points.
  • Anticipate. Usually a manager knows if an employee will cry, become defensive, and/or get angry. Ponder this when planning what could happen. Managers should have tissues ready, let HR know they’re having the conversation, or plan to have someone with them if they have concerns about the employee’s reaction. Select this person carefully—s/he should not be a coworker of the employee. It’s best if it’s someone from HR.
  • Prepare for surprise. Sometimes, a manager won’t be able to anticipate how the employee reacts. If the employee starts lodging complaints, the manager needs to know how to refocus the discussion. Managers will need to hear a complaint, but then remind the employee that they’re there to talk about a performance or discipline issue. Managers should report the complaint immediately after the meeting, so HR or upper management can take action.
  • Document. Managers can use their preparation bullet points or script to recap, adding notes on how the meeting actually went. The employee doesn’t have to sign off on the documentation, but should know of the document’s existence.

Tough conversations aren’t what most, if any, managers look forward to in their day-to-day work. However, sometimes they still need to take place. With a little preparation, and even help from HR, we can make tough conversations a bit easier for everyone.


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  1. Avatar Kerry-Ann DP on October 11, 2018 at 12:37 pm

    Great tips! One of the things I would add under Schedule is being mindful of the TIMING of the conversation. Especially if you do not know how the conversation will go, so if you think there is a potential for the conversation to go sideways – then you should schedule it either closer to lunch so that you and the employee involved have the ability to reset; or later in the day.

    • Karina Schultheis Karina Schultheis on October 15, 2018 at 2:01 pm

      That’s a great point Kerry-Ann – timing is everything, as they say. Thank you for sharing!

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