Tough Talks – How to Have Difficult Conversations with Employees

by Dr. Tricia Groff

One of my clients, a business owner, reached out to me and said, “How do I tell this person that they need to keep their personal stressors from impacting everyone at work without sounding like a jerk?”

The situations may change, from telling employees they are underperforming to telling them their attitude is alienating everyone around them to telling them they are being fired. (My perennial favorite is how to handle bad breath and body odor).

Leaders across all levels of experience, age and title often feel inept about how to address difficult conversations. They are smart and skilled, and their reluctance often stems from their strengths: kindness, a desire for harmony, and insight into the downstream impact of conversations.

Guidelines that Help

Difficult conversations with employees may never feel easy, but here are some guidelines to make leaders feel less alone as they walk through them.

Waiting makes it worse. The longer leaders wait, the more time, energy and focus they lose worrying about the impending meeting. Everyone knows this at a logical level, but most people rationalize delaying the conversation by waiting for the right time. I always ask myself, “Will I ever want to have this conversation?” and “Will waiting make it better?” Usually, the outcomes of waiting include more stress, a worse situation, an erosion of patience and fewer chances for a positive outcome. 

All conversations should have a goal and a follow-up plan. Whenever I help leaders prepare for a difficult conversation, I ask them what they are trying to achieve. The goal governs the approach, creates clear expectations about outcomes, and provides a path for follow-up. The follow-up plan needs to include the timeframe and what action items will be reviewed. Follow-up provides emotional safety for employees because they know where they stand.

Time and place matter. Leaders can best help the employee in question and others in the organization by paying attention to the unique variables that govern time and place. For example, Friday afternoons are great times to meet with particularly disruptive employees who may need the weekend to cool down. If an employee has two important meetings, one may want to avoid scheduling a difficult conversation in the middle of them. Coffee or lunch outings are never appropriate for difficult conversations — the social atmosphere lacks privacy and sends mixed messages.

Consult with HR or other trusted advisers. Many initial difficult conversations can happen one on one, with appropriate documentation. In some situations, leaders may want HR present. The upside to having only two people in the room is increased openness and vulnerability. The downside is that it makes the organization legally vulnerable in he said/she said scenarios. 

Small companies without dedicated HR may want to consult with another leader who is stable and trustworthy. This person can also act as a witness if necessary. Single business owner-leaders should document everything and consult with an adviser or attorney as appropriate.

Deal with emotions. Many people try to mask all emotion or hold it in until they explode. When leaders are angry, it can be helpful to vent to someone else first. If leaders are nervous or frustrated, they can let the employee know that the conversation is difficult. I’ve had people tell me first-hand that an employer’s own stress or empathy made difficult conversations easier.

Leaders who are uncomfortable with emotion themselves often have difficulty tolerating it in others. If they rush to make an employee’s emotions go away, they risk coming across as cold, glossing over an issue, divulging too much or making promises they can’t keep. 

There’s power in encouragement. Difficult conversations with well-liked employees can be especially hard. Leaders can honor good employees with a straightforward approach that integrates tough feedback with encouragement. This combination of honest and specific feedback helps employees feel valued and respected. 

Difficult conversations require a leader’s utmost courage. When leaders can step up to the plate, they help their employees grow, protect other people on the team and allow their organizations to thrive.

Pitfalls to Avoid

On the flip side are things I tell people to not do.

Do not ask people to lunch or coffee and fire them.

Do not set a meeting five days ahead. It’s one thing if one-on-ones are regular items. However, if such meetings are not normal occurrences with an employee, they will raise anxiety. By the time the meeting occurs, the heightened anxiety will guarantee that it will be much muddier than it needed to be. 

Do not reprimand people in public (unless you are purposely trying to shame them, and you want them to hate you). Some people have said to me, “I’m so angry, I don’t care.” The problem is that this mindset makes the leader and the company more liable to negative ramifications.  

Tricia Groff, Ph.D., is an executive advisor and executive coach who works with high achievers and their organizations. She is also a licensed psychologist who brings 20 years of behind-the-scenes conversations to her recommendations for workplace wellness and profitability. Dr. Groff is the author of Relational Genius: The High Achiever’s Guide to Soft-Skill Confidence in Leadership and Life.

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