How to Have Tough Conversations With Employees

A high-performing, effective staff is often integral to a financial planning firm’s success.

However, we all know not every hire turns out to be the best fit—for the firm or the employee. If you’re a business owner or have management responsibilities, you’ve likely handled an unhappy or underperforming employee situation. When that happens, a properly prepared and honest conversation can effectively bring issues to light, set a course for improvement and clearly communicate the follow-up and stage for future action.

Here are some guidelines for having some of these tough conversations.


Prior to meeting with the employee who is disengaged, unhappy or underperforming, gather specific examples. And be sure to remove your emotions. Look objectively at what is happening and what you want the employee to be able to do differently.

State the Purpose

Start the meeting by stating the purpose. If you did not coach or counsel previously on the matter at hand, open with a statement such as, “We are meeting today to discuss and resolve an issue I have observed regarding [what is happening].” Assure the employee that he or she will have time to share his or her perspective on the situation.

If you have already coached or counseled on the matter, open with a statement such as, “We are meeting today because previously we talked about [the situation]; we agreed to [corrective actions] and I have observed [what the results are currently].”

Be Clear and Specific

When discussing the employee’s behavior, be clear and specific. Describe what you see as the problem, giving some examples of what the employee has done and how it has affected you and other coworkers (these items should be documented). Discuss what should stop, start or change and why.

Be up-front about the situation and don’t downplay, sugar-coat or apologize for having the conversation. Describe your thoughts and feelings using phrases including, “I am concerned/disappointed/frustrated,” and “I feel that …” or “I have observed …” Avoid phrases that increase the employee’s defensiveness such as, “You do or don’t” and “You are …” Keep to the employee’s observed behavior and its effect on the financial planning practice.

Ask for a Response

You can conclude the previous steps by saying, “Now you have a picture of how I see the situation. I need to understand your assessment of the situation. What is your understanding of what has been happening?

Ask the employee what the best way is to resolve the situation. What does he or she need from you? You need to listen for, or ask, if the employee has any facts that would change your assessment of the situation.

Anticipate Possible Responses

If it does not appear it will escalate to a dangerous situation, let the employee vent, then paraphrase your understanding of the employee’s feelings. Determine and acknowledge what has relevance to the situation and what is a diversion.

If there are tears or other emotional displays, simply say, “I see you are upset, and I understand these issues may be difficult to discuss. Do you want to stop for a few minutes?” Most employees will be able to collect themselves and continue. You may have to ask, “Do you want to stop for a few minutes?” several times in the conversation. Do not postpone the meeting because the employee is tearful and emotional unless you think there may be psychological issues and an expert is needed.

If the employee is unwilling to talk about the situation or answer questions, ask open-ended questions to get the employee to open up, or pause until the employee becomes uncomfortable.

If the employee is unwilling to acknowledge the problem, to agree on the fairness of the solution or to resolve the issue, you should document the discussion and schedule a follow-up meeting. The purpose of the follow-up meeting is for the employee to discuss and resolve the situation. This establishes the fairness of the process and an opportunity for the employee to help resolve the issue.

Discuss Specific Consequences

The employee should be told the specific consequences of failing to improve his or her performance. The consequences should be listed in any written document or follow-up letter.

If the situation involves underlying mental or physical issues, you should not attempt to solve them alone; perhaps there is a need for the employee to seek an expert for help. If you think the employee may be under the influence of drugs or alcohol or have mental or emotional problems, get a human resources expert to help you approach these issues.

What to Document

Any discussions (coaching, warnings, written, unwritten) should be documented.

Coaching or Verbal Warnings can have follow-up letters sent to employees outlining the discussions and expectations.

Written Warnings are signed by the employee acknowledging that they have read and understood the contents. At every stage of the written warning(s) process, the document should contain what happens if the issues are not resolved. As an example – “Failure of employee to correct the problem or occurrence of any incidents may result in termination of employment.”

Follow Up and Conclusion

After you and the employee agree on what actions need to be taken to show improvement, schedule regular check-in meetings to gauge progress. At the check-in meetings, determine whether the employee is making progress. Document what has happened since the last check-in meeting. Make your expectations clear.

There should be a clear conclusion to this process. Possible outcomes could be: the employee has improved; you have reassigned the employee to other work, or you have terminated the employee. Never let any outstanding issue “drop off the radar” or be ignored without a resolution.

Giving the Right Support

Give the employee enough time to turn things around. Emphasize that you need the employee to communicate with you on issues that aren’t being resolved or when help is needed. Be sure to give positive feedback and encouragement at the check-in meetings. Make the encouragement relevant to the amount of progress; don’t overdo or ignore.

An unhappy or underperforming employee can often turn the situation around. Sometimes he or she just needs to have an honest conversation about the issue and have clear guidance on expectations along with the support to meet those expectations.

There are times when an employee has disagreed with the action plan, placed blame elsewhere and/or refused to talk about the situation. If the employee has improved to your expectations, then you may need to look at the employee’s attitude going forward and its affect on the team. If the employee has not improved, then you have documented the process, and the stage could be set for possible termination.

This article is for informative purposes only and is not to be construed as legal advice.

Mary Dunlap, CFPÒ, of Mary Dunlap Consulting, helps financial planning firms attract, develop and retain the best people for their teams. She is a member of the Society for Human Resource Management. Contact her at