Before You Counsel: Five Questions a New Supervisor Should Ask

BY GRANT SHEPHERD · OCTOBER 11, 2026

Adapted from The First-Line Supervisor: Leading from the Front and The Difficult Officer: Leading the People Who Test Your Leadership.

Most difficult employee situations eventually arrive at the same place: a conversation the supervisor would rather not have. The subject may be attendance, communication, judgment, productivity, or a pattern of small failures that has finally become impossible to ignore. The quality of that conversation is often decided before the employee enters the office.

1. Was the expectation clear, and did the officer understand it?

Accountability should never begin with discipline. It begins with clear expectations. Before you can fairly hold a deputy accountable, that deputy must understand exactly what success looks like. Surprises destroy trust. Clear expectations build it.

Questions can reveal whether the employee understands the issue. Asking the employee to explain the expectation in their own words is more useful than asking, ’Do you understand?’ Most people will answer yes simply to move the conversation forward. Their explanation shows whether the message actually reached them.

Clarity does not require hostility. The supervisor can state the purpose in plain language: this is the concern, this is why we are meeting, this is the standard, and this is what needs to change. Directness often reduces anxiety because the employee no longer has to guess where the conversation is going.

2. What facts have I verified, and is there a pattern?

Preparation begins by separating what the supervisor knows from what the supervisor feels. Frustration may be justified, but it is not evidence. The supervisor should be able to identify specific behavior, dates or examples when appropriate, the expectation that applied, and the effect the behavior had on the assignment or team.

That preparation protects both people. It keeps the supervisor from unloading months of irritation in one meeting, and it gives the employee something concrete to address. ’You are unreliable’ invites an argument about character. Explaining the documented pattern of unscheduled absences and the assignments that required coverage creates a conversation about behavior.

Before the meeting, I also consider what explanation the employee may reasonably offer. That does not mean preparing a rebuttal to every possibility. It means entering the room willing to learn whether information is missing. A conclusion formed without listening is not accountability; it is performance theater.

Listening has limits. Once the facts are established, an explanation should not become an endless detour away from responsibility. The supervisor must distinguish between context that changes the decision and context that merely makes the employee’s choice easier to understand. Understanding behavior does not automatically excuse it.

3. Did the officer have the training, equipment, and support needed?

New deputies often need repetition before confidence develops. A supervisor can become frustrated when the same question is asked more than once, but frustration is not instruction. If I wanted them to become capable deputies, I had to remain consistent enough for the lessons to take hold.

Remedial training should not be treated as humiliation. When properly used, it is an opportunity to correct a gap in knowledge, judgment, or performance before the problem happens again.

Once I understand someone’s goals, I look for opportunities to help them grow. If report writing needs improvement, I have them review reports with me and explain why one report is stronger than another.

The plan also has to be realistic. A supervisor cannot demand that a quiet employee become charismatic or that an inexperienced rookie instantly demonstrate veteran judgment. Expectations should focus on job behavior: timely completion, appropriate communication, correct use of policy, dependable attendance, and independent decisions within the employee’s level of responsibility.

4. Does the problem call for teaching, clearer direction, or an accountability conversation?

Before labeling anyone as weak, arrogant, slow, or difficult, I had to observe. I had to determine whether a problem came from inexperience, unclear instruction, an old habit, a lack of confidence, or a refusal to meet the standard. Those causes can look similar from a distance, but they require different responses.

Every deputy remains responsible for the same essential performance, but the path toward that performance may differ. One employee needs a direct order. One needs to explain the policy back to the supervisor. One needs a deadline. One needs the supervisor to stop rescuing him. Different coaching is not favoritism when the standard remains consistent. Favoritism changes the expectation based on who the employee is. Leadership changes the method based on what the employee needs to reach the expectation.

One deputy once asked me, “Who has the best pod?” I answered, “It isn't yours.” He wanted to promote, but his daily habits did not match his stated goals. Before an inspection I pointed out deficiencies, yet they remained. During our counseling I told him, “Your words tell me you want to promote. Right now your actions tell me something different.” Then I asked, “If you were the supervisor, would you be okay with one of your deputies leaving work like this?” That conversation changed his approach. He later became deputy of the Quarter, earned Field Training Officer, and pursued supervision. Accountability should produce growth—not simply punishment.

Whenever possible, coach first. Explain the standard, explain why it matters, document the conversation, and give people an opportunity to improve. Discipline exists to correct behavior, not satisfy emotion.

5. What specific improvement will I expect, and when will I follow up?

The employee should leave knowing what improvement looks like. ’Do better’ is not a plan. The supervisor should identify the behavior that must stop, the behavior that must begin, the time frame, the resources available, and what will happen if the pattern continues.

After the meeting, documentation should reflect the conversation rather than exaggerate it. The record should identify the concern, the employee’s significant response, the direction or assistance provided, and the expected follow-up. Loaded descriptions may feel satisfying in the moment and damage the credibility of the record later.

Follow-up is where many coaching efforts fail. The supervisor has the difficult meeting, feels relief that it is over, and waits until the next major problem. Employees need to know whether their effort is producing improvement. A short acknowledgment of progress can reinforce change before the next formal evaluation.

Follow-up must also identify continued failure. If the supervisor repeatedly announces consequences and never acts, the conversation becomes noise. The employee learns that discomfort is temporary and the standard will eventually disappear. Consistency does not require rushing to discipline, but it does require doing what the supervisor said would happen.

Document expectations, coaching, improvement, recognition, and deficiencies. Good documentation tells the complete story and protects the deputy, the supervisor, and the organization.

A difficult conversation should not make the supervisor feel powerful or the employee feel small. It is to place the truth where both people can see it and make the next expectation unmistakable. What happens after that will reveal whether the employee is ready to move forward.

Put the conversation into practice

Prepare the meeting with Before You Counsel an Employee, then use the Difficult Conversation Planner to organize the discussion. For related templates, explore the Conversations and Documentation Pack.

About the author

Grant Shepherd is the pen name of a veteran correctional supervisor with nearly two decades of experience in detention operations, field training, leadership development, and first-line supervision. Having spent years mentoring deputies and developing future leaders, Grant believes leadership is earned through consistency, humility, accountability, and service to others. The Difficult Officer: Leading the People Who Test Your Leadership examines the employees and situations that challenge supervisors to adapt, communicate clearly, and hold people accountable without giving up on their ability to grow.

Sources: Grant Shepherd, The First-Line Supervisor: Leading from the Front (2026), chapters 2, 7, and 9; The Difficult Officer: Leading the People Who Test Your Leadership (2026), chapters 4 and 6.

Editorial disclosure: AI assistance was used to select and arrange passages from the author’s books and format this article. The article body retains the wording of those passages.

Read more leadership articles