I’m a new supervisor in a county parks department. I was a team member before I was promoted, and I now supervise my team.

I enjoy my new position and am learning a lot. However, I am having several problems making the shift from peer to supervisor. I was friends with many of my peers and generally had good relationships with my team members. Now I’m the boss. I want to be liked, but I feel the need to assert my authority.

I’m getting to the point of having a difficult conversation with a direct report who is not meeting my performance expectations. Another direct report who has longer tenure than me seems to challenge my ideas in staff meetings on a regular basis. 

How do I conduct these difficult conversations, so I don’t ruin relationships?

It is a rough transition from peer to supervisor. Supervising others requires a shift in mindset and behavior. The more conscious you are about the shifts, the less difficulty you will experience in making the shifts. As a supervisor, you now operate in a different world requiring different attitudes and behaviors.

Shifts in Mindset and Behavior

Here are some of the common shifts:

Before    After
Peer Supervisor
Team member Team leader
Self-centered  Other-centered
My picture  Bigger picture
Individual contribution Team contribution
My responsibility   Our responsibility
Do work Do work + work through others






Typical Situations That Require a Difficult Conversation and Action         

There are many rewards and joys moving up to a supervisor or manager position. However, there are some challenges as well. Given your new responsibilities as supervisor, one challenge is confronting certain situations requiring correction. 

Having difficult conversations with subordinates is now part of your job description. Typical situations requiring such conversations include those with team members who

  • Are not performing as required (for instance, their work is messy, late and/or incomplete).
  • Arrive late to work or leave early.
  • Constantly question your authority, approaches, or ideas but don’t provide their ideas or proposed solutions.
  • Do not contribute to team discussions or are actively disengaged.
  • Regularly create tension or conflict with other team members.
Since anticipating a difficult conversation causes us anxiety, stress, and trepidation, the usual default behavior is to avoid the difficult conversation. Avoiding the conversation usually allows the negative behavior to continue, which impacts other team members and you.

Overcoming Our Fears

There are many rewards and joys moving up to a supervisor or manager position. However, there are some challenges as well. Given your new responsibilities as supervisor, one challenge is confronting certain situations requiring correction. 

  • You won’t be liked.
  • More conflict will arise.
  • You or the employee will get emotional and you won’t know how to handle the emotions.
  • The employee will turn others on the team against you.
  • You won’t be competent in successfully conducting the conversation.

Everyone has fears. Courageous people confront their fears, challenge the fears, and then act anyway. (See Career Compass #58--“Overcoming Deep-Seated Fears.”)

You overcome fears by acknowledging them and then asking yourself: How likely is my worst fear? Can I handle it? If I do nothing, what is the outcome or the cost to the team, or the organization or the people we serve?

For instance, if you fear that you will no longer be liked, you may conclude that respect as a supervisor is more important than being liked.

In terms of fearing an escalation of the conflict, it is often the case that avoiding the conflicts enables the negative behavior to continue and usually get worse.

With respect to people getting “emotional,” you can ask questions and model behaviors to help the conversation be productive. See the tips below.

If you deal with the poor behavior, others on the team will appreciate it. They will respect that you took action.

Choosing the Problem

In the scenario described below, a former peer and now a subordinate is questioning every idea you propose as a new supervisor. You fear that the staff person is undercutting your authority as a supervisor.

As a supervisor, you have two possible problems. If you act and conduct the difficult conversation, you may be disliked by the employee. If you don’t act, the nay-saying and opposition will continue and get worse, threatening your authority as a supervisor, promoting disengagement among others, and generally undercutting the team.

Which problem do you choose? You can’t avoid a problem.

Deciding What Matters Most

Another way of deciding how to deal with an oppositional employee is to decide what matters to you the most.

First, ask yourself what matters: I want to be liked or I want to develop a great, highly functioning team.

Second, ask yourself “how can I . . .?”  For example, “How can I effectively confront the nay-saying employee so he doesn’t undercut my authority as a supervisor and my ideas and solutions to enhance team effectiveness?”

What matters most to you? Being liked or being effective as a team leader? (See David Dye’s post “Do You Struggle to Manage Your Emotions? You Are Not Alone” in the Winning Well blog, Dec. 8, 2018.)

Getting Ready for the Conversation

For any important task, you must prepare. You are ready for the difficult conversation if you are:

  • Certain that standards and expectations are understood by the employee.
  • Compassionate and have considered what may be happening or motivating another person.
  • More focused on the future than the past.
  • Willing to listen, reflect, and explore what the other person is experiencing and are open to the possibility that you could be wrong about your perceptions or conclusions.
  • Prepared to work with another person moving forward.
  • Clear about the issue and what you want. Ask yourself:
    • What is the specific behavior that concerns you or the team?
    • What is the impact on the team, you or others?
    • What is the cost of doing nothing?
    • What is the desired outcome?
    • What are non-negotiables for you?

Tips for the Conversation

Here are 15 suggestions to facilitate the conversation:

  1. Don’t avoid difficult conversations; confront your fears and act.
  2. Focus on one issue only (save another issue for another conversation).
  3. Be ready for the conversation; select an appropriate place; conduct the conversation when you are not stressed out.
  4. Be present; avoid distractions (close your office door, mute your phone and computer); focus on the other person.
  5. Don’t “ambush” the other person; let the other person know in advance about the one-on-one meeting and the topic so they can anticipate the conversation.
  6. Use open-ended questions to explore what is happening and what can be done (see below for sample questions).
  7. Acknowledge the other person’s perspective (even if you do not agree).
  8. Be calm; manage your emotions.
  9. Be comfortable with silence (since many people are uncomfortable with silence, silence after asking a question often prompts the other person to respond).
  10. Don’t dwell on past problems; be forward-looking.
  11. State your clear expectations going forward.
  12. Support well-intentioned mistakes; if a staff person is trying to do good work, a mistake offers an opportunity to learn.
  13. Explore how you can support the other person.
  14. Leave responsibility with the other person; don’t jump in to solve the problem; let the other person figure it out; ask “how are going to address the problem?”
  15. End with an action item or two and schedule a follow-up meeting.

The goal of the conversation is not only to correct the negative behavior but to conduct the conversation in such a way to preserve the relationship.

Using Powerful Questions

In a difficult conversation, you want to use open-ended questions (not “yes” or “no” type questions) to elicit responses from the other person. 

Here are some powerful questions:

  • I want to understand what is happening from your perspective. Can you help me understand?
  • What happens if you continue with this behavior and don’t take any action? What are the consequences?
  • What would you like to do about this situation? What are some options?
  • What would be the best outcome for you?
  • How can I support you?
  • How will we be accountable to each other?
  • What does success look like for you?

Getting Guidance from a Coach

To correct the negative behavior as well as maintain the relationship, it is a good idea to get guidance and advice from a formal or informal coach. The coach can be your current manager, a former boss, or a trusted colleague inside or outside the organization. Getting advice on how to conduct the difficult conversation will also strengthen your resolve to actually confront the situation.

A Sample Conversation

Let me demonstrate how these tips can be put into action.  Here is a typical situation demanding a conversation:

The Situation:

Tom used to be a peer but now is a subordinate.  He is a long-term employee but did not get the supervisor job that you recently won.  Now, Tom is questioning your ideas and proposed approaches on a regular basis in team meetings.  You feel that Tom is questioning your new role and authority as team leader.  You are trying not to react defensively in staff meetings, but it is becoming increasingly difficult.  Tom’s behavior is causing some team members to feel uncomfortable and you even fear that others may be emboldened to join in and question your authority.

The Conversation:


Tom, thanks for having coffee with me. As I mentioned yesterday, I wanted to meet with you to discuss our interaction in team meetings. You are a long-time county employee, so you have a lot of knowledge about how to do things around here. And I have my own ideas as a new supervisor. My observation is that at staff meetings you frequently question my ideas. For instance, you questioned the way I proposed to handle budget preparation by forming a working group. The staff meeting before that you raised objections to how we should provide office coverage.

I want to encourage all staff to bring forth ideas and solutions, even if they are different from my ideas. However, I sense there is something going on between you and me that contributes to you questioning me in public on a regular basis. How do you see this situation?


I’m just trying to tell you when things won’t work out, that’s all.


(Pause.) I understand that you have a lot of institutional knowledge and have ideas about what will or won't work. I would like to understand your perspective about this friction we seem to be having. Is it because we were previously peers on the same team and now I’m your supervisor?


You are relatively new, but I’ve been here a long time. And I know what will work and what won’t.


How do you think I have reacted, and other staff members have reacted, to your fairly frequent objections in our staff meetings?


I don’t know.


(Pause.) The way I react to frequent objections to my proposed solutions is that I perceive you as questioning my role and authority as a supervisor. I sense that it may also cause others to feel uncomfortable.


I don’t see a problem.


As your supervisor, I can tell you that I feel there is a problem. I have also had several staff members come to me and indicate that our apparent friction makes them uncomfortable. So, there is a problem that we need to address. Going forward, how could you contribute yet not appear that you are opposing me on a lot of issues? What’s one suggestion that you could offer?


I don’t know. What do you think?


You must have one idea. (Silence.)


Well, I could try to suggest another approach or idea instead of saying that your idea won’t work.


Yes, that is a good approach for sharing your institutional knowledge.

What else might work? (Silence.) May I suggest another option?




One possibility is that you pick your spots and only object in public to proposed solutions that are especially important to you or to the team. (Pause.)


Well, I could do that.


Do you have another option when you disagree with my approach in a staff meeting?


I guess that I could bring it up to you in private.


Yes. I know that sometimes I may be off base, and I would thankful for your feedback in private.

I appreciate your openness to consider different approaches. Going forward, which options feel best to you?


Well, I’d be willing to offer another idea instead of an objection. And if I really object to something, I’ll bring it up at a one-to-one meeting in private.


Good. How can I help or be of support?


If I come off as too strong, you could let me know in private.


That makes sense. 

Moving forward, let’s talk about what “success” looks like for each of us. For me, success would be that my role and authority as supervisor are respected and that all team members contribute their good ideas as we try to address the problems that we face.

Tom, how about you? What does success look like?


I want you to respect my knowledge of how this place works and the opportunity to share my ideas.


Okay. We will both support each other to be successful.

Let’s both monitor our interaction and see how we’re doing. Let’s talk at our next one-to-one meeting.



Debriefing the Conversation

In this conversation with Tom, I used some of the tips above. For example, I

  • Let Tom know in advance that I wanted to have a conversation about our interaction in team meetings.
  • Made an observation and asked Tom for feedback.
  • Provided a few specific examples.
  • Asked open-ended questions.
  • Used silence to prompt a response from Tom.
  • Acknowledged Tom’s perspectives.
  • Asserted that there was in fact a problem.
  • Asked Tom for options.
  • Focused on the future.
  • Asked how I as the supervisor can help.
  • Identified the follow-up.

Practicing and Improving

Effectively conducting difficult conversations is like any other activity. With practice, you get better at it. So, the process is to:

  • Prepare for conversation.
  • Do it.
  • Debrief with yourself or a trusted coach or colleague (What went well? What did not go so well? How can I improve the conversation next time?)
  • Practice another conversation.
  • Debrief again.

The Joys of Formal Leadership

As you make the shift from peer to supervisor, you take on more responsibility. And periodically you will need to have difficult conversations with subordinates.

While some conversations in your new role may be difficult, the upside to taking on a formal leadership role is great. The role of supervisor provides a tremendous opportunity to

  • Build a better team and enhance the group’s performance.
  • Develop others.
  • Develop yourself.
  • Improve the lives of staff and service recipients.

I have been blessed with the opportunity to lead. You will be blessed, too.


What are the difficult conversations that you need to have with others? 

What is your biggest fear? 

To conduct the conversation, what are one or two tips that you can use?

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frankbenest80pxSponsored by the ICMA Coaching Program, Career Compass is a monthly column from ICMA focused on career issues for local government professional staff. Dr. Frank Benest is ICMA's liaison for Next Generation Initiatives and resides in Palo Alto, California. If you have a career question you would like addressed in a future Career Compass, e-mail careers@icma.org or contact Frank directly at frank@frankbenest.com. Read past columns at icma.org/careercompass.