I am a hard-working and newly promoted project manager in the Public Works Department of a mid-sized city. Things are pretty dreary in the organization—we’ve experienced budget cuts even lay-offs and everybody feels overwhelmed. Like others, I am dealing with quite a number of projects.

I would like to enroll in a well-regarded certificate program for project management but of course our Director has gutted the training budget in the department. I’m afraid that my manager would not be sympathetic to my request that she find the training dollars and the time off. However, I think the certificate program would strengthen my project management skills and energize me.

I do not have much of a relationship yet with my manager and she seems a bit gruff. How do I create a safe environment so I can propose the certificate program without being thrown out of her office?


To be successful over time, we often must conduct difficult and even courageous conversations with supervisors or peers. Such a difficult conversation may be about a colleague not carrying one’s weight, or a conflict with a peer, or the desire to be given more room to operate by your supervisor. In any case, you need to create some “safety” so you can confront the situation. To have a productive exchange, it needs to be safe for you and for the other person.

To create a safe environment for a difficult conversation, I would suggest a number of related approaches:

1. Demonstrate value

First and foremost, you must demonstrate that you are a reliable and productive team member. As staffing has been reduced, those who perform well and can be counted on to become very valuable commodities. Since you are newly promoted, you need to spend the next 4-6 months showing everyone, especially your manager, that you are a key and valuable staff member who produces tangible results. Of course, as you perform in your assignments and volunteer for new projects, you must ensure that your manager is aware of your efforts and the results produced. (See Career Compass No. 17: The Subtle Art of Promoting Your Value.)

Over time, you should go out of your way to help the manager with her priorities and projects and take problems off her plate. She will be more open to assisting you as you become helpful to her and more indispensable.

2. Create rapport

As you interact with your new manager, you can work to slowly create rapport. To do that, take some time to get to know who she is and what is important to her. Ask questions and listen intently.

To find out something about your manager’s family and non-work- related interests, you can disclose a little bit about your family and/or leisure pursuits and see if that encourages your manager to disclose any of her interests. Don’t give the third degree. Take cues from her about what she is comfortable in discussing.

Over time, you can have conversations not just about work but about some non-work topics which help build rapport and connections.

3. Understand the concerns of your manager

As you develop “positive regard” for your manager, you will identify her concerns. Even if you do not agree with her concerns and issues, you must acknowledge them because they are “real” to your manager. For instance, your manager may feel that a certificate program may cost too much given that training monies have been stripped from the budget; the training program will take you away from work and there is not coverage; and/or there is simply too much work.

Before you can develop responses to the concerns, you must identify and acknowledge them. As Steven Covey said, “seek to understand before being understood.”

4. Confront your fears about the conversation

Many of us do not like confrontations and certainly do not like the feeling of being turned down. So we avoid the conversation.

To minimize the fear, acknowledge it. Your manager may say “no.” The manager may say that you must be aware of the reduced training budget. She may say that you would be further burdening others. She may outright reject your request. Are these the worst consequences that can happen? How likely are the feared consequences? Can you live with any and all of these possibilities? If so, you can proceed.

Everyone is fearful of something. Courageous people confront their fears but still take action.

5. Prepare for the conversation

Preparing for the conversation makes it easier. In your mind, or on paper, you may wish to:

  • Identify your goals, which are hopefully aligned with those of your manager (for example, becoming a more productive and effective project manager);
  • Acknowledge possible concerns of the manager;
  • State the “facts” (see below);
  • Propose specifically what you want;
  • Be prepared to respond to the concerns raised;
  • Develop a back-up or Plan B proposal.

You may wish to practice the conversation with a trusted colleague or coach or friend, especially in respect to keeping the conversation even-toned and responding to any objections.

6. Select a good time and a safe or neutral location

Depending on your manager, it may be helpful to hold a difficult conversation at the beginning of the day (if your manager arrives early) or end of the day (if she stays late). To avoid distractions and create some privacy, it may also be a good idea to invite your manager for a cup of coffee at a nearby café.

7. Use “I” language

To minimize defensiveness from the other party, you should use “I” language:

“I believe. . .”
“I feel. . .”
“I hope. . .”
“I am concerned that. . .”

8. Focus on the “facts”

To help create a safe environment for any difficult conversation, you should start the conversation by identifying some facts or making statements that the other party will not generally dispute. For instance, using “I” language, you could state the following:

  • “I am a new project manager trying to become a better project manager.”
  • “I know that we have less staffing and demands have not diminished.”
  • “I am committed to the team and to helping produce tangible team results even with reduced resources.”
  • “I would like to improve my project management skills in order to enhance my value to the department.”
  • “I believe that the training program would be of value to me and the organization.”
  • “I know that it is difficult for you to manage our constrained resources.”
  • “I believe that you can count on me to maintain my performance even if I were engaged in the training program.”
  • “I have developed an approach so that we can maintain coverage while I am away at the training classes.”

These “fact” statements help set the stage for the rest of the conversation.

9. State directly what you want

You need to put your proposal on the table and directly and non-defensively ask for approval and support. In this case, you may state that you want to free up some monies so that the city pays for the certificate program and that you want work time off so you can participate.

10. Sell the benefits

After stating your proposal, you should quickly identify the benefits from the manager’s point of view. For example, participation in the training program would:

  • Make your more productive and valuable to the department;
  • Keep you energized and excited about your project management role;
  • Allow you to share what you learn with other project managers and team members so everyone can benefit.

11. Inquire about any issues and respond

At this point, you may indicate that you know that the manager may have some concerns and inquire what some of the issues may be. Be open and acknowledge whatever issues are stated. By asking questions, you can demonstrate openness to any perceived issues, again even if you do not agree that the concern is legitimate.

As you propose what you want, you can explain how you may deal with some of the possible concerns, responding to such questions as: From which accounts do you propose to transfer the monies to pay for the training program? Who has agreed to provide more office coverage while you participate in the program? How will you follow up to ensure that you get any information from the meetings missed in your absence?

If you feel that any of these issues cannot be overcome in the mind of the manager, you may wish to provide a Plan B. For example, as an alternative proposal, you may agree to pay half the tuition, or you propose to take the courses on your own time but the city pays the tuition.

12. Show a little vulnerability

In the hope of promoting some openness, you may wish to demonstrate some vulnerability. For example, even though your request may get rejected, you could say: “I am a new project manager and would like to enhance my skills. I need your support.”

13. Don’t force a decision or resolution

If you sense that the manager is not ready to say “yes,” ask her to think about your proposal and suggest that you two can discuss it at a follow-up meeting next week.

Regardless of the difficult topic and the outcome, you should express appreciation that the other person considered what you have said and your interests and concerns. In this case, whatever the manager decides about the certificate program, you should thank her for the consideration and commit in your mind and heart to maintain your sense of excellence. You will have other difficult conversations in the future and you want your manager to remain open and positive whatever you bring to her and about you as a professional and a person.

To be effective, you must confront situations and engage in difficult if not courageous conversations. The question is, how do we create safety for ourselves and others so we can have the conversation?


A good resource is the book by Kerry Patterson et al, Crucial Conversations—Tools for Talking When Stakes Are High.


Career Compass is a monthly column from ICMA focused on career issues for local government professional staff. Dr. Frank Benest is ICMA's senior advisor 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.

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