How to engage your employees in great career conversations without fear

by Caela Farren, PhD, MasteryWorks, Inc.

Managers inspire, guide and support career development. Career conversations between managers and employees are the single most important factor in building, motivating and developing a highly skilled, professional workforce.

Career conversations are becoming more difficult. Job loss, corporate restructure, and worrisome finances are taking a toll on career plans. Strategies and tactics change rapidly in some organizations, which directly affects career options. The workforce is far more diverse – multicultural, multi-generational, global, technically diverse. Employees feel stressed by their workloads and lack of job security, making career conversations more challenging – yet far more important.

Managers admit they are afraid to have career conversations with employees because they don’t feel confident that they have the answers to their questions any more. Here are four ways to have great career conversations.

Be prepared – anticipate tough questions    
If you don’t have immediate answers, postpone answering and suggest revisiting those issues later or try brainstorming answers with your employee. Prepare yourself for questions such as:

  • Will my job be here tomorrow or in six months?
  • What options do I have to be secure at work?
  • How can I possibly achieve my career goals in this economy?
  • What can I do to recover from mistakes I’ve made and repair my reputation?
  • How can I talk about my accomplishments without sounding arrogant?
  • How do I learn about other options in the organization without turning off my manager?
  • How do I stay current with all the changes in this business? Who do I need to know? What do I need to do?

Place yourself in the shoes of your employees and anticipate their concerns. It’s more important to anticipate the questions than have all the answers. The object is to create an honest and authentic dialogue. 

Ask questions – get personal and real    
The best way to get to know an employee is to ask powerful questions. If you ask the right questions, employees realize that you care, which establishes confidence and trust. Both of you will learn new things about one another that will establish a bond of respect and open doors of opportunity. It’s not until you really know someone that you’re able to give advice as to options and next steps available to help craft a career.

You can’t give advice to employees on options if you don’t know the individual’s interests, skills, passion and aspirations. Together, you should thoroughly explore topics such as ‘how am I unique?’ and ‘how is the world of work changing?’ Employee career choices must be related to the changes that can be predicted in industry, profession and organization. Once you both see and understand these elements, new goals that couple uniqueness to opportunity will appear, such as a new project or position or a change to another division or profession.

Plan how you start a conversation
If you start a conversation thoughtfully and with your objective in mind, you’ll be amazed at the conversational journey you have. Examples of starting questions are:

How are you unique?  When you have a really good day at work, what talents and personal traits do you draw on? What are your most important values and how does your work fit into those values? If you had to choose between working with people, data, things or ideas, which mixture would you choose? What would be your ideal job?

What are your capabilities?  What are the critical skills in your job and how would you rate yourself? Choose three people who can rate your work and what feedback would you expect from them? What are some ways to get feedback for your reputation at work? Which skills are most and least valued by your team or organization? Which ones do they say you have?

How is the world of work changing? How have the changes in the organization affected you? Where are your best opportunities? What are the key issues driving your company? How can you help solve them? What are the major trends in your industry and how will they affect your job? What are the skills you will need in the future?

What are your aspirations? What career goals do you have? Which ones are realistic? Which fit into the organization and why? Which goal do you want the most? Which goal will position you best for the future? Where do you see yourself in ten years?

How can you accelerate your learning?  How do you learn the best? What would you like to do to increase your skills? What is the perfect learning job? What training or learning programs interest you? Who would you like as a mentor and how can I help get you that support?

Tell the truth – engage employee as a partner    
If you don’t know the answer, tell your employee. Tell the truth. Don’t pretend you know. Don’t make up stuff. Don’t make promises you can’t keep. Turn your lack of knowledge into a joint exploration and shared experience. Talk about working together to get an answer. Have a discussion where the two of you can figure out how best to answer difficult questions.

Each career discussion enables you to evaluate your own career. Ask yourself:

  • What are your three greatest strengths? What have you achieved that support these strengths?
  • How would you describe your reputation? Who is important for your reputation?
  • What profession are you in? What level of mastery have you attained? What are your aspirations?
  • What contributions would you like to make this year using your unique strengths and experience? What do you need to learn to make an even greater contribution to the organization? What training do you need to attain in order to broaden your career options? 

A longer version of this article first appeared at