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About the AuthorCaela Farren,, Ph.D. is President of MasteryWorks, Inc. - a leading Career Development solution to large to mid-size companies, including Sprint, Lockheed-Martin, and Capitol One. MasteryWorks provides enterprise web portals, training, consulting, and an assessment framework for employees and managers. For more than 30 years, Caela has been a tireless advocate around complex issues redefining the workplace. She envisioned the current climate by more than a decade, when she published the book, “Who is Running Your Career: Creating Stable Work in Unstable Times” (Bard Press, 1997). Through MasteryWorks, she oversees solutions that create the foundation for impact-filled “career conversations” - centered on increased contribution, performance, and fit. Her strategic approach consistently delivers on employee engagement and retention goals for her clients.
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Five Surefire Tips for Great Career Conversations - Without Fear
by Caela Farren, Ph.D., MasteryWorks, Inc.


"The object is to create an honest and authentic dialogue with your employees."
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. As important as ever, these career conversations are becoming more difficult.

    Why more difficult? We are living in tumultuous economic times. Job loss, corporate restructure, and worrisome finances are taking a toll on career plans. Strategies and tactics continue to change rapidly in organizations, which directly affects career options. The workforce is far more diverse – multi-cultural, multi-generational, global, technically diverse, etc. Motivators for working people are necessarily quite different and not readily apparent. 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.

1. Be Prepared - Anticipate Tough Questions    
    There will always be some tough questions employees may throw at you. 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?”

A recent On-Boarding seminar with 500 new employees brought the following questions to the instructors:
  • “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?”

   Be ready. 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 with your employees.

2. Follow a Process – Determine Your Objective    
    There are five critical keys to opening an effective career conversation with an employee. They are the five A’s: Appreciate, Assess, Anticipate, Align, and Accelerate.
  • Appreciate Uniqueness - help employees recognize their unique talents, skills, abilities, personality traits, passion and accomplishments to make career choices that fit.
  • Assess Capabilities – help employees discover their capabilities, build reputation, and assess individual and team performance in order to build strong networks in their industry, organization, profession, job and personal life.
  • Anticipate the Future – help employees consider and anticipate future trends in an industry, organization and profession and how the trends will affect future choices.
  • Align Aspirations – help ensure that individuals see how their aspirations, talent, goals and passion are in “sync” with the mission, goals and strategies of the organization.
  • Accelerate Learning – connect individuals to mentors, projects, and learning opportunities to help achieve their goals and support long-term organization strategies.

Manager's 5 Key Roles
2009 MasteryWorks, Inc.

Five A's Model

3. Ask Questions - Get Personal and Real    
    The best way to get to know an employee (and to help one understand him/herself better) is to ask powerful questions. Appropriate questions will prompt thinking and self-reflection. If you ask the right questions, employees realize that you are prepared. They will also know 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 “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 will appear on the horizon, such asa new project or position or change to another division or profession, etc. that couples uniqueness to opportunity.

4. 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 covering the five A’s are:
  • How am I 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 my capabilties? – 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 my 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 I accelerate my 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?

    Career Maps should define knowledge, skills and abilities within each of the professions in an organization. They will reflect a consensus of opinion regarding the application of all or any part of the nine elements to each profession.

5. 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.

    Use these discussions to appreciate and honor your own career. Each career discussion enables you to evaluate your own career by asking yourself the sampled questions: What are your three greatest strengths? What accomplishments 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?

    Share your own concerns and challenges with employees where appropriate. There’s an organic life to these questions that can open up thoughts about your own future choices. You’ll see how questions provide some nice soul-searching for you and open some doors in thinking about your own abilities and future aspirations. You’ll be surprised to discover where these questions will take you and your employees.

    Never lose sight that your career conversations are aimed at building, motivating and developing employees. Career conversations help open doors for career choices, build trust, and engage people to realize the mission and strategies of your organization. back to top

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