Lorem ipsum dolor sit amet, consectetur adipiscing elit. Vivamus convallis sem tellus, vitae egestas felis vestibule ut.

Error message details.

Reuse Permissions

Request permission to republish or redistribute SHRM content and materials.

Five Sure-Fire Tips for Great Career Conversations

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? 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 affects career options directly. The workforce is far more diverse—multicultural, multigenerational, global, technically diverse.

Motivators for working people are necessarily quite different and not always readily apparent. Employees feel stressed by their workloads and lack of job security, making career conversations more challenging yet far more important. Some managers admit that 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. Anticipate Tough Questions. There will always be some tough questions employees throw out. If managers don’t have immediate answers, postpone answering and suggest revisiting those issues later or try brainstorming answers with the employee. Prepare 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?”

Managers should place themselves in the shoes of their 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 employees.

2. Follow a Process to Determine Objectives. There are five critical keys to opening an effective career conversation with an employee: 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. Help employees consider and anticipate trends in their industry, organization and profession, and how the trends will affect 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.


3. Ask Questions—Get Personal and Real. The best way to get to know an employee (and to help one understand himself or herself better) is to ask powerful questions.

Appropriate questions will prompt thinking and self-reflection. When a manager asks the right questions, employees realize that their manager is prepared. They know that their manager cares, which establishes confidence and trust.

The manager and employee learn new things about one another that will establish a bond of respect and open doors of opportunity. It’s not until one really knows someone that they’re able to give advice as to options and next steps available to help craft a career.

Managers can’t give advice to employees on options if they don’t know the individual’s interests, skills, passion and aspirations. Together, they should thoroughly explore the questions “How am I unique?” and “How is the world of work changing?” Employees’ career choices must be related to the changes that can be predicted in their industry, profession and organization. Once managers and employees see and understand these elements, new goals will appear on the horizon (i.e., a new project, position, or change to another division or profession that couples uniqueness to opportunity).

4. Plan How to Start a Conversation. If a conversation is started thoughtfully and with an objective in mind, managers will be amazed at the conversational journey they’ll have. Examples of starting questions:

How am I unique? When the employee has a really good day at work, what talents and personal traits do they draw on? What are their most important values, and how does work fit in with those values? If they had to choose between working with people, data, things or ideas, which mixture would they choose? What would be their ideal job?

What are my capabilities? What are the critical skills in the employees’ job, and how would they rate themselves? Choose three people who can rate their work; what feedback would they expect from them? What are some ways to get feedback about their reputation at work? Which skills are most and least valued by the team or organization? Which ones do they have?

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

What are my aspirations? What career goals do they have? Which ones are realistic? Which fit into the organization and why? What goal do they want the most? Which goal will position them best for the future? Where do they see themselves in 10 years?

How can I accelerate my learning? How do they learn the best? What would they like to do to increase their skills? What is the perfect learning job? What training or learning program interests them? Who would they like as a mentor, and how can you, as their manager, help them get that support?

5. Tell the Truth—Engage Employees as Partners. If you don’t know the answer to a question, tell the employee the truth. Don’t pretend to know. Don’t make up stuff. Don’t make promises that can’t be kept. Turn a lack of knowledge into a joint exploration and shared experience. Talk about working together to get an answer. Have a discussion in which the two of you can figure out how best to answer difficult questions.

Use these discussions to appreciate and honor your career. Each career discussion enables individuals to evaluate their career by asking themselves the sampled questions:

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

Share concerns and challenges with employees where appropriate. There’s an organic life to these questions that can open up thoughts about future choices and provide some nice soul-searching for both parties and open some doors in thinking about one’s own abilities and future aspirations.

Never lose sight that 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 the organization.

Caela Farren is founder and CEO of MasteryWorks, Inc., a career development solutions firm based in Falls Church, Va.

Adapted with permission from MasteryWorks, Inc. © (2009) MasteryWorks, Inc. All Rights Reserved.


​An organization run by AI is not a futuristic concept. Such technology is already a part of many workplaces and will continue to shape the labor market and HR. Here's how employers and employees can successfully manage generative AI and other AI-powered systems.