Blindsided: The Employee Conversations You Should Be Having (But Probably Aren’t)

By: Betsy Hagan

According to a Right Management survey of over 4400 employees and managers in 15 countries, 82 percent of today’s workforce would be more engaged in their work if managers conducted meaningful career conversations with them on a regular basis. And yet that same research found that two-thirds of managers are failing to support their employees’ career development.

So why is having regular and meaningful “What’s next for me?” conversations falling short in terms of a priority for managers?

In Manager Boot Camp, I hear managers often complain of a lack of time, information, and motivation; the fear of losing a great employee; and not being supported by the organization as reasons to put off talking to employees about their career interests and aspirations. While I empathize that managers are often faced with the reality of time constraints and competing priorities, avoiding these critical conversations can have serious repercussions if it becomes the reason your very best people walk out the door. When managers don’t know what an employee aspires to be or how they feel about future employment opportunities, they create a blind spot for their organizations to see potential risk of unplanned employee turnover, something that can be devastating to productivity and the bottom line.

Making time to talk to employees is only the first step. To create meaningful dialogue, a manager must let go of a belief that they must have the answer to the “What’s next for me?” question. Managers don’t own the development of their employees’ careers; employees do. Your job is to facilitate thinking about their career journey. To do that effectively you don’t need answers, but you must know the right questions.

Meaningful career conversations: Stop telling and start asking

Powerful questions can promote reflection, insight, ideas, and sometimes even discomfort in others. Questions keep the conversation focused on the employee and reinforce employee ownership of career development. Effective questions demonstrate that you respect and value the other person. So, when I am engaged in a career conversation, I am prepared with questions to consider career opportunities from three different perspectives: how they can contribute to the organization, their strengths and weaknesses, and their interests and passions. Encouraging exploration of “What’s next for me?” through multiple perspectives often gives employees greater insight into what they can achieve.

To help prepare for your next career development conversation I’ve listed below some of the more powerful coaching questions I’ve collected over the years.

Conversation starters:

• What career issues are on your mind today?
• What career decisions do you have to face now?
• What are your plans for future career growth?¹
• Two or three years from now, where would you like to be professionally?²
• What are your goals for the meeting today?
• What would you hope to accomplish in this career development discussion?

Exploring general career aspirations:

• What is important to you in terms of work?
• How are you defining “success”?
• What is the most rewarding part of your job or of jobs you’ve had in the past?
• What are some things you enjoy doing that you are not doing now? What do you NOT like doing?
• What would you like to look back on and say you were most proud of in your career?
• What career goals have you considered?
• What would you do if you knew you wouldn’t fail?¹
• What would be your next goal after you achieve your current one?

Exploring organization alignment:

• Is there something more that you could do that would make a greater contribution to our organization?²
• What big problems do you see in our organization that you would like to help solve?
• Is there a new task or role you could take on that would make better use of your talents?²
• What additional value could you provide? What would it take to “release” this?
• What challenges would you like to face that might help you grow?²

Exploring skills/knowledge/capability

• What careers are best suited to your skills and abilities?¹
• What do other people tell you-you’re good at?
• What do you feel are your key development areas?
• What skills do you feel you need to practice more?
• What progress have you made so far?
• What are your barriers to career success?
• Name three things you do very well? Explain…

Exploring interests and passions at work

• What professional or career-related opportunities are you most excited about pursuing?³
• What brings you joy/energy in your work today?
• What activities in your job have you enjoyed the most and found most interesting? Which have you disliked?⁴
• Considering what motivates you, what is important to you in your next job?⁵
• What are you willing to work hard for?
• What demotivates you at work?
• If you could spend the rest of your life doing the most amazing thing you’ve ever dreamed of, what would you be doing?

Whether you use these or create your own, just remember that powerful questions usually have these characteristics:

They reflect curiosity, not judgment. A powerful question comes from a place of genuine curiosity. Be interested in the employee sitting in front of you and wanting to know their story.

They take time to answer. A powerful question cannot be answered quickly. It requires thoughtful consideration. Give people enough time to think and respond thoughtfully.

They make us accountable to our goals and our priorities. A well-turned question can create clarity around our objectives for the future after which we can identify the root of the obstacles or barriers that may keep us stuck.

¹ Career Coaching Questions – East Central University
²Adapted from Strategic Employee Development Guide, Manager’s Guide
³The Leader-as-Coach: 10 Questions You Need to Ask to Develop Employees
⁴11 Career Development Questions You Need to Ask Your Employees
⁵Career Coaching Competency: Powerful Questioning

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About the Instructor: Betsy Hagan

Betsy is an independent consultant specializing in organizational effectiveness and talent development. Her background includes 15 years of senior leadership experience in corporate Human Resources and Program Management with Hewitt Associates LLC, a $3 billion dollar HR consulting and outsourcing company located in Lincolnshire, Illinois.