6 Tips for Holding a Great Career Conversation

Employees who assume their annual performance review is the only time to raise career development questions could be missing important opportunities to do just that. A yearly discussion is far less likely to advance your career as much as a series of short 1:1 meetings held at monthly intervals with your manager. 

Ideally, managers should initiate career development discussions, but if not, it’s up to the individual employee to arrange such meetings. Asking for career-focused meetings can be intimidating, but most managers are more than willing to coach employees. After all, the greater your skill set, the more use you are to your department and the larger organization. Below are 6 tips to help you get the most out of regular career growth meetings, including a series of 1:1 questions to ask your boss about your about professional development. 

Schedule a Meeting

Career discussions are best held without interruptions and when professional development is the only topic on the agenda; hallway conversations, “water cooler” moments, and similar informal update meetings are not the ideal format for discussing your career. Your first step, then, is to contact your manager and request a career development meeting. Once it’s on your manager’s calendar, it’s more difficult to ignore or forget your request. 

Be aware that your manager’s schedule has to be flexible so he or she can respond to emergencies and unforeseen events. If he or she cancels the meeting, be sure to let him/her know you understand — and immediately suggest a date and time to reschedule.

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Set Your Agenda 

Include an agenda in the meeting request, so your manager understands the topics you want to discuss. This provides a framework for the meeting and demonstrates that you’re proactive. 

Possible topics include:

  • An assessment of your current skills
  • Advice on how to develop your skill set
  • Feedback on your current performance
  • A review of your career goals
  • A better understanding of career opportunities within the organization

Asking the Right Career Development Discussion Questions

Consider which questions to ask your boss about career development before your 1:1 meeting. The questions you ask should be in line with your agenda and prompt candid, insightful discussion.

Possible career development discussion questions include:

  • How can I better serve the needs and objectives of the department and the company?
  • What What knowledge and skills should I develop to help achieve department goals?
  • What is one thing I could be doing 10 percent better?
  • Can you give me one piece of advice to improve my work performance?
  • Are there any upcoming department or team changes that offer an opportunity for me to enhance or add to my skill set?
  • Are there any opportunities for me to take the lead on an upcoming project?
  • Are there any employee/managers you would recommend me to job shadow?
  • Can you suggest someone on the organization who would be willing to mentor me?
  • Can you recommend any extra assignments or training to help further my career goals?
  • What is the growth potential of my current role?
  • How do you see me getting to the next step in my career? 

Limit yourself to a few discussion questions per meeting. The goal isn’t to get all the information you want at once — it’s to create an ongoing career conversation that becomes part of your relationship with your manager.

Understand the Company Landscape

Before initiating a career discussion, familiarize yourself with the company’s current situation and leadership goals. Pushing for career advancement might not be the best course of action if the company is going through a period of slow growth or a financial slump; instead, focus the discussion on the skills you need to better serve the company at its current stage. In doing so, you’re showing a commitment to the company while still honing your abilities.

Learn to read your manager, as well. Some managers are perfectly fine with employees whose career aspiration is the manager’s own position, especially if the manager sees his or her current role as a career stepping stone. Others may find overly ambitious employees threatening — in which case, you can “sell” your career advancement plans as a way to make the manager’s job easier. 

Stay Positive

Career discussions can take unexpected turns. Your request for a frank assessment of your skills may yield unpleasant feedback, or the boss may not see your career goals as realistic. 

Try to remain positive in such cases. Arguing the point with your boss can sabotage future career discussions. Take any feedback and constructive criticism seriously and with the assumption that it’s designed to make you a better employee. Emphasize to your boss that you value your current position and want to be of value to the department. Ask for advice on how to move forward and improve. Sometimes, the most important career advice is that which makes you the least comfortable. 

Recap and Reschedule

Take notes during the meeting, and send your boss a summary of your conversation once it’s over. Review any feedback and create a plan to work on action points that arose from the discussion. Above all, schedule another career development meeting, using the information from the previous meeting to guide your agenda.

Managers tend to favorably perceive on employees who proactively work on career development. Your goal is to keep moving forward, working month-by-month with your manager to secure the skills, training, and experience you need to make your career dreams a reality.

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