learning and development

What Are Career Conversations + Benefits of Encouraging Them

Explore the essentials of career conversations, their key elements, and how to overcome common obstacles for professional growth.

Kinjal Dagli

Sr. Content Marketing Manager at Together

Published on 

November 20, 2023

Updated on 

Time to Read

mins read time

Nearly 50.5 million Americans quit their jobs in 2022.

That number is higher than the 47.8 million of 2021 and the highest in the last two decades. It means that organizations across industries are struggling with retention, people are quitting in droves, and it is high time managers start having meaningful career conversations with their team.

What is a career conversation?

A career conversation is a strategic dialogue between an employee and another party, typically their manager, about the employee's career goals and aspirations. This discussion is not just about immediate job responsibilities but encompasses broader aspects of the employee's career trajectory, including their strengths, areas for growth, and long-term professional objectives.

  • For professionals and job seekers, these conversations are a crucial tool for navigating career transitions and seeking professional growth.
  • For managers, these discussions are essential for improving motivation and engagement, and for planning employee development.

Career conversations, when done right, foster a supportive and growth-oriented workplace for the management and the employees alike. Here are some benefits of having such conversations:

5 Key elements in a career conversation

Whether you are a manager or team member, understanding the key elements of a career conversation will enable you to have meaningful and productive discussions at your next meeting. Just make sure you focus on the following:

1. Preparation and clarity

Both the employee and manager should come prepared with clear objectives for the conversation.

  • Employees should clearly understand and articulate their career goals, strengths, areas needing improvement, and the kind of support they seek. To prepare, reflect on your career path, gather relevant achievements or feedback, and be ready to discuss these aspects openly.
  • Managers should prepare by understanding the employee's role, performance, and potential growth areas within the organization. Managers should be transparent about the opportunities available and the realistic pathways for career advancement.

2. Open and honest dialogue

The conversation should encourage frank and open discussion about career aspirations, strengths, weaknesses, and opportunities.

  • Employees should be forthright about their career aspirations, concerns, and feedback they’ve received. It is important to express your expectations from the organization and management clearly and constructively.
  • Managers should provide transparent feedback on the employee's performance and potential career paths within the organization. It also means listening actively to the employee's aspirations and concerns, acknowledging limitations where they exist, and discussing possibilities and challenges openly.

3. Goal setting

Identifying specific, actionable career goals is crucial for both employees and managers, because that means both will be working towards the same targets.

  • Employees should define specific, achievable career goals that align with their aspirations and skills. This could include short-term objectives like learning new skills or long-term goals like attaining a particular role.
  • Managers should assist employees in setting realistic and relevant career goals. This involves understanding the employee's ambitions and guiding them to set goals that are aligned with both their personal development and the organization's needs.

Managers must also help employees break down these goals into actionable steps and provide the necessary support to achieve them.

4. Feedback and guidance

The manager should provide constructive feedback and guidance to help the employee navigate their career path.

  • Employees should actively seek feedback on their performance, strengths, areas for improvement, and career progression. It involves asking for specific advice on how to achieve their career goals and being open to constructive criticism.
  • Managers must provide clear, actionable feedback to employees about their current performance and potential career paths. This includes highlighting areas of strength and offering specific advice on areas for improvement.

Managers should also guide employees in understanding the skills and experiences needed to progress in their careers and help them navigate the path to achieving their career goals.

5. Follow-up and action plans

A career conversation should conclude with a clear action plan and follow-up steps to ensure ongoing career development.

  • Employees should take responsibility for implementing the action steps discussed in the conversation. This includes pursuing the agreed-upon goals, acquiring new skills, and seeking additional feedback or support as needed. It also means keeping track of their progress and being proactive about scheduling follow-up discussions.
  • Managers should schedule regular check-ins to monitor the employee's progress towards their goals. It involves providing ongoing support, resources, and adjustments to the action plan as necessary. 

Managers should also hold themselves accountable for facilitating the employee's development and offering continued guidance.

eBook Make The Perfect Match Read our best tips and tricks to effectively pair mentors + Mentees

Common obstacles in conducting career conversations and how to overcome them

By recognizing and addressing challenges like lack of preparation, time constraints, fear of honest feedback, and misaligned expectations, both employees and managers can engage in more meaningful dialogues.

1. Lack of preparation

Lack of preparation leads to unfocused and unproductive discussions. 

Employees sometimes enter these conversations without a clear understanding of their career goals, strengths, and areas where they need improvement. This lack of clarity can make it challenging for them to articulate their aspirations and understand how their goals fit within the broader organizational context.

On the other hand, managers may not be adequately prepared with a thorough understanding of the employee's performance, potential, and the career opportunities available within the organization. This results in providing vague or non-actionable feedback.

To overcome this challenge, it's essential for both parties to prepare thoroughly. 

  • Employees should reflect on their career path, achievements, and areas where they seek growth. They should also consider specific questions or guidance they need from the conversation. 
  • Meanwhile, managers should review the employee's performance history and be aware of potential opportunities or challenges within the organization that could impact the employee's career development.

Setting an agenda for the meeting can also be beneficial, as it ensures that the conversation remains focused and productive. This preparation helps in creating a more meaningful and effective career conversation, where both parties can engage constructively.

2. Time constraints

Time constraints pose a significant challenge in conducting career conversations. 

Both employees and managers often have packed schedules, leading to postponed or rushed conversations that fail to address critical career development aspects. To combat this, it’s crucial to prioritize these discussions as key components of professional development. 

Scheduling dedicated time for career conversations, well in advance, and ensuring that this time is respected and uninterrupted, can greatly enhance their effectiveness. This commitment to setting aside time demonstrates the value placed on career development, encouraging more thoughtful and productive discussions.

3. Fear of honest feedback

The fear of honest feedback is another hurdle in career conversations. 

This fear can stem from employees worrying about receiving negative feedback or managers hesitating to provide constructive criticism that might be perceived unfavorably. Such apprehensions can lead to guarded or superficial conversations, hindering meaningful dialogue about career growth.

To overcome this, it's important to cultivate a workplace culture where honest feedback is valued and seen as a vehicle for growth. Encouraging open and transparent communication, where feedback is delivered constructively and received with an open mind, can transform these conversations into opportunities for professional development. Such conversations also strengthen the trust between employees and managers.

4. Misaligned expectations

Misaligned expectations can significantly hinder the effectiveness of career conversations. This occurs when there’s a discrepancy between what employees envision for their career progression and the opportunities or pathways available within the organization.

Employees may have aspirations that don’t align with current organizational roles or possibilities, while managers might struggle to effectively communicate the realities and constraints of career development within the organization.

To address this, it’s essential for both parties to set clear expectations from the outset. Open dialogue about career goals, organizational opportunities, and potential challenges helps in aligning individual aspirations with what the organization can realistically offer. Such clarity ensures that career conversations are grounded in reality, making them more productive and focused on achievable outcomes.

The role of mentorship in career conversations

People that have mentors are vastly more prepared for having meaningful and impactful career conversations. That’s because mentorship provides a framework for ongoing, developmental dialogue, offering both guidance and support in navigating career paths.

Mentors, with their experience and insight, can offer invaluable perspectives, helping mentees to clarify their career goals, understand industry dynamics, and identify opportunities for growth. They can also provide constructive feedback, develop professional connections, and serve as role models. 

This relationship enhances career conversations by adding depth and continuity, ensuring they are not isolated events but part of a sustained effort towards professional development and success. For both mentors and mentees, this relationship enriches the career development process, making it more holistic and effective.

Speaking of mentor-mentee relationships, Together provides a structured yet flexible environment for these crucial discussions. Whether you're looking to mentor others or seeking guidance for your own career path, Together can help you navigate these conversations with ease. 

Book a demo to explore the platform today

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