The Modern Leader: Building Careers and Teams with Intentional Conversations

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Looking back on the early stages of my career, I see all those annual performance reviews as missed opportunities. The long wait between each review left me in the dark, trying to figure out where I stood. That once-a-year discussion felt like a high-stakes event, which was hardly welcoming or fair. We all seek feedback—it’s the guiding light for our professional growth and development.

However, when feedback time came around, it often zoomed in on the past rather than paving a path to the future. My leader would recount the dos and don’ts of my year, but seldom inquired about my career aspirations or discussed shaping my current role to help me advance. This lack of direction was disheartening, subtly implying that my professional growth wasn’t a priority. I felt stuck, uncertain of my role and worth within the organization.

Career conversations shouldn’t just be a yearly checkpoint. They should be a continuous dialogue that aligns with the ever-evolving nature of both career goals and business needs. Below, are best practices for making these discussions a regular part of your work life. And to wrap things up, there’s a quiz that will let you reflect on how effectively you’re guiding your team—and your own career—forward.

Integrating Career Conversations

In addition to the standard objectives of one-on-one meetings, integrating career conversations is an essential practice for any forward-thinking leader. Career conversations not only boost engagement, retention, and overall job satisfaction but are crucial for understanding your direct report’s aspirations, aligning them with organizational goals, and planning for long-term development.

Below, are best practices for incorporating career conversations into your one-on-one meetings.

Schedule Regular Career-Focused Discussions

Career growth should be an ongoing dialogue, not confined to annual reviews. By dedicating time during regular one-on-ones to career matters, you signal that their long-term development is a priority, ensuring that growth is continuously on the agenda. A cadence of a career conversation depends on what the career aspirations are and what opportunities are currently available, but monthly to at least quarterly is a reasonable frequency.

Link Career Goals with Business Objectives

Begin career conversations by exploring each direct report’s aspirations, interests, and goals. Questions about their vision for the future or areas of work they find most fulfilling can reveal valuable insights. This understanding allows leaders to tailor development opportunities that resonate with both the direct reports’ interests and organizational needs. This alignment helps them see the bigger picture and understand how their growth and development contribute to the organization’s success.

Create Personalized Development Plans

Based on these conversations, work together to create a personalized development plan. This plan should include specific, measurable, achievable, relevant, and time-bound (SMART) goals. Regularly reviewing and updating these plans is essential to keep them relevant and effective.

Provide Growth Opportunities

Offer resources and opportunities aligned with your direct report’s development plan. This could include training programs, mentorship, or stretch assignments that challenge and expand their skillset. For instance, if they show interest in a leadership role, consider assigning them to lead a small project team, providing a safe environment to develop and demonstrate their leadership skills.

Celebrate Milestones and Reassess Goals

Recognize and celebrate (every chance you get) when direct reports reach milestones in their development plans. Positive reinforcement encourages continued growth and shows that you value their efforts. Be ready to recalibrate goals as needed to match evolving interests and business conditions.

Encourage Networking and Professional Development

Encourage your direct reports to network beyond their immediate roles, by attending workshops, conferences, or networking events. These experiences not only contribute to their professional growth but also benefit the organization by bringing in fresh perspectives and ideas.

Questions to prepare for a Career Conversations:

  • Do you have any career goals?
  • What do you love (like) about your work?
  • When do you feel energized and engaged at work (in your flow state)?
  • What do you hate doing?
  • Where do you struggle or procrastinate most?
  • What’s hard for you at work?
  • What do you want to learn/develop?
  • What interests you or where are you curious?
  • Do you feel supported at work? If not, how can I support you more?
  • What motivates you (money, title, free time, interesting projects…)?
  • Do you feel connected to your team?
  • Do you feel you can ask your team members for help?
  • How do you want to receive feedback?
  • How do you describe success in your current role?
  • What do you do that makes you good (at your role)?
  • Does the mission/purpose of your company make you feel your job is important?

Integrating career conversations into your one-on-one meetings is a powerful way to demonstrate your commitment to your team’s personal and professional growth. By understanding individual aspirations, aligning them with business objectives, creating personalized development plans, leveraging resources, celebrating milestones, and encouraging networking, you can help your direct reports navigate their career paths with fulfillment while simultaneously driving your organization forward. Such practices not only nurture talent within your organization but also foster a culture of continuous learning and development.

Want to Deepen Your Understanding? Take These Self-Assessment Quizzes

Leader Self-Assessment: How well are you developing your team?

Evaluate your performance as a leader on a scale from 1 (less than 50% accurate) to 4 (entirely accurate).

I coach my direct reports through a process of self-development by assisting them in:

  1. Recognizing their most proficient skills and areas of expertise.
  2. Identifying the abilities and proficiencies they are most eager to improve.
  3. Understanding and fostering their strengths and areas for growth in ways that preserve and boost their self-esteem.
  4. Gathering feedback from a variety of sources and knowing the questions to ask for precise and impartial feedback.
  5. Learning to proactively manage their professional image and the way others perceive them.
  6. Effectively utilizing the career development tools and resources our organization offers.
  7. Assessing organizational dynamics, as well as challenges and changes that may affect their career goals.
  8. Exploring and assessing opportunities to enrich their current role.
  9. Write realistic career goals with specific and measurable outcomes and timelines.
  10. Identifying specific training and developmental requirements to fulfill their career goals.
  11. Crafting an actionable career strategy and acquiring the necessary resources for its execution.
  12. Executing the necessary actions to create and sustain a supportive network of contacts for their career growth.

Now that you’re identified your biggest opportunities to improve as a leader, what resources do you need to improve? What support do you need?

Your Career Self-Assessment: Your Own Development

Evaluate how you take ownership and manage your own career development on a scale from 1 (less than 50% accurate) to 4 (entirely accurate).

  1. I can articulate the values (personal priorities I need to consider) to feel committed to my job.
  2. I am aware of the work-related activities that I find most enjoyable.
  3. I can respond to the question, “What are your superpowers?”
  4. I have requested that my manager evaluate my strengths and areas for development.
  5. I have solicited honest feedback from colleagues regarding my reputation.
  6. I have asked for input from clients (whether internal or external to the organization) on my performance and how I could better meet their expectations.
  7. I can identify three individuals (excluding my manager) from whom I have sought career advice.
  8. I understand the business challenges and trends facing my organization and can assess their impact on my career opportunities.
  9. I can describe the cultural norms that influence the political landscape within my organization and their implications for career management.
  10. I am knowledgeable about alternative career paths beyond vertical progression.
  11. I have identified activities or projects within my current role that would enhance my work experience and support my career goals.
  12. I have formulated at least one written career goal that meets both my needs and the organization’s.
  13. I have identified specific developmental areas to focus on to achieve my career goals.
  14. I have identified development activities and resources to address my developmental needs.
  15. I am tracking my accomplishments and their impact, which I regularly communicate with my manager.
  16. I have a written career plan.

Now that you’re identified your biggest opportunities to take more ownership of your career, what resources or support do you need?

The road to impactful leadership is paved with consistent, thoughtful conversations that fuel not just the business’s engine but also the aspirations of those who drive it forward. Embedding career dialogues into your regular interactions isn’t just about check-ins; it’s about forging a path that aligns individual ambitions with collective success. Apply these best practices and use the quizzes to reflect on where you may need to focus more attention – both for your team and yourself. If you want a partner to gain guidance on where to take your own career or how to show up as the impactful leader you want to be, I’m here for you.