Resource Round-up: Essential Tips for Navigating Career Conversations Like a Pro

Explore this resource round-up for mastering career conversations, featuring essential tips and a curated selection of guides, podcasts, and videos. Equip yourself to navigate these important discussions effectively, whether you’re a seasoned manager or just beginning your journey!

Every three months at work, we host what I refer to as a “mini managerial mastermind.” It’s a structured meeting with managers from across our organization swapping best practices and resources, all in the spirit of growth and improvement. Yep, I’m lucky enough to work for a company that doesn’t just talk the talk about growth mindsets—they walk the walk, too!

These meetings are a goldmine of insights, especially considering the mix of fresh-faced and seasoned managers sharing their two cents. It’s fascinating to hear from people who’ve practically seen it all and from those who are just starting to figure it all out.

As part of the team that puts these meet-ups together, I partner with another manager to gather extra resources that align with the topic of the quarter. This time around, we’re diving into how to have career conversations. I’ve already shared one of my go-to resources for having meaningful career conversations – a detailed guide with tips on how to prep and facilitate discussions. But for those who prefer to soak up knowledge through your earbuds or watch experts on your screens, here are a few additional resources from LinkedIn learning, podcasts and short YouTube videos to check out.

LinkedIn Learning:

LinkedIn Learning is an online education platform offering over 21,000 courses in business, technology, and creative fields, designed for individual learners and teams. For individuals, it costs $39.99 monthly or $239.88 annually (approximately $19.99 per month), making the annual option significantly more cost-effective. Each subscription includes access to all courses, personalized recommendations, and offline viewing options. New users can explore the platform with a one-month free trial, which provides full access to all courses and features.

Having Career Conversations with Your Team | LinkedIn Learning: Instructor Jenny Blake introduces a coaching framework that guides team members to identify ideal outcomes and plan their growth. Learn how these discussions differ from performance evaluations and how to integrate the four-stage Pivot Method into regular meetings, fostering a strong development culture and actionable insights (this session is 59 min long).

Podcasts:

Three Steps to Career Conversations – Coaching for Leaders In this episode of Coaching for Leaders (one of my favorite leadership podcasts) Russ Laraway outlines a practical framework for meaningful career conversations. He introduces three steps—understanding your team’s dreams, aligning their goals with organizational needs, and offering actionable feedback—to empower leaders to unlock potential, improve retention, and foster mutual success in the workplace (podcast length is 36 min).

How to have a career conversation – Squiggly Careers Hosts Sarah Ellis and Helen Tupper discuss six actionable ideas to facilitate effective career conversations, emphasizing the importance of regular discussions to enhance engagement at work (podcast length is 40 min).

How to Have Courageous Career Conversations from the Making Sense of Work podcast Vanessa Iloste, HR VP at Sephora Asia, discusses the complexities of career conversations on the “Making Sense of Work” podcast. The first ten minutes of the podcast is about the challenges around COVID so skip ahead ten minutes if you want to get to the heart of the career conversation tips. Vanessa emphasizes the need for curiosity in the conversations. She likes to use the phrase “what if” as a way to brainstorm different options for career growth. Then she guides employees on the “how” to chart their growth and stay market-ready by building relevant skills (podcast is about 46 min long).

Videos:

How to Have a Career Conversation with your Staff – FOR MANAGERS In this video, Helen Bryant (a leadership and training coach) provides managers with guidance on conducting effective career conversations with their employees. She emphasizes the importance of building trust, understanding employees’ aspirations, setting clear goals, and offering constructive feedback to foster professional growth and development (video is 9:38 min long).

How to Have a GROW Coaching Conversation – WITH QUESTION TIPS This YouTube video outlines the GROW coaching method, providing tips for each stage: Goal, Reality, Options, and Will. Key tips include setting clear, achievable goals, assessing the current situation accurately, exploring alternative strategies or paths, and committing to action steps. She emphasizes asking open-ended questions to facilitate effective coaching conversations (video is 14:12 min long).

If you’re a manager wanting to sharpen your skills in facilitating career conversations, I’m here to help. Sign up for a one-on-one mentor session with me, and I’ll provide personalized guidance to ensure you’re fully prepared to lead these impactful discussions.

Thanks for reading! xx

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Danielle Cullivan

Career Insight Studio

Danielle Cullivan is a seasoned leader in tech with over 20 years of experience in Fortune 500 companies. She is also the creator of Career Insight Studio, a career and lifestyle blog dedicated to providing insights and new perspectives for working women. Danielle lives in the Pacific Northwest with her husband and high-school-aged son, and visits her college-age daughter as often as possible! 

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