Episode summary

Do you know what your direct reports want out of their careers?

Leadership and development expert Steph Wong makes the case that it’s your job as a manager to know.

Steph shares with us the approaches and tools she uses to guide people in developing their careers, and how meaningful career conversations can help your team do their best work – at their current jobs, and beyond.

Why it matters

As managers, we have a tremendous amount of potential influence on our direct reports’ careers – not just within your current organization, but also wherever they may go in the future (and yes, someday they will leave!). We have a responsibility to wield this influence with care and buy-in, and if we do it well, it will bring out the best in them in their current jobs as well.

Putting it into action

  1. Care about your direct reports as humans, not just employees
    In order to have meaningful, honest, and open conversations about career development, your direct reports have to feel that you genuinely care about them and are interested in their lives – this can’t be faked!

    You have to build a rapport and trust with them and this takes self-awareness on your part.  The ways you communicate with them – how you hold conversations, how you ask questions, your gestures, etc. – all feed into how rapport and trust is built.
  2. Help your direct reports build self awareness to ultimately figure out what they want in their careers
    “What do you want to do with your career?” can be daunting for many.

    Try these exercises and frameworks to help you and your direct report to together identify themes in what motivates and energizes them at work as a starting point to more thoughtfully plan their careers.

    (These exercises largely draw on the book Designing Your Life by Bill Burnett and Dave Evans. For more information, visit: https://designingyour.life).
    • Adjectives exercise
      One’s awareness of oneself is just one side of the coin. Help your team members understand how they show up at work in the eyes of others. Ask them to each write 5 adjectives to describe each other – the collated adjectives for each person should help them identify key themes on how they are perceived and what others notice about them.
    • Good time journal
      Invite your direct report to document everything they do for a period of time, in and out of work, scoring each event or activity based on how engaged they were and whether they gained or lost energy from it. At the end of it, they should be able to step back and recognize patterns in what keeps them engaged and energized in life and at work. (You can use the good time journal worksheet.)
    • AEIOU
      Have your direct report identify some significant positive and negative experiences at work. For each, ask them to reflect on: What activity they were doing, what was the environment like, what were the interactions with the people there, were there any objects being made or used, who the users there were and how they affected the experience. This exercise provides a deeper understanding of the factors that enhance or detract from their satisfaction at work.
    • Odyssey
      Career planning can be an exercise in imagination. Odyssey planning helps you envision different careers and acknowledge different parts of yourself that you may have forgotten or not realized before. Use it with your direct reports by asking them to make three 5-year plans, as if they had three lives: One based on their current life trajectory, one where whatever they were doing now completely disappeared as an industry, and one where they had all the resources in the world and didn’t care what other people thought. What are the elements from the different lives that they would want to start to incorporate in their career planning? (Learn more in this video and use this worksheet.)
  3. Design experiences for your direct report that gives them joy
    After you’ve worked with a team member to identify what energizes, engages, and motivates them — and what doesn’t — tailor their work and responsibilites to better match their strengths and interests. They’ll get more satisfaction and growth out of work, and you’ll have a happier team that is able to do their best work.

Share your insights & experiences

Have you had an interesting or enlightening experiences with career conversations, whether for yourself or for your direct reports? Have you tried any of these exercises? How did it go?

We‘d love to hear from you at [email protected]!

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