Don’t be afraid of having thoughtful career discussions with your key people. Don’t tell me you’d be at a loss for words (or topics), but here are some starting points:

  • At our firm, what have been your proudest accomplishments and biggest disappointments? Why?
  • What energizes you and what drains you?
  • Rank the following in importance to you:
    • financial rewards
    • firm culture
    • security
    • friendships
    • intellectual challenge
    • non-financial recognition
    • autonomy
    • power
  • Where would you like to be in three, five, or seven years?

Expect the first few conversations like this to be tentative and maybe even awkward at first. People may suspect you of ulterior motives, like trying to gauge whether they’re loyal, truly ambitious, goal-directed, or self-disciplined. Don’t worry. As you begin having these conversations more and more regularly, they’ll become familiar with it and trust will grow.

Make sure the meeting is all about them, and follows whatever agenda they seem to be setting.

Remember the goal above all is for you to listen and learn, not to judge, critique, or even (at this point) try to play coach or psychiatrist. Just listen.

But you also will need to follow up. Ask them, subject to the firm’s priorities, what they’d like to work on more and less; where they feel they could use more experience (or simply more “exposure”) in order to advance their own career goals. Help them define some concrete objectives—and prepared to support them in working towards those goals, but also hold them accountable if the firm gave them all they needed to get there and through inattention, laziness, or lack of focus, they fell well short.

This may sound simple—it’s all about having a conversation—but few things are more important. And in your heart you know that; you know it from all the “rest” of your life. What’s one of the strongest ways to build the bond between you and your spouse, you and your kids, or you and a good friend? It’s to talk, honestly and openly and without an agenda of your own.

You might want to try this at work every once in awhile.

Because if your top talent feels that they can’t talk to you, they’ll find someone else they can talk to. Who may not have your firm’s best interests at heart.

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