What’s the biggest challenge you’re facing? You can make the “challenge” question more specific (“on this project”) or more general (“in your job”). Are you making progress? If employees feel “stuck,” frustration sets in. Help me understand what led to … Instead of asking “Why?” about a problem, start the question this way—it’s wordier, but less accusatory. Is it clear what we’re doing and why? Ask employees this question with regard to company goals, directives, policy changes, and the vision for the future. How can I help? Per Doug Conant, the “ultimate leadership question.” But only ask it
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