One of my direct reports struggles to comprehend crucial aspects of their role but (1) refuses to ask for help and (2) gets defensive when I proactively set aside time to coach/train them. As a leader, I always pride myself on being approachable and adjusting my teaching methods to the individual instead of “one size fits all”. How would you approach this in a caring, respectful way that shows you are dedicated to this persons development without making them feel “dumb”?

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You could try asking them that very same question. "I've noticed you've been struggling a bit adjusting to the role and I'd like to help you meet expectations. What's the best way for me to provide you with feedback and development opportunities?"

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Put it back on them. Present them with the same information you have laid out here, explain what you are attempting to do and why, and ask them how they would like to be coached and what they would need to get better at asking for help, because not changing anything about their behavior puts them at risk of not meeting performance expectations.

Brené Brown has one of my favorite quotes and if I could tattoo it on my arm I would “Clear is kind”, some times as leaders we avoid healthy confrontation by hinting at the problem instead of simply addressing it.

Be upfront and pull them in to coaching and development conversation with you. This is way if THEY tell you what they need and they still don’t actively participate in their own development- that opens you up to a different conversation. But you’ve at least given them the chance to show up for themselves.

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Sounds like they are frustrated with the job and perhaps the training thus far? As an autistic, I like simple, step-by-step, written instructions. Is there someone else that can coach him? Maybe a different person with have a different way of training that your DR will understand.

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Sad thing is you're already approaching them in a caring and respectful way. None of us are perfect, no one knows everything, and all of us need to work on our game in some form or fashion. Just keep trying, if they don't adjust it might be time to reevaluate their role and status at the company. You can only do so much until it's on them.

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