{ "media_type": "text", "post_content": "One of my employees is the only one in the firm who knows how to use a critical piece of outdated software. I overheard them speaking about accepting a job interview. Should I get them to train another employee?", "post_id": "613166b6867abe001d020466", "reply_count": 7, "vote_count": 5, "bowl_id": "55375ce690f5eebe1d2a0f88", "bowl_name": "Tech" }

One of my employees is the only one in the firm who knows how to use a critical piece of outdated software. I overheard them speaking about accepting a job interview. Should I get them to train another employee?

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You should have done that long before you heard they were interviewing. Get documentation and another person trained.

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If it’s biz critical, immerse yourself in the software. Document it. Understanding it yourself will help you source their backfill more effectively. It’s also a good time to do some introspection around why you allowed a single point of failure to exist for so long. People who keep the lights on with systems like this are important, and these jobs are often thankless. What can you, as a leader, learn from this experience and change to improve outcomes going forward?

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Piggybacking on the single point of failure, no one person should carry the weight of a task as important as that. All it takes is one offer, one accident, one mistake, for all of it to come crashing down if that person were to leave.

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Is there any documentation on what they do with that software? Start by getting something documented.

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Would you be open to counter-offering their other offer?

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Have them train more than one employee. Then, the problem won't repeat.

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