When I get in front of a hundred business owners and ask them to stand if they have a dedicated long time employee who needs to retire but won’t, I have a room full of people standing up.

Henry was with the company since it started 37 years ago. As a dedicated account executive, your customers, employees, suppliers, and you – all love him. The problem is, at 71 years of age Henry has physical and memory issues that are seriously affecting his performance and worsening by the day. He is hard of hearing and he is forgetting to follow-up and follow-through with clients on critical issues. These challenges, combined with his inability to keep up with technology, social media and a whole new sales strategy, have resulted in your company out-growing Henry’s skill sets. In fact, you don’t want to believe it but Henry has become a liability. So what do you do?

The business owners I work with are compassionate, often to their detriment. They consider their people and their people’s families an extension of their own. They feel an overwhelming sense of responsibility to take care of them. They struggle greatly with this sensitive issue because if not approached and communicated properly, negative feelings from various stakeholders can result in serious implications – not to mention, they will not be able to live with themselves. It’s easier to procrastinate, keep paying Henry, and let him become more of a team mascot than a producer. The problem is that this isn’t good for Henry as people are losing respect for him, and it’s not good for your company, your employees, or their families.

It takes incredible self-awareness to understand that you are not doing Henry any favors by ignoring the issue. It is making you feel like you are doing a good deed, but not serving Henry long term. Henry is a long-term valued member of your team who wants the best for the organization. He may very well appreciate you working with him on a transition strategy that is professional, thoughtful and reflects the values that Henry has brought to the organization – rather than pretending the issue does not exist.

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Your company is a team. Each player has a role, and the execution of that role is critical to the future of your company’s survival. If you were coaching a professional hockey team, and your long time goalie who had taken you to a number of successful finals had lost his edge, you might park him on the bench. But now you have a back-up goalie who really isn’t able to perform that position either…you are fooling yourself and you are putting your team and their families at risk if your lead goalie needs a break or gets injured because you don’t have a suitable replacement.

As an Advisor and Disruptor, my job is to pose realistic questions and implications regarding scenarios you are facing in your organization so that you make the tough decisions – especially the uncomfortable ones. As a business owner, if you procrastinate in dealing with Henry, the bottom line is that you are setting dangerous precedents that are jeopardizing your entire team and their families. You are doing this by allowing a non-performer to hold a critical position on the team.

Business is a team based performance activity, and as the owner of the team, you take overall responsibility for performance – that means ensuring you have the right coaches and talent on the team who can play their position. So you need to start a dialogue with Henry concerning his future.

Remember that if you ask Henry when he is retiring, he doesn’t have to answer that question, and if he does, legally he doesn’t have to leave on the date he indicates.

There are civilized ways to start this conversation, and there are ways to put things in writing so that whatever is decided between the two of you will now be a solid plan. Check with your advisers and consultants prior to meeting with Henry, and lay out a plan that sees him leaving at a certain point with dignity and the respect from all of your stakeholders. Like most things, putting it off will only end up in disaster.


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