Boss in Midlife Crisis Hires Cute but Lazy Women

By Lindsey Novak

December 25, 2014 4 min read

Q: Our boss/owner is in a midlife crisis and is ruining his business. His wife used to come in every day so things ran smoothly, and she kept track of things. She slowly got less involved and stopped coming in. The business had been good for about 15 years. Recently, he started hiring incompetent, inexperienced "girls" who don't deserve the jobs. He hired one with a cutesy baby-doll personality but no work experience in the field. He allowed her to hire her 22-year-old girlfriend, who knows nothing about anything. They are darling, of course.

I have tried training them, but after months of my correcting both of them, neither cares about learning, and I end up having to redo things. They also need to learn many other things, such as polite communication, manners — far too much to mention. If I could teach it all to them, I wouldn't know where to start. And they don't want to learn anyway.

The rest of us here are baby boomers with lots of work experience, common sense and strong work ethics. We need the business to continue to be successful because we need our jobs, but it won't take long for it to run into the ground if he stays dazzled in this life phase. How do we show him the light, short of calling his wife?

A: Don't call the owner's wife. Try a business approach to enlightening a boss who has taken a vacation from reason. Tell him you'd like to present a PowerPoint to him of the company's history of success that you think he will want to use for future meetings.

Writing this presentation will take a bit of research, organization and preparation, as you will deliver it as if you were leading a motivational sales meeting. The presentation will be in three parts — positive, negative and positive.

First review the success his company has experienced. Mention all who were involved in that phase. (His wife is one you can point to.) Talk about the major events that contributed to company growth.

Next comes the negative portion. You will mention events that may have taken away from past success, perhaps his wife's being less involved, the hiring of less experienced individuals, extended required training times and any other negative activities. This cannot be a personal attack on any person in particular.

This business owner had the wherewithal to grow a business. He is not naive about the work and devotion it took. Successfully delivering a message means knowing when to stop, so don't overdo it. Your secret goal is to alert the owner to the changes you see in his business style and direction, not to humiliate him. End on a positive note, mentioning all who have invested time and have developed careers at his company and how they look forward to growing his business in the future. If you present it with care, your boss should appreciate the work that went into it, even if he chooses never to use it. And don't expect changes overnight. This type of problem has to sink in emotionally, as well as intellectually.

You also need to let the two "girls" fail. Correcting a person's mistakes at work protects that person from eventually being fired. Each of them has been in the job long enough to absorb the training, and being a good trainer doesn't mean you should perform the person's job. When the errors hurt the company, you can point to the inability of the employee to learn the job. The boss may need to see the losses before he admits that his recent hiring decisions have caused a downturn.

Email your questions to workplace expert Lindsey Novak at [email protected], and follow her on Twitter @I_truly_care. To find out more about Lindsey Novak and to read features by other Creators Syndicate writers and cartoonists, visit the Creators Syndicate website at

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