Are You a Spineless Business Owner Dominated By Your Staff?

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Milquetoast [milk-tohst], noun: a very timid, unassertive, spineless person, especially one who is easily dominated or intimidated. (per

Raymond, a (now former) client of mine, is a milquetoast. Are you?

Do you let other people run your business? Do you shy away from confrontation? Are you afraid to ask the hard questions? Are you intimidated by stronger personalities? Raymond is.

Raymond has a bookkeeper named Helen. I’ve never met Helen but I had the displeasure of dealing with her over the past few months and the even greater displeasure of talking with her on the phone just two weeks ago. I’m guessing Helen is aged somewhere between 50 and 150. I’m sure she’s a great bookkeeper and very loyal to Raymond. Unfortunately, she doesn’t know a thing about technology. But don’t tell Helen that. She knows it all. At least she thinks she does.

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That became obvious after Raymond’s company purchased a software upgrade from my company. In the world of technology there is software and there is service. Anyone who has any experience with technology knows that purchasing software entitles you to the software and oftentimes support from the manufacturer.

However, consultants like us offer an additional value. We implement, configure, customize, integrate and train our clients so that they get the most from their system. This is provided for an additional charge (in our case we charge an hourly rate). You know this, right? And so did Raymond and Helen too. At least, I thought they did -- they signed a contract with my firm at the time of purchase that explained the services we provide and the rates we charge.

But I guess I assumed too much. Because a few weeks after receiving her software, Helen called us wanting help.

“We would like you to come here and install this software,” she said to our project manager. “And make sure all of our prior data moves over. And make sure it’s working with our other software systems. And provide us training.”

That’s fine. Except that Helen had never purchased a block of hours from us to provide services. As written in our contract, we don’t provide services without a block being purchased. That’s the way we do it. That’s the way many technology firms operate.

But Helen refused to believe that. And she knows it all, right? So she didn’t pay, and we didn’t provide any services. She continued to demand services. I continued to refuse. I emailed explanations. I called her. My project manager did the same. She accused us of poor service, in her own dominating, arrogant way. She was not nice.

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Ultimately, I went over her head. I emailed Raymond -- her boss and owner of the company. I explained the situation.

And his reply? “Your attitude is costing you our business.”

He sided with Helen!

Why? Who knows? Maybe he believed her more than me. Maybe they don’t like me (wouldn’t be the first time). Maybe he didn’t read the contract either. Maybe she has secrets about him. It could be for any reason.

But the bottom line is that Raymond, after paying thousands of dollars, was now stuck with software that didn’t work and because his bookkeeper refused to pay for services, he couldn’t get any help. This is Raymond’s business and Raymond’s money. And yet he’s letting other, less competent people make decisions for him. Could Helen and Raymond find another company to provide these services? Sure, but they’ll ultimately have to pay them too.

Raymond is a milquetoast. Are you a milquetoast? Does your sales director determine pricing without your input? Does your HR person override your decisions regarding benefits or compensation? Does your warehouse manager buy product without telling you?

Are these decisions being made on your behalf because you’re afraid to get too involved, upset people or rock the boat? If you are, then you’re a lousy manager, and an even worse business owner. You will lose money and be the victim of bad decisions made by people who shouldn’t have the power to make those decisions.

Related: Fight Overthinking, That Destroyer of Decision Making