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Thinking of doing business with my company? You should proceed with caution. I've made mistakes, and some of my clients have suffered because of them.



My 10-person firm sells popular business software and then provides services such as consulting, training, support, and customizations. We have more than 500 clients. Most are happy, but some are not. The unhappy ones are not to blame. Their dissatisfaction is almost always my fault. In the effort to get a sale, and sometimes long after the sale, I've made errors in judgment. I didn't take the high road when I should have. I took the easy way out. I'm pretty sure that other information technology professionals have done the same. But this is about me, not them.



Am I kidding here? No. To prove it, here are a few real-life examples, with names changed, of how I messed up and failed my clients. I've tried to learn from these mistakes, and you should be on the lookout for warning signs such as these before you give the green light to any IT project.



1. I sold cars to unlicensed drivers.



To this day, I'm amazed by the number of people who will spend a ton of money on software for their entire business after a single demonstration. I spend more time picking out a pair of sneakers than some clients have spent evaluating a business application.



Barr Landscaping turned to my firm to put in a help-desk system so they could track service issues from the time a ticket is opened to the completion of a customer survey. After one demonstration of our product, Alan Barr, the owner, gave me a thumbs-up and said enthusiastically: "This looks great. Let's get started!" Buying new software should require product research, multiple demos, on-site testing, reference checking, and planning. None of which he had done.



Knowing this, did I take the high road and refuse to move forward? Nope. I said "Super," arguing to myself that he's going to buy from someone, so it may as well be me. I kept my fingers crossed. I took his money. I hoped for the best. And I made him sign paperwork releasing my firm from any liability. Not surprisingly, the software wasn't exactly right and he had to spend a lot more to customize it. We no longer work together.



Have you done all your homework before buying technology? I've learned now to ask questions.



2. I've sent boys to do a man's job.



Need IT training or support? I've learned the hard way about assigning the right person to the job.



We didn't do that for AVM Manufacturing. They purchased a customer relationship management [CRM] product. AVM is a small company with a small budget. Like many IT firms, my company is also small, and my resources are limited. I have experienced people who are certified in the products we sell. I also have people who aren't. I'd like to send my most qualified people out all the time, but if we're busy, that isn't always possible. And clients can be impatient. So the big, important, profitable jobs get our best first.



And AVM? Well, they didn't. I had a bad feeling as I knowingly sent an unqualified person out to perform an installation. My hunch was right. Things took much longer, and my guy almost hosed their entire database. Thank goodness for backups. We got fired. I learned my lesson here, too.



3. I hoped that a Little Leaguer could strike out A-Rod.



Mildred is a nice bookkeeper who a few years ago celebrated her 60th birthday. Unfortunately, she almost didn't make it to 61. At the time, she was put in charge of her company's accounting software upgrade. They might as well have made her manager of the New York Yankees. Nice lady, but wrong skill set.



Yet the owner of the company insisted. I knew she was ill-suited for the job, but I didn't argue further. I kept my mouth shut. I just wanted to sell them the software. As expected, putting Mildred in charge was not a good choice. The project went badly. And here's the thing: The client wound up spending way more money on our services than planned, just to cover Mildred's inexperience.



By not drawing a line in the sand and insisting on a more qualified employee to work with, I failed that client, too. Want your project to be successful? Make sure you've got the right person on the mound. Having learned my lesson, I'll do my best to warn you if he's not.



4. I'd rarely commit.



I dated my wife for seven years before she finally proposed. It wasn't exactly a proposal. She told me to you-know-what or get off the you-know-what. I used to conduct myself the same way with clients.



They would ask me to commit to a fee, and I'd hem and haw. I'd whine that there are too many variables, too many question marks. At best, I'd give a wide estimate ["Gee, that should take between 50 and 892 hours"]. Maybe this was because I had been burned many times before by unexpected complications beyond my control.



I've come to realize that I was doing my clients a big disservice by refusing to commit to a fixed price on projects. How could a client have confidence in me if I didn't have the confidence in me? This nagged at me. Just like my wife. Now I've learned to make commitments. I give firm estimates. I put my skin in the game.



5. I said yes too quickly.



John, a manager at an engineering consulting firm, asked me early in the process of reviewing a CRM application if the software "synchronizes with my BlackBerry contacts." I said, "Of course." He was happy with my response. I was happy that he was happy.



As it turned out, the software did sync this contact info -- only not the contact info he was talking about. He had created certain user fields that were very important to him, and they did not transfer over. Needless to say, John was not happy. I, therefore, was not happy.



John's not an expert at CRM software. I was supposed to be the expert. I was supposed to dig deep, ask the tough questions, get the details. In the heat of trying to get the sale, I didn't really dig deep enough. Important stuff was glossed over. I naively assumed too much and brushed aside important questions. And by doing this, I failed John. We no longer work together.



Now when clients ask about features and functionality, I try my best to show, show, show. I've learned that I can't read people's minds. And saying yes all the time can build unrealistic expectations. It all catches up with you in the end.



Are you still, after reading this, interested in buying technology services from a firm like mine? I know I've failed some clients in the past. But I've learned. And at least now you know what questions to ask.