Mike Boucher ('07)

Careers In House Profiles Dec '12

Founder and CEO, Dakota Legal Software

Originally drawn to law school in order to apply a background in software and hardware to improving technology law, Mike Boucher is now Founder and CEO of Dakota Legal Software, where he coordinates senior management and technical experts to make the company successful. "I use what I learned in law school to guide my company to develop technology that will help lawyers and legal professionals."

Q. Why did you go to law school? I originally decided to go to law school to apply my extensive software and hardware background to improving the state of technology law. Seeing some truly miserable reasoning in a few key cases led me to believe that I could contribute to society by applying a thorough understanding of science and technology to legal decisions and processes related to technology.

Q. Tell us about your current work. I do not do much of our own legal work, but being able to quickly assess a legal position or argument helps me work with our lawyers effectively. For example, by understanding the legal reasons why a lawyer might initially approach a particular situation with a risk-averse posture, I am sometimes able to help our lawyers achieve personal breakthroughs in their risk tolerance that they might otherwise find imprudent, or even terrifying. My team includes some of the most knowledgeable people in law and legal technology, and my favorite part of the job is watching them work and learning from them.

The three most important skills in my current position are flexibility, arrogance, and humility, usually in that order. I approach very difficult problems from many different perspectives and with a willingness to define success in many different ways. Once I've carefully analyzed a difficult problem and decided on a path to solution, I find arrogance to be an indispensable tool in committing to a course of action and dismissing the inevitable uncertainties that will try to consume all of my time and energy with second-guessing myself. On the other hand, when it becomes obvious even to me that I have made a mistake, my team will still follow me down the next path if I have the humility to admit my mistakes rather than blame others or try to spin a loss as a win.

Q. What about Colorado Law helped prepare you for the position? The faculty at Colorado Law provided the right combination of guidance and support with the freedom to choose and investigate a nontraditional direction. Once I decided that I was going to start my current company after law school, I got a lot of help from across the entire school including professors, the law library faculty, and the registrar. The other important factor is that my experience at Colorado Law never stopped. I take advantage of the opportunities to maintain my engagement with the school even now, years after I stopped taking classes.

Q. Tell us about your professional networking experiences? I established LinkedIn connections with students, professors, and guest speakers. I volunteered to drive guest speakers to and from the airport as often as I could, then followed up with a short note to them to thank them for taking the time to discuss a particular topic of interest that we discussed in the car. I prepared thoroughly before contacting alumni, guest speakers, or others so that they would come away from our contact with a favorable impression.

Q. If you could go back and do something different in law school, what would it be? I would have taken notes by hand instead of on my computer. I missed some class material because I couldn't resist the urge to format my notes as I went instead of just leaving misspellings and strange spacing for after class. If I had transcribed the notes from paper to my laptop after class then that would be one more time that I saw the information and one more chance to remember and synthesize the material.

Q. What final piece of advice do you have for current and prospective law students? Believe the things that the faculty tell you, no matter how improbable. When they tell you that you're not supposed to learn law but you are supposed to learn to think like a lawyer, you probably should not spend all of your time trying to memorize the law. When they tell you that your grade is completely determined by a single test at the end of the year, spend more time figuring out what the professor thinks is important and less time deciding which decisions you personally find just or unjust.

When guest speakers in class tell you that you can contact them with further questions or help on a project then do it. Tell them that you would like a way to keep in contact so that you can accept their generous offer and ask whether they would be open to accepting a LinkedIn invitation. Contact them where it would be helpful to do so, but only after you have thoroughly prepared yourself to use their time wisely.