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Legal Speed Dating: 4 Questions to Ask Yourself and A Lawyer to See if You Are Compatible

Dan Cooper, Partner and Growth Catalyst with Acumen Impact July 24, 2018

As an attorney in Kansas City, I am often introduced to and network with professionals that are thought leaders in the community. It is my pleasure to bring you this guest blog post from a business leader in Kansas City.

-Jeff Coppaken

Finding the right lawyer for your business is hard. If you are like most of my executive coaching and mastermind clients, you ask your network if anyone “knows a lawyer that …” and you’ll get a couple of responses. Great.

In the initial call you’ll ask questions about expertise and client list and so on but those aren’t the real deep questions that will allow your business to thrive through this relationship. So, how do you make sure which lawyer will be the best fit?

Here are 4 real business questions you can ask yourself and a potential lawyer to see if you are a match.

What Is Your Philosophy on Business Risk?

When I owned my first business, it drove me crazy when my lawyer would tell me “No” without any explanation, alternatives, or solutions to do what I wanted to accomplish in a legal and risk adjusted way. You can never get rid of all the risk.

We would argue (actually argue!) about the appropriate amount of risk to take and an agreed upon way to move forward. I want to know where I’m taking risks, but I also want someone to work with me to maximize my outcomes and minimize time and investment.

Where do you fall on the risk continuum? Knowing that, what kind of lawyer should you partner with?

How Important Is Winning?

Many times, there are opportunities to create partnerships or joint ventures with other people and companies. There will also be a point in your career where you will be involved in a legal proceeding. If you haven’t, you are lucky, or don’t own a business or have any employees. Life is too short to negotiate with a “win at all cost,” attitude, and trust me, it will cost you. One sided contracts and legal matters starve businesses of time and resources that are better spent elsewhere. How you deal with these matters will show the business community what kind of person you are. It will get around. That said, there are times where you need to die on a hill. But make sure you are ready to do so and it’s worth it.

How Do You Look at Business Relationships?

It’s amazing to me the number of times where owners or CEOs are going into a matter with only the next conversation in mind and are in the weeds versus taking the time to think through the best outcome and work towards that. If you are seeking a lawyer on a particular matter, start with the end in mind. They have done this a lot more than you and can tell you possible outcomes for your situation.

What Are All the Alternatives to The Situation You Present Your Attorney?

The amount of levers in any matter are many. Money, time, effort, etc. are few things to consider. What is right for you? Is your lawyer asking these questions: What mix would you be open to? What kind of partnership makes sense? How else can you provide equity to key personnel? Ask about alternatives. A good lawyer will know them.


When looking for a business lawyer, you’ll save a lot of time, effort, money, and sanity if the both of you are on the same page about how you like to run your business, mitigate risk, negotiate, and seek alternatives. It’s worth the time on the front end before you get too deep into your date.

Dan Cooper is a partner and Growth Catalyst for Acumen, a mastermind community that exists to sharpen, challenge and inspire CEOs and Owners through affinity-centric advisory teams, executive coach and leadership acceleration workshops.