"Ask more questions" — How I Contract Interview with Sterling Miller

how i contract interview Mar 27, 2024

We have had the great pleasure to interview Sterling Miller, three-time General Counsel, currently CEO & Senior Counsel at Hilgers Graben PLLC. Sterling is also the author of three books, Ten Things You Need to Know as In-House Counsel blog, and a writer for Thomson Reuters.

This interview is part of the How I Contract interview series designed to offer various perspectives from experienced lawyers and contract professionals on what works in contracts in the real world.

Dive in! 


What was your biggest challenge when you started working with contracts? If you could go back in time, but keep all the knowledge and experience you have now, how would you deal with it?

Generally, the biggest challenge was the fact that I had been a litigator for the first six years of my career.  So, I had to learn contracts from the ground up. 

Even though I had a contracts course in law school, it doesn’t really teach you how to draft contracts or review contracts. 

And this was before the internet or all of the great resources we have today, like How to Contract or Contract Nerds

So, I made a lot of mistakes.  But, I learned from them and that’s always valuable.

If I had a time machine, I think the main thing I would change is to ask the business more questions about the deal and the objectives. 

I think drafting contracts goes much faster if you have spent 30 minutes with the business understanding what they want to get out of the deal.  When I was starting, I was terrified of clients knowing that I didn’t  know a lot.  So, I kept my mouth shut way too much. 

I would go with “ask more questions.” 


How have your contract drafting techniques changed over the years? What did you stop doing? What did you start doing?

To start, I am not so picky. When I started, I would – like most young lawyers – argue every point and work hard to get my version of the contract accepted. I would spend time (agonizing) on word choice, formatting, etc. 

Over time I realized there are many contracts where you can live with “good enough” and just get on with it.  Only a minority of contracts that come across your desk need an A+ effort. Learning how to live with “good enough” was a big change and saved me a lot of time. 

I also created a lot of checklists which helped me get through the pile even faster.  Big fan of checklists.


What are the three most important things to know about contracts?

Three things come to mind:

  1. Boilerplate matters.  These clauses are where you should spend a large amount of your time.
  2. Save your drafts every few seconds (and don’t trust autosave).
  3. Try to get the business to truly partner with you on a contract (especially a non-template, big-dollar agreement). The business tends to think everything in the contract is legal’s responsibility and not theirs. Convincing them otherwise and solving the hard issues together is a much better way to go.

What’s your biggest lesson learned in contracts?

Learn the business' risk tolerance and do not substitute your aversion to risk in place of what the business is okay living with. 

As long as the right person at the right level is making the call then just get going. 

If the SVP of Sales doesn’t care about a liability cap, make your points about why one is a good idea and then draft the contract without the liability cap. But, document somewhere the discussion where you advised the SVP on the downside of doing so. 

I think lawyers slow down a lot of deals by fighting battles they shouldn’t fight.


What mistakes should contract lawyers and professionals avoid when working with contracts? How would you avoid them?  

You need to read the contract several times before you start in with changes, etc. 

Many times, lawyers (myself included) just start going. 

By doing so, we miss a lot of nuance and may end up misreading a redline or comment because we are moving too fast. 

I think slowing down and using the three-passes technique is the best way to minimize mistakes, i.e.,

1) quick pass to see what’s what,

2) second pass and plugging in the definitions,

3) third pass where you truly get to work. 

Seems like a pain but it works.


What’s one of the easiest ways to screw up a contract?

Ignoring the definitions. 

I print those out and have them handy when I read the contract. 

It’s amazing what people will bury in the definitions that can really come back and bite you or surprise you. 

I also like to print out the entire contract and use that version to mark up. Reading a complicated contract online is very hard and I think we miss things because it’s not easy to flip back and forth, etc. Printing it out solves the problem.


Are there any simple hacks our readers can use right away to improve their contract drafting and negotiation skills?

A few things I do:

  1. Start in the back and work toward the front. Contracts are very different creatures when you read them back to front. I am not sure why and maybe it is just me, but I find them easier to read that way.
  2. As I mentioned earlier, print out the contract vs trying to read it all on the screen.
  3. Never accept hyperlinks that the other side can change when they want to. Either print out and make an exhibit that is subject to the amendment process or add language that if they change the hyperlink you have the ability to terminate the contract.   


If you could give a shoutout to one (or more) person who has influenced your life in contracts (or is your mentor), who would that be?

My high school English teacher, Joe Berry. 

He’s no longer with us but he once told me that everything is a story including contracts. 

They (contracts) are just really poorly written stories.  You can do better by making better stories, i.e., make them easier to read. 

Great advice.

The second would be Jeff Everett. 

Jeff worked for me when I was general counsel and spent a lot of time answering my questions about how contracts worked. I was humble enough to ask and he was generous enough to teach.


What interview question would you like to be asked and how would you answer it? 

I would like to be asked, “What is to next big leap in contracting?” 

To which I would say, “There are two things. The first is artificial intelligence which can truly redline a contract or respond to redlines. The second is a “UCC” for contracts, i.e., standard terms and conditions for a multitude of contracts that are fair, and balanced, and anyone using them can rely on them without harming their company (regardless of which side of the table you are on). That may be out there. If it is, I haven’t seen it.


Who should we interview next? Why?

David Tollen

He is the author of The Tech Contracts Handbook. It is a fantastic book for anyone trying to learn how to deal with SaaS and other technology contracts. Then I think you can find any litigator and ask them what the biggest problems they see with the contracts they litigate over are. That may be a two-parter.


Thank you very much, Sterling!

Want to learn more about how other experienced lawyers and professionals excel at contracts in the real world? Check out these interviews.

Join 6,000+ lawyers and professionals who receive our free weekly contract training newsletter. 

Sign up now