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The Millennial General Counsel

The Millennial General Counsel

Interview of Ian Connett by Courtney Cregan, UpCounsel

October 2016

I recently had the opportunity to sit down with Ian Connett, the 30-year-old legal director of Collective, one of the hottest advertising technology companies in New York.

Ian followed a somewhat “non-traditional” path to becoming a legal director at such a young age — the average age of general counsel and legal director at “unicorn” startups is 43 — and in the conversation below he discusses how he got to where he is today.

He also talks about what it’s like to be among the first millennials running an in-house department, how the legal industry is evolving, and where he thinks it’s headed next. (Hint: Think Elon Musk and SpaceX.)

You’re in a unique position, given that you’re much younger than the average general counsel. What is it like to be a millennial GC? Do you find yourself approaching challenges differently? Does it work against you?

I definitely notice surprise in the eyes of people who meet me after we’ve worked together virtually. Typically, one might expect to see a few more gray hairs on the “head” of Legal!

While I am on the younger side, for the most part, youth isn’t really an advantage in this profession. However, I’m lucky to have had the opportunity to shadow some terrific general counsels after law school. I guess it’s like a golfer who does well on the PGA Tour at a young-ish age. I think it has less to do with talent, and more to do with coaching. If you’re focused and surround yourself with great teachers, then learning how to manage a legal department by age 30 is totally attainable.

There’s also a big upside to companies hiring millennial GCs. We grew up with technology. We’re comfortable using innovative tools, and it’s more obvious to us how technology can make legal departments — and, in turn businesses — more streamlined and efficient.

Today, there are plenty of 30-something CEOs and CTOs, so why not GCs?

You took a somewhat “non-traditional” route out of law school. Why not go to a big law firm straight out of law school like most young lawyers?

The most important thing I learned in law school was that I didn’t want to be a “lawyer” in the traditional sense.

I knew early on – after taking Moot Court, a courtroom simulation course often required at law school – that I was not going to be a traditional courtroom attorney, à la “My Cousin Vinny” or Atticus Finch.

An in-house internship during my 2L year paved the way for me to go in house quickly out of law school – after one year of law firm practice – which is fairly unusual. Typically, attorneys spend 5 or 10 years practicing at a big law firm before making that move.

Millennial GCs grew up with technology. We’re comfortable using innovative tools.

Making a decision to go “in house” directly after law school was what saved me from becoming the lawyer I knew I didn’t want to be. I consciously did not focus on the traditional law school success criteria, like law review, clerkships, moot court competitions, for example. Instead, I sought out opportunities to work with legal departments at companies I admired, and networked with other in-house professionals.


To use familiar startup and engineering lingo, you might say I hacked the legal profession – or the traditional path young attorneys follow out of law school. Today, there are more opportunities to “hack” the profession the way I did. It’s more common than many think.

Can you tell me what it’s like to be the “legal guy” at a startup in tech?

Working in the tech world is a dream for attorneys. Yes, there are mountains of contracts to plow through, but the documents you’re working on are the strategic building blocks of the company, ultimately determining its success or failure. Good documents are critical, especially when supporting startups.

In a way, drafting contracts is a lot like writing code, but for human behaviors. Contracts are essentially nothing more than a series of “if … then” statements for your enterprise – much like programming languages. Framing it this way makes it exciting for me. Contracts are more than just words; they create futures.

What else can attorneys expect when taking an in-house role?

It’s very different from a traditional law job. Being responsive at all hours is the reality, whether you are a millennial GC or not. Of course, if you like what you do and who you work for, this isn’t a problem. I find that I want to be responsive if I like who I am working with and believe in the overall mission.

Making a decision to go “in house” directly after law school was what saved me from becoming the lawyer I knew I didn’t want to be.

Time also becomes a luxury. You lose the bandwidth to spend hours and hours on a research memo or court motion. You also have to cultivate boardroom etiquette and the ability to deliver opinions quickly and confidently. It’s not just what you say, but how you say it!

As you might imagine, especially with startups, budgets come into play a lot. Developing a consistent way to forecast the company’s legal spend during the fiscal year is critical. I recommend all GCs understand and leverage e-billing technology to do this.

Your typical mid-sized company should have between 10 to 20 outside firms on retainer to handle specialty, high-risk matters, such as IP, employment law, securities or litigation. As a legal budget owner, I am responsible for and need to manage this spend, or else the law firms will bill me out of a job!

What about the stereotype of legal as being antagonistic to sales … Is that something you wrestle with?

Absolutely. One of the most difficult parts of our job as in-house attorneys is to counter the perception that legal is preventative to sales. Any attorney who can figure out a way to get contracts done quickly and properly will be worshipped like a god by their sales team, because so many of us are seen as preventative to the sales process.

Developing a consistent way to forecast the company’s legal spend during the fiscal year is critical. 

My “secret sauce” has been to brand myself as a sales enabler. This requires an emphasis on customer service and relationship building both outside and inside of the organization. I want my sales teams to be excited to send me the contract, not dreading it! Of course, the challenge is doing this while avoiding excessive risk. This is where technology can really help.

Anything in particular?

Automated drafting tools and workflows can significantly cut down the contract lifecycle. Machine learning and analytics will play a bigger role in tackling this problem as well. As these technologies proliferate, the tech-savvy attorneys who know how to use them will be very desirable.

And since I’m basically a one-man show, I love services like UpCounsel. It means in-house folks can save time and do more for less.

Ha. We weren’t fishing, I swear. But thanks for that.

For someone considering whether or not they want to become a general counsel, should they worry about accumulating deep knowledge of a subject matter or specialty?

I find that breadth of knowledge is far more important than depth in my position. I handle day-to-day operations and farm out specialty matters to the experts.

Using a medical analogy, as general counsel, you’re more like a general practitioner — not a surgeon. You’re able to diagnose critical problems in a range of legal areas and refer them to the appropriate specialist for triage (i.e., your outside counsel).

Would you recommend the path you’ve taken in your career to attorneys fresh out of law school?

Yes. Opportunities are growing in-house, and in the legal tech startup space. The industry is being disrupted by new technology (just like everything else), so why not be a part of the disruption and control your post-law school career destiny? 

Any attorney who can figure out a way to get contracts done quickly and properly will be worshipped like a god by their sales team.

What other advice would you give to someone interested in going in house? Is there anything in particular they should know, or anything that is different from what they might learn or hear in law school?

One key to success is something they don’t teach in law school – how to effectively communicate with business folks. GCs who are not reliable communicators do not last. They lack what is perhaps the most critical legal skill of all: Trust.

That’s why I don’t read too many legal textbooks these days; instead, you’re much more likely to find me in the “Business” or “Self-Help” section at my local bookstore.

I read a lot about effective communication, leadership and marketing. I also read a lot about evolutionary biology and new technology, because to understand where the law is headed, and prepare accordingly, you need to know where humanity is headed first.

And where we’re headed, trust me, there is a demand for legal minds! 

To understand where the law is headed, and prepare accordingly, you need to know where humanity is headed first

How do you think the legal industry is changing?

Drastically, but positively. Technological disruption is freeing up lawyers to do more of what they like, lessening administrative burdens. In the future, attorneys will focus more on what they love to think about. Not what they hate!  

I find it funny that law students get depressed thinking our profession is dying when the legal questions we face at the advent of incredible developments – like space colonization and human cloning – are knocking on our door. I tell them to take a break from Torts 101 and instead read about what Elon Musk and Jeff Bezos are doing. I argue there’s no better time to be interested in law. But, you have to get interested in humanity first.

Technology is giving us the ability to find new solutions to legal problems, and while the younger generation of attorneys may be the ones who are adopting them, they’re accessible to attorneys of all ages. We attorneys should be doing everything we can to modernize the profession. Millennials are coming of age, so it’s inevitable they will start running corporate legal departments. I hope to see many more and to become less of an anomaly in the profession!

I. Connett, Esq.

San Francisco, California

Ian Connett