"When we let our ego be in the driver’s seat, the work suffers" β€” How I Contract Interview with Alexandra Sepulveda

how i contract interview Apr 24, 2024

We have had the great pleasure to interview Alexandra Sepulveda, Senior Commercial Counsel at Gusto, ex-Uber, ex-Udemy, and ex-Unity.

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.

 Let's 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?

My biggest challenge when I started working with contracts is one that I think a lot of folks earlier on in their careers probably face: Prioritization of which clauses to redline/stand your ground on. 

When you are inexperienced, knowing which provisions truly matter is hard because you haven’t yet seen an agreement fail to get to the execution stage because the parties could not agree. 

If you are earlier on in your career, finding mentors who are outside of your work is a great way to get different perspectives on contract provisions.

You don’t have to share sensitive, privileged information with that mentor.

You can ask general questions like, “How have you successfully navigated carve-outs to the limitation of liability when the two sides don’t see eye to eye on what carve-outs are appropriate?” Or, “What do you think is the market for coverage for IP infringement?”

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

When I first started working on contracts, I looked at them from a litigators’ perspective because that’s where my career started.

Viewing a contract in terms of “What could go wrong?” is a very different perspective from where I am now, which is much more, “How could this become a bigger opportunity for the company and how do we make sure this is set up for long term success?” 

Once I took my first in-house job, I was given responsibility for the IT division’s legal work, in addition to doing food law work. That’s where I started having to shift my perspective from protecting the company at all costs to getting the best deal I could considering all the circumstances involved — including the relative bargaining strength of the parties.

I also now consider how I strategically put in my redlines.

Comments are a point of strategy; sometimes saying nothing at all, but letting the redline stand on its own, speaks volumes.

If you could write a short e-mail to your younger self when you were just starting to work with contracts, what would you write?

Dear self,

That personality you are trying to hide in order to fit into a corporate environment?

1) You can’t hide it, it is coming out despite your attempts to silence yourself in meetings and multiple rewrites of your emails; and 2) It is your superpower.

It doesn’t work for everyone you encounter, and that’s ok!

It works more than you think it does, though, so keep going and refine it.

If you could share just one practical, real-life contract tip, what would that be?

It took me longer than I would like to admit to get myself real training on the differences between redlining in Google Docs versus Microsoft Word.

It is not training likely to be given by your customer or firm.

It is worth investing in attending training on this.

The tools are different and you need to know how to effectively switch between the products to deliver an effective redline.

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

One of the easiest ways to screw up on a contract is to be overly focused on winning every point or wanting to be right.

When we let our ego be in the driver’s seat, the work suffers.

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

When you’re dealing with a long contract, consider using an issues list between you and the other side rather than trading redlines back and forth. 

Sometimes as legal professionals, we can get really entrenched in the words used in a clause rather than focusing on the overall issue that’s being addressed. 

Layer into this the fact that legal professionals come from different backgrounds and approaches and you have a situation where both sides might be overly concerned with words at the expense of aligning on the concept.

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?

Maureen Sheehy
and Roger Cook

Maureen Sheehy, who was my law firm mentor, could communicate a plethora of responses to an opposing party on a call with a simple “Mmm-hmmm.”

Your response, particularly in a charged situation, doesn’t always have to be your full response.

You can indicate that you have heard the other side, but that you may not agree with it.

This provides you with the space to avoid giving your full position there and then and buys you time to come back with a thoughtful written follow-up.

Roger gave me one of my first opportunities to negotiate an agreement on my own.

We started off the call with a vendor and after about five minutes Roger said something along the lines of, “Well, I’m leaving, Alexandra has got this.”

Sometimes just being seen and trusted can do wonders for your negotiating posture and confidence.

We can all do that for the folks on our teams who are earlier on in their careers.

It can be something as simple as an NDA, but letting colleagues have an opportunity to lead even if THEY think they aren’t quite ready (but you think they are) is a fantastic learning experience.

Who should we interview next? Why?

You should interview Anya Ryjkova.

I worked with her closely on a project at Uber and she is a superstar! 


Thank you very much, Alexandra!


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

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