GC Sidebar: Alisha Cieslak, former Chief Legal and Risk Officer at Gordon Food Service

In this GC Sidebar Season 2 episode, Paragon Legal CEO Trista Engel speaks with Alisha Cieslak, former Chief Legal and Risk Officer at Gordon Food Service, about modern GC leadership, building legal teams from the ground up, and navigating business uncertainty in a rapidly changing environment.

Alisha shares why today’s general counsel must operate as business leaders first, translating legal risk into business strategy and helping organizations adapt to evolving challenges including AI, cyber threats, geopolitical instability, and operational pressure. Drawing from her experience building two legal departments, she also discusses how legal leaders can create scalable, business-oriented teams that combine in-house talent, flexible legal resources, technology, and outside counsel.

She also reflects on the importance of relationship-building across the business, developing future leaders, and creating legal functions that drive both operational efficiency and strategic value.

Full episode now available.

Read the Full Conversation

Prefer reading over watching? Below is the complete transcript from our GC Sidebar interview with Alisha Cieslak, former Chief Legal and Risk Officer at Gordon Food Service.

Trista Engel:
Welcome to GC Sidebar, a short and sharp conversation series with leading general counsel about the decisions, reflections, and people behind the title.

I’m Trista Engel, CEO of Paragon Legal, and today I’m joined by Alisha Cieslak, former Chief Legal and Risk Officer at Gordon Food Service, a 125-year-old family-managed food service distributor.

Alisha has twice been the first legal hire, building legal functions from the ground up at both Benteler and Gordon Food Service. She has paired that work with long-standing community involvement, including board service with the Special Olympics of Michigan and the Grand Rapids Chamber of Commerce. Alisha, I’m so happy to have you here. Thank you so much for joining me.

Alisha Cieslak:
Thanks for having me, Trista. I’m looking forward to the conversation.

Trista Engel:
All right, let’s jump in. What’s one thing you’re most focused on for 2026, and why?

Alisha Cieslak:
As I enter 2026, I’m beginning a purposeful transition from my role. I’m looking to join an organization that’s growing and where a strong culture is a competitive differentiator.

My 12 years at Gordon Food Service deeply ingrained a passion for the food industry, so I’m excited about the legal issues facing the industry today. We have the “Make America Healthy” movement, shifting consumer expectations, and, of course, volatility that comes with changes in administration.

But for GCs more broadly, it’s not just about industry-specific dynamics. We’re all navigating the convergence of AI, professionalized cybercrime, shifting geopolitics, cost pressures, and talent fatigue. These aren’t just CEO problems. They’re business continuity problems.

I’m focused on how a skilled GC acts as a bridge, translating those external shocks into internal strategies.

Trista Engel:
That’s a great point. There are regulatory uncertainties that will affect the food industry differently than other industries, but there’s also a broader business continuity challenge we’re all facing in these fluctuating and uncertain times.

Alisha Cieslak:
Exactly. Every business appreciates certainty, but strong general counsel know how to stay agile and adapt during periods of uncertainty.

Trista Engel:
What’s the most valuable lesson you’ve learned as a GC?

Alisha Cieslak:
There are so many, but the most valuable lesson I’ve learned is that a modern GC has to be a business leader first, whose work is informed by the law.

In the boardroom, I leave legal jargon at the door. My role is to frame legal issues in terms of ROI, business strategy, revenue acceleration, market-entry speed, and operational efficiency.

I’ve also learned to let go of perfectionism, which can be difficult for lawyers. Often, the need for perfection comes from fear or insecurity. But as you gain experience and sharpen your judgment, you learn how to make decisions and navigate uncertainty in a way that builds trust with leadership.

That allows you to move faster, keep the business moving, and become someone who guides the organization through challenges while adding value where it matters most.

Trista Engel:
Those are two incredible lessons, and both reflect the reality that this role is much bigger than legal. It’s about being a business leader sitting at the table and thinking about the trajectory of the company, not just the legal issues in front of you.

Alisha Cieslak:
Absolutely.

Trista Engel:
What’s one career moment that changed your trajectory?

Alisha Cieslak:
For me, it wasn’t a single event. It was the realization that I needed to transition from being a great lawyer to becoming an enterprise leader.

Early in my career, I focused on finding the perfect legal answer. But while building legal functions at Benteler and Gordon Food Service, I started seeing the bigger picture.

I stopped just leading lawyers and started building leaders. I intentionally invested in developing my team and creating opportunities for them to gain visibility and build trust with leadership.

That gave me more time to get into the field, visit facilities, participate in strategic planning, and build succession plans for the future. With that broader perspective, I began to understand that the legal view is not the only view. It’s a critical input into business decisions, but it’s only one part of the equation.

When you sit on the executive team of a multibillion-dollar company, you aren’t just the lawyer in the room. You’re responsible for advancing the company’s strategic aspirations while also protecting and preserving family legacies.

That shift in perspective changed everything for me.

Trista Engel:
I love that perspective. Legal touches every function in the business, so it’s incredibly important to understand how the company operates on the ground. Not every in-house lawyer gets the opportunity to do that, so I really appreciate that part of your story.

Alisha Cieslak:
It takes time to earn those invitations into the room. It requires intentional relationship-building. But over time, if you demonstrate excellence in your core responsibilities while showing a willingness to learn and lead in different ways, management teams become very receptive to that.

It also builds credibility with the business and operations teams when you truly understand the rules, processes, technology, products, and operations firsthand.

Trista Engel:
You’ve built two legal teams from scratch, and today GCs have a wide range of resourcing options beyond just FTEs and outside counsel. What’s your approach to resourcing your legal team?

Alisha Cieslak:
This is the question I’m most excited about.

Since I started practicing in-house more than 15 years ago, I’ve always heard the phrase “do more with less.” But I think we’re in a really exciting moment because we finally have the tools to do it.

To be successful, a GC has to apply the same operational rigor to the legal department that a COO applies to operations.

My approach to legal staffing centers around three ideas.

First, business-partner orientation. I want generalists who can deeply understand a line of business, product line, or business unit and manage those relationships effectively.

Second, specialists who support core business functions that require deep institutional knowledge and consistent legal support.

Third, the technology, processes, tools, and templates that support those people and keep the business running efficiently.

Law firms remain extremely important, but I’ve also learned that flexible legal talent is a powerful and often underutilized resource for GCs.

I’ve had tremendous success using flexible legal resources during maternity leaves, periods of attrition, and other transition periods. They helped us maintain service levels without overburdening the internal team.

And many of those flexible resources were former in-house counsel who already understood the pace, expectations, and operating style of an in-house environment.

Technology is also evolving rapidly. Today, GCs are managing AI from multiple angles simultaneously: establishing company guardrails, advising on how AI is embedded into products and services, and using AI internally to automate lower-value work like NDAs, due diligence, and discovery so legal teams can focus on more strategic work.

Trista Engel:
That’s such a strong framework because it really captures the full ecosystem of legal resourcing—internal teams, outside counsel, flexible legal talent, and technology.

It’s also a much more sustainable and forward-thinking way to resource a legal department while preventing burnout and allowing in-house lawyers to focus on higher-value work.

Alisha Cieslak:
Exactly. The GC toolbox now contains all of these options.

Sometimes there’s hesitation because onboarding new resources takes time, but that time investment is going to happen regardless. If you can direct that effort toward your highest and best use, it helps reduce burnout, overload, and disengagement.

And the work becomes much more fulfilling for in-house lawyers when they’re focused on strategic discussions instead of constantly being in the trenches.

Trista Engel:
If you weren’t an attorney, what would you be?

Alisha Cieslak:
I truly love being a general counsel, so I’d probably still work somewhere at the intersection of law, business, and policy—perhaps around food, nutrition, or hospitality.

But if I really stretch, I’d probably be a sommelier or a professional organizer.

Whether it’s a chaotic closet or a complicated wine list, I have a natural drive to bring order, structure, and a high-quality experience to everything I touch.

I’m also an amateur pasta chef at home, so maybe I’d commercialize that.

Trista Engel:
You are truly multifaceted. And I’ve never heard anyone connect being a sommelier and a professional organizer before, but somehow it makes perfect sense.

Trista Engel:
And the bonus question: Paragon turns 20 this year. What’s one memory from 20 years ago that still stands out to you?

Alisha Cieslak:
Twenty years ago, I was graduating from college and heading to law school.

Looking back, I’d tell that version of myself to hold onto the curiosity, ambition, and desire to make an impact. And honestly, that’s the same enthusiasm I’m carrying into this next chapter of my career in 2026.

Trista Engel:
I love that. Taking your own advice is one of the hardest things to do.

Well, this was such a great conversation, Alisha. Thank you so much for joining me today.

Alisha Cieslak:
Thank you so much, Trista. It’s been a pleasure.

Trista Engel:
All right, that’s a wrap on today’s episode of GC Sidebar. Catch more great conversations at paragonlegal.com. Thanks for tuning in.