“Restructuring ideas don’t sleep —because business doesn’t live in theory. It lives in reality.”
In this Spotlight, Pivot’s Stephanie Wickouski shares insights from her career in bankruptcy and restructuring law: where strategy, finance, and human judgment converge.
The Role and Approach: Strategic Advice in Context
Q: What does “strategic advice” mean in bankruptcy and insolvency work?
SW: Strategic advice means formulating a course of action to navigate a distressed situation to maximize value and protect a client’s interests– all within a challenging business environment and complex legal system. Strategy demands innovation, while striking a balance between legal precision and business pragmatism.
Bankruptcy strategy means using the legal system to accomplish business objectives — and identifying paths forward that others might overlook.
Q: What initially drew you to this field, and how has your perspective evolved?
SW: I’ve always been fascinated by why some businesses succeed and others fail. The summer before I started law school, I read a Wall Street Journal article about a major retail chain that collapsed because bankruptcy laws were too rigid to allow reorganization.
I knew then that I wanted to be right there — at the intersection of law, business, and finance. Over time, I’ve seen bankruptcy law, business and finance become inextricably interwoven. On a macro level, bankruptcy law evolves with business realities and financial innovation. On a micro level, no advice should be given — and no decision made — without seeing all three dimensions simultaneously.
Q: When advising clients in distress, what’s your first step?
SW: Every situation has many layers — business pressures, financial realities, and both economic and non-economic stakes. Before developing a strategy, you have to understand the full landscape: what’s at risk, who’s at the table, and what your client truly wants to achieve.
This starts with hearing everything that a client wants to tell you. Don’t rush to be directive. Ask questions but don’t ever cut a client off. If you don’t let someone talk, you’re going to miss something important.
Navigating Complexity
Q: Can you share an example of a complex or challenging situation you’ve helped navigate?
SW: I once advised a client in a crisis involving multiple jurisdictions, competing creditor groups, and intense public scrutiny. The complexity wasn’t just legal or financial — it was geopolitical and personal.
I drew on a principle from Harvard Business School’s Deepak Malhotra and Max H. Bazerman’s Negotiating Genius: focus on aligning interests rather than emphasizing opposition. By identifying even partial alignment, you can achieve outcomes that far exceed what a purely adversarial approach can deliver. Of course, alignment isn’t always perfect. You’ll always have holdouts — so you need a plan (or two) for managing them. As a former bankruptcy judge once said, “Never underestimate hold-up value.”
Timing is everything. Know when to make a deal — and don’t let the moment pass. Leverage shifts fast, and the best agreements happen when your position is strong, but the counterparty still has something to lose. When the other side has zero leverage, they have nothing to lose. Perhaps counterintuitively, that is not the best time to negotiate.
Clarity and composure are critical. High-pressure environments make people emotional — even professionals. I once watched a major Chapter 11 case derail because the lead negotiator – a prominent restructuring professional – lost his cool in a creditors’ meeting. The best decisions are made in the clear zone — when you are calm, steady, focused.
Q: How do you develop long-term strategies in fast-changing situations?
SW: Restructuring ideas don’t sleep. Today’s solution can be tomorrow’s obstacle. Strategy is an iterative process that requires continual recalibration.
Q: How do innovation and strategic thinking shape the future of restructuring?
SW: Innovation drives this field. Data analytics, generative AI, and cross-disciplinary collaboration are how we assess risk and value.
These tools improve insight — they don’t replace judgment.
Personal Reflection and Career Advice
Q: What do you find most rewarding about your work?
SW: It’s most rewarding to move a difficult situation to a successful resolution.
Q: What advice would you give to someone starting out in this field?
SW: My advice is the same no matter where you are in the field: Don’t listen to bad advice. Trust your intuition. Don’t let fear, greed, or outside noise override your judgment. Be a clear listener and communicator. Be diplomatic but direct. Always do your best — and never, never, never give up.
One more thing: make sure this field is right for you. Don’t stay in any profession that’s at odds with who you are — physically, intellectually, or spiritually. I’ve seen unhappy people in restructuring because the work doesn’t fit their makeup. It doesn’t have to be that way.
Final Thought
SW: At its best, restructuring isn’t about simply solving a math problem — it’s about finding a new direction when the old route no longer works.