To succeed in today’s workplace, you must think like a CEO—whether you’re just starting your career or negotiating an executive contract. Jotham Stein, Principal of the Law Offices of Jotham Stein and author of Negotiate Like a CEO, joins podcast host Molly McGrath to explore how employees at every level can apply CEO-level strategy to protect themselves, plan ahead, and negotiate with confidence.
With over 25 years of experience representing employees from entry-level to the boardroom, Jotham breaks down what it takes to own your power in any professional setting.
Why You Should Think Like a CEO from Day One
One of the strongest lessons Jotham shares is this: always think like a CEO when approaching your employment agreement. CEOs never walk into a job blindly. They negotiate protective clauses—like severance packages, termination terms, and bonuses—before they sign anything. Employees should do the same.
Many professionals wait until things go wrong to think about their rights. But by that point, options may be limited. If you approach your job like a CEO does—strategically, thoroughly, and with your long-term well-being in mind—you can avoid the pitfalls that catch so many off guard.
Think Like a CEO by Planning for the Unexpected
The best way to stay protected in your role is to think like a CEO and plan ahead. Older companies often have procedures for offboarding and employee exits. But younger startups or fast-growing firms may not.
This lack of structure means you could find yourself without a safety net if leadership changes or layoffs happen. Don’t rely on HR to do all the work for you. Ask about performance expectations, severance terms, and internal grievance processes before signing your offer.
As Jotham advises: “Hope for the best, but prepare for the worst.” A little foresight today can protect your future.
Do Your Research and Leverage Your Value
Thinking like a CEO also means doing your homework. Before you accept a position, research the company thoroughly—its leadership team, turnover trends, financial backing, and employee reviews. Sites like Glassdoor, LinkedIn, and even news archives offer valuable insights.
If you discover red flags, consider whether it’s worth it. If everything checks out and you have unique value to offer—such as a rare skillset or competing job offer—use that as leverage.
CEOs negotiate from a place of strength. You should, too. Even if you’re new to the workforce, your ability to think like a CEO and advocate for yourself will set the tone for your entire career.
Maintain Emotional Control During Negotiations
One of the most overlooked workplace skills is emotional intelligence. When navigating interviews, salary conversations, or tough feedback, it’s important to stay calm and grounded.
Letting emotions take over can cost you credibility—or even your job. Instead, think like a CEO and treat every conversation as a professional exchange, not a personal battle.
CEOs make decisions based on facts, not feelings. Adopting that same mindset helps you stay focused on the outcome you want, even in high-pressure situations.
The Hidden Costs of Staying Silent
Workplace power dynamics often make people afraid to speak up. However, failing to negotiate early can lead to long-term career dissatisfaction. Some managers don’t train or support new hires properly, especially in toxic work cultures.
That’s why one of the most important lessons is to think like a CEO and speak up early. If you sense poor communication, unclear expectations, or limited growth opportunities, don’t stay silent. Seek clarity. Ask questions. And if necessary, walk away.
Well-informed, empowered employees don’t wait for permission to advocate for themselves. They move forward, find better opportunities, and create success on their own terms.
Final Thoughts
You don’t have to sit in the corner office to think like a CEO. Whether you’re in HR, marketing, legal, or sales, CEO-style thinking means protecting yourself, planning ahead, and negotiating with purpose.
Want to take this even further? Visit HiringAndEmpowering.com to explore our free tools, templates, and negotiation tips. Our blog features actionable strategies to build a fulfilling, protected career, and our weekly podcasts dive deeper into workplace trends, legal tips, and leadership growth.
Written by Molly Hall McGrath