The knowledge economy, an “economic system in which… the key element of value is the greater dependence on human capital and intellectual property as the source of innovative ideas, information, and practices,” (Wikipedia) is on it’s way out. In today’s fast-paced, information-saturated world, knowledge alone isn’t enough.
The most valuable professionals aren’t just those who know the most—they’re the ones who can make the best decisions and solve the toughest problems. As Adam Grant, author of Hidden Potential, puts it, “The hallmark of expertise is no longer how much you know. It’s how well you synthesize.”
For Executive Assistants (EAs), Chiefs of Staff (CoS), and other right-hand partners, this couldn’t be more relevant. Your role isn’t just about managing tasks—it’s about managing complexity. It’s about knowing what matters, what doesn’t, and how to guide your Executive’s focus in the right direction. More than ever, EAs and Force Multipliers must evolve into strategic problem-solvers who not only anticipate challenges but also proactively find solutions.
We’ve moved beyond the knowledge economy into what Dan Shipper, CEO and cofounder of Every, calls the “allocation economy,” where the ability to prioritize and deploy resources effectively is the real competitive edge. In his article, “The Knowledge Economy Is Over. Welcome to the Allocation Economy,” Shipper explains, “We’ll go from makers to managers, from doing the work to learning how to allocate resources—choosing which work to be done, deciding whether work is good enough, and editing it when it’s not.”
As an Executive Assistant or Chief of Staff, you’re at the center of this dynamic, constantly making judgment calls on what deserves attention, time, and action, and helping your Principal do the same.
Judgment and Discernment Defined
Let’s start with the basic definitions.
Judgement (according to DIctionary.com) is simply “the ability to judge, make a decision, or form an opinion objectively, authoritatively, and wisely, especially in matters affecting action.” Judgment is the ability to make decisions, evaluations, or conclusions based on available information. It is often associated with assessing situations, people, or choices and determining what is right, wrong, good, or bad. Judgment can sometimes carry a negative connotation if it is rushed, biased, or based on assumptions rather than understanding.
Discernment (Dictionary.com) is the “ability to recognize small details, accurately tell the difference between similar things, and make intelligent judgements using such observations.” Discernment is a deeper, more thoughtful process of perceiving, understanding, and interpreting a situation before forming a judgment. It requires wisdom, intuition, and patience to see beyond the obvious and consider nuances. It is more about seeking truth, clarity, and insight rather than making a quick determination.
Discernment and judgement work together. Discernment comes first – it helps you gather deeper insights. Judgement follows – you use discernment to make a well-informed decision. Both are critical for Force Multipliers.
In The Almanack of Naval Ravikant by Eric Jorgenson, Ravikant is quoted as saying, “I would love to be paid purely for my judgement, not for any work. I want a robot, capital, or computer to do the work, but I want to be paid for my judgment.” Me too, Naval. Me too.
Problem Solving, Judgement, & Discernment: The Competitive Edge That Sets You Apart
As I was reading Exit Interview by former Amazon employee Kristi Coulter, she reminded me of Amazon’s lifeboat exercise, otherwise known as a meeting where management “stack ranks” employees based on who they would keep on a lifeboat and who they would throw overboard. It’s similar to the idea of going into battle with your co-workers. Who would you want by your side?
As a leader, the employees and team members I wanted to go “into battle with” were those who were resilient, insightful, self-motivated, solution-oriented, adaptable problem solvers. It didn’t matter their tenure, job specific role, or title. What mattered was whether or not they could solve problems and take action.
Okay, maybe we need less ruthless analogies, but the sentiment remains the same. Are you this person for your Executive and your team?
Joe Hudson’s insight applies here as well: “Your job isn’t to work hard, your job is to have great ideas.” You can be the hardest-working, strategic business partner in the world, but if you’re focused on the wrong priorities, that effort is wasted. The most impactful EAs and Chiefs of Staff aren’t just doers—they’re thinkers, advisors, and problem-solvers who bring clarity to complex issues.
And in the future, problem-solving will be one of the most valuable skills any professional can have. Automation and AI will take over repetitive tasks, but the ability to analyze complex issues, make judgment calls, create solutions, and lead others to adapt and adopt changes will always be in demand.
How to Strengthen Your Judgment, Discernment, and Problem-Solving Skills
Building these skills takes practice, reflection, and intentional learning. Here’s how you can develop this critical expertise:
1. Develop Self-Awareness
- Recognize your biases and blind spots.
- Notice when emotions cloud your decision-making.
- Regularly reflect on past choices—what worked, what didn’t, and why.
2. Become a Better Problem-Solver
- Break problems down into their root causes instead of just addressing symptoms.
- Use frameworks like first principles thinking (reducing a problem to its most basic truths) to find innovative solutions.
- Apply second-order thinking (considering long-term consequences) to ensure decisions don’t create bigger problems later.
- Approach problems with a solution-oriented mindset—instead of just flagging issues, present well-thought-out options.
3. Ask Better Questions
- Use Socratic questioning to uncover deeper truths.
- Challenge assumptions: Is this true? What’s missing? What are the alternatives?
- Seek clarity before acting—don’t just take things at face value.
4. Learn from Experience
- Keep a decision journal to track choices, reasoning, and outcomes.
- Analyze both mistakes and successes to refine future judgments.
- Observe and learn from people with strong discernment and problem-solving skills.
5. Gather Diverse Perspectives
- Avoid echo chambers—seek out opinions that challenge your views.
- Engage with people from different industries and backgrounds.
- Read widely—books, case studies, and news from multiple sources.
6. Practice Pattern Recognition
- Identify trends and recurring themes in challenges you face.
- Look at past situations to see how similar problems played out.
- Strengthen intuition by paying attention to past decisions.
7. Strengthen Critical Thinking
- Separate facts from emotions and assumptions.
- Embrace ambiguity—great judgment isn’t about having all the answers but making the best decision with available information.
- Use decision-making models like OODA (Observe, Orient, Decide, Act) to think through situations methodically.
8. Seek Wise Counsel
- Find mentors or trusted advisors who challenge your thinking.
- Study how great leaders make decisions.
- Engage in thoughtful discussions and debates.
9. Slow Down When Necessary
- Not every decision needs to be made instantly—pause and reflect when needed.
- Use the 10/10/10 rule: How will this decision feel in 10 minutes, 10 months, and 10 years?
10. Trust Your Gut—But Verify
- Intuition is valuable but should be tested against logic and evidence.
- Experience strengthens gut instincts—validate them through analysis.
11. Stay Curious and Keep Learning
- Expose yourself to new ideas, industries, and challenges.
- Take on projects that stretch your thinking.
- Keep refining your ability to see nuances and make informed decisions.
The Future Belongs to Problem-Solvers
As an Executive Assistant, Chief of Staff, or Force Multiplier, your ability to cut through the noise, identify what truly matters, and guide your Executive’s decisions is what makes you invaluable. But beyond that, your role is evolving. Executives increasingly need trusted partners who don’t just execute tasks but solve high-level problems.
The future belongs to those who don’t just collect information but know how to connect the dots, make sound judgments, and solve problems proactively. AI can process data, but only humans can think critically, navigate ambiguity, and apply discernment to real-world situations.
Want to future-proof your career? Start by sharpening your judgment, problem-solving abilities, and decision-making skills.
Need help? Consider joining The Force Multiplier Academy! The Force Multiplier Academy is a career accelerator for right-hand partners. Through over 40 hours of on-demand course content, live group coaching calls, guided strategic exercises, and 25+ tools and resources you can implement immediately to get results, you’ll leave the Academy ready to increase the effectiveness of your Principal, impact the bottom line, land that promotion or next job, confidently navigate your career, and more. Click here to learn more.
