Julia Schmidt, author of The Executive Support Guide to Building a Successful Career Strategy, explains how mastering a new mindset is key to futureproofing your career
Key Takeaways:
The ‘Five Whys’ method uncovers root causes of problems.
Analytical thinking is the number one skill for 2025.
Executive support roles are shifting from task execution to strategic advisory through analytical insight.
Analytical thinking has emerged as the most critical skill for professionals across all industries. According to the World Economic Forum’s Future of Jobs Report 2025, nearly 70% of employers now rank it as a top priority, placing it above creativity, leadership, and resilience.
As technology accelerates, the ability to assess complex information, solve problems, and make sound decisions becomes essential not only for navigating change but for creating value where machines fall short. For those of us working in administrative and executive support roles, sharpening our analytical thinking isn’t just a competitive edge; it’s a strategic imperative. With business environments becoming more complex and data-driven, the ability to analyze information, identify patterns, and support decision-making with clarity has become a key differentiator. It enables professionals to navigate uncertainty, adapt to evolving technology, and contribute meaningfully to organizational goals.
Whether it’s preparing a briefing, managing stakeholders, or improving workflows, applying analytical thinking empowers executive support professionals to go beyond task execution and become trusted advisors. And the good news? Like any other skill, it can be learned and refined – with practice, intention, and the right mindset.
Choosing an Analytical Mindset
Let’s be honest, how often do we jump to conclusions based on instinct? I’ve done it too. But I’ve learned that pausing to ask better questions often leads to better outcomes. That pause is the start of analytical thinking. One of the most important elements in developing an analytical mindset is strengthening our ability to pause and refrain from coming to conclusions based solely on gut feelings and without dedicating time to understanding the problem or situation, assimilating facts and trends, and adopting a more structured and disciplined approach to handling any situation.
Enhancing our analytical mindset will help us structure a mental process governing problem-solving and decision-making across multiple domains. It’s a form of brain power, also called analytical intelligence, which embraces skills like analysis, comparison, evaluation, critique, and judgment abilities.
It’s part of our daily life at work and business:
- Enhance communication with data-driven precision
- Support problem-solving with result-oriented strategies
- Foster compromise through critical thinking
- Improve business efficiency via data analysis
Provide significant insights for informed decision-making in research work
Applying Analytical Thinking to Drive Business Impact
These are real examples of how I’ve seen or experienced executive support professionals making a difference by thinking analytically. You might recognize yourself in some of them.
1.Translating data into executive insight
Use dashboards, internal reports, or AI tools to extract strategic signals from data, summarizing only what is relevant to the executive’s current priorities. Turn scattered numbers into business narratives that clarify opportunities, risks, or decisions.
Impact: Increases decision speed and alignment with corporate KPIs.
2. Integrating analytical reviews into leadership routines
Structure key weekly and monthly rhythms (1:1s, board prep, investor updates) with executive-grade briefings backed by curated data. Ensure meetings shift from status reporting to strategic decision-making.
Impact: Positions the Assistant as a partner in shaping strategic cadence and alignment.
3. Mapping stakeholders and communication risk
Analyze power–interest grids, message impact, and timing to proactively advise your executive on how to adapt messaging across internal and external audiences (e.g., employees, board, media).
Impact: Reduces reputational risk and strengthens stakeholder relationships.
4. Conducting analytical calendar and workflow analysis
Use historical data and contextual foresight (product cycles, regulatory timelines, market events) to proactively shape the executive’s calendar around strategic imperatives, not just requests.
Impact: Elevates prioritization from reactive to predictive, with better ROI on executive energy.
5. Leading post-mortem reviews with structured debriefing
After high-impact projects, events, or crises, lead structured post-reviews that identify patterns, decisions, blockers, and lessons learned, then suggest process improvements.
Impact: Builds institutional learning and eliminates repeat inefficiencies.
6. Supporting financial and vendor decisions with cost–value analysis
Evaluate supplier contracts, subscriptions, and vendor KPIs using a comparative matrix (price, value added, ESG impact, stakeholder feedback). Include risk-based reasoning in procurement decisions.
Impact: Ensures procurement aligns with long-term value, not just short-term cost.
7. Utilizing AI tools for diagnostic and prescriptive insights
Use AI tools not just for drafting but for generating “what-if” scenarios, risk analysis, and proposal alternatives. Pair AI speed with your human judgment.
Impact: Increases Assistant’s productivity and supports scenario-based thinking.
8. Acting as a constructive challenger in decision-making
Use analytical skills to test assumptions, surface alternative viewpoints, or flag ethical concerns, especially when quick decisions carry long-term consequences.
Impact: Reduces blind spots and improves quality of executive-level decisions.
9. Designing information workflows with data integrity in mind
Audit the quality, relevance, and flow of the information your executive receives. Build systems to reduce data noise while ensuring the right signals surface at the right time. Impact: Shields the executive from overload and supports signal-based leadership.
10. Evaluating executive dashboards and reporting tools for relevance
Periodically audit the dashboards, trackers, or reports your executive receives, asking: Is this helping the executive make faster, better decisions? Identify outdated metrics, missing KPIs, or irrelevant data points. Work with internal teams to improve the signal-to-noise ratio and align reports with evolving business goals.
Impact: Enhances decision quality by ensuring reports reflect real-time priorities and reduce cognitive overload.
The Power of Asking “Why” Five Times
One of my favorite tools and one I use often is the “Five Whys” technique. Simple, powerful, and surprisingly effective, it is a method that helps us uncover the root cause of a problem by asking “why?” repeatedly.
Originally developed by Toyota as part of its lean manufacturing philosophy, this approach is now widely used across industries to promote structured problem-solving.
How it works
When faced with a problem, instead of jumping to conclusions, you ask, “Why did this happen?” Then, based on the answer you receive, you ask “why” again. You repeat this process up to five times or until you reach the root cause that is actionable and meaningful.
Example
Problem: The executive’s report was submitted late.
- Why was the report late?
Because the data was not ready on time.
- Why wasn’t the data ready?
Because the team didn’t receive input from one department.
- Why didn’t that department provide input?
Because they didn’t know the deadline.
- Why didn’t they know the deadline?
Because it wasn’t communicated clearly.
- Why wasn’t it communicated clearly?
Because there is no standardized reporting schedule.
Root Cause: Lack of a standardized reporting process.
With this insight, the solution is no longer about chasing missing files or sending reminders but rather about establishing a clear, consistent process that prevents delays altogether.
The Five Whys method encourages you to slow down and think deeply so you solve the right problem, not just the visible symptoms. For Executive Assistants, it’s a practical way to strengthen your analytical lens and offer strategic solutions.
The Five Whys method encourages you to slow down and think deeply so you solve the right problem
Boosting Your Analytical Thinking Skills
“Freethinkers are those who are willing to use their minds without prejudice and without fearing to understand things that clash with their own customs, privileges, or beliefs. This state of mind is not common, but it is essential for right thinking.” – Leo Tolstoy
This quote reminds us of the importance of staying curious, challenging the status quo, and embracing diverse perspectives. Analytical thinking thrives when we remain open to different viewpoints, ask thoughtful questions, and stay committed to learning. It’s not about knowing all the answers but about knowing how to frame the right questions.
Here are some practical strategies to keep developing your analytical mindset:
Be an active learner
Regularly attend webinars. Take short online courses on analytical thinking. Join cross-functional project teams to expand your knowledge base and sharpen your critical thinking.
Ask the “why” behind the “what”
Use the Five Whys technique to dig deeper into problems and uncover root causes. Don’t settle for surface-level answers.
Strengthen your communication with logic and structure
Practice explaining your ideas clearly, supporting your proposals with data, logic, and evidence. Avoid overcomplicating, as clarity is power.
Visualize to understand
Embrace tools like ChatGPT, ChartAI, or Whimsical to turn data into charts, diagrams, or simplified narratives. This helps you and others see patterns, compare options, and make better decisions.
Embrace diverse viewpoints
Promote collaborative analysis. Invite feedback from others with different experiences to test your assumptions and refine your thinking.
Call to Action: Think Smarter, Lead Stronger
Analytical thinking is no longer just a desirable skill; it’s your competitive advantage. When AI can generate content and process data at scale, your value lies in asking the right questions, challenging assumptions, connecting the dots, and turning complexity into clarity. That is the power of analytical thinking. If you want to elevate your role, influence strategic outcomes, and stay future-relevant, start treating analytical thinking as a daily practice and not just an occasional skill. Examine patterns. Interrogate problems. Visualize ideas. Interpret data. Challenge defaults. And most importantly, make space to think before you act.
Start small, stay consistent, and choose progress over perfection. Because the more you practice thinking analytically, the more you lead with intention, precision, and impact.
Now it’s your turn.
What decision can you make better today by pausing to ask “why”? What process can you improve by seeing it through a more analytical lens?
The future of your career isn’t just automated; it’s analytical, and it starts with you.
