Mastering Deeper Thinking: 10 Tips for Smarter Conversations and Better Results

As a team coach, I often challenge leaders to think deeper and broader. Why? Deeper questions often reveal more effective and inclusive solutions. In our fast-paced world, it's effortless to succumb to reactive thinking, yet the transformation occurs when we take the time to pause, reflect, and expand our mental capabilities.

Want to elevate your leadership and team interactions? Here are 10 strategies to cultivate deeper thinking that you can apply in your next conversation or meeting.

1. Engage the Right Stakeholders

How to: Ask, “Do we have the diversity of perspectives needed to solve this problem?” Identify any missing voices—whether it’s a future client, a younger generation, or a different department. If they cannot be present, then assign someone on your team to actively represent that viewpoint. This ensures decisions are more inclusive, innovative, and future-focused.

2. Challenge Your Thinking

How to: Regularly question your assumptions. Ask yourself, “Is there another way to approach this?” or “What am I missing?” or “What model or assumptions am I using that are limiting or creating biases?”. Encouraging alternative viewpoints helps broaden your perspective.

3. Prioritize Mentally Tasking Tasks

How to: Tackle the most challenging tasks when your mind is sharpest—often in the morning. Save repetitive or less demanding activities for later. When working with a team, be sure to separate a problem-solving process from the general updates and task assignments. Deep thinking requires focused energy.

4. Seek Emotional Intelligence

How to: Pay attention to emotions—yours and others. Ask, “How do I feel about this?” or “What might this person be experiencing?” Emotional insight leads to more compassionate and effective decisions.

6. Listen More Than You Speak

How to: During conversations, aim to listen actively for 75% of the time. Ask open-ended questions like, “Can you tell me more?” Or “and what else?” Resist the urge to jump in with your added thinking or solutions. Give each person the space to share and adjust for clarity. Hearing and respecting others makes them more open to working together on a solution that may not have been theirs.

7. Use the Feynman Technique

How to: Break complex ideas down as if teaching a five-year-old. Simplifying concepts not only clarifies your understanding but also uncovers gaps in your knowledge.

8. Work on Subduing Your Ego

How to: Approach every situation with humility. Replace “I know this already” with “What can I learn here?” Leading with curiosity cultivates trust and creates opportunities for deeper conversations.

9. Practice a Deeper Point of View & Values

How to: Zoom out. Ask, “What’s the bigger picture?” or “How will this impact others long-term?” or "What's really going on here?" Bring your company values into the conversation: "What might our values say if they could talk?" These types of questions encourage strategic thinking and help you identify win-win solutions.

9. Engage an AI Co-Pilot

How to: Treat AI as a valuable member of your team and a brainstorming partner. Use generative AI tools to enhance ideation and creativity by prompting with clear context. Give it a role to play; provide background reports or data for it to review in advance; let it be the role or department in the room that was unable to attend.

You can ask your AI all the questions above. Other examples are, “What are three fresh approaches to solving [a specific problem]?” or “Draft a list of questions to deepen my team’s thinking on [x].” Be specific, include details about your goals, and refine responses as needed. AI can help uncover perspectives you might not have considered and save valuable time.

10. Follow Up with Plans Timely

How to: Make a habit of revisiting decisions and plans promptly. Whether it’s a project update or a check-in after a meeting, timely follow-ups ensure accountability and keep deeper insights actionable. This prevents the stalling of subsequent steps and guarantees a concentration and dedication to ongoing enhancement. Not every solution works out as planned and it is important that revisiting results and adapting is part of the process.

Most important, keep learning and stay curious. Read books, attend workshops, or follow thought leaders who inspire you. Ask your AI co-pilot for related concepts, research, or applications that can expand your perspective of a problem you are solving. Each new piece of knowledge adds depth to your decision-making toolbox.

Why It Matters

Deep thinking isn’t just a skill—it’s a superpower for today’s leaders. By committing to these strategies, you’ll unlock fresh perspectives, strengthen team dynamics, and create solutions that resonate across your organization.

Ready to give it a try? Take one or two questions from these strategies and ask them in your next meeting or conversation. Don't forget to ask your AI co-pilot too. Small shifts lead to big results.

Let’s elevate the way we think—and lead.

Are you interested in learning more about integrating AI into your team's processes and innovation? Please reach out.

About the Author

Leanne Terrace is an executive leadership coach, AI strategist, and thought leader with a passion for helping professionals maximize their impact with minimal time investment. With extensive experience in coaching leaders and guiding teams, Leanne combines her expertise in AI tools with a practical approach to personal branding and visibility. Known for her engaging and motivational style, she empowers clients to confidently share their insights and expand their influence.

Leanne’s latest initiative, "AI Leveraged Leader," equips leaders to harness AI for efficiency, growth, and clarity. Her team of experts helps identify the best tools to maximize the ROI for team productivity, innovation, and execution.