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Rapport prompt: “What would make this a valuable conversation for you today?”Context: “When have you felt most like yourself lately?”Permission: “Is it okay if we explore what sits underneath your decisions and habits?”
Core beliefs and principles: What they see as right/wrong, fair/unfair.Priorities and trade-offs: What they choose when they can’t have everything.Non‑negotiables: Lines they won’t cross.Definitions of success/failure: What “a good life” or “a good day” means to them.Moral intuitions: Gut reactions to dilemmas (e.g., honesty vs. loyalty).Role models and heroes: Who they admire and why.Emotional triggers: What reliably makes them proud, angry, or moved.Time/money attention: How they allocate scarce resources.Stories they tell: Moments they’re most proud/ashamed of.Boundaries: What they protect (e.g., family time, integrity).Aspirations: Long-term goals and the “why” behind them.
If you had to turn your beliefs into 3 personal principles, how would you phrase them? What small behavior this week would best honor these principles?If you have a wish to have a super power what would it be? Why do you want to have it?If your best friend described your character, what 3 traits would they name?When have you felt most proud of who you were, not just what you did?Complete the sentence: I am the kind of person who…If you only have 1 more day to live,What value am I honoring today?What activity, person, or cause would I dedicate my last day to?How would I naturally express myself if this were my last chance?What strength, lesson, or ability can I share before the day ends?
“When you’re short on time, what gets done first, and what waits?”“If you had to choose between meeting a deadline and maintaining quality, how do you decide?”Follow-up: “What trade-off there feels hardest? Why?”
“What’s a line you don’t cross at work/in relationships?”“What would make you say ‘no’ even if everyone else said ‘yes’?”
“What does a ‘good day’ look like for you?”“How do you define success five years from now?”
“A close friend lies to avoid trouble. Do you confront them or protect them? How do you think it through?”“You can win by bending a rule slightly. Do you do it? Why/why not?”
“Who do you admire, and what about them stands out?”“What qualities do your favorite teammates/friends share?”Who are your hero? What makes them special with you?
“What reliably makes you angry? What does that reaction protect?”“What recent moment made you feel deeply proud?”Tell me about a place you want to spend the rest of your life? Any special things from that place attract you?If you have a collection with no limit on the budget, what will it be about? Why it is matter to you? What impact do you want this collection to have, and on whom?Follow up questions:Which materials and why?How would you measure success beyond revenue?Who do you collaborate with first, and why them?...
“If you got an unexpected free day, how would you spend it?”“What do you never mind paying extra for? Why?”
“Tell me about a decision you’re glad you made even though it was hard.”“What’s a regret that changed how you act now?”Who is the person that make the most impact with you since you started your career? What was the story which make that person special?Share with me about the movie that make the most impact to you? What was that movie about?
Energy orientation: Solitude vs. social refuel; interaction appetite.Information style: Concrete facts vs. patterns/possibilities.Decision style: Speed vs. certainty; principle-based vs. outcome-based.Structure preference: Plans/routines vs. flexibility/spontaneity.Conscientiousness: Follow-through, reliability, detail orientation.Openness: Novelty seeking, curiosity, creativity.Agreeableness: Collaboration, empathy, conflict style.Emotional regulation: Stress response, recovery habits.Risk posture: Comfort with uncertainty and stakes.Autonomy needs: Direction vs. freedom balance.
“How do you recharge after a demanding day—people or quiet?”“Ideal collaboration cadence for you (daily standups, weekly deep dives, async docs)? Why?”
“When deciding, do you start with data or with a gut sense of the pattern? Example.”“Do you prefer deciding quickly with 70% info or slowly with 90%+? When does each work best?”
“What level of planning makes you effective (detailed plan vs. broad direction)? Example of each.”“How do you behave in high ambiguity? A time you thrived vs. struggled.”
“Describe a complex goal you delivered end-to-end. What habits enabled it?”“What typically derails your follow-through? Your countermeasures?”
“What new idea/skill excited you recently? What did you do with it?”“How do you seek feedback, and what do you do when it stings?”
“How do you give hard feedback? Receive it?”“What’s your conflict default—avoid, confront, mediate? When does it serve/hurt you?”
“Early signs you’re overloaded? What’s your reset plan?”“What pressure improves your performance—and what kind degrades it?”
“Biggest smart risk you’ve taken at work. How did you size it?”“What’s your ideal autonomy: clear goals and free methods, or close guidance?”
Curiosity patterns: Topics/tasks that spark “I want to know more.”Flow activities: Work that makes time disappear.Intrinsic enjoyment: Tasks done without external rewards.Preferred problems: Types of puzzles they keep returning to.Attention share: Where spare time/reading/podcasts go.Admired work: Roles/outputs they find cool or meaningful.Energy signatures: Activities that reliably energize vs. drain.Skill–interest gap: Things they like but haven’t mastered (yet).Growth itch: Areas they feel compelled to try/level up.Avoidance patterns: Topics/tasks they skip (anti-interests).“What topics or tasks do you research for fun?” Why?“When did you last lose track of time doing something?” What were you doing?“What problems do you never tire of solving?”“Which parts of your current role do you look forward to most? Least? Why?”“What would you do on a free day with no obligations?”“Whose job would you try on for a month?”“Which activities leave you more energized after doing them?”“What do you avoid even when it’s important—what about it turns you off?”“What are 3 skills you’re excited to build this year? Why these?”“What is a small, non-obvious skill or habit that has significantly improved your life, and why?”What's a small change you've made in your daily routine that has made a big difference in your well-being?
Map each domain to choices you can change now:Values → Boundaries, decision principles, purpose lensInterests → Project selection, learning plan, exposure experimentsPersonality → Workstyle agreements, tools/rituals, team/process designLook for alignment sweet spots:High-values alignment + high-interest + personality-fit context = sustainable performance/engagement.Watch for friction patterns:Value–role conflict (e.g., integrity vs. sales pressure)Interest–task mismatch (enjoyment low, proficiency high → delegate/rotate)Personality–process mismatch (need for autonomy vs. micromanagement)
Why → Vision, mission, values → Values, Interests, PersonalityWho → Target users & their problemsWhat → Solution & value propositionHow → MVP & success metricsLaunch → Test & validateScale → Iterate & grow
Define your Values (principles you won’t compromise) Define your Interests (topics, industries, causes you want to be associated with) Define your Personality (tone, style, voice, e.g., “practical & direct” or “empathetic & inspiring”) Define your Skills (what you’re known for and can credibly demonstrate)
Identify your target audience (who you want to influence: recruiters, peers, clients, mentees, companies) Understand their needs and pain points (what they seek in someone like you) Map out where they spend attention (LinkedIn, conferences, communities, podcasts, etc.)
Define your unique value proposition: what you offer that others don’t Craft a personal tagline (1 sentence that captures you) Decide your brand archetype (e.g., Mentor, Explorer, Builder, Challenger) Gather evidence of credibility (case studies, testimonials, achievements)
Write a short bio (2–3 sentences for intros) Write a long bio (1–2 paragraphs for profiles or pitches) Define your content themes (3–5 recurring topics you’ll talk about) Decide your tone of voice (formal, friendly, bold, thoughtful, etc.)
Optimize online profiles (LinkedIn, GitHub, personal site, etc.) Build a content plan (posts, blogs, talks, videos) Engage in communities & networking (share, comment, collaborate) Seek speaking or publishing opportunities (conferences, articles, podcasts)
Create signature projects (portfolio, frameworks, open-source, training) Collect testimonials or recommendations
Questions used for coaching
Foundation: Build safety and context
Values
What in someone’s mind reflects their values
Core beliefs and principles
Priorities & trade‑offs
Non-negotiables & boundaries
Success & meaning
Moral dilemmas (scenario-based)
Role models & admiration
Emotions & triggers
Money/time choices
Emotional triggers - Stories & defining moments
Personality
What in someone’s mind reflects their personality (workstyle)
Energy & interaction
Information & decisions
Structure & planning
Conscientiousness & follow-through
Openness & learning
Agreeableness & conflict
Emotional regulation & stress
Risk & autonomy
Interest
What in someone’s mind reflects their interests
Putting VIP together in practice
Build a personal brand as a product
Simplified View
If you want a leaner sequence to remember on how to build a product:
Personal Brand as a Product — Step-by-Step Checklist
1. Foundation (Why you, why now?)
2. Audience Discovery (Who is this for?)
3. Positioning (What makes you stand out?)
4. Messaging (How will you communicate?)
5. Visibility (Where will you show up?)
6. Proof of Work (What demonstrates your brand?)
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