While it seems like a casual conversation starter, answering kickstarts a sophisticated power dynamic test that most executives fail without realizing. Even when speaking with gatekeepers vs. decision makers.
Let's turn how you answer this question into your strategic advantage.
The 90-Second Reality Check
Your first 90 seconds after hearing "Tell me about yourself" will either doom you to mediocrity or establish you as a standout force against your competition.
You must artfully advance your perception, build excitement about your expertise, and distance yourself from other candidates.
But your answer isn't just about making a strong first impression—it's about engineering the power dynamics that will define your entire negotiation journey.
The interview is the negotiation, and every response shapes your leverage. I'm not conflating ideas—I'm correcting them.
These opening moments establish your executive presence, create crucial leverage points, and set the psychological foundation for every subsequent conversation.
Get your answer right, and you will transform from candidate to strategic partner. Or better yet, position yourself as the top executive that others clamber to learn from.
Get it wrong, and you'll negotiate from a position of weakness before you even reach the compensation discussion.
I often receive pushback on the 90-second time constraint:
"Jacob, how am I supposed to explain my 25-year career in a minute and a half and engineer all the required power dynamics?"
You're not.
Your answer isn't about cramming decades of your detailed past.
It's about creating momentum and keeping the conversation interesting, engaging, and valuable.
Your past matters only as context for the future you'll build together while leading in your new role.
While others recite their history, you'll focus on what matters most to them: understanding their challenges and establishing a shared purpose in solving them.
Think more sales discovery and less history biopics.
Your goal isn't to be impressive; it's to find alignment.
You must demonstrate your confidence and enthusiasm for the opportunity while leading the conversation forward with curiosity and asking sharp questions.
This approach will help you actively engineer power dynamics by becoming the problem solver instead of an evaluated candidate.
Context-Specific Examples: Adapting Your Narrative
Before diving into my recommended framing, let's look at examples of what I'd consider strong starts across different executive scenarios:
For the Growth-Stage Tech CEO Role:
For the Turnaround CFO Position:
For the Corporate Innovation Role:
Each example follows a winning pattern: Begin with relevant experience, then bridge directly into meaningful dialogue about their challenges.
This approach transforms a standard intro into a strategic conversation starter.
The Strategic Framework For Your 90-Second Story
Most executives, investors, and board members want to spend their limited time solving problems. They want to quickly assess your competence and trust you can do the job.
As such, the lightning-fast 20-second overview examples that I shared above, pivot toward leading questions about solving company priorities, and will most often suffice.
However, depending on the personality on the other side of the table, you'll also need to prepare to go deeper. Just in case.
Yes, some will want more, and you all know who you are.
Your response must cover a five-ingredient recipe that builds relevant momentum in those instances.
It's intended to be a script. Rather, it's a storytelling flow.
Credit to influence and storytelling master Ravi Rajani, who shared this framework with me years back. You'll noticed that it's adapted from every Disney movie you've ever seen.
The recipe has two parts context, followed by equal parts conflict, turning point, and transformation.
Your deeper 90-second story follows this structure:
- 40%: Context - professional foundation and skill development.
- 20%: Conflict - A key challenge you faced.
- 20%: Turning point - Your response.
- 20%: Transformation - Results and value created.
End with a targeted question that bridges the conversation to your interviewer's needs and get right back into discovery mode.
Here's my story as an example of how to structure yours:
Context:
Why this works: Establishes authentic roots in your field and shows early signs of core competencies.
Context:
Why this works: Validates expertise through others' perspectives rather than self-promotion, focusing on growth trajectory over granular details.
Conflict:
Why this works: Creates authentic connection and deeper engagement through vulnerability - many executives relate to the disconnect between success and fulfillment.
Turning Point:
Why this works: Demonstrates intentional decision-making and strategic thinking in career transitions.
The turning point also helps executives communicate short stints, getting fired, or any other friction you may dread discussing from your past experiences. It's best to address insecurities on your own terms and take extreme ownership. You smooth the pitfalls and make your journey appear more intentional and strategic.
Transformation:
Why this works: Quantifies impact and establishes relevant credibility.
Question:
Why this works: A great question shifts focus to the interviewer's needs—or, in this case, my client's ambitions.
Notice how each element flows naturally into the next, creating a narrative arc that ends by engaging your interviewer in dialogue.
Funny enough, this approach is similar to mastering a sales deal and engaging with a prospective client.
For those sales leaders reading Execs and the City today, I bet you're already great at this, but you haven't yet connected the dots for yourself.
Food for thought.
Advanced Power Dynamic Management
Understanding and controlling interview dynamics separates exceptional executives from merely qualified candidates.
Here are a few additional considerations that I'll explore in later guides on interviewing.
The Strategic Interrupt
- Create natural pause points for engagement.
- Use interruptions to gauge interest and pivot.
- Example: "That experience with turnarounds taught me... [pause] ah, well, it appears very similar to what you're working on now. Let me ask first..."
Be a Well of Information, Not a Fountain
- Hint at expertise without overwhelming.
- Create curiosity that invites questions.
- Example: "I developed a framework for this at Goldman that doubled deal flow... I'm sure we'll get into that later. Have you thought about..."
Monitor Body Language and Tone
- Match or slightly exceed your interviewer's energy level.
- Watch for engagement signals to adjust depth.
- Example: When they lean forward during a discussion of growth strategies, dive deeper into that topic. When they glance at their phone during operational details, pivot to the strategic level. "I want to be mindful about our time. We can get into those details later..."
Master situational awareness and you control the conversation.
Notice when they begin taking notes or when they transition from scripted questions to genuine dialogue. These micro-moments are where real power transfer happens.
Most crucially, recognize when they start sharing organizational challenges unprompted—this is your signal to transition from candidate to strategic partner and valuable consultant.
Miss these signals, and you've surrendered power before you even get a shot at a second call.
Red Flag Behaviors to Avoid
Even accomplished executives can undermine their position with subtle missteps that signal desperation or misalignment.
Here are the critical patterns that diminish your leverage and authority in these pivotal conversations.
The Resume Reciter
- Chronologically listing every role.
- Getting lost in historical details.
- Missing social cues about relevance.
- Failing to connect past to present.
The Title Dropper
- Over-emphasizing prestigious employers.
- Name-dropping without context.
- Focusing on roles rather than impact.
- Missing the "so what" factor.
The Agenda Pusher
- Forcing prepared stories regardless of flow.
- Ignoring interviewer signals.
- Missing opportunities to adapt.
- Failing to read the room.
The Desperation Telegraph
- Over-explaining qualifications.
- Apologizing for gaps or transitions.
- Seeking constant validation.
- Fear of rocking the boat or asking tough questions.
Watch for these behaviors in yourself, but also take notice of them in your competition.
Every time another candidate falls into these traps, they're creating space for you to demonstrate strategic value.
While they're reciting their history, you'll be solving future challenges. While they're dropping names, you'll be building authentic connections. While they're sticking to their script, you'll be leading a meaningful dialogue about what matters.
The difference between landing a transformative role and being another qualified candidate often comes down to this: Are you the executive they're evaluating, or the leader they're eager to collaborate with?
Avoid these red flags, and you'll consistently be the latter.
Mastery Levels in Action
When executing this framework, there are three distinct levels of success:
Novice Level
- The interviewer knows you're qualified and capable.
- Your experience aligns with the role requirements.
- Basic competency is established.
Intermediate Level
- Personal connection is established.
- The interviewer shares their own related stories.
- Rapport moves beyond professional credentials.
Master Level
- The interviewer begins solving challenges with you during the conversation.
- They're already envisioning you in the role.
- The power dynamic shifts from interview to consultation.
- You're projecting as the solution to their future challenges and asserting the interview journey ahead.
The journey from novice to master isn't about accumulating more answers—it's about transforming the fundamental nature of the conversation.
At the novice level, you're participating in their process. At the intermediate level, you're building connections. But at the master level, you're actively shaping the opportunity and defining the role around your unique value proposition.
The difference?
Masters understand that qualification is merely table stakes—the real game is becoming integral to their future success before an offer is even extended.
Just wait until we start talking about more about creating unfair leverage advantages later.
Beyond the 90-Second Rule
Here's what separates truly exceptional executives in this context:
They understand that sometimes the process carries on for months, especially for big-time C-Suite decisions, mergers and acquisitions, or significant re-org of behemoth conglomerates.
If you don't know how to navigate this effectively, you've likely:
- Not done the proper research on the organization, role, or individual.
- Not asked the right questions to steer the conversation into meaningful territory.
- Overestimated your qualifications or found yourself in a poor-fit process.
- Failed to demonstrate empathy and appear overly self-interested.
- Failed to be consistent in your messaging and demonstration of your leadership characteristics.
Remember: The interview process at this level isn't a sprint—it's a sophisticated dance of competence, character, and strategic alignment.
Every interaction builds upon the last, creating a compelling narrative of your leadership potential.
The most successful executives understand that their "Tell me about yourself" story evolves throughout this journey, becoming richer and more relevant with each conversation.
They recognize that while the first 90 seconds open the door, it's their consistent demonstration of strategic value that keeps it from closing.
The Power Dynamic Shift: From Good to Impressive
A crucial distinction to mention: there's a difference between leaving a good impression and trying too hard to be impressive.
Being casual, relaxed, and empathetically curious is more critical to success than proving your impressiveness through past achievements or having perfectly polished answers.
This is counterintuitive advice from what you'll get from average career coaches and content gurus.
Here's a more concise example that demonstrates this principle:
"Let's see. I led a decade-plus career as a marketing and product executive in Silicon Valley before founding and leading a multi-million-dollar senior executive career consulting company.
Now, there are several areas we can explore from here—wins, losses, and some severe screw-ups—but before we go on, I'd like to understand why we're on the phone today.
I suspect you're working on a go-to-market strategy for the coaching industry and need fresh perspectives. What are some of the challenges you're facing? How can I best show up for you today?"
This approach works because it:
- Is short and direct.
- Asserts the conversation forward.
- Provides an agenda for possible talking points.
- Creates intrigue without overwhelming detail.
- Makes the conversation about them — not you.
This is a less polished and unscripted tight answer where the emphasis is shifted to them. In a pinch, ask more questions and you'll be able to provide better answers.
The most powerful executives understand this paradox: True influence comes not from proving your worth, but from demonstrating genuine curiosity about others.
When you shift from showcasing achievements to exploring possibilities, you transform the entire dynamic.
This isn't just interview strategy; it's executive presence in action.
The ability to be simultaneously accomplished and approachable, confident yet curious, is what separates truly influential leaders from those who merely hold senior titles.
By making the conversation about them while maintaining your proven track record as context, you create the perfect conditions for authentic connection and strategic alignment.
In the end, the most impressive thing you can do is stop trying to be impressive.
Focus instead on being genuinely interested in their challenges and authentically eager to solve them together.
That's how you turn a standard interview into a compelling conversation about the future.
Next Steps
Before our next deep dive on answering "What's next for you?", your homework is to:
- Write your 90-second pitch following the context, conflict, turning point, and transformation approach.
- Practice with friends, family, or mentors until it feels natural.
- Start a standing weekly meeting with a handful of other executives in transition or preparing for networking events and practice with each other.
- Create at least three variations for different strategic contexts.
- Record yourself and analyze your delivery.
Remember: You're not there to talk about you, even when the question is "tell me about yourself." You're there to create a strategic opening to discuss their challenges and how you can solve them.
Stay fearless, friends.
