Own Your Story, Build Your Leverage

The "Why did you leave?" question is a trap. Master strategic vulnerability to own your narrative, build trust, and gain critical leverage in executive interviews.

"Why did you leave?

Four words that make even seasoned executives sweat.

Even as a (mostly) objective confidant for thousands of executives, I've had to pull on my best mud boots to trudge through the sticky situations leaders delicately try to explain when looking for their next opportunity.

Sometimes, you're frustrated with hostile working conditions.

Sometimes, the performance expectations are untenable.

Sometimes, you are the one who created hostile working conditions and untenable expectations, and you're running from your self-inflicted mess.

Sometimes, it's just time.

Then there are the times when non-performance factors come into play, such as a spouse taking a new role or a lifestyle change to live closer to family. Babies, children's education, work visas, restructurings, aging parents, sabbaticals—you name it.

Either way, organizations and executives fall out of alignment all the time.

So why is it so hard to answer questions about why you want to leave or why your last role didn't work out?

Own Your Story, Control Outcomes

After engineering power dynamics in your first 90 seconds and mastering the "what's next?" question to demonstrate strategic vision, you might think explaining a transition would be straightforward.

But your answer is particularly treacherous because, more often, you will reveal more about your executive presence than the actual circumstances of your departure.

I've noticed that the general perception and most career advice regarding executive-level interviewing is incorrect.

While it's not wrong to be confident and optimistic about interviewing or to prepare your ass off—the buck doesn't stop there.

The purpose of interviewing is to understand (and to be understood).

That means understanding both the good and the bad for you and the employer.

Wouldn't you like to know what you're getting yourself into? Where is the dirty laundry? What are the precise pros and cons? Where are the bodies buried?

How do you get the best intel and nail due diligence better than your competition?

Truth Becomes Power Through Strategy

Think of strategic vulnerability like an interviewing and negotiation master key.

When you share a carefully chosen insight about your journey, you're not just answering a question—you're creating psychological safety that invites reciprocity.

After all — nobody is perfect. A healthy reminder of that is refreshing for everyone.

Elite negotiators use strategic vulnerability all the time.

Chris Voss developed this into 'tactical empathy' — a technique for creating trust by being the first to show genuine understanding and openness and inviting others to do the same.

When you take the lead in showing measured vulnerability, people naturally reciprocate, creating a space where more meaningful information and influence can flow.

Drop the poker face.

Your calculated openness about failures will make others spill their organizational secrets.

When you acknowledge, for instance, that you misjudged product-market fit in your last role but extracted specific insights from that experience, you're not showing weakness—you're demonstrating the kind of reflective leadership that makes others feel safe sharing their challenges.

When handled skillfully, this approach transforms the traditional interview power dynamic.

Instead of an interrogation, it becomes a strategic discussion where both parties feel comfortable exploring real challenges and opportunities.

This collaboration is how we mastermind the most significant compensation wins later.

The foundation of trust and mutual respect you build now becomes your negotiation leverage when it matters most.

Suppose you haven't worked hard to understand and take ownership of the harmful elements of your career.

If you can't confront your ghosts with clear-eyed honesty, you're telegraphing a deeper truth about your leadership capacity.

Your answer's deflection or sugarcoating betrays a weakness far more damaging than any specific career setback—the inability to own your narrative and learn from your journey.

Why would an employer open their kimono when you're still wearing armor?

Most executives miss this crucial truth—your ability to own your story directly impacts their willingness to share theirs.

Every bit of authenticity you withhold becomes a brick wall between you and genuine organizational insight.

As Jocko Willink teaches through "extreme ownership," true leaders take absolute responsibility for everything in their world—successes and failures.

When you demonstrate this level of radical accountability for your career journey, you create the psychological safety others need to be equally candid about their organization's challenges and opportunities.

Own your failures like trophies.

They're often worth more than your wins.

The goal isn't to spill all your secrets. It's to demonstrate emotional intelligence through calculated openness that invites others to do the same.

Getting this right is how you move from being evaluated to being consulted—creating an environment where authentic strategic dialogue can flourish and your negotiating leverage becomes palpable.

The Sugarcoating Trap

Too often, leaders trap themselves in talking about a tough career transition in what I call the "compliment or BS sandwich."

You'll immediately recognize the BS sandwich, as more than half of your company's emails follow a similar structure.

The BS Sandwich: Positive fluff + softened negative + enthusiastic positive = instant credibility killer. Stop it.

When you find yourself unprepared, you may naturally manifest the following answers to "Why aren't you with XYZ company anymore?"  

Nervously Buying Time

"Ah, you see. I am so glad you are asking about this thing (this thing I really didn't want to talk about)."

Positive Spin Bread

"I have had a great experience at XYZ Satanware.io (even though it has only been 4 months). The team, the vision, the (soul-suckingly inefficient, no product-market-fit, overfunded vaporware) product—all exceptional."

Negative Meat

"I recognize that I want to get closer to working hands-on with the customer (because XYZ Satanware.io never once paid attention to the customer anyway), and we weren't in alignment on the overall vision of the company (because the CEO bait-and-switched the role and micro-managed every leadership decision anyway)."

Positive Spin Bread

"I'm not in a hurry to leave (please get me the hell out of here, but don't assume I have no negotiation leverage), but I am entertaining other leadership opportunities at companies like yours where we can find stronger mutual alignment (Please don't lie about this role. My heart and career can't take anymore)."

Notice how each layer of this answer screams insecurity and inauthenticity.

When you sugarcoat tough transitions, you're not just failing to answer the question—you're undermining your executive presence with every forced positive spin.

Remember: you're not crafting a Yelp review of your last role; you're demonstrating how you process challenges and extract value from complex situations.

You need to respond to negative stories with a growth mindset and share what you've learned from your good and bad experiences.

Ownership Is Strength, Especially When It's Uncomfortable

Let's get real. These conversations are challenging and uncomfortable.

GOOD.

That's why you're in the running to earn the big bucks. If you feel uncomfortable, you're growing. Embrace it.  

The cliche is true that it's not what you say; it's how you say it. Words matter. Delivery matters.

But toxic positivity is just another form of bullshit—and nearly all executives fall victim to it. It doesn't matter if the glass is half full or half empty when it's full of piss.

Stop putting a positive spin on piss. Call it like it is.

If you're struggling to explain a challenging work situation — and let's face it, the employee usually takes the blame — focus first on understanding why it happened and owning your part of the failure.

Ask yourself the hard questions:

• Did you ignore red flags during the interview?

• Were you desperate for any job that would pay the bills?

• Did you compromise on your values for a bigger paycheck?

• Did you fail to set clear boundaries early in the role?

• Were you afraid to speak up when things started going sideways?

• Did you stay too long, hoping things would magically improve?

• Had you researched the leadership team's track record?

• Did you have an honest conversation about expectations during onboarding?

The deeper your understanding, the more confidently you can communicate the lessons learned and how you'll prevent similar situations in the future.

Example Responses & Considerations

In our previous discussions, we explored how to engineer power dynamics in your opening 90 seconds and shape strategic vision through your "What's next?" response.

Now, let's apply those same principles to transform your transition story from a defensive explanation into a powerful demonstration of leadership thinking.

Here are a few considerations about how you can craft more effective responses.

The Four Corners of Control

1. Context Control

Frame the situation before they can make assumptions.

Remember: the moment you wait for someone else to guide your narrative is the moment when you surrender control of your future.  

💬

"Rather than waiting to be downsized in the merger, I started conversations with the board about a transition that would minimize disruption to our team and customers. [PAUSE]

Now that I think about it more—being proactive allowed us to execute a more thoughtful six-month handover that preserved key client relationships."

2. Narrative Control

Own your story's direction and why what you learned makes you a better fit for the next opportunity.

💬

"While leading the turnaround, I discovered my real passion isn't merely fixing broken operations—it's transforming how organizations approach sustainable growth. [PAUSE]

That insight drew me to your focus on building scalable processes. I'd say we're a much stronger match."

3. Emotional Control

Maintain executive presence while showing strategic vulnerability.

💬

"Looking back, I made an error in judging product-market fit. [PAUSE]

But that experience shaped how I now evaluate opportunities, including developing a framework that's helped our last three launches exceed revenue targets. Now, I choose products that meet X criteria..."

4. Outcome Control

Bridge to future value, connecting past experiences to their needs.

💬

"Those lessons in stakeholder management during the crisis directly parallels the challenges you've mentioned about aligning your global teams.

I'd like to hear more about how you approach those coordination issues. I suspect I have a few lessons to share with you."

These four elements of control—Context, Narrative, Emotional, and Outcome—work together as a system.

Context Control: "Frame it before they do."
Narrative Control: "Your story, your rules."
Emotional Control: "Vulnerability without weakness." Outcome Control: "Turn past pain into future gain."

When mastered, they transform potentially tricky conversations about transitions into opportunities to demonstrate strategic leadership.

Let's examine how to adapt this framework across specific scenarios that senior executives commonly face.

Example Scenarios & Considerations

Each example demonstrates how to maintain command of your narrative while building strategic connections.

Three Critical Transition Types

1. The Active Recruitment

When you're pursued for a new opportunity while you're still employed, the key is to balance your current success with future opportunities.

Most executives find it easy to keep leverage in these scenarios.

💬

"To be honest, I'm not actively looking to leave. I've had a successful three years at XYZ Corp, including a 40% increase in enterprise sales.

However, when your team reached out, the opportunity to scale a global operation spoke to me.

Leading globally excites me, but that has not been part of our growth plans at XYZ Corp."

Notice how this response:

- Demonstrates loyalty while showing ambition.

- Quantifies current success.

- Shows professional maturity in handling the transition.

- Aligns the move with strategic career planning.

This approach isn't just about responding to an opportunity—it's about positioning.

By leading with success and following with strategic growth limitations, you create a narrative in which your next move isn't about running from something but running toward something bigger.

The measured tone and specific metrics transform what could be seen as professional dating into a thoughtful evaluation of mutual fit.

Most importantly, you maintain optionality.

You're not desperate or unhappy—you're successful but ambitious.

That's the sweet spot where real negotiating power lives.

2. The Voluntary Departure

When you depart without another role, the emphasis shifts to demonstrating strategic self-awareness and intentional career management.

Most executives are terrified that they will lose leverage in these scenarios, but I've found that the problem is primarily self-imposed limitations and a lack of sophisticated negotiation skills. When wielded correctly, voluntary departures increase leverage.

💬

"I don't find my current work fulfilling. I enjoy leading a larger team and having increased responsibility, and I've learned a lot.

But I made a mistake when evaluating the product, and we're much further away from growth, which really excites me. I have learned that I can make a bigger impact on an organization that's further along.

I'm evaluating other opportunities that are a better fit for me, but I am not actively looking for a chance to leave.

Instead, I'm taking my time to make a smart decision with my next steps and avoiding a poor fit moving forward. Does that cause any alarm or hesitation? It's not easy to talk about, but I respect being candid."

This response succeeds because it:

• Shows mature self-awareness by acknowledging the mismatch without blame.

• Demonstrates strategic thinking by explaining the specific growth limitations.

• Uses tactical empathy by addressing potential concerns head-on ("Does that cause any alarm?").

• Projects confidence through deliberate pacing ("taking my time").

• Balances vulnerability with strength by owning the decision while showing clear direction.

Also, notice how each element builds credibility:

• "I don't find my current work fulfilling."

  • Direct honesty establishes trust.

• "I made a mistake when evaluating."

  • Takes ownership of the decision

• "I'm evaluating other opportunities."

  • Shows strategic approach to career

• "Does that cause any alarm?"

  • Invites open dialogue

• "I respect being candid."

  • Reinforces professional maturity

This level of thoughtful transparency transforms what could be seen as a weakness into a demonstration of leadership capacity.

How's that?

It breaks down each element while showing why each piece matters in building credibility and maintaining leverage.

3. The Performance Misalignment

When handling role misalignment, such as a layoff or termination, focus on learning and growth while maintaining professional dignity.

All executives fear that their leverage is eviscerated in these scenarios—but again—I find this is self-imposed and only true if the executive loses confidence and only possesses a rudimentary understanding of negotiation.

💬

"The role required a different leadership style than what had made me successful previously.

While I delivered strong operational results, including 25% growth, I failed to build the right coalitions at the board level.

That misalignment taught me crucial lessons about stakeholder management and establishing clear expectations early.

I'm now looking for opportunities to apply these insights while staying true to my track record in scaling operations."

This approach succeeds by:

• Owning the narrative without making excuses ("different leadership style").

• Balancing achievements with honest reflection (25% growth vs. board alignment).

• Demonstrating a growth mindset through specific lessons learned.

• Connecting past challenges to the future value proposition.

• Maintaining professional dignity while showing vulnerability.

The common thread across all these scenarios isn't just what you say—it's the confidence that comes from deeply understanding your story.

True leverage isn't about having the perfect situation; it's about owning your narrative completely.

Whether you're crushing it in your current role or navigating a challenging transition, your power lies in your ability to reflect honestly and communicate authentically.

Remember: Your career story isn't a highlight reel—it's a growth journey.

The executives who command the highest compensation aren't the ones with perfect trajectories; they're the ones who can articulate their evolution with clarity and purpose.

Perfect careers command average salaries. Battle scars, well-explained, command empires.

When you embrace this level of ownership, every situation—even the challenging ones—becomes a platform for demonstrating your leadership capacity.

That's when you stop playing defense and start commanding the value you deserve.

Common Pitfalls to Avoid

• Treating the conversation like a transaction instead of a strategic dialogue.

• Focusing on qualifications while neglecting culture and leadership fit.

• Missing opportunities to demonstrate genuine curiosity about their challenges.

• Inconsistency between your stated values and demonstrated behaviors.

• Racing to answers instead of exploring deeper organizational context.

Remember: Executive interviews aren't about proving yourself—they're about demonstrating how you think, lead, and build relationships. Creating alignment trumps being impressive.

When you approach these conversations with authentic curiosity and measured vulnerability, you transform what could be an interrogation into a meaningful strategic discussion.

Moving from Theory to Practice

Before our final piece next week on "How Much Money Do You Want?" here's your strategic homework:

Draft your transition stories using the Four Corners of Control

• Context Control: Frame your situation.

• Narrative Control: Own your story's direction.

• Emotional Control: Balance vulnerability with strength.

• Outcome Control: Bridge to future value.

Pressure test your narrative

• Practice with trusted advisors who will challenge your thinking.

• Record yourself and study your delivery.

• Create variations for different strategic contexts.

• Pay attention to where you default to defensive language.

Build your practice environment

• Join or create a weekly executive transition group.

• Test different approaches with your network.

• Get comfortable with strategic vulnerability.

• Refine your ability to pivot from past events to future value.

Remember: The goal isn't to explain your past—even when directly asked about it. You must instead create strategic openings demonstrating your leadership capacity and inviting authentic dialogue about their challenges.

Need help applying this? Upgrade to paid for monthly live sessions with Jacob.

Stay fearless, friends.