I spent 40 minutes last month listening to a CFO answer a simple question: “What’s your career plan for the next three years?”
She talked about her current reporting structure. Her board relationships. The systems implementation she’s overseeing. The team she’s building. Forty minutes of describing what she does – not one sentence about what she’s actually for.
When I pointed this out, she went quiet. Then: “I’ve never thought about my career that way.”
She’s not unusual. Most executives I work with can’t answer the question “What percentage of your role is task execution versus strategic judgment?” in under ten seconds. They’ve spent years becoming excellent at doing without examining whether what they’re doing is what will keep them valuable.
That uncertainty – the gap between what you do and what you’re for – is where AI career vulnerability lives. And no industry statistic, no reassuring article about “the human touch,” and no LinkedIn course on prompting is going to close that gap for you.
Only honest assessment will.
Why Generic AI Risk Assessments Fail Executives
You’ve probably seen the headlines. Citigroup’s own analysis says 54% of banking jobs have high automation potential – the highest of any sector. Other reports tell you that managerial roles face only 9-21% automation risk compared to entry-level positions. Some studies say AI will create more jobs than it eliminates.
Here’s the problem: none of that tells you anything about you.
Industry statistics tell you about industries. Only your PURPOSE AUDIT™ tells you about YOU.
The CFO reading the Citigroup report might feel reassured – she’s not in a back-office role, after all. She’s strategic. She’s on the executive team. But that comfort comes from looking at the wrong data. The question isn’t whether CFOs as a category will be automated. The question is whether her specific mix of tasks, judgment, relationships, and strategic contribution is positioned for what’s coming.
The Stat-Comfort Trap
Executives love aggregate data because it feels objective. “Only 9-21% of managerial roles at risk” sounds scientific. It also conveniently avoids the uncomfortable work of honest self-assessment.
The trap works like this: You read a statistic that suggests executives are relatively safe. You conclude that your position is secure. You never actually examine what percentage of your week goes to work that AI can now do faster, cheaper, and with fewer errors.
Meanwhile, the executive down the hall – the one who actually ran the numbers on their own role – is already repositioning toward the work AI can’t replicate.
The Competence-as-Shield Trap
Being excellent at your job has never felt less protective. I’ve watched brilliant executives discover that decades of expertise in financial modeling, market analysis, or technical architecture – skills that took years to develop – can now be approximated by tools that a junior analyst can operate.
The uncomfortable truth: competence at tasks that are becoming automatable isn’t career security. It’s career vulnerability disguised as strength.
This doesn’t mean your expertise is worthless. It means the application of that expertise needs to shift – from execution to judgment, from analysis to decision-making under uncertainty, from producing outputs to orchestrating outcomes.
The PURPOSE AUDIT™: Tasks vs. Purpose in Your Role
The distinction that matters most in the AI era isn’t between jobs that will be automated and jobs that won’t. It’s between the tasks within your role and the purpose you serve.
This builds on Huang’s purpose vs task framework, though with an important caveat: while the framework is useful, it requires executive-specific application. Huang’s perspective – influential as it is – comes from someone with a vested interest in AI adoption. The radiologist example he uses (where AI-assisted diagnosis actually increased demand for human radiologists) is compelling, but it doesn’t address the identity disruption and transition pain that executives experience when their roles fundamentally shift.
You won’t be replaced by AI. You’ll be replaced by an executive who knows what percentage of their role is judgment and what percentage is task execution.
The PURPOSE AUDIT™ framework asks you to categorize every significant activity in your role into one of three buckets:
Bucket 1: Pure Task Execution These are activities where the output matters more than the judgment. Generating reports. Synthesizing data from multiple sources. Creating first drafts of communications. Scheduling and coordination. Monitoring dashboards. These tasks can often be done faster and more accurately by AI tools – and increasingly, they will be.
Bucket 2: Judgment-Dependent Tasks These activities require human judgment, but the judgment is applied to relatively structured problems. Evaluating vendor proposals against defined criteria. Reviewing work for quality. Making hiring decisions with clear role requirements. Approving budgets within established parameters. AI can augment these tasks significantly, but human oversight remains valuable – for now.
Bucket 3: Irreducibly Human Purpose This is the work that AI cannot replicate: setting aspirational direction for an organization, navigating political dynamics, building trust with stakeholders who need to believe in you specifically, making decisions when values conflict and time is short, reading emotional undercurrents that data doesn’t capture. McKinsey’s research identifies aspiration, judgment, and creativity as “only human” leadership traits that provide an irreplaceable competitive edge.
Running Your Own PURPOSE AUDIT™
Take your calendar from the past two weeks. For every block of 30 minutes or more, ask: “If AI could do this task at 80% of my quality, would the outcome be meaningfully different?”
If the answer is no – if an AI-generated first draft, analysis, or summary would serve almost as well as your personally-crafted version – that’s Bucket 1.
If the answer is “it depends on the specific situation” – that’s likely Bucket 2.
If the answer is “no technology could substitute for my specific presence, relationships, or judgment in this moment” – that’s Bucket 3.
Most executives who complete this exercise discover something uncomfortable: 40-60% of their time goes to Bucket 1 activities. They’ve become highly-paid task executors without realizing it.
Run Your Own PURPOSE AUDIT™
The 19-page worksheet walks you through separating your automatable tasks from your irreplaceable purpose – the same framework used throughout this article.
Includes the Task-Purpose Inventory, the “Would AI Do This Better?” filter, and a completed example for reference.
Time investment: 30-45 minutes
Worked Example: The CFO Assessment
The CFO I mentioned earlier ran this audit. Here’s what she discovered:
- 25% of her time: Financial reporting, variance analysis, board deck preparation (Bucket 1)
- 35% of her time: Budget reviews, forecast adjustments, vendor evaluations (Bucket 2)
- 15% of her time: Strategic capital allocation decisions, M&A judgment calls, CEO advisory relationship (Bucket 3)
- 25% of her time: Meetings that could have been emails (a category unto itself)
Her Bucket 3 percentage – the irreducibly human work – was 15%. That’s the real measure of her current positioning.
The goal isn’t to eliminate Bucket 1 work overnight. It’s to see clearly where you stand, so you can make intentional choices about where to invest your development energy.
Career Assets Inventory: What Transfers and What Doesn’t
Assessment isn’t just about vulnerability. It’s also about identifying what you bring to whatever comes next.
Your career assets inventory examines three categories:
Transferable Capabilities These are skills that remain valuable regardless of how your role evolves: strategic thinking, stakeholder management, team leadership, crisis navigation, communication at the executive level. These capabilities don’t disappear when tasks get automated – they become more important.
Context-Dependent Expertise This includes deep knowledge of specific systems, processes, industries, or organizations. It’s valuable, but its transferability depends on where you’re headed. A CFO’s expertise in healthcare revenue cycle management transfers beautifully to another healthcare role – less so to a technology startup.
Relationship Capital Your network isn’t just who you know – it’s who would take your call, advocate for you, and collaborate with you on new ventures. This asset compounds over a career, but it can also decay if your relationships are all in sectors facing decline.
The executives who navigate AI disruption well aren’t starting from zero. They’re leveraging decades of accumulated assets – but they’re honest about which assets actually transfer to where they want to go.
The loss is real, but it’s smaller than you think. What transfers is bigger than what doesn’t.
Calculate Your Actual Runway
The RUNWAY READY™ Calculator measures all three dimensions: financial months, psychological readiness, and network quality. Most executives discover their real runway is different than they assumed.
PDF workbook explains the framework. Companion spreadsheet does the math.
Time investment: 20-30 minutes
RUNWAY READY™: The Three Dimensions of Transition Readiness
Vulnerability assessment tells you where you stand. Readiness assessment tells you what you can actually do about it.
The RUNWAY READY™ framework examines three dimensions that executives often assess incompletely – or avoid assessing entirely.
Financial Runway
This isn’t just “how many months of expenses do you have saved.” Executive financial runway involves complications that generic advice ignores.
The Real Calculation
Start with your monthly burn rate – but be honest about it. Not the budget you aspire to, but what you actually spend. Include the private school tuition, the country club dues, the second home. These aren’t judgments about lifestyle choices – they’re data points for calculating runway.
Then factor in the executive-specific elements:
- Unvested equity: Those RSUs vesting over the next two years? Walking away means leaving money on the table. How much?
- Deferred compensation: Many executives have significant deferred comp that disappears if they leave before specific dates.
- Bonus timing: Is your bonus tied to a performance period that’s almost complete? Leaving now versus in six months could mean a significant difference.
- Healthcare costs: Executive healthcare often includes benefits that are expensive to replicate privately.
- Severance negotiation potential: Research shows C-suite executives receive an average of 16 weeks severance, but this varies widely and is often negotiable.
The financial runway calculation isn’t about reaching a specific number. It’s about knowing your actual constraints so you can make decisions from clarity rather than assumption.
Financial runway isn’t just savings divided by expenses. It’s how many months you have before the pressure to accept the wrong opportunity becomes unbearable.
The Uncomfortable Truth
Most executives overestimate their runway because they’ve never stress-tested their assumptions. They assume they could “cut back if needed” without calculating what cutting back would actually require. They assume their spouse’s income provides a cushion without discussing what that would mean for family dynamics. They assume they could find something comparable “within a few months” without researching actual market timelines.
Honest financial assessment isn’t pessimistic. It’s protective. Knowing your real runway lets you make proactive choices while you still have options.
Psychological Readiness
This is the dimension executives most resist examining. It’s also often the dimension that determines whether a transition succeeds or fails.
Identity Investment
How much of your sense of self is tied to your current title, company, or role? This isn’t a judgment – it’s a measurement. After 20 years as a technology executive, “CTO” isn’t just what I do; for many, it’s become who they are.
The executives who struggle most with transition aren’t the ones who lack skills or financial resources. They’re the ones whose identity is so fused with their current position that any change feels like loss of self.
I’ve sat with leaders in this moment more times than I can count. There’s a particular kind of silence that happens when an executive realizes their decades of expertise might need to be rebuilt. Everything they’ve become professionally suddenly feels uncertain.
That uncertainty isn’t your enemy. It’s the beginning of understanding what you’re actually protecting – and what you’re ready to release.
Uncertainty Tolerance
Some people find ambiguity energizing. Others find it paralyzing. Neither response is wrong, but knowing your honest tolerance level matters for planning.
If uncertainty makes you anxious, you need a longer runway and a more detailed plan before making changes. If you thrive in ambiguity, you might be able to move faster – but you also need to watch for impulsive decisions driven by restlessness rather than strategy.
Grief Acknowledgment
Whatever path you take, something will be lost. Even the best transitions involve letting go of aspects of your current identity, relationships, and routines.
If this section makes you uncomfortable, that’s useful data. The discomfort isn’t a problem to solve – it’s information about what matters to you.
The psychological readiness factor isn’t about eliminating discomfort. It’s about understanding your emotional landscape well enough to navigate it intentionally.
Network Readiness
Your professional network is either an accelerant or an anchor – and many executives discover they’ve been measuring the wrong things.
Quality Over Quantity
LinkedIn connections aren’t relationships. Conference acquaintances aren’t advocates. The question isn’t how many people you know – it’s how many would respond meaningfully if you reached out with a specific ask.
The network audit examines:
- Depth: How many relationships are deep enough that the person would advocate for you, not just introduce you?
- Breadth: Are your connections concentrated in one industry, one company, or one function – or distributed across multiple domains?
- AI-Era Relevance: Are your strongest relationships in growing sectors or declining ones? A robust network in an industry facing structural decline is a depreciating asset.
The Network Mirage
Many executives believe their network is stronger than it is because they’re measuring activity rather than mobilizability. You might have active relationships with dozens of people – but how many of those relationships would survive you asking for something significant?
Honest network assessment often reveals concentrated risk: relationships clustered in one company, one industry, or one era. The executive whose entire network comes from a 15-year tenure at one organization has a different readiness profile than one who has built relationships across multiple companies and sectors.
Your Composite Vulnerability Profile
The three assessments – PURPOSE AUDIT™, Career Assets Inventory, and RUNWAY READY™ – don’t produce a single score. They produce a profile with multiple dimensions.
Different profiles suggest different strategic responses:
High Task Ratio + Low Runway This is the urgent profile. Significant vulnerability with limited resources for transition means you need to start repositioning within your current role while simultaneously building runway. The four executive career paths include options for this situation, but the window for proactive choice is narrower.
High Task Ratio + Strong Runway You have time to be strategic. Use it. This profile allows for more significant pivots or even complete reinvention – but don’t let comfortable runway become comfortable complacency.
Low Task Ratio + Strong Network You’re better positioned than most. Your focus should be on amplifying what’s already working – increasing your Bucket 3 activities, deepening your most valuable relationships, and building thought leadership around your irreducibly human contributions.
High Psychological Resistance + Any Profile This is the hidden variable that can undermine any strategy. If your identity is tightly fused with your current role, even strong financial position and clear skill transferability won’t make transition feel possible. The inner work may need to come first.
The executives who navigate this well aren’t the ones who move fastest. They’re the ones who take time to understand what they’re actually protecting – and what they’re ready to release.
The Real Test
Here’s the question that integrates everything: Could someone who uses AI tools well do your current job at 80% of your effectiveness?
Not “could AI replace me” – that’s the wrong frame. The right frame is: “Could a less experienced executive, armed with current AI tools, deliver most of what I deliver?”
If the answer is yes, that’s not a verdict. It’s information. And information is the foundation of good strategy.
What Your Assessment Reveals – And What to Do Next
Assessment creates clarity, not action. The PURPOSE AUDIT™ tells you where you’re vulnerable. RUNWAY READY™ tells you what resources you have. Neither tells you which direction to move.
That’s the work of path selection – and it’s the focus of the four executive career paths framework: Transform, Pivot, Reinvent, or Portfolio.
Different starting points require different paths. An executive with a 45% Bucket 3 ratio and strong financial runway has different options than one with a 15% ratio and golden handcuffs. Both can navigate successfully – but the strategies differ.
If you’re ready to move from assessment to strategy, the TRANSITION BRIDGE™ framework provides the decision architecture. But don’t rush there. Assessment that gets skipped or shortcut tends to produce strategies that don’t actually fit.
Your Immediate Next Steps
- Download the PURPOSE AUDIT™ worksheet and complete the time categorization for your past two weeks
- Run an honest financial runway calculation – not the optimistic version, the realistic one
- Identify your top 10 relationships and assess each for depth, breadth, and AI-era relevance
For executives navigating career transitions, having structured assessment tools makes the difference between reactive scrambling and proactive positioning.
The assessment is private. No one sees the results but you. There’s no judgment here – only clarity.
Frequently Asked Questions
How long does a complete assessment take?
The full PURPOSE AUDIT™ takes 45-60 minutes if you’re being thorough. The RUNWAY READY™ financial calculation takes 30-60 minutes depending on the complexity of your compensation structure. Psychological and network assessments are ongoing reflections more than timed exercises. Most executives complete initial assessment across all dimensions in a weekend.
What if I don't like what the assessment reveals?
That’s common – and it’s useful information. Discomfort with results often indicates areas where assumptions have been doing the work of analysis. The executives who benefit most from assessment are the ones who let the data change their view, not the ones who adjust the data to match their preferred narrative.
Is this assessment valid across different industries?
The framework applies across industries, though specific task-to-purpose ratios vary significantly. A CFO in manufacturing will have different Bucket 1/2/3 distributions than one in technology. The methodology is consistent; the results are personal. For industry-specific application, the Pillar 5 articles provide deeper context for CFO, CMO, CTO, General Counsel, and professional services roles.
How often should I update my assessment?
Significant reassessment makes sense annually or when major changes occur – new role, new company, major AI tool deployment in your industry. Light-touch review of your task-to-purpose ratio quarterly helps you notice drift before it becomes vulnerability.
What if my financial runway is shorter than I expected?
This is uncomfortable but addressable. Short runway doesn’t mean you can’t navigate transition – it means you need to navigate differently. The Transform path allows evolution within your current role while building resources. The Portfolio path can create additional income streams while you’re still employed. Knowing your real constraints early gives you more options than discovering them in crisis.
Should I share my assessment results with anyone?
That’s your choice. Many executives find value in discussing results with a coach, mentor, or trusted peer. Others prefer to process privately before deciding on next steps. If you share within your organization, be thoughtful about what that signals – not everyone responds well to an executive who appears to be planning their exit.
What's the difference between this and a skills assessment?
Skills assessments tell you what you can do. This assessment tells you what you’re for – and whether that purpose is positioned for value in an AI-augmented world. Many executives have strong skills that are becoming commoditized. The PURPOSE AUDIT™ helps you distinguish between skills that are appreciating and skills that are depreciating.
What if I'm already in transition?
The assessment is still valuable – perhaps more so. Understanding your vulnerability profile helps you evaluate opportunities against your actual positioning rather than your assumed positioning. Many executives in transition make choices based on comfort or familiarity rather than strategic fit. Assessment provides the data for better decisions.
Whatever surfaced as you read this – recognition, resistance, relief – is information worth holding.
There’s no requirement to act today. The assessment is private, non-judgmental, and entirely in your control. You can close this page and return to your current trajectory. Many executives do.
But if something in these frameworks resonated – if you recognized yourself in the Stat-Comfort Trap or felt the weight of the identity question – that recognition is the beginning of seeing clearly.
Whatever surfaced during this assessment – recognition, resistance, relief – is data. And data beats assumption every time.
The executives who navigate this era well aren’t the ones with the most certainty. They’re the ones who built their strategy on honest assessment rather than comfortable assumptions.
When you’re ready, the tools are here. The path forward starts with knowing where you actually stand.
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About the Author
Cherie Silas, MCC
She has over 20 years of experience as a corporate leader and uses that background to partner with business executives and their leadership teams to identify and solve their most challenging people, process, and business problems in measurable ways.
