Women's Leadership Success

Women Leaders Psychological Safety: How Kerry Siggins Turned "You're Erratic" Into Her Best Leadership Lesson
Last updated: September 3, 2026
Trusted by leaders at Stanford University, Ernst & Young, Autodesk, MGM Grand Resorts, and Farmers Insurance
Executive Summary: The word that stung most in StoneAge CEO Kerry Siggins' toughest feedback moment was the word that was true. Here's her litmus test for real feedback, how she builds psychological safety without losing accountability, and how women leaders navigate the double bind.

Quick Takeaways:

If feedback "stings," there's probably truth in it worth examining
Psychological safety and accountability aren't opposites — done right, they build each other
The double bind is real: women who are direct risk being called aggressive
Influence matters more than being right — and it changes how feedback lands
U.S. employee engagement hit a decade-low of 31% in early 2026

Jump to:The Feedback Story · Spotting Valid Feedback ·Safety vs. Accountability · The Double Bind ·Action Plan · FAQ

As an executive leadership coach with over 30 years of experience (MA, MFT, PCC) working with Fortune 50–1000 companies, I've watched brilliant women leaders freeze in two different ways: some can't tell which feedback to take seriously and which to release, and others have been burned so badly by being called "too direct" that they've gone quiet. Both patterns erode psychological safety — theirs, and their team's.
This is Part Two of my conversation with Kerry Siggins, CEO of StoneAge and author of Talk With Trust: How to Own Feedback, Spark Growth, and Build Stronger Teams. In Part One, we walked through her SHARES framework for difficult conversations. Here, we go deeper into the moment that started it all — the day a trusted colleague told her she was "erratic" — and what she's learned since about telling real feedback from noise, building psychological safety without losing accountability, and the double bind that so many women leaders still navigate every day.

The Feedback That Almost Cost Kerry Siggins Her COO — And Changed Her Leadership
Kerry had spent a year having what she thought were deep, honest conversations with her COO. Then, in a discussion about his role and growth path, it came out all at once: "You think you're this inspiring CEO who disrupts the industry, but really what you are is erratic, and you're really hard to work for. You're the problem." Kerry's first instinct was to fire him. She paused instead — because, as she told me, "I don't want to react in the moment."
That pause is the whole story. Kerry went home, sat with the feedback, and asked herself a simple question: what's true about this? She landed on one word — erratic — and traced it back to something real: her fast pace and love of new ideas could look, from the outside, like constant direction-changing. She decided, in that moment, to become a "cool, calm, and collected, unflappable leader." It changed how she led. It also cost her the relationship — the way the feedback was delivered damaged the trust between them beyond repair, and her COO eventually left the company. Both things were true at once: the feedback was a gift, and the delivery broke something. That tension is exactly why psychological safety matters — not as comfort, but as the structure that lets hard truths get said before they explode.
How to Tell Valid Feedback From Noise
Kerry's litmus test is disarmingly simple: if it stings, there's probably some truth to it. She described being called "disingenuous" by someone recently and letting it go completely — because it didn't sting. She knows who she is on that dimension. But "erratic" stung, because some part of her recognized it. That sting is data.
The follow-up question matters just as much: is this feedback about who I am, or about someone else's perception and unmet need? "Just because something hits your identity," Kerry said, "doesn't mean that person is right or wrong — it just means they're seeing things differently." Her advice for women leaders receiving feedback that challenges their identity: get curious, ask for examples, and then decide. "Do you want to be right, or do you want to be accurate?" Accuracy requires asking questions. Being right just requires defending your position.
She also named something every leader has lived: most of what reaches you has already been filtered. The brain can only process a tiny fraction of available information, and the person giving you feedback is filtering it further through their own fear of your reaction. The fix is direct: ask "what are you not saying right now?" and genuinely invite the rest.
Psychological Safety vs. Accountability: Why They're Not Opposites
Most leaders treat psychological safety and accountability as a tradeoff — soft versus firm, safe versus serious. Kerry rejects that framing entirely. "There can be accountability in how you're addressing any kind of challenge through dialogue," she said. Her practice: after a hard conversation, put recurring check-ins on the calendar — not as a punishment, but as a standing space to talk about progress, struggles, and wins. "My manager really cares about me" and "I'm being held accountable" become the same sentence, not opposite ones. Accountability only becomes destructive to psychological safety when it's used as a weapon instead of a rhythm.
This is the same territory I mapped out recently in a LinkedIn post on the three pillars of trust — and two of them apply directly here.
Trust isn't built in one big moment. It's built in the small moments people learn they can count on you. — Sabrina Braham, MA, MFT, PCC
Authenticity breaks when a leader hides a mistake to protect their image instead of admitting when they're wrong — exactly what Kerry avoided by sitting with "erratic" instead of dismissing it. And reliability breaks when accountability only shows up when something goes wrong instead of on a consistent rhythm — which is precisely why Kerry's recurring check-ins work: the consistency itself is what makes accountability feel like care instead of a threat.
The Double Bind: When Direct Reads as Aggressive
I asked Kerry directly: women leaders often face a double bind — direct enough to be respected reads as aggressive; warm enough to be liked reads as weak. How do you navigate it? Her answer came from experience: a fellow board member once told her, in front of a long-time customer, that she was "aggressive" and an "overachiever" — framed as a flaw. "There's no way he would have ever said that to a man," she said.
This isn't just anecdote. New 2026 research out of INSEAD confirms the bind is still fully intact: promotion-focused language — bold, action-oriented, opportunity-framed — tends to clash with gendered expectations for women leaders, while prevention-focused, risk-aware language can reinforce perceptions of low competence, a tension that gets sharper under crisis or high pressure. Separate research on women serving as corporate board directors found something even more troubling: the constant work of switching between "warmth" tactics and "competence" tactics to avoid backlash is itself a driver of the disproportionate burnout many women in leadership report — the double bind isn't just unfair, it's exhausting in a measurable way.
Kerry's shift wasn't to soften herself — it was to change what she was optimizing for. "I changed my perspective: do I want to be right, or do I want to influence?" When someone in a meeting takes her idea and repeats it as their own, she no longer takes it personally. "That's a great idea, let's build on that" gets her further than proving the idea was hers first. Influence, not being right, became her north star — and it's a reframe available to any woman leader caught in the double bind.

You don't have to shrink to be trusted.
The FREE Leading Before You're Ready Playbook gives you language and a framework for navigating exactly this — leading with directness and building the trust that gets you promoted.
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Implement This Week: Building Psychological Safety Without Losing Accountability

(10 minutes) Recall the last piece of feedback that stung. Write down exactly why it stung — what did it touch that you believe about yourself?
(15 minutes) Separate what's accurate from what's someone else's unmet expectation. Ask: is this something I need to work on, or a relationship I need to manage?
(5 minutes) Identify one relationship where you suspect you're only getting filtered information. Plan to ask directly: "What are you not telling me?"
(20 minutes) Put one recurring check-in on the calendar with a direct report — framed around progress and support, not correction.
(This week) Bring one piece of feedback to your own team: "I'm working on X, and I'd love one honest thing I could do better." Modeling receptivity is the fastest way to build a feedback culture.
(Ongoing) The next time you're told you're "too direct," ask for a specific example before deciding whether to change anything. Success metric: you leave with clarity, not just a feeling.

Common Mistakes Leaders Make With Feedback and Safety

Treating every sting as truth. Not all feedback that hurts is accurate — some reflects the other person's ego or fear, not your reality. Examine it before you internalize it.
Defending instead of asking. Over-explaining your intentions in the moment shuts down the other person's willingness to keep talking, even if it doesn't feel defensive to you.
Using accountability as punishment. If check-ins only happen when something goes wrong, people stop seeing them as safe — and stop bringing you the truth early.
Softening yourself to avoid the double bind. Shrinking your directness doesn't resolve the bind — it just trades one cost for another, and the research suggests the constant self-regulation itself carries a burnout cost. Shift toward influence instead of retreat.
Reading body language as neutral....

Last updated: August 27, 2026
Trusted by leaders at Stanford University, Ernst & Young, Autodesk, MGM Grand Resorts, and Farmers Insurance
Executive Summary: Most women leaders avoid difficult conversations to protect relationships — and that avoidance is what actually destroys trust. StoneAge CEO Kerry Siggins built the six-step SHARES framework after a piece of brutal feedback changed her leadership. Here's exactly how it works.

Quick Takeaways:

Difficult conversations delayed almost always get harder, not easier, over time
The SHARES framework has six steps you can prepare in under ten minutes
Organizations with regular feedback see 14.9% lower turnover rates
Wanting to "be right" is the single biggest killer of workplace trust
Feedback without a credible next step leaves people hopeless, not motivated

Jump to:
Why It Happens ·
The SHARES Framework ·
Examples ·
Action Plan ·
FAQ

As an executive leadership coach with over 30 years of experience (MA, MFT, PCC) working with Fortune 50–1000 companies, I hear the same confession from brilliant, accomplished women leaders almost every week: "I know I need to have this conversation. I just keep putting it off." If you've been carrying a difficult conversation you haven't had yet — with a direct report, a peer, a boss, even a spouse — you are in very good company, and it is costing you more than you think.
On this episode of the Women's Leadership Success Podcast, I sat down with Kerry Siggins, CEO of StoneAge (an employee-owned manufacturer of high-pressure water jetting equipment) and author of the new book Talk With Trust: How to Own Feedback, Spark Growth, and Build Stronger Teams. Kerry built her career on hard conversations — including one that nearly ended her leadership before it began. What she learned from it became the SHARES framework, a six-step system for women leaders navigating difficult conversations without torching the relationship in the process.

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Why Women Leaders Avoid Difficult Conversations — And What It Actually Costs
Nobody avoids a hard conversation because they're lazy. Women leaders avoid difficult conversations because they're afraid of the consequence: a damaged relationship, an angry reaction, a reputation for being "too much." As Kerry put it on the show, "We're all not having a conversation that we know we need to have because we're afraid of the consequences." The problem is that the consequence of silence is almost always worse than the consequence of speaking.
The research backs this up. Recent workplace data shows organizations with regular employee feedback see 14.9% lower turnover, while highly engaged teams — the kind built through honest dialogue — report 21% greater profitability (Careertrainer.ai, 2026). On the trust side, the numbers are sobering: employer trust fell to 76% in the 2025 Edelman Trust Barometer, and a 21-point gap now separates how much executives trust their organizations (91%) versus how much individual contributors do (70%). Every unspoken conversation widens that gap.
Kerry's own turning point came from a conversation she didn't get to control. Her COO — her right-hand operational partner — had been quietly building resentment for a year. It came out in a blowup: "You think you're this inspiring CEO who disrupts the industry, but really what you are is erratic, and you're really hard to work for." Kerry's instinct was to fire him on the spot. Instead, she went home and sat with it. That single piece of painful, poorly-delivered feedback became the foundation for Talk With Trust — and for the SHARES framework she now teaches leaders everywhere.
Your team is asking themselves this question constantly, whether they say it out loud or not: can I trust you? I broke this down recently on LinkedIn into three pillars — and it's the exact groundwork that makes a framework like SHARES actually work, instead of just sounding good on paper.

Trust isn't built in one big moment. It's built in the small moments people learn they can count on you. — Sabrina Braham, MA, MFT, PCC

Notice how closely this maps to what goes wrong in most difficult conversations. Performance trust breaks when someone overpromises or makes excuses instead of owning a miss. Authenticity trust breaks when someone says what people want to hear instead of what's true, or hides a mistake to protect their image — the exact trap Kerry's "articulate your experience" step is built to avoid. And reliability trust breaks when standards shift with someone's mood, or follow-through only happens when it's convenient — which is precisely why the SHARES framework's final step, endorsing a path forward, matters so much: a plan you don't follow through on costs you more trust than no plan at all.
This is the same shift Kerry made the day she got called "erratic" — she stopped waiting to feel ready to lead differently and just did it.

The SHARES Framework: Six Steps for Difficult Conversations That Build Trust
SHARES is a simple, repeatable system women leaders can use to prepare for any hard conversation — a performance issue, a peer conflict, a hard truth with a boss, even a conversation with a spouse. Each letter is a step you move through, in order.
S — Specify Your Ideal Outcome
Before you say a word, get clear on what you actually want from this conversation. Not "to be right" — an actual outcome. "I want to keep this relationship strong. I want to see behavior change. I want this to build trust, not break it." Kerry's insight: most difficult conversations go sideways because neither person has named the outcome they're going for. Stating it out loud — even to yourself — changes everything that follows.
H — Have Your Facts and Feelings Ready
Facts alone feel cold and clinical. Feelings alone feel like an ambush. You need both: the observable behavior ("you were late to this meeting") and the impact it had ("we waited, and had to repeat ourselves for you, which was frustrating for the team"). Preparing both in advance also does something else important — it gives you time to calm down before you walk into the room.
A — Articulate Your Experience
This is the step Kerry calls her favorite, because it's the one most leaders get subtly wrong. "I feel like you don't respect me" still sounds like a judgment wearing an I-statement disguise. Articulating your experience instead sounds like: "I'd like to share my experience of this situation. The story I'm telling myself is that you don't respect me — and I want to check whether that's accurate. What was your experience?" Owning your perspective as a perspective, not a verdict, opens the door instead of slamming it.
R — Reflect With Questions and Dialogue
The goal of any difficult conversation isn't to be right — it's to be accurate. And the only way to get accurate is to ask questions and actually stay in dialogue. Kerry shared a story of giving tough feedback to an employee who wasn't a direct report. Rather than delivering a verdict, she asked what was going on. What she learned changed the entire conversation — from correction to genuine understanding, without letting go of accountability.
E — Endorse a Path Forward
Feedback without a credible next step doesn't motivate people — it leaves them hopeless. Kerry described a boss early in her career who told her she wasn't getting in front of decision-makers and to "come back with a plan." She didn't know how to fix it and didn't feel safe saying so. She eventually quit. Now she builds the path forward together with the other person: What are you trying? What's working? What isn't? That collaborative plan is what turns feedback into change — and what creates real accountability without punishment.
S — Stay Emotionally Grounded
People tend to mirror the emotional energy in the room. If you walk in braced and defensive, you'll get braced and defensive back. Kerry's practice: feel your feet on the floor, take a breath, and become "the mirror that calms people down" rather than the one that escalates them. Staying grounded doesn't mean suppressing emotion in the other person — it means giving them room to have their reaction without matching it.
SHARES in Practice: Three Real Application Examples
The promotion conversation. A director wants to raise her hand for a VP role but suspects her boss has reservations. Using SHARES, she opens with her outcome ("I want clarity on what would make me ready for this role"), shares the facts of her track record alongside how the uncertainty has felt, then asks reflective questions instead of defending her resume — walking out with an actual development plan instead of vague reassurance.
The peer conflict. Two directors keep clashing in cross-functional meetings. Instead of escalating to their shared VP, one initiates a SHARES conversation: names the outcome (a working relationship that doesn't derail meetings), articulates her experience without accusation, and asks what's driving the friction from the other side. They leave with a path forward neither would have found by avoiding the topic.
The marriage parallel. As I shared with Kerry on the show, this isn't only a workplace tool. Simply naming the outcome you want at the start of a hard conversation with a spouse — "I want us to leave this in a better place" — changes the entire trajectory before either person says another word.

You don't have to figure this out alone.
The FREE Leading Before You're Ready Playbook gives you the exact framework to walk into your next leadership conversation — or your next promotion case — with real confidence, even before you feel ready for it.
GET THE FREE PLAYBOOK
Implement This Week: Your SHARES Action Plan

(15 minutes) Name the one difficult conversation you've been postponing. Write down the consequence you're avoiding by not having it — and the consequence of continuing to avoid it.
(10 minutes) Write your S: specify the outcome you actually want....

Executive Summary: Workplace betrayal doesn't just cost you a relationship — it costs you trust in your own judgment. Dr. Debi Silber joins Sabrina Braham to unpack a stage-based path back to confidence, using real coaching stories instead of easy platitudes, so leaders can rebuild what betrayal breaks: themselves.

Quick Takeaways:

Betrayal breaks trust in yourself, not just in the person who betrayed you
Losing your voice in meetings is often a betrayal symptom, not a confidence problem
Recovery moves through stages — you can't skip to "just get over it"
Your intuition can be rebuilt with a simple daily practice
78% of employees say they trust their employer most of any institution (Edelman, 2026)

As an executive leadership coach with over 30 years of experience (MA, MFT, PCC), I've sat across from directors, VPs, and C-suite leaders who could run a board meeting flawlessly and still couldn't shake the feeling that they didn't trust their own read on people anymore. That's what workplace betrayal does. It doesn't announce itself as trauma — it shows up as hesitation, over-checking, and a leader who used to speak up in meetings suddenly going quiet.

In this episode of the Women's Leadership Success Podcast, I sit down with Dr. Debi Silber, a holistic psychologist and founder of the PBT Institute, for a workplace betrayal recovery conversation about what betrayal actually does to a leader's confidence, judgment, and career trajectory — and what it takes to rebuild.
Why Workplace Betrayal Hits Differently Than Other Career Setbacks
Most leadership content treats betrayal like a subcategory of stress or conflict. Dr. Silber's central point in this conversation is that it isn't. A layoff, a missed promotion, even a bad performance review — these are painful, but they don't usually make you question your own perception. Betrayal does. When someone you trusted — a boss, a peer, a mentor — acts against you, the injury isn't just what they did. It's that your internal compass, the one that told you this person was safe, was wrong. That's a different kind of damage, and it requires a different kind of recovery.
This distinction matters for women in leadership specifically. Executive presence is built on decisiveness and trust in your own judgment — the "gravitas" that research consistently identifies as the core pillar of how leaders are evaluated for advancement. When betrayal quietly erodes that self-trust, it doesn't just hurt personally. It shows up publicly, in hesitation during exactly the moments a leader is expected to be most sure of herself.
A Client Story: When Betrayal Shows Up as "Losing Your Voice"
I shared a story with Dr. Debi about a client I'll call Jenny. Jenny was sharp, capable, and well-respected — until a workplace betrayal knocked something loose. She stopped negotiating. She stopped advocating for herself in meetings where she used to be the first voice in the room. From the outside, it looked like a confidence problem. It wasn't. It was betrayal doing exactly what it does: convincing a capable leader that her own instincts couldn't be trusted anymore.

The Real Cost: What Betrayal Quietly Takes From Leaders
Left unaddressed, workplace betrayal tends to produce three patterns in otherwise strong leaders:

Loss of personal power. Leaders stop negotiating for themselves — raises, promotions, credit for their work — because some part of them no longer trusts that speaking up is safe.
Self-protective isolation. As Dr. Debi put it in our conversation, many people conclude it's "better to keep everyone at a distance than risk that chance that someone may get close to us again." It feels like self-protection. It functions like a ceiling on your influence.
Eroded intuition. The instinct that once flagged red flags in coworkers or bosses goes quiet, because the last time it "worked," it still let you get hurt.

Ready to rebuild the confidence workplace betrayal quietly took from you? Download our FREE Leading Before You're Ready playbook and get:

? A framework for rebuilding executive presence when your confidence has taken a hit
? Practical language for reclaiming your voice in meetings within days, not months
? The mindset shift that lets you lead before you feel "fully ready" again
? Tools used with clients who've gone on to earn promotions and six-figure roles
Get the Leading Before You're Ready Playbook ?
How to Notice You're Still Carrying It
One of the most useful moments in this conversation is Dr. Debi's answer to a simple question: how does someone even realize betrayal is still affecting them? Her answer wasn't a checklist of symptoms — it was three places to look: your health, your work, and your relationships. If any of those three areas feels "off" in a way you can't quite explain, unresolved betrayal is worth considering as a root cause, not just stress or burnout.
Workplace Betrayal Recovery: Why You Can't Skip to "Just Move On"
A recurring frustration Dr. Debi and I discussed is how often people are told to "just get over it" — as though healing from betrayal were a decision instead of a process. In her framework, recovery moves through stages, not a single leap. You can't talk yourself into Stage Four while you're still standing in Stage One. Trying to skip ahead is exactly why so many leaders feel stuck: they've done the mental work of "deciding to move on" without doing the deeper work each stage requires.
The practical implication for leaders: if you've told yourself to "get over" a workplace betrayal and it hasn't stuck, that's not a willpower failure. It's a sign you skipped a stage.
Rebuilding Trust in Your Intuition
Dr. Debi was direct about this: "we have to rebuild trust in our intuition, in our wise inner guide, whatever you want to call it." The practice she described is simple — the next time something feels off with a coworker or a boss, a small signal that something "feels shady," pause and name it instead of dismissing it. Every time you notice the signal and honor it, even in a small, low-stakes way, you rebuild the muscle betrayal weakened.
Rebuilding Identity: Keep What You Love, Release the Rest
The second piece of the framework is about identity, not just instinct. As Dr. Debi framed it: figure out "what are all the parts you love" about who you are — those come with you into the next chapter. The rest doesn't have to. This isn't about becoming a different person. It's about consciously choosing which parts of your pre-betrayal self are worth rebuilding and which parts were never serving you anyway.
That reframe — "you're rewriting a new script" — is the shift from surviving betrayal to authoring what comes after it. A useful self-check Dr. Debi offered: picture the version of you on the other side of this, fully rebuilt. Would she do the things you're currently doing and saying? If not, that gap is exactly where to start.
Implement This Week: A 4-Step Action Plan

Step 1 (15 minutes): Run the three-area check. Write down one honest observation each about your health, your work, and your relationships right now. Look for the thread connecting them.
Step 2 (10 minutes/day): Practice the intuition pause. Once a day, when something feels slightly off in an interaction, pause and name it silently instead of dismissing it. Track how often your read turns out to be accurate.
Step 3 (30 minutes): Do the "parts you love" inventory. List the traits, habits, and strengths you want to carry forward. Separately, list what you're willing to release. Keep the first list somewhere visible.
Step 4 (ongoing): Use the future-self test. Before a hard conversation or decision this week, ask: would my fully rebuilt self do this? Let the answer guide you, not the fear in the moment.

Success metric: By the end of one week, aim to catch and honor your intuition at least five times — even in small moments. That's the rebuild in motion.

Common Mistakes Leaders Make After a Workplace Betrayal

Mistake 1: Treating it as a confidence problem instead of a trust problem. Confidence-building tactics (power poses, affirmations) don't address a broken intuition. They mask the symptom while the root cause stays untouched.
Mistake 2: Trying to "just get over it" without moving through the stages. Deciding to move on isn't the same as doing the work each stage requires. This is why the same hurt tends to resurface in new relationships and new roles.
Mistake 3: Isolating as a permanent strategy. Keeping everyone at a distance feels protective short-term. Long-term, it caps your influence, your network, and your visibility for the next promotion.
Mistake 4: Trying to heal alone. You don't have to do this without support — a coach, a trusted peer, or a mentor can see the gap between where you are and your future self faster than you can see it yourself.

People Also Ask
What is workplace betrayal, exactly?
Workplace betrayal happens when someone you trusted at work — a manager, peer, or mentor — acts against your interests in a way that violates that trust. It's distinct from ordinary workplace conflict because it damages your trust in your own judgment, not just your view of the other person.
How is betrayal different from burnout?
Burnout is typically caused by chronic overwork or lack of resources. Betrayal is caused by a specific breach of trust and often produces symptoms — hesitation, isolation, eroded intuition — that can look like burnout but require a different kind of recovery.
Can you really rebuild trust in your own intuition?
Yes. Dr. Debi Silber describes it as a practice, not an event: consistently noticing and honoring small intuitive signals rebuilds the confidence in your own perception that betrayal damaged.
How do I know if I'm still carrying an old workplace betrayal?
Look at three areas: your health, your work, and your relationships. Unexplained tension in any of them can be a sign that an old betrayal hasn't fully been processed.
...

Executive Summary
AI strategic thinking for women executives is no longer optional — it's the dividing line between leaders who get exposed and those who get elevated. Executive coach Sabrina Braham and author Barry O'Reilly reveal how to build your judgment system, accelerate decisions, and think strategically at the highest level.




Quick Takeaways


Barry O'Reilly's defining insight: "AI is not going to replace leaders — it's going to expose them."
Most executives have never documented their judgment system — and AI makes this gap impossible to hide.
Decision velocity + decision advantage are the two metrics separating leaders who accelerate from those who stall.
Misty Schaefer, VP at American Airlines, uses AI voice notes and scenario planning for orders-of-magnitude better decisions.
The biggest missed opportunity in AI leadership is not learning together — yet the fastest learners do exactly that.







There's a line on the back of Barry O'Reilly's new book that every woman executive needs to sit with:

"AI is not going to replace leaders. It's going to expose them."

AI strategic thinking for women executives is no longer a competitive edge — it's fast becoming the baseline expectation at the director, VP, and C-suite level. I'm Sabrina Braham, executive leadership coach (MA, MFT, PCC) with 30+ years of experience, and host of the Women's Leadership Success Podcast — top 1.5% globally with almost 900,000 downloads. My clients include leaders at Stanford University, Ernst & Young, and Autodesk. And what I see in my coaching practice right now is a clear divide emerging: women executives who are building AI-enhanced judgment, and those who are still relying on invisible, inarticulate intuition they've never made explicit.

AI is about to make that gap impossible to hide.

This is Part 2 of my conversation with Barry O'Reilly — author of Artificial Organizations: Build Better Judgment, Speed, and Results with Machine and Human Intelligence, keynote speaker at Gartner's CFO Conference, and one of the most sought-after AI leadership advisors in the world. In Part 1, we covered how women leaders can use AI to build personal career confidence and grow into bigger roles. Here, we go deeper — into the strategic leadership capabilities that will define who rises at the executive level in 2026 and beyond.

New research from Chief and The Harris Poll (2026) confirms that 85% of senior women leaders are now active players in their organization's AI strategy — and 68% are focused on using AI to amplify human talent, not replace it. The leaders pulling ahead are those who've moved beyond productivity tools into something more fundamental: AI-enhanced judgment systems.







The Uncomfortable Truth: AI Will Expose Leaders Without a Judgment System
When Barry walks into executive rooms around the world, he asks a deceptively simple question: "Show me your system for making this decision."

The silence that follows is telling.

"Often, a lot of the time, they just don't have a system," he explains. "They've never systematically written down all the steps they're going to go through to make an actual decision." For most leaders, the judgment system — the internal algorithm for weighing options, prioritizing inputs, and reaching decisions — has never been made explicit. It works. But it has four critical limitations:

It's not visible — others can't observe or learn from it.
It's not repeatable — it can't be consistently applied by or handed off to others.
It's not challengeable — if it's in your head, no one can push back on its blind spots.
It's not improvable — you can't deliberately tune what you can't see.

In my 30+ years of executive coaching, this is one of the most consistent patterns I see in women leaders who are passed over for promotion despite exceptional performance: their judgment is excellent — but it's invisible. They can't teach it, transfer it, or demonstrate it in the way boards and senior leaders need to see. AI strategic thinking for women executives forces this reckoning, and the leaders who embrace it rather than resist it will define the next decade of leadership.

Here's what my Leading Before You're Ready playbook addresses directly: building the judgment, presence, and strategic clarity that precedes you into every room — before you hold the formal title. AI doesn't change that mission. It accelerates it.




What Is a Judgment System — and Do You Have One?
A judgment system is the explicit process and criteria you use to make leadership decisions: the information you seek first, the variables you weigh, the sequence you follow, and the principles that guide your final choice.

For most leaders, this system exists — but it lives entirely in their heads, accumulated through years of experience and pattern recognition. It works. But it has critical limitations that AI strategic thinking for women executives can directly address.
The Judgment System Exercise Barry Uses With Executive Teams
Here's the exercise Barry runs at the opening of his executive engagements — and one I now recommend for every leader I coach:

Name a key decision coming up for your team. Be specific: a resource allocation decision, a product investment, a market expansion choice.
Draw out your judgment system for making that decision. What information do you look for first? What criteria matter most? What's your sequence of evaluation? What would make you say yes — or no?
Share your judgment system with your peers. This is where the transformation happens. A VP of Marketing and a VP of Finance, both making the same type of decision, suddenly realize they weight customer behavior and market size differently — and neither has ever made that explicit in shared decision-making.
Identify the gaps. Where is your information current and reliable? Where is it outdated, incomplete, or missing entirely? What would better information change?

"Suddenly you have groups of people sitting around going, 'I've never done this before,'" Barry explains. "And they're right. Most executive teams have never made their collective judgment infrastructure explicit."

From a coaching perspective, I want to highlight what this exercise does beyond improving decision quality: when you can articulate how you make decisions — not just what decisions you make — you demonstrate the executive presence that earns trust and bigger responsibilities. This is exactly what I teach in the Leading Before You're Ready playbook.






Judgment Infrastructure: The Data Ecosystem That Feeds Your Decisions
Once leaders map their judgment systems, Barry introduces a second connected concept: judgment infrastructure — the data ecosystem that feeds your decision-making algorithm.

Barry asks leaders: "Across your company, how are you getting the information you need to run your judgment system?" The answers reveal how fragile most leadership data environments actually are.

"I have a spreadsheet I get once a month." "Our customer records are three months out of date." "I usually get that information from a conversation with someone else, so it depends on who I ask."

The principle is clear: the output of any system is determined by the quality of its inputs. Poor-quality, delayed, or incomplete information fed into even an excellent judgment system produces poor decisions. For women executives in tech leading AI-adjacent organizations, understanding how to design and govern your information ecosystem — not just receive reports — is a defining capability for 2026.


Decision Velocity + Decision Advantage: The Two Metrics That Define Executive Performance
Barry's work with high-performing organizations has surfaced two metrics that consistently predict which leaders — and companies — pull ahead:

Decision velocity: How fast can you move from problem identification to a well-reasoned decision? Not impulsive speed — calibrated speed supported by quality process.
Decision advantage: How current, accurate, and comprehensive is the information available to you when you need to decide? Real-time — or three months stale?

"That is how companies, startups, businesses power ahead," Barry explains. "They learn faster, they make decisions at a high velocity, and the information to support those decisions is to hand in real time."
 



AI dramatically accelerates both metrics. A meeting co-pilot that captures and synthesizes every conversation means you're never walking into a decision without full context. Barry describes his own routine: "I run a process either the day before, the morning of, or even five minutes before I meet someone. It runs all the last conversations we've had against my judgment system for the meeting I'm about to have." He shows up to every conversation with full context, clear priorities, and the calm that comes from genuine preparation.

That calm is not incidental. As I always tell the executives I coach: your cognitive and emotional state in high-stakes situations is a performance variable. Anything that reduces cognitive load — like AI capturing your meeting context — directly improves your effectiveness in those moments. AI strategic thinking for women executives isn't just a professional tool. It's a confidence tool.


Case Study: How Misty Schaefer Uses AI to Lead American Airlines Strategically
The most vivid example Barry shared of AI strategic thinking in action involves Misty Schaefer Sern, VP of Consumer Technology at American Airlines — responsible for AA.com, the mobile app, and every digital touch point the world's largest airline uses to serve customers.

Misty's natural trait: she has her best ideas on the move — walking the terminal, talking to ground staff, observing what's happening at the gate. The traditional problem: those ideas used to evaporate between the inspiration and the desk.

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Executive Summary: Most women leaders know AI could accelerate their careers—but don't know where to start. Executive coach Sabrina Braham and author Barry O'Reilly reveal the Traits, Tasks, and Tools framework that eliminates AI paralysis, builds confidence in unfamiliar leadership roles, and helps women leaders AI career growth into bigger opportunities—starting this week.

Quick Takeaways:

69% of women say AI has opened new career pathways—but only for those who start using it now (ANSR Women in Tech Report, 2026).
The Traits, Tasks, Tools framework reveals how to match AI to the way you personally do your best work.
Use AI to pressure-test your thinking—never to hand over your judgment. That distinction changes everything.
Asking AI "What questions should I be asking as a VP?" instantly elevates your perspective without years of experience.
The worst thing you can do in a time of AI uncertainty is nothing. You must be in it to learn it.

You know you should be using AI. You've heard the urgency, seen the headlines, maybe even opened ChatGPT, stared at that blinking cursor—and quietly closed the tab.
Here's what I want you to know: that moment of hesitation doesn't mean you're behind. It means you haven't yet found your entry point.
I'm Sabrina Braham, executive leadership coach (MA, MFT, PCC) with 30+ years of experience, and host of the Women's Leadership Success Podcast—top 1.5% globally with over 950,000 downloads. I coach senior women leaders at Stanford, Ernst & Young, Autodesk, and across the tech industry. And one of the most common things I hear from directors, VPs, and C-suite executives right now is: "I don't know where to start with AI."
New research backs this up: Chief and The Harris Poll surveyed 1,000+ senior women leaders in 2026 and found that while 85% are active players in their organization's AI strategy, the approach matters enormously. The leaders who get ahead aren't the ones who automate the most—they're the ones who build human capability alongside AI. And according to the ANSR Women in Tech Report 2026, 69% of women who do engage with AI report it opens entirely new career pathways in product strategy, transformation leadership, and AI governance.
In this episode of the Women's Leadership Success Podcast, I welcome back Barry O'Reilly—author of Artificial Organizations: Build Better Judgment, Speed, and Results with Machine and Human Intelligence, keynote speaker at Gartner's CFO Conference, and one of the most sought-after AI leadership advisors in the world. Since our last conversation, Barry has been traveling globally—observing how leaders at every level are (and aren't) adapting to AI. His findings are equal parts sobering and energizing.

This is Part 1 of a two-part series. Here, we focus on women leaders using AI for personal growth, confidence, and career advancement. In Part 2, we go deeper into how AI can transform your strategic thinking and decision-making as an executive leader.

Why Women Leaders Are Paralyzed at the AI Starting Line
After keynoting Gartner's CFO Conference and spending months in leadership rooms across North America, Barry reports seeing the same pattern everywhere: hesitation.
"People don't really know where to start," he says. "They constantly hear about new tools arriving in the market. They hear that everything they were meant to do last week is no longer the right thing to do this week. And it all leads to hesitation—which, counterintuitively, is the worst possible response."
I know this directly from my coaching practice. I've spoken with women leaders who are brilliant, accomplished, and deeply capable—who are also avoiding AI entirely because they don't know what to do first. And I understand it, because I was there too. When I first started exploring AI, I treated it as if it were smarter than me—as if whatever it said must be right. That mindset kept me small.
What changed? Doing the exercises in Barry's book. Going through them shifted me from intimidated observer to active director. Now, AI is my servant—I correct it, challenge it, redirect it. My creative and analytical output has genuinely expanded as a result.

"Counterintuitively, the worst thing you can do when there's uncertainty is do nothing. Because you don't learn anything." — Barry O'Reilly

This matters especially for women in tech, where the stakes are already high. The ANSR 2026 report found that despite women producing 43% of the world's female STEM graduates, only 14% hold C-suite seats. The gap isn't pipeline—it's systems. AI fluency is rapidly becoming one of those systemic differentiators. The women who build it now will have compounding advantage; those who wait will face a steeper climb.
My Leading Before You're Ready playbook is built on exactly this truth: you don't wait to feel fully prepared. You use every available tool—coaching, community, AI—to think and show up at the level you're stepping into.

The Traits, Tasks, and Tools Framework: The Smarter Way to Start with AI
Most people approach AI for women leaders career growth backwards. They hear about a tool, jump into it, hunt for something useful to do, get mediocre results, and conclude AI isn't for them. Barry's Traits, Tasks, and Tools framework—one of the most referenced frameworks in Artificial Organizations—completely resequences this.
The problem: "Most people with this technology just jump straight into the tool. They try to figure out a task to use it for. And only if ever do they ask themselves how they actually do their best work." That backwards approach locks you into the tool's opinions about how work should be done—which may have nothing to do with how you create your best thinking.
Trait-First: Start With How YOU Do Your Best Work
Before you open any AI tool, answer honestly: When do I do my best thinking?

Are you a talker? Your best ideas emerge in conversation and dialogue.
Are you a writer? You process and synthesize by putting things on paper.
Are you a visual thinker? You need diagrams, maps, and frameworks to see clearly.
Do you need solitude and quiet to generate insight, or energy and people?

Barry's personal discovery here is instructive. Dyslexic and self-described as a D-student in English literature, he'd spent years trying to write like he imagined writers wrote—sitting quietly, composing prose. "I drank a lot of wine and sat by a lot of fires, but I didn't create much content." Once he recognized that his natural trait was talking, everything changed. He hired a journalist to interview him conversationally, used transcription to capture the output, and went from blank pages to 10,000 words of book content in roughly three hours.
That's not a productivity hack. That's a trait-matched workflow—and it's what women leaders using AI for career growth need to build for themselves.
Task-Next: Where Does Your Leadership Create the Most Value?
Once you know your traits, identify the tasks where you create outsized value. Not the email and calendar management—the strategic work that shapes your team, your organization, and your career trajectory. This might be:

Synthesizing complex information into clear executive recommendations
Preparing for high-stakes meetings and presentations
Developing your team's thinking and capability
Building strategic scenarios and options for decision-making
Crafting your executive narrative for visibility and advancement

Tool-Last: Find What Matches Both Your Traits and Your Tasks
Only now do you select tools. Barry matched his "talker" trait and "content creation" task to meeting co-pilots and transcription tools. For women leaders with different trait profiles:

If you're a talker preparing for board presentations: Use voice-to-text capture combined with a generative AI to structure and refine your speaking points. Tools like Otter.ai for capture and Claude or ChatGPT for synthesis are a natural combination.
If you're a writer preparing strategic memos: Use AI as a sophisticated thinking partner—share your draft, ask it to steelman the opposing view, and challenge every assumption.
If you're a visual thinker: Use AI to generate frameworks and then render them in tools like Miro or Canva. Ask AI to "map this decision as a 2x2 matrix" and then build on what it generates.

How AI Builds Leadership Confidence in Unfamiliar Territory
This is the angle I brought to this conversation that Barry told me he'd never considered—and it's at the heart of what I see women leaders needing most right now.
A director gets promoted to VP. A leader's company downsizes and she inherits three departments overnight. A high-potential executive gets tapped for a stretch role she doesn't feel prepared for. These are the moments when imposter syndrome spikes, when visibility feels risky, when the gap between who you are today and who the role requires feels widest.
I asked Barry: "How can women leaders use AI to build their confidence in these transitions?" Here's how he frames the three levels of AI impact:

Level 1 – Productivity: You bolt AI onto your existing workflow. Emails are faster, documents generate quicker. Real but modest—5 to 10% improvement.
Level 2 – Performance: You use AI to pressure-test your thinking and challenge your mindset before high-stakes situations. Your judgment improves, and better decisions follow.
Level 3 – Executive Presence: AI offloads cognitive load by capturing conversations, tracking decisions, and surfacing context. You arrive at every meeting calm, prepared, and fully present. This is where careers accelerate—and where women leaders using AI for career growth unlock the biggest competitive advantage.

My own experience makes this concrete. I started using AI to help reorganize a storage shed—asking it to help me think through what goes where, what organization system would work best. After three days of working on it together, AI said to me: "You're getting better at this." And the following week, when I had a larger project,...