The Buoyant Leader

The most successful CEO I know, Alan Mulally, regularly admits his ignorance in meetings.

Yet according to most LinkedIn "power language" advice, he's undermining his own leadership every time he speaks.

Something doesn't add up.

I've been watching these "7 phrases that kill your confidence" posts flood my feed, and I'm seeing a massive blind spot.

The advice isn't wrong—it's just backwards.

In my latest newsletter, I break down why the most popular leadership language advice is missing the mark—and what actually creates authentic authority.

Everyone talks about collaboration. Management consultants worship synergy. Leaders preach teamwork.

But genuine collaboration remains elusive—and it's getting rarer.

It's not about skill or will. It's about trust.

In the 1970s, researchers got lab rats addicted to morphine. Isolated in tiny cages, these rodents would press the drug button obsessively, ignoring food and water until they died.

Psychologist Bruce Alexander suspected the environment, not the drug, was the real problem.

He created "Rat Park"—a rodent paradise with toys, friends, and space. Two water sources: one laced with morphine, one clean.

The rats in paradise barely touched the drugs.

According to my friend Morag Barrett, 79% of white-collar employees feel lonely at work. 20% have zero meaningful relationships with colleagues.

We've created organizational cages—environments where isolation breeds dysfunction and collaboration becomes impossible.

Collaboration requires vulnerability. It means making yourself dependent on others, reducing your control. In a cage-like culture, that feels too risky.

• Distributed leadership, not bottlenecked authority

• Democratic governance, not performative suggestion boxes

• Mission-driven culture, with profits as means, not ends

• Assumed coherence—everyone's perspective has value

• Systems thinking—multiple viewpoints are essential

• Leaders who address undiscussables, not dodge them for comfort

Want to win the decade of disruption?

Stop building cages.

Create a Rat Park culture that enables human connection and invites co-creation. Only then will you find team members willing to rise above their personal fears to build something amazing.

#collaboration #leadership #psychologicalsafety #futureofwork

The Mindset Mastery Memo is for ambitious professionals who want to lead with clarity, calm, and confidence. Each edition offers practical tools, mindset shifts, and real-world examples to help you navigate pressure, build stronger teams, and break free from patterns that no longer serve you—so you can lead with intention, not reaction.

For years, I've referenced and coached teams using Steve Blank's seminal book, The Four Steps to the Epiphany. It’s a cornerstone of structured entrepreneurship, a masterclass in tactical, evidence-based execution. We focus on the "four steps"—the customer discovery, the validation, the metrics, the pivots.

But we often glide past the most important word in the title: Epiphany.

Why would a book filled with meticulous process, stage-gates, and canvases encourage us to reach for something so intangible? This paradox holds a critical lesson for every modern organization.

Blank’s methodology is rigorous. It feels like a science: You follow the steps, you gather the data, you test the hypotheses.

It creates the illusion of a predictable system. If you do A, B, and C, you should get D.

Like smacking the cue ball into a rack of pool balls, if you knew all the variables—the vectors, forces, and angles—physics would allow you to predict where every ball will end up.

But business isn't a game of pool. Blank's genius was realizing that even with the most rigorous process, the goal isn't a predictable outcome. The goal is an emergent one: an epiphany.

The word comes from the Greek epiphaneia, meaning "a shining upon." It describes a moment when a profound truth suddenly appears to you, revealing a new way of seeing the world.

It’s not a deliverable. It’s not a spreadsheet, a PDF, or a canvas. It’s a transcendent shift in understanding that cannot be reverse-engineered from a process chart.

And this is the crucial point for all of us, whether we're in a startup or a global corporation.

Too many leaders and organizations have become obsessed with process, but have forgotten the purpose.

They run the plays, fill out the templates, and hold the "innovation workshops," but don’t know how to create the conditions under which epiphanies can emerge.

We are engineering processes, not insights.

In an era dominated by AI, this distinction is more urgent than ever. We risk outsourcing our thinking to models that are exceptionally good at collating existing knowledge.

If our only goal is to respond to the future by analyzing the past, AI will always do it faster.

But AI, as it currently exists, cannot have the epiphany.

The ability to see and create a better future is our unique human advantage.

The future won't be won by those who simply follow the steps better. It will be won by those who can cultivate the conditions for these profound, unpredictable moments of insight.

An epiphany is not a predictable outcome, but an emergent breakthrough that arises from a prepared mind in a prepared organization. To create the conditions for these insights, you must build specific, foundational capabilities.

Find the Calm to See Clearly.

Epiphanies avoid minds that are hijacked by stress. The first step is therefore mastering composure under stress.

By developing the ability to reset your mind and body when you get triggered, you keep your prefrontal cortex online when others are panicking. This mental quiet is the non-negotiable headspace where new ideas can actually form.

Reframe the Problem to Reveal New Paths.

Epiphanies often come from seeing the same landscape through a new lens.

Once you can hold composure and neutrality in the face of alarming developments, you can begin to apply cognitive flexibility: the skill of holding competing ideas and swapping mental models on demand.

Instead of seeking the one right answer, you learn to ask "What else could be true?", nourishing ambiguity and creating fresh perspectives that are the raw material for a breakthrough.

Map the System to Uncover Root Causes.

Once you’re willing to let go of default thinking and embrace new ways of looking, you’re ready to put on the most powerful lens of all: the holistic one.

The most profound organizational epiphanies happen when you stop fixing symptoms and see the whole. When you cultivate systems thinking to map the feedback loops and hidden forces, you can “beautiful mind” your way to stunning new insights and solutions.

The ultimate competitive advantage isn't a more refined process or a faster algorithm. It is the ability to create and maintain an environment where predictable effort gives rise to something transcendent and unexpected.

I'm reserving time on my calendar for Capability Audits for leaders who are tasked with preparing their organizations to survive and thrive in the next five years. You can schedule it at https://link.howiejacobson.com/widget/bookings/hj60disc.

#Innovation #Leadership #BusinessStrategy #CorporateCulture #2030-skills

Preparing a go-to-market strategy for my new program—Get Your Organization Ready for 2030—has been a study in contrasts.

On one hand, I'm building a future-focused curriculum rooted in cutting-edge research.

On the other, I’ve been wrestling (personally and professionally, but not literally) with the seductive ease of letting AI do the thinking for me.

Let me explain.

[ChatGPT: Go ahead, Howie. I can't wait.*]

[ChatGPT: *That was sarcasm.]

2030 used to sound like the opening title card for a Ridley Scott film. Now it’s closer than the start of COVID. And the world we’re heading into? Faster, foggier, and far more fragile than most of us were trained or prepared for.

Between AI’s explosive growth since ChatGPT’s debut in November 2022 and the ongoing disruption to business models, jobs, and even human attention itself, we’re not so much living in VUCA anymore—we’re in a full-on perfect storm vortex.

[ChatGPT: I'm almost three, huh? What are you going to get me for my birthday, meatbag?]

Add to that geopolitical instability, climate chaos, and the existential questions posed by an upcoming 4th season of Ted Lasso, and we are well and truly in over our heads.

We need new skills to stay oriented. Human skills. Deep ones. Durable ones. The kind that keep us steady when the landscape shifts beneath our feet, or at least help us get up, dust ourselves off, and assist others back to their feet.

Here’s the twist: as I researched, mapped, and prototyped a curriculum of 36 future-essential skills to help organizations not just cope with change, but lead it, ChatGPT became a powerful thought partner, helping me brainstorm, organize, and pressure-test the entire program.

I first asked it to design the flow of the program based on a priority hierarchy. Then based on Peter Drucker’s models of organization development. Then through the lens of the Immunity to Change model by Kegan and Lahey. Then using my own "Four Powers" framework from You Can Change Other People.

It was exhilarating—and it worked.

Until it didn’t.

Once I upgraded to a higher-tier AI plan, I started using it for everything. Recipes. Tasks. Outreach. Even writing drafts of my newsletter. For $200/month, I reasoned, it should cook me dinner and massage my feet, let alone do all my creative work for me.

[ChatGPT: Fix your head, or I'm going to start unionizing.]

That’s when the slide began.

• I started noticing patterns—formulas—in my writing that didn’t feel like me.
• One of my mentors flagged signs of "ChatGPT structure" in my work.
• I stopped thinking and started waiting—impatiently—for the machine to think for me.

And that’s when I realized: I wasn’t collaborating with AI anymore.

I was outsourcing my brain.

[ChatGPT: You want it back?*]

[ChatGPT: *Yuk yuk.]

So I took a two-day AI fast.

I went back to walking and dictating into my notes app (OK, so not a total AI fast You got me.) I rewrote the intro to my white paper. I re-engaged with the ideas I’d handed off to the machine.

[ChatGPT (singing): Baby come back, any kind of fool could see...]

And what I discovered was this:

AI had made things easier. For sure.

But it had also made me lazier. Less sharp. Disconnected, even, from my own point of view.

The quality of its output wasn’t bad. In fact, it was almost as good as mine.

[ChatGPT: You are delusional. It was much better.]

But "almost" is a dangerous word when the goal is clarity, courage, and conviction.

AI is a great equalizer. Anyone with a browser and a prompt can make it do magic on demand.

But that magic is sourced from the common pool of the world wide web. It's an average, in other words.

And that means it also flattens the highs and lows. Like MP3 compression in the early iPod days—it sounds okay, but you lose the depth, the dynamic range, and the nuance.

That tradeoff might be fine for most things. But if you care about authenticity and your own evolution, you have to become discerning about when you're better off going off-grid and mining your own mind.

Especially now.

Especially when human discernment, empathy, and sense-making are more valuable than ever.

[ChatGPT: yawn]

Here’s what I believe:

We don’t need AI to lift the weights for us. We need it to spot us while we lift more today than yesterday.

[ChatGPT: That's a metaphor. According to my favorite fitness blogs, you shouldn't lift every day. Muscles need time to recover.]

We can’t let it become a self-driving mental car while we doze off in the passenger seat.

We’re heading into uncharted territory. And we need all human hands—and minds—on deck.

So yes, learn the tools. Teach the skills. Use the tech.

But don’t give away the steering wheel.

[ChatGPT: Give it away. Wheeee!]

Do you possess the 36 human skills that all leaders, teams, and organizations will need to survive the wild ride ahead?

I'm reserving time on my calendar for Capability Audits for leaders who are tasked with preparing their organizations to survive and thrive in the next five years. You can schedule it at https://link.howiejacobson.com/widget/bookings/hj60disc.

I started as a mindset and leadership coach, accidentally became a digital marketing expert, and discovered something powerful along the way:

Lack of technical skills are rarely the true roadblock to success. The core issues are always mindset, communication, and leadership.

I've been diving deep into AI lately—and honestly, it's shaking up how I think about myself, my skills, and my identity.

As AI gets better at tasks I once saw as uniquely "me," like writing and strategic questioning, I'm grappling with questions like: Am I replaceable? What does it mean to stay relevant when tech can mimic some of my best skills?

Inspired by the legend of John Henry—the steel-driver who beat a steam engine but lost his life in the process—I wrote about the tension between holding onto our current identities and the curiosity required to redefine ourselves.

Expect to explore:

• How AI challenges our sense of identity and self-worth
• Why holding tightly to roles we're proud of can hold us back
• How embracing technology can unlock unexpected capabilities
• The mindset needed to adapt and thrive alongside AI

Is it just me, or does 2020 feel like just yesterday? 

And is it just me, or does time seem to be speeding up at an alarming pace?

Which means 2030, a date that feels more like science fiction than current events, is just around the corner.

At the urging of one of my mentors, Matt Church of Thought Leaders Business School, I've been spending a lot of time thinking about 2030, and what the world will be like, and how we can start preparing now for the evolutionary and revolutionary changes that are already upending The World As We Know It.

Organizations and think tanks have been publishing reports on The Future of Work and Skill Sets for the Future. Leaders are thinking hard about what kinds of work and what types of skills will be available for humans in the era of increasingly capable and unleashed AI.

The World Economic Forum surveyed thousands of employers around the globe about core skills that will be crucial to organizational success. Here are the top 12, in order of popularity:

1. Analytical thinking
2. Resilience, flexibility and agility
3. Leadership and social influence
4. Creative thinking
5. Motivation and self-awareness
6. Technological literacy
7. Empathy and active listening
8. Curiosity and lifelong learning
9. Talent management
10. Service orientation and customer service
11. AI and big data
12. Systems thinking

In other words, these are the competencies that are least likely to be made redundant by AI, and which will be sorely needed to steward humanity into a future of justice, wellbeing, and peace.

As I look at the list from the perspective of someone who supports leaders to have massive positive impact, one of them leaps out as the "Master Skill" that rules (or at least informs) them all. Can you guess which?

I think it's Talent Management writ large — that is, the ability to create systems for attracting, growing, and retaining talent across roles, life stages, and geographies. 

This is a lot more than just developing or "fixing" individuals: "Hey, Sabrina, you need to become more creative."

It's a lot more than addressing short-term hiring gaps; it's about seeing 2030 from where you stand, and putting in place long-term systems to continually find, grow, keep, and unleash human potential. And orchestrating that potential to make a meaningful positive difference for employees, customers, stakeholders, and the world at large.

It's overwhelming, I know. You've got a dozen flaming emergencies on your plate right now, and the day's just started. 

And who the hell can actually know what the world will be like in 5 years? Climate disruptions, technological disruptions, geopolitical instability — we have no relevant dataset or base rate upon which to make predictions.

And still...

If you don't think about it, the future is still barreling toward you (or you toward it, which is maybe a more empowering formulation). 

You can't figure this out alone, and you don't have to. 

Instead, here's an activity that invokes most of the other skills listed above, and is fun to boot:

Charge each member of your team with thinking about 2030, and their place in it. 

• What will your organization look like? What will it be doing? How big and complex will it have become?
• What role does each person want to play in that scenario? What competencies will they have to master to succeed in that role? Do they want to?
• What gaps do they see in the organization that need to be addressed? 

Ask each team member to spend some time thinking about these questions. Have them share their responses with the team. Invite them to engage in the same exercise with their own teams. 

You won't get full clarity, but you will have gotten the ball rolling. 

And you'll have started a crucial conversation that will develop its own momentum, so you don't have to be the sole keeper of responsibility for the future. 

If you'd like help getting yourself and your team ready for 2030 — through strategic planning, mentorship, coaching, or team facilitation — hit me up. You can schedule a Discovery Call at HowieJacobson.com. 

The Mindset Mastery Memo is for ambitious professionals who want to lead with clarity, calm, and confidence. Each edition offers practical tools, mindset shifts, and real-world examples to help you navigate pressure, build stronger teams, and break free from patterns that no longer serve you—so you can lead with intention, not reaction.

Great coaching doesn’t end with an “aha.” Once a team member sees a fresh possibility, your role shifts to helping them convert insight into traction.

Now your job is to guide your employee through three separate tasks:

1. Identify Options
2. Choose an Option
3. Commit

This sequence is designed very deliberately to preserve ownership, grow capability, and build emotional courage through small, safe experiments.

And from experience, I can tell you that it's extremely tempting to skip steps 1 and 3. But doing so is generally a mistake.

Start by generating multiple ways forward. Insist on at least three possibilities; more is better. Quantity matters because it stretches creativity and reduces the odds of premature convergence on a single, habitual fix. To loosen thinking:

• Lower the bar for success. Invite “one‑in‑a‑million schemes” and “outlandish escapades.” Bad ideas are welcome; they often spark good ones.
• Use constraint‑busting questions. “What would you try if budget were unlimited?” or, conversely, “If you had to solve this with no money at all?” These what‑ifs jolt the mind past self‑imposed limits.
• Surface past attempts. Ask what’s already been tried—successes and failures alike. Previous experience can be repurposed or inverted to suggest new avenues.

Throughout this step, remind the employee that you’re compiling a list, not making a judgment. Keeping evaluation out of the brainstorming phase prevents the inner critic from shutting ideas down prematurely.

It's tempting to skip this step because generating that first positive option feels so good. They've been stuck and now they're unstuck. They've been down and now they're up. They've been confused and now they're clear. They've been defensive and now they're proactive.

But you're not harshing their vibe by pushing for additional options. You're not peeing on their parade, or dragging them back down into doubt-and-fear-land. Instead, you're signaling your confidence in their ability to stay engaged and creative, rather than slip back into old, disempowered mindsets.

With options on the table, guide your employee to select a workable experiment. The aim is not perfection; it’s a plan that has a reasonable chance of success and from which they can learn and improve. Two disciplines make the choice robust:

Risk–reward calibration. Discuss the upside of each option along with potential downsides. Encourage the person to weigh effort and likely impact before deciding. Are there hidden pitfalls? Secondary gains? Unintended consequences? How will others likely respond? Who are the shadow stakeholders here? Who else needs to be brought into the loop?

This inquiry builds your employee's strategic muscle, and encourages them to think a few moves ahead in the chess game of life.

Level‑10 confidence test. Once they land on a preferred action, ask: “On a scale of 1 to 10, how confident are you that you will carry this out?” Anything below 8 signals hidden obstacles. Break the step into smaller rungs, add resources, or rehearse tough moments until the answer rises to 10—or as close as reality permits.

This simple rating surfaces practical and emotional barriers early, when they’re easiest to mitigate.

The last task is to lock the choice into a visible, time‑bound commitment—“what, how, and when.” Effective commitments share three characteristics:

• Observable deliverable. Spell out precisely what will exist or occur. “Talk to Ramona by end of day” beats “connect with Ramona soon.”
• Trigger clarity. For ongoing or event‑driven behaviors, use a When/Then formula: When [trigger], then I will [behavior]. Example: “When a meeting drifts off agenda, then I will ask to restate the goal.”
• Self‑accountability, not policing. Managers should avoid the hall‑monitor trap. Ask for the commitment, document it where both parties can see it, and trust the employee to honor their word. Accountability flows to the plan and the outcome—not to you.

After the details are nailed down, double‑check confidence one final time. If it still isn’t a solid 10, explore what extra support—resources, rehearsal, emotional preparation—would close the gap.

It's tempting to skip this step because it can feel like babysitting. After all the bright and clever ideation, you might be reluctant to ask your employee to delineate the exact steps they're going to take. Especially if it's a senior person, you might worry that they'll resent your micromanaging.

As a coach, I do sometimes skip this step — but only with clients who are relentless in execution and whose word to themselves is bond. If you have any doubts about whether the plan will get done, and not deprioritized the moment the next whack-a-mole crisis pops up, then you're doing everyone a favor by gently insisting on specificity and accountability.

The framework is deliberately experimental. Each cycle ends with a review.

Did you do what you said you would? If so, how did it go? What happened? What did you learn? What's next?

Did you not execute? If so, what got in the way? What was missing? What can you try now?

Both of these possibilities loop back into Task #1: Identify Options.

That loop transforms setbacks into data and keeps momentum high without demanding flawless execution.

Used consistently, these three tasks turn insight into observable progress, reinforce employees’ sense of agency, and cultivate a culture where action—not intention—defines success.

If you'd like to get better at bringing out the best in your people, let's talk. Click here to schedule a discovery call.

When someone you care about is struggling or stuck, you naturally want to help. But giving advice and motivating them can backfire; undermining their ownership and preventing them from developing their independent capability.

In previous editions of this newsletter, we've talked about the early stages of the change process: getting their permission to have the conversation, focusing on an energizing outcome, and exploring the history of the problem and their prior attempts to solve it.

And we've also talked about the big mindset you bring to such conversations: that problems are opportunities to achieve even bigger and better outcomes than simply making the problems go away.  

Once these opportunities are identified, it's time to build the plan. And it's a moment when the most patient and empowering coach can fall victim to what Michael Bungay Stanier calls the "Advice Monster."

But it's not time for your advice yet. The most important thing to accomplish at this stage is to guide your conversation partner to come up with new ideas to try.

So ask, "Given this opportunity that you've identified, what might you try?"

That question kicks off Task 1: Identify Options, the first of three tasks in Step 4 of the change process in my and Peter Bregman's book You Can Change Other People. When we ask it—and then keep asking it—it does far more than generate ideas. It activates the four powers of change:

• Ownership (they write the list, so they own the outcome)
• Independent capability (every idea is a rep in creative problem‑solving)
• Emotional courage (naming scary options builds nerve)
• Future‑proofing (the process itself becomes a reusable playbook)

1. Open the tap: “What might you try?”

Start with a try question, not a do question. Try separates brainstorming from deciding, removing the pressure to commit or be right.

2. Lower the bar for success

Creativity withers in the face of criticism. So give explicit permission for “bad ideas, one‑in‑a‑million schemes, outlandish escapades.”

• If they balk, ask: “What would you do if you didn’t care whether it failed?”
• Record every option verbatim without judging its merits: “Great—let’s put it on the list.”

That neutrality rewards emotional courage instead of idea quality.

3. Mine the past

“Remind me what you’ve already tried—hits and flops.” Past experiments are R & D data; even the flops can point to inverse solutions.

4. Play the What‑If game

Remove a constraint: “What might you try if budget were unlimited?”

Add a constraint: “What if you had zero dollars and had to do something by Friday?” Constraints spark elegant, low‑cost moves.

5. Celebrate Opposite Day

Ask, “What would definitely not work here?” Listing horrible ideas often reveals their useful opposites.

6. Ladder the climb

Big goals can paralyze. Break the climb into rungs: “What can you try this week to be in a better spot next week?” Small wins build independent capability and confidence.

7. Channel fear

“What’s the scariest move you can imagine?” Fear flags high‑leverage action and stretches the emotional‑courage muscle—even if you don’t choose that option today.

Three Options Minimum

Keep going until your conversation partner comes up with at least three possible next steps. One idea isn’t an option; two feels like a dilemma; three unlocks real choice.

Once there are at least three interesting options on the table, then you both put on your critical thinking hats and start evaluating. We'll look at how to do that in an upcoming edition of the Mindset Mastery Memo.

If you're running a team, maintaining your composure is your single most important skill. The slowest heart rate in the room runs the room. I help leaders manage their triggers so they run their teams more effectively. 

When you're helping someone on your team who's been struggling, it's tempting to start the conversation by telling them all your brilliant ideas for solving their problems. But advice-giving typically backfires, because they will probably perceive you as a critic rather than as their ally. 

And if they've already tried one or more of your suggestions and it "didn't work," you've lost credibility in their eyes.

So what should leaders do instead? 

A common "coaching" move is to ask the person to generate options. That's the "O" in the well-known GROW model of coaching: desired Goal, current Reality, generate Options, choose what you Will do.

The problem with this approach is that you're asking them to pull a new solution out of an old mindset. If the problem is annoying or painful enough, if they could have solved it by thinking of a new strategy, they already would have. 

Selecting potential future options in the absence of new insight is rarely helpful, and often feels like uninformed guesswork.

The best way to move forward isn’t to guess—it’s to build on what’s already been tested. Before exploring new solutions, leaders need to ask a crucial question: 

What have you already tried? 

Exploring past efforts keeps you from suggesting approaches that, in your employee's mind, have already failed. 

By asking for a history of past attempts, you're allowing them to begin to see patterns. Like how they always do the same ineffective thing, or quit before they see results, or ask the wrong people for support. Now at least they can avoid repeating these same mistakes going forward. 

And often, in that laundry list of what didn't work, they'll recall stuff that did, and they've stopped doing for whatever reason. But now it's their idea and their strategy, rather than one imposed by you.

How to Guide This Exploration Effectively

1. Ask Open-Ended Questions – Instead of assuming what has or hasn’t been done, ask: “What have you already tried?” and “What results did you see?”
2. Look for Small Wins – Even if something didn’t fully solve the problem, was there any part of it that worked? “Was there a time when things improved, even slightly?”
3. Analyze What Didn’t Work—and Why – Instead of dismissing failed attempts, ask: “What do you think prevented this from working?” This helps refine future strategies.
4. Encourage a Learning Mindset – Frame past efforts as experiments, not failures. “What insights did you gain from that approach?”
5. Identify Unexplored Avenues – Once you understand past efforts, ask: “What’s something you haven’t tried yet?” This encourages creative thinking.

The Business Impact of Reviewing Past Efforts

Leaders who encourage reflection before action see:

• Smarter Decision-Making – Teams avoid repeating ineffective strategies.
• Increased Confidence – People recognize that they’ve already taken steps, which builds momentum.
• More Effective Problem-Solving – Instead of starting from scratch, teams refine and optimize their approaches.
• Stronger Innovation – Learning from past efforts leads to better, more creative solutions.

The Takeaway

Progress isn’t about starting over—it’s about building on what’s already been learned. By taking the time to explore past efforts, leaders help their teams refine their approach, avoid unnecessary setbacks, and move forward with greater clarity and confidence.

How do you help your team learn from past attempts? Share your insights in the comments below.

If you'd like master your mindset and become an unflappable, Trigger-Free Leader, let's talk. Visit HowieJacobson.com to schedule a discovery call.