The CEO Playbook

The best leaders interview for curiosity, not perfection.  " I interview how people think," says Millard 'Mickey' Drexler, Chairman of Alex Mill. “I don't care where you were educated. Tell me about where you grew up.” 'Mickey' says he’s less interested in rehearsed answers and more interested in the unscripted details that reveal how someone notices the world around them. "One worked at Starbucks, so I said, 'If you were running Starbucks,  what would you do better?'  I'll never forget, someone said, 'It's all perfect.'  I said, 'What about the messy counters?'" What small “tells” do you look for when interviewing someone?

FAILER-FAVE (pronounced FLAY-vər FLAYV) presents “How To Fail As A CEO” Episode (Yeah, boyeeeeee!) 13. Speaking of gender, lyricist “Flavor Flav” helps fulfill needs of Olympic athletes including being the U.S. women's water polo team's official 💰 hypeman, a model for disruptive advocacy. “House of Cards” diabolical disrupter “Frank Underwood” said, “What if I tell you, your boss doesn't pay you for your time? He pays you just enough to keep you showing up tomorrow. If he paid you too much you’d quit & build your own. If he paid you too little you'd leave & find better. So he keeps you trapped in the middle. Earning enough to survive, but never enough to escape. They call it a job, but it's really a system. Your effort creates the wealth, your boss collects the profit, & you get the scraps dressed up as a salary. They convince you that a promotion is freedom when it's really just a shinier cage with a higher rent. Your boss doesn't need you rich he needs you dependent, because dependent workers stay loyal while free people walk away. If you want to really be free & want to learn more, then...” Breathe, self-sooth & listen courageously to a counter to Frank’s employee/employer sentiment in an excerpt of my 2022 keynote at LinkedIn TalentConnect. “What has been allowed to exist for too long is the idea that retention success means keeping you. We don't need to retain people anymore, y'all. It’s not your choice what they choose to do. Who you are is who you are. If you can’t be who you are, where you are, change where you are, not who you are. Whatever your life was & whatever their life is & how they are the same, is not true. So don't create an environment where people need to come & fit in or stay. Instead, understand that they're coming with all this, give them the choice of whether or not they want it to be told & do not retaliate. I don't mean the type of retaliation that is HR investigateable & obvious. I'm talking about the retaliation where you don’t invite me to lunch anymore, you take me off the list for promotion, you say ‘I wonder if Caroline is late because she doesn’t have a husband & has to drop her daughter off at daycare so we gotta start at 8.’ Take what they’ve lived, understand them deeply, advance them with protection & air cover, & be the place that puts the best of talent out into the world.” About his clock William Jonathan Drayton Jr. said, “The reason why I wear this clock is because, you know, time is the most important element, and when we stop, time keeps going." When/where is your talent coming or going, CEO? Do you know when Talent [Daylight] Savings Time starts & if we’re “falling back” or “springing forward?” ************************************************* So if the failure-lessons are “The Biscuits” then the purpose-learnings are “The Tea.” As Kermit-The-Frog would say, “Sip Curiously!” 🍵 Until next week, Fa[re]il Well My Friends, Fail Well. 🤝🏿 Oh & PURPOSE-fully, LinkedIn The CEO Playbook peeps. 😎

Not sure where to start with improving your workspace? Try this quick quiz inspired by one of my favorite books, “A Pattern Language” by Christopher Alexander. - Is there a wall behind you? So no one can sneak up on you. - Is there a wall to one side of you? Too much openness makes you feel exposed. - Do you work in at least 60 square feet? Otherwise, you’ll feel cramped. - Do you have a view to the outside? You’ll feel confined in a room without a view. - Can you face in different directions at different times? - Do you have at least one co-worker within talking distance? Any questions to which you answered “No” may be a good place to start. During a busy season, even turning your desk a few degrees or swapping out a chair can make a surprising difference.

When we talk about feeling motivated and engaged at work, we use words like "purpose" and "passion." The author Jennifer Breheny Wallace says there is an essential need beneath all of this — mattering. Jennifer describes mattering as "the feeling that you are valued and that you add value." She goes on to say — "It is the drive to matter that shapes human behavior for better or for worse. Mattering is the story that employees tell themselves about their place in the company. Am I valued? Do I have a voice here? Would I be missed? When an employee can answer YES to these questions, they feel seen, appreciated, essential. They feel like they matter, they will give energy to their roles, and they will stay more loyal." I really like this notion of mattering as the most fundamental of needs — not just in the workplace, but in society more broadly. So much of what ails us is a crisis of mattering. We often talk about the human need for dignity, for love, for status, but these objectives all sound loftier, and harder to achieve. Status is a zero sum game. Dignity is subjective. If we love everyone, the meaning is diluted. But making the people around us feel that they matter? This seems like an excellent goal for all of us.

In a crowded marketplace, the businesses that win aren’t always the ones with the best products. They’re the ones that make their value unmistakably clear. I was walking through the Bryant Park Holiday Market in New York City. A swirl of lights, music, and more than a hundred vendors all trying to grab attention. Most booths were charming. Clever names. Cute displays. Plenty of personality. But they all blended together because you had to stop and figure out what they actually sold. Then I saw it. A simple sign. No fancy design. No clever branding. Just three words: “Gifts for Golfers.” Instant clarity. Who they serve. What they offer. Why someone should stop. In a sea of generalists, they stood out because they were specific. And it made me think about how often we bury our own value under jargon, creativity, or complexity. We assume people will get it, but most of the time they’re busy, distracted, and making decisions in seconds. So here’s the real filter to use: Can someone understand who you help and how at a glance? Because whether it’s your LinkedIn profile, your website, or the way you introduce yourself, clarity is a competitive advantage. The easier you make it for people to see themselves in your message, the faster the right opportunities find you. Clarity isn’t the opposite of creativity. Clarity creates space for the right kind of creativity that attracts the people you’re meant to serve.

On the twelfth [day] week of [🎄] “How To Fail As A CEO,” [my true love] failure sent to meeeeeee…Episode 12, sans Partridges, Pears, & Trees. In the literary classic “There’s A Monster At The End Of This Book” the first-astonished-then-embarrassed philosopher Grover asserts, “the monster ‘twas indeed me.” Big “A,” Big “I,” alleges Grover becomes increasingly distressed because the title suggests a monster is at the end. He repeatedly begs & pleads with the reader to stop turning the pages to avoid meeting the feared creature. His futile attempts to prevent progress include tying pages together with rope, nailing them shut with boards, & building a brick wall. These efforts fail as they are just illustrations easily "bypassed" by turning the page. The final page reveals that the only character present is Grover, who is the "monster" the title referred to all along, signaling that the things one fears may not be so scary after all. Thematically, this meta-narrative for young minds offers a CEO’s warm & weird inner child some reflective reasoning on the potential-of-the-possible. Interactively, a legacy far beyond benevolence is gilded when the future-proofing influence of a CEO is wielded. With born & bred ambition, the role offers transformative opportunities to re-condition something individually noticed, into a refurbished thing equitably & collectively known. Davos, anyone?!?! With full “who da monster” energy, what could social media be if it was molded into the best version of itself for any & all, powered by the people that need it least but can change it most…I am talking to you & your change agendas, CEOs, politicians, academics, et al, in my “davos culture” voice. Grovey-Grove’s scholarly groove challenges us to break the fourth wall & speak directly to the “consumer,” leverage humor & friendship to thwart anxiety & fear, & foreshadow the better as it’s being built. It’s a generous contextualization platform from which we can embark upon “social media” reform to enable how we ALL BEST PERFORM! Powerfully WE can… …oust hiding hurt; own heeding hope. …foreclose harm havens; construct healing homesteads. …remodel hostility housing; design health hosting …eradicate humiliation’s hospice; hospitate humanization’s hostel. You da monster [CEO] boo, so whatcha gonna do to upgrade a place that haunts us into one that flaunts us as us? Hue-man to human can really happen?!?! ION know, but I know who does. To Switzerland I go. Toodles. **Caroline caroling** Oh, one more piece of business. I move to induct formerly embarrassed now empowered “Grover the Great,” into the CEO Hall of Fame. All those in favor say, 👁️. ************************************************************* So if the failure-lessons are “The Biscuits” then the purpose-learnings are “The Tea.” As Kermit-The-Frog would say, “Sip Curiously!” 🍵 Until next week, Fa[re]il Well My Friends, Fail Well. 🤝🏿 Oh & PURPOSE-fully, LinkedIn The CEO Playbook peeps. 😎

Early in your career, people chase you for your work. Later, you’re the one chasing everyone else—and your own projects may fall to the bottom of the list. That change isn't necessarily about motivation, but rather, how you respond to external expectations. In my Four Tendencies framework, I explain how some people easily meet their own aims, while others do way better when someone else is expecting results from them. If this sounds like you, it might help to identify your own Tendency so you can set up the systems that make it easier to follow through on the work that matters most. Take the free quiz here: bit.ly/3MVoWXr

Do business leaders today choose new forms of media over legacy media in order to avoid tough questions? If so, is this a mistake? Andrew Ross Sorkin thinks so. Andrew told me the following story. "Many years ago I was about to go on stage with an executive, and right before the interview the CEO said, 'throw them as hard as you can.' And I remember thinking, 'Huh, no one ever says that to me.' When the interview was over, I said, 'What were you doing?' I thought maybe he was trying to throw me off. And he said, 'If you throw them underhand, both us lose. I knew that if you threw it hard and I could hit the ball out of park, I would win the game.' And I think there is a lot of value to that. And unfortunately I think right now there are not a lot of people who are following that lesson."

I’ve developed a lot of different skills over the years, but what stood out most from my conversation with Robert Herjavec were his thoughts on curiosity and discipline. These two traits create the bridge between potential and progress. The best leaders I’ve met share something powerful: emotional intelligence, storytelling, and the ability to enroll others in a mission bigger than themselves. Discipline keeps you consistent when excitement fades. Curiosity keeps you expanding when comfort tempts you to stop. The more you cultivate both, the faster you grow, and the further you can take the people you lead. What lesson resonates most with you?

AI is giving us back hours. The real question is what we do with them. We’re already seeing the upside: faster analysis, quicker ideation, tasks that used to take hours now taking minutes. That’s real progress. But unless we’re intentional, the time we gain quietly gets absorbed into the noise of daily work. If we want AI to improve our lives rather than simply accelerate them, we have to choose how we reinvest that space. One option: create room for strategic thinking. Most of us rarely pause long enough to ask where we’re heading, what we should double down on, and what we should stop doing altogether. Those quiet moments often reveal opportunities we’ve been too busy to notice. Another: deepen human connection. In a world where information is abundant, trust is rare. Rapport, presence, and real relationships are still the things that move careers forward and no model can replace them. As AI takes on more of the busywork, the opportunity isn’t to simply do more. It’s to do what matters with more clarity, more intention, and more heart.