Building a CIO Office to Impact 1,200 Families
My favorite part of my job is working with C-suite officers. Right now, I’m helping build the Office of a CIO ahead of a corporate split. Day 1, she inherits a brand-new company. We meet daily and work through org design, capital allocation, and technology needs. Her org alone is 1,200 people. Impacting that many families is something I don’t take lightly. I take the role with humility and approach it the same way I do my own investing: Long-term, disciplined, and future-obsessed.
Customer Obsession Turned $6M Into $5B
Coach went from $6M to $5B because Lew Frankfort focused on one thing: Customer obsession. Function. Difference. Emotion. That’s brand power. #Branding #Leadership https://t.co/dSE0pXRsTs
Value Over Novelty: Prioritize Meaningful Innovation
Not all innovation is good. Just because something is new doesn't mean it's better. Focus on meaningful innovation that truly adds value rather than chasing every new trend.
Spot Red Flags in Discovery Calls, Move On
Founders: Discovery call warning signs: 🚩 Vague answers about current challenges 🚩 'Need to talk to my boss' responses 🚩 No current spend on similar solutions 🚩 'No rush' timeline signals 🚩 Deflects all pricing questions Seeing 2+ flags? Move on to better opportunities.
Adaptability Fuels AI Revolution: Build Windmills, Not Walls
Build Windmills, Not Walls: Michael Gerstenzang Cleary Gottlieb’s managing partner until last month, Gerstenzang shares insights about the importance of adaptability, the AI revolution, and more. LINK: https://t.co/vXUH338qAL https://t.co/SZIJHMLcnA
AI Enhances, But Can't Replace Human Insight in Journalism
A wonderful evening with the @Columbia Knight-Bagehot Fellows — journalists taking a deep dive into business, economics, finance and technology at a moment when rigorous reporting has never mattered more. We talked about leadership, resilience and AI — and the responsibility...
Optimistic AI Startups Can Disrupt the Doomsday Narrative
So many doomsday predictions from the biggest AI players...who also need to justify massive capex. If you're a startup with a more optimistic and nuanced take on the future of work, this is your opportunity. The dominant narrative is ripe...
Roku Hires Former Snap, Meta Exec to Lead Ads
Roku taps Patrick Harris, a veteran of Snap and Meta, to run advertising sales.... https://t.co/0mYOElGbjg via @variety
True Career Power Comes From Sovereignty, Not Branding
You don't need a better brand. You need Sovereignty. You can have a great personal brand and still feel like a passenger in your own career, waiting for permission, chasing recognition, tying your worth to a job title. Professional Sovereignty is the...
Every Great Tech Team Needs Vision, Design, Execution
Every iconic tech company follows the same pattern. I’ve seen it repeat again and again. → The visionary founder who bends reality → The designer who shapes taste and experience → The quiet engineer who makes it actually work Different names. Same archetypes. Apple had them. Tesla had...
Specify AI Skills, Processes, and Problems, Not Vague Demands
Leaders, telling people they need “AI skills” is vague. What specific skills are helpful? What specific processes are you replacing with AI automation? What specific problems will AI solve in your organization? There are a lot of tools out there, and no...
Sarandos Accuses Paramount of Misinformation as WBD Negotiates Rival Deal
Ted Sarandos Slams Paramount for ‘Flooding the Zone With Misinformation’ as Warner Bros. Discovery Initiates New Talks With Rival Suitor https://t.co/rpsvBCV0vj via @variety
Likability Beats Intelligence for Earning More Money
Hard truth: Being likable will make you make more money than being smart 9/10 times.
Executive Ownership Drives Successful Business Transformations
Business transformations require strong executive ownership and decisive decision-making. Don't delegate all choices; leaders must guide consensus to navigate the inherent risks and ensure success beyond just a tech upgrade. #BusinessTransformation #Leadership #ChangeManagement https://t.co/3eDHQ4CWSO
Design Hybrid Work Intentionally; Leadership Shapes Future
Last month I had the pleasure of speaking at the Vienna-based International Organizations HR Network (VBIO) at the United Nations in Vienna on rethinking hybrid work. Three reminders: • There’s no one-size-fits-all hybrid model. Design it intentionally. • Hybrid isn’t an HR issue,...
Daily Habits, Not Promotions, Drive Lasting Success
Don’t obsess about getting promoted. Embrace daily attitudes and activities that earn promotions. Don’t concentrate on living a fruitful life. Practice life-giving habits. Dreams frustrate until they distill into daily habits. From: https://t.co/JXkB2kNxzc
Leaders Already Possess AI Skills—Just Unlock Them
One reassuring thing about teaching leaders to work with AI: They've been building AI skills their whole careers... without realizing it. The trick is unlocking what they already know so they can level up with AI. Judgment, context, and institutional...
Retention Beats Acquisition: Tight Onboarding Drives PLG Success
I sat down with Melissa Kwan, founder of eWebinar, and one line stuck with me: “Getting customers to sign up is the first date. Not the last day with you.” Melissa has built eWebinar to just under $2M ARR. No...
Defense Secretary Ousts Senior Adviser, Halts General Nomination
NEW: Defense Secretary Pete Hegseth has forced the ouster of a senior military adviser to Army Secretary Dan Driscoll, defense officials said, marking the Pentagon’s chief’s latest intervention into the service’s internal affairs amid long-simmering tension between two of the...
CEOs Must Publish Transparent AI-Forward Memos
100% agree. This is why I’ve been pushing for organizations to publish AI-Forward CEO Memos that are honest and transparent. CEOs need to be more proactive in communicating the impact of AI, and make the next steps for employees more...
Focus on Actions, Not Outcomes, for Lasting Progress
The Focus Most Get Wrong Don’t focus on what you want. Concentrate on what you do. Glance at the future. Concentrate on present action. Long-term goals are good for direction. Reject the seduction of results. Commit to daily rituals. https://t.co/JXkB2kNxzc https://t.co/SopVInPjlZ
Turn Envy Into Curiosity: Study Success, Not Resentment
The older I get, the more I realize envy is just misdirected admiration. Instead of resenting what someone else built, default to curiosity. Study it. Ask what it required. Ask what sacrifices they made. Ask what it cost. If you’re...
When Leaders Feel Obligated, Teams Suffer
A lot of people take on leadership roles, not because they want to, but because someone told them they “should” or they “had to” to achieve success. They approach the role like a transaction, not a responsibility. Now there are teams...
AI Boosts Productivity but Amplifies Workload and Burnout
A provocative new Harvard Business Review article is challenging everything we thought we knew about #AI in the workplace. “AI Doesn’t Reduce Work—It Intensifies It” shares findings from an eight-month study that reveal a counterintuitive truth: instead of lightening workloads, AI...
When CEOs Outshine Teams, Hiring Is Failing
Early on, the CEO is “the best person at the company” at some things. Often sales (passion + knowledge) or product vision. But by 100 people, if the CEO is “better than everyone” at 𝘢𝘯𝘺𝘵𝘩𝘪𝘯𝘨, the CEO has hired poorly, and...
Pause, Listen, and Question Your Own Assumptions
Everyday Pauses: Resisting the impulse to speak. Keep your lips together. Listen to understand. Shifting to curiosity. Humility learns. Ego knows. Ask yourself, “What might they understand that I don’t?” Challenge your own wisdom.
Choose the Letter: Prioritize Product Over Business Wrapper
Are you an envelope entrepreneur or a letter entrepreneur? Someone who's about the container, the business on the outside, or someone who's more focused on the letter, the product inside? You can be both, but I think most are definitely one or...
Choose Action over Blame to Keep Moving Forward
When something goes wrong, you have two choices: blame or action. The blame loop keeps you stuck. The action loop moves you forward. https://t.co/5vP2blgpeS
AI Wins, Workforce Burns: Address Fear Separately
You can “win” your AI rollout and still lose your workforce. A recent study of 430 manufacturing employees found that even successful AI transformations increase emotional exhaustion. Translation? Your KPIs can trend up, 📈 while motivation trends down. 📉 The...
GE Aerospace Eyes Explosive Asia Pacific Aviation Growth
bbaviation7 had an exclusive interview with Nakul Gupta, Vice President Sales and General Manager for Asia Pacific at GE Aerospace, where he shares what’s driving the rapid growth of aviation across the region from his perspective. We talk about how his...
AI Shows KPI Design Must Prioritize Impact Over Proxies
What #AI reveals about performance measurement: proxies get optimized. If you measure speed, you may lose quality. If you measure output, you may miss impact. In the ML era, KPI design is a leadership discipline. https://t.co/FfVafJZaUk @mitsmr #MWC26 https://t.co/NqyEiNAj50
Give Second Chances: Key to Employee Engagement
One of the best tools for employee engagement: second chances. Part of the reason some employees check out is that they’ve been tossed aside after making a mistake. No one has ever let them live it down, and that mistake...
Core Skills for 2026: Leadership, Data, EPR, Governance
The most valuable skills for 2026 are not mysterious. Delivery leadership, data literacy, EPR fluency, governance, and communication keep reappearing. These skills survive restructures, tech shifts and policy cycles. Career Navigator 2026 outlines the full skills picture.
Scaling a Startup Is Harder Than Starting One
Why it’s never been easier to start a company, and never been harder to scale one with Brian Halligan Brian is Sequoia in-house CEO coach, long-time CEO and co-founder of HubSpot , and more than anyone I’ve ever met, a...
Revamp Agile Now to Harness AI’s 2026 Edge
Agile was built for a different era. Here are 7 urgent reasons leaders must revisit agile practices if they want real advantages from AI in 2026. #Agile #AI #DigitalTrailblazers https://t.co/RZY9U0X8ws
ROI Works for Pebbles, Not Sand or Rocks
ROI is a good way to prioritize tactical tasks, or 'Pebbles.' ROI is not a good way to prioritize tiny tasks (‘Sand’) nor the most important large things (‘Rocks’). Here’s why: https://t.co/gy7ac3Aqmy
Structure Unlocks Clarity, Stops Rambling
Most people don’t ramble because they lack ideas. They ramble because they lack structure. Before you build slides, write paragraphs or even rehearse. Ask yourself: What pattern of organization best serves my message? Structure is not restrictive, It is liberating. When you choose...
Empower Employees, Not Just Automate, to Meet Expectations
Automation alone is not the answer. Institutions that replace people instead of empowering them will struggle to meet rising customer expectations. https://t.co/3KhyMMpnPe
Automation Shifts Jobs to Higher‑Level Human Oversight
The future of work will look something like what Boris is describing. Anthropic is hiring engineers because people who know what they’re doing still have to tell the agents what to do, review their work, and integrate that work into...
Redefining CIO: Embrace AI Leadership Structures
Thinking about a CAIO? Or evolving the CIO role instead? I explore what uplifting AI leadership should look like - and what structures actually work. #CIO #CEO #AI https://t.co/3nnLLxqhZt
Visible Goalposts Boost Team Effort Near Finish
Runners will sprint the last 100 feet of a race because they see the finish line. Justin Su'a calls this the goal gradient effect where you increase your effort as you get closer to completion. Use this to your advantage by setting...
CIOs Must Rethink IT for Real AI Impact
World-class IT in the AI era looks very different. I share provocative lessons for CIOs who feel under fire to transform IT and show real impact. #CIO #ITLeadership #AI https://t.co/VjbvwFzWSu
Great Leaders Give Needed Support, Not Deserved Criticism
There’s a powerful leadership lesson in watching Trae Turner. When you’re in a tough season, people can either give you what you deserve — criticism, frustration, distance — or they can give you what you need — encouragement, belief, support. The best...
AI Widens Gap: Leaders Must Keep Learning
AI is accelerating the divide between leaders who learn continuously and those who fall behind. Standing still is not a https://t.co/fRpFGuoNlH the full episode: https://t.co/niO7fXOQML https://t.co/vMRrQNi6cA
Limited Context Forces New Work Practices for AI Agents
Eventually, as a result of the context limitations of AI agents, we’ll start to change and improve our work practices to aid in their success. One of the most interesting issues with AI agents is because of their inherently limited...
AI Users Outpace Non‑Users; Human Judgment Remains Priceless
AI won’t replace people, but people who use AI will replace those who don’t. 👥 At the #CiscoAISummit, leaders discussed how 70% of code is now AI-generated, but human judgment remains "priceless." The CIO's job is now as much about culture...
Not Now Masks Indecision: Useful Pause or Avoidance?
When you say “not now” instead of “no”… …you are avoiding making a decision. That’s good, if waiting means you can make a better decision (e.g. more data, more options to pick from). That’s bad, if you’re just non-committal. Cross things off the list.
Surround Yourself with Allies Who Push, Not Praise
Build relationships that make risk-taking more likely. Choose people who kick you in the pants over those who affirm your excuses. Trust allies who believe in your potential, fuel your courage, and challenge you to get off your butt.
Boards Must Prioritize Cyber‑Risk Oversight, Says Expert
My comments on the role of corporate boards in overseeing the management of cyber-risk. In today's New York Post. Link on my website... Type JS.TC into any web browser.
Spot the #1 Sign Management Lacks Business Command
What’s the #1 tell that a management team doesn’t actually have command of their business? I spoke with Paul Stansik , an operating partner at ParkerGale Capital , about the relationship between boards and their portfolio companies. Paul works on...