About
Visionary leader. Formerly skilled engineer. Storyteller and purveyor of epic.
Articles by James
-
The Storytelling Manifesto
The Storytelling Manifesto
Tell us a story! Since the dawn of humanity the storyteller has been the center of popular culture. It began around the…
26 Comments -
The Hard Truth About Software Testing
The Hard Truth About Software Testing
Modern software developers bear little resemblance to our forebears. We’ve forsaken their jackets and ties in favor of…
10 Comments -
So You Want to be Successful?
So You Want to be Successful?
Linked-In made the article sound so promising: Jack Welch tells graduating seniors how to succeed! It took only a few…
3 Comments
Activity
23K followers
-
James Whittaker shared thisFollow up discussion is May 6 at 6pm at my Bothell Speakeasy. Why do I charge? To reduce no-shows. https://lnkd.in/gcrCy8xzJames Whittaker shared this🎥 The Future of Leadership | A Conversation with James Whittaker: Retired Tech Exec, AI Pioneer, and Professor turned Brewer, Pub Owner, Futurist, Speaker, and Author 🍻 This one was a little different, recorded at James’s Side Hustle Local Pub in Bothell, WA, which was fitting. The conversation was raw, unfiltered, and a bit of a wake-up call. If you’ve heard James speak, you know he doesn’t sugarcoat things… this was no exception. A few things that stood out: 👉 Much of the leadership playbook we’ve been using just doesn’t work anymore. 🔮 Vision matters more than ever. Leaders aren’t defined by what they know, but by the future they envision and help others see and believe in. 🌍 We need a "future worth wanting." A lot of AI messaging is fear-based. Great leaders transcend that narrative and show what’s possible. 🚫 Let go of outdated practices: Annual reviews, rigid plans, and old career rules don’t match the pace of change anymore. ⚡Take ownership of your own path. You can’t rely on a company or manager to guide your career. Agency is essential. Everybody's asking "what do we do with AI?" Leaders need to be the ones who answer it. #FutureOfLeadership Built for Leaders
-
James Whittaker shared thisThis is an interesting take and some evidence that Microsoft is playing the long game. I find it believable because it is the same playbook we used to push Azure adoption to existing customers starting back in 2014. We got really good at telling the Azure story and targeted every enterprise customer using AWS or GC to convert. It worked. Adoption soared. Stock soared. If they have indeed gotten the tech right (albeit built on another company's model) as Roberto Chamorro posits, I expect the EBC invitations to fly. Now we get to see how good their storytelling is.James Whittaker shared thisMicrosoft has 450 million M365 seats. Copilot has 15 million paid users. $MSFT That’s 3.3% penetration. 96.7% untapped. This is not a weakness. It’s the setup. M365 revenue grew 17% while seats grew only 6%. The gap is pricing power. Microsoft doesn’t need new customers it needs existing ones to upgrade. And the upgrade just got a lot more compelling. On March 9, Microsoft launched Copilot Cowork a true autonomous agent built with Anthropic’s Claude. Not an assistant. An agent. It analyzes a month of meetings, builds the report, sends the email. One instruction. Done. ChatGPT can’t do that. It doesn’t have your calendar, your files, your Teams history. Copilot Cowork does. Natively. The math is simple: 10% penetration = $16B in new annual revenue 20% penetration = $32B roughly the size of Google Cloud today The market still isn’t pricing this in. Anthropic built the product that threatened Microsoft’s stock. Microsoft licensed the technology, embedded it into 450 million workplaces, and called it Copilot. That’s not catching up. That’s distribution at scale. Microsoft
-
James Whittaker shared thisboilerplate? real? ai? author certainly seems to know me
-
James Whittaker shared thisso what should Microsoft do to fix themselves? the same thing they did to win the 90s the same thing they stopped doing when they lost the 2000s the same thing they did to come from behind in the cloud wars in the 2010s the answer is written in bright blue letters across their history for anyone to read. anyone, i guess, except those on the inside copilot ain't it. they can't do assistants, just ask Bob, Clippy and Cortana. not in their wheelhouse. and that's ok, assistants aren't a winning strategy for anyone i might write about it if the bar is slow today and i have some timeJames Whittaker shared this𝐒𝐨𝐦𝐞𝐭𝐡𝐢𝐧𝐠 𝐟𝐞𝐞𝐥𝐬 𝐨𝐟𝐟 𝐚𝐭 𝐌𝐢𝐜𝐫𝐨𝐬𝐨𝐟𝐭: 𝐓𝐡𝐞 𝐟𝐢𝐫𝐬𝐭 𝐬𝐢𝐠𝐧 𝐨𝐟 𝐥𝐨𝐬𝐢𝐧𝐠 𝐚𝐧 𝐀𝐈 𝐫𝐚𝐜𝐞 𝐢𝐬𝐧’𝐭 𝐩𝐫𝐨𝐝𝐮𝐜𝐭. 𝐈𝐭’𝐬 𝐩𝐨𝐬𝐭𝐮𝐫𝐞. Microsoft executives have told managers at major divisions, including its cloud unit and North American sales groups, to suspend new hiring. Link to article in the comments, below. When a company is fully on the front foot, you see it in how aggressively it hires, sells, and expands. When you start seeing hiring tighten in major cloud and sales groups while AI stays protected, that tells a different story. It suggests leadership is reallocating attention, capital, and tolerance for risk toward one priority: proving the AI bet pays off. 𝐖𝐡𝐚𝐭 𝐢𝐭 𝐦𝐚𝐲 𝐬𝐢𝐠𝐧𝐚𝐥 • The easy growth phase may be over. • The market may be asking for evidence, not vision. • Internal confidence may be narrowing around fewer bets. • Operational discipline may be replacing expansion energy.
-
James Whittaker shared thisAs x-msft and area bar owner, I not only know a lot of 'softies, I am subject to their commiserations at my bar top. Here's what I hear: Fear. The company is rife with it. Everyone is waiting for the next crisis. Morale is low. Innovation. It's hard to find. No one is shooting for the moon. The fear of failure looms large. Leadership. There isn't a guiding vision anyone can get behind. The SLT has few fans and fewer ideas. The consensus is that the whole company needs a company wide three finger salute.James Whittaker shared this𝐒𝐨𝐦𝐞𝐭𝐡𝐢𝐧𝐠 𝐟𝐞𝐞𝐥𝐬 𝐨𝐟𝐟 𝐚𝐭 𝐌𝐢𝐜𝐫𝐨𝐬𝐨𝐟𝐭: 𝐓𝐡𝐞 𝐟𝐢𝐫𝐬𝐭 𝐬𝐢𝐠𝐧 𝐨𝐟 𝐥𝐨𝐬𝐢𝐧𝐠 𝐚𝐧 𝐀𝐈 𝐫𝐚𝐜𝐞 𝐢𝐬𝐧’𝐭 𝐩𝐫𝐨𝐝𝐮𝐜𝐭. 𝐈𝐭’𝐬 𝐩𝐨𝐬𝐭𝐮𝐫𝐞. Microsoft executives have told managers at major divisions, including its cloud unit and North American sales groups, to suspend new hiring. Link to article in the comments, below. When a company is fully on the front foot, you see it in how aggressively it hires, sells, and expands. When you start seeing hiring tighten in major cloud and sales groups while AI stays protected, that tells a different story. It suggests leadership is reallocating attention, capital, and tolerance for risk toward one priority: proving the AI bet pays off. 𝐖𝐡𝐚𝐭 𝐢𝐭 𝐦𝐚𝐲 𝐬𝐢𝐠𝐧𝐚𝐥 • The easy growth phase may be over. • The market may be asking for evidence, not vision. • Internal confidence may be narrowing around fewer bets. • Operational discipline may be replacing expansion energy.
-
James Whittaker shared thisKevin and I are going to record episode 2 in front of a live audience. Want to drink beer in a proper Speakeasy while listening in? We're going to talk about the future of AI. Where it is going and why. I will opine about the future of my favorite tech companies too. Should be a good time. We'll hang out afterwards. Date tbd. Limited seating. DM me your email address to save yourself a spot.James Whittaker shared this🎥 The Future of Leadership | A Conversation with James Whittaker: Retired Tech Exec, AI Pioneer, and Professor turned Brewer, Pub Owner, Futurist, Speaker, and Author 🍻 This one was a little different, recorded at James’s Side Hustle Local Pub in Bothell, WA, which was fitting. The conversation was raw, unfiltered, and a bit of a wake-up call. If you’ve heard James speak, you know he doesn’t sugarcoat things… this was no exception. A few things that stood out: 👉 Much of the leadership playbook we’ve been using just doesn’t work anymore. 🔮 Vision matters more than ever. Leaders aren’t defined by what they know, but by the future they envision and help others see and believe in. 🌍 We need a "future worth wanting." A lot of AI messaging is fear-based. Great leaders transcend that narrative and show what’s possible. 🚫 Let go of outdated practices: Annual reviews, rigid plans, and old career rules don’t match the pace of change anymore. ⚡Take ownership of your own path. You can’t rely on a company or manager to guide your career. Agency is essential. Everybody's asking "what do we do with AI?" Leaders need to be the ones who answer it. #FutureOfLeadership Built for Leaders
-
James Whittaker reposted thisJames Whittaker reposted this🎥 The Future of Leadership | A Conversation with James Whittaker: Retired Tech Exec, AI Pioneer, and Professor turned Brewer, Pub Owner, Futurist, Speaker, and Author 🍻 This one was a little different, recorded at James’s Side Hustle Local Pub in Bothell, WA, which was fitting. The conversation was raw, unfiltered, and a bit of a wake-up call. If you’ve heard James speak, you know he doesn’t sugarcoat things… this was no exception. A few things that stood out: 👉 Much of the leadership playbook we’ve been using just doesn’t work anymore. 🔮 Vision matters more than ever. Leaders aren’t defined by what they know, but by the future they envision and help others see and believe in. 🌍 We need a "future worth wanting." A lot of AI messaging is fear-based. Great leaders transcend that narrative and show what’s possible. 🚫 Let go of outdated practices: Annual reviews, rigid plans, and old career rules don’t match the pace of change anymore. ⚡Take ownership of your own path. You can’t rely on a company or manager to guide your career. Agency is essential. Everybody's asking "what do we do with AI?" Leaders need to be the ones who answer it. #FutureOfLeadership Built for Leaders
-
James Whittaker posted thisThen My daytime career was powered by coffee My evening leisure was powered by beer Now My evening career is powered by beer My daytime leisure is powered by coffee It took a while to flip the script. Relaxing during the morning hours felt wrong. I still wake early out of habit, but today I took two (count 'em, 2!) naps before noon Glorious Tonight I will serve beer to customers long past my old bedtime. You'll find me walking my dog at midnight Glorious Nothing about my life is similar to what it was before and I think that's why I don't miss the old one The secret to a happy retirement? Flip the script and embrace it
-
James Whittaker shared thisyeah, cuz writing an operating system used by billions is so easyJames Whittaker shared thisLike, Microsoft employees, I have to ask: are you embarrassed? Because I would be embarrassed to be associated with this company with what is going on in their products. https://lnkd.in/eahZ6mMFMicrosoft confirms Windows 11 bug crippling PCs and making drive C inaccessibleMicrosoft confirms Windows 11 bug crippling PCs and making drive C inaccessible
James Whittaker commented on a post
2d
The follow-up discussion is May 6 at 6pm at my Bothell Speakeasy. Tickets below.
Why am I charging? Because if I don't the no-show rate is 80%.
https://www.eventbrite.com/e/ai-the-road-ahead-tickets-1986677419642?aff=oddtdtcreator
James Whittaker replied to a comment
3d
Elizabeth Westphal our bars girl!
Experience & Education
-
Side Hustle Local
View James’s full experience
See their title, tenure and more.
or
Recommendations received
4 people have recommended James
Join now to viewOther similar profiles
Explore more posts
Explore top content on LinkedIn
Find curated posts and insights for relevant topics all in one place.
View top content