I took me a long time to warm up to AI at work. But the ability to move conversation to the center of the experience (plus a consistent context) have resulted in the single biggest paradigm shift of my career. Let me back up... I have a longtime love/hate relationship with AI. Joanna Maciejewska's famous… Continue reading All of a sudden, AI is helping me do my job better… much better
Author: Robert Deupree Jr.
The folly and the power of AI
A buddy in the UK posted this picture with the message: My Outlook AI-generated theme today. Where does the river go to beyond the bridge, or is this just a flooded road? Thinking that it might be funny, I asked another AI (Claude) to tell me the story of this picture. The resulting story was so… Continue reading The folly and the power of AI
Photo Tip #28 | Audiophile’s regress
If you were to travel back in time to the 1970’s or 1980’s, seek out hardcore videophiles, and compare our typical video technologies, they’d hang their heads in shame. Our phones have several times the resolution of their big-screen TVs. But if you were to seek out hardcore audiophiles and compare our typical audio technologies,… Continue reading Photo Tip #28 | Audiophile’s regress
Introducing the Ford Analog
Coming next year: the Ford Analog. A solid, old-school, easy-to-work-on, steel panel car with no plastic, no computers, and no screens. This is my dream car. Sadly, it's just a dream so far. I believe in market research and evaluating personas, but sometimes... just sometimes, I want someone to build exactly what I want to… Continue reading Introducing the Ford Analog
That book you’ve been meaning to write
Have you been writing a book for years, or even decades? I've discovered the true value of AI art and a life hack to get you unstuck with your book. Let me explain. I have a love/hate relationship with AI art. Some days, it seems designed to populate the Internet with uncanny valley seven-fingered nightmare-inducing… Continue reading That book you’ve been meaning to write
Inclusive language, 1978 vs. today
Picture it: A veteran's hospital, 1978. I learned inclusive language in 5 minutes. It was fun. Picture it: A corporate inclusivity seminar, this year. I was confused into silence. Not fun. I'm not here to "bash the woke". I don't mistrust the hearts of those who want to be allies for others. And yet, our… Continue reading Inclusive language, 1978 vs. today
Business books are mostly dead
There are days when it'd be nice to listen to an audiobook to help me do my job better. Well, I would listen to business books but I can’t stay awake through an entire chapter. I’m sure some business books are good and all, but as C. S. Lewis would say, they tend to be… Continue reading Business books are mostly dead
Is Polly Plummer the Narrator of the Narnia Books?
If you've read the Chronicles of Narnia, you probably remember the Narrator's voice. The Narrator does far more than tell a story — he or she walks you through the adventures scene by scene. The Narrator is emotionally present and his or her personality permeates the entire story. The Narrator often speaks directly to the… Continue reading Is Polly Plummer the Narrator of the Narnia Books?
Photo Tip #51 | Expand/collapse in OneNote
An insomnia-inspired tribute to OneNote and the Hallmark Channel.
Photo Tip #59 | Move cursor with phone space bar
My favorite Photo Tips are the ones that I’ve never heard of (even when everyone else knows it). I have a tough time placing my phone cursor exactly where I want. It’s so frustrating that I typically long-press a word and simply retype it. But many phone keyboards (including Gboard, SwiftKey, Samsung Keyboard, iPhone, etc.)… Continue reading Photo Tip #59 | Move cursor with phone space bar
“Try not to bring it to life.”
I am a huge advocate for diversity and representation in both computer science and science fiction. Attending the Richard Tapia Celebration of Diversity in Computing Conference was one of the highlights of my career. That said, in an age where we're all striving *not* to build murderous sentient AI machines, please break the mold with… Continue reading “Try not to bring it to life.”
I love mashups because I am a mashup
One of my favorite songs growing up was Rockaria (which I mispronounced "Rock-a-ria" instead of "Rock Aria") by the Electric Light Orchestra. In the song, a rocker falls in love with an opera singer. By the end, the two cultures have blended into something new. And as the night grew older everybody was as one… Continue reading I love mashups because I am a mashup
Why I love poetry
Choose an Option- by Lewis Carroll I love poetry because it captures how things make me feel. Of course, a glossary always helps. GLOSSARY "You seem very clever at explaining words, Sir", said Alice. "Would you kindly tell me the meaning of the poem 'Jabberwocky'?" "Well, 'toves' are something like badgers--they're something like lizards--and they're… Continue reading Why I love poetry
Star Wars 8 and Windows 8 | In defense of magnificent failures
Star Wars 8, The Last Jedi was my least favorite film in the series. Windows 8 was my least favorite version of Windows. Yet upon further reflection, I truly appreciate them both. Here's why. I'm not sure how the brain's filing system is supposed to work but mine stores objects in semi-random buckets organized by… Continue reading Star Wars 8 and Windows 8 | In defense of magnificent failures
Photo Tip #58 | Dock and undock OneNote with one click
Now that the full desktop version of OneNote has made its triumphant return, here is a quick way to dock and undock your notes quickly. Why? Because you can keep a narrow but-always-visible note pane on the side that won’t interfere with other apps, even when you Maximize them. For example, it’s my favorite way… Continue reading Photo Tip #58 | Dock and undock OneNote with one click
Photo Tip #57 | Browse back to a fork in the road
I hope that this tip is not too specific to my own needs but Ctrl + browser back button is my friend. Let’s say you're browsing along and come to a fork in the road with multiple links. Sure, you can Ctrl + click to open new tabs for each interesting link. But what if… Continue reading Photo Tip #57 | Browse back to a fork in the road
Photo Tip #56 | Start a new Word, PowerPoint, or Excel file from your browser
Photo Tip #55 | Cool ways to select text
This tip is specific to Microsoft Word and Outlook. We all know how to use our mouse to click and drag a block of text. But what if you want to select blocks of text that are not connected? What if you want to select a vertical block? Simple. Try holding the Ctrl or the… Continue reading Photo Tip #55 | Cool ways to select text
Photo Tip #54 | PowerPoint is a basic video editor
Today’s Photo Tip is a reminder that you can use PowerPoint as a basic video editor. I’m a Camtasia user but edited the following video entirely in PowerPoint. https://youtu.be/BB8Fa4h1ViQ The original PPTX file is here:Download ...and the resulting video is a pure Save As -> MP4 video output.
Photo Tip #53 | Words of respect in HD
A few years ago, I asked some trusted friends if I should post this graphic and they all agreed no. They worried that it was too easy for readers to misinterpret my intent. But in the wake of recent violence against Asian Americans, I've decided to take a chance. One telltale form of respect or… Continue reading Photo Tip #53 | Words of respect in HD
Photo Tip #52 | Information ≠ data
Do you remember that joke from the 90’s?... A lost helicopter pilot flies by tall building with a handwritten sign that reads, “WHERE AM I?” The people in the building quickly respond with a large sign, “YOU ARE IN A HELECOPTER”. That's when he realizes he’s flying over Microsoft. One of the most difficult concepts… Continue reading Photo Tip #52 | Information ≠ data
Photo Tip #50 | Dragging and shaking windows
Many people know about dragging and shaking windows – but many do not. Many people know about dragging and shaking windows in Windows 10 – but many do not. So how do you reach an intelligent and well-informed audience who don't know what they don't know? They won't hit Play on a video but they… Continue reading Photo Tip #50 | Dragging and shaking windows
Quote of the day | Weak on dragons
I love this C.S. Lewis quote and think of it often in meetings. Our inspiration needs to draw from sources beyond business and technology books. Even the most mundane meetings need a little whimsy and adventure to break complacency and fuel imagination. (For example, my review of "The Road Ahead" by Bill Gates: An optimistic and… Continue reading Quote of the day | Weak on dragons
Quality with an attitude
I wouldn't normally rave about a YouTube video but this is an exception. As with any job, it takes a certain level of effort to create something good. It takes so much more to create something of true quality. I've done just enough video editing to be dangerous and respect the effort required here. When… Continue reading Quality with an attitude
Photo Tip #35 (revisited) | Windows Clipboard – now with history
Today’s tip is from Michael Brittenham. If you are running Windows 10 or 11, you can turn on and access the history of things you’ve copied. Just type Windows key + V. Not geeky enough for you? You can also synchronize that history across all of your Windows 10 or 11 devices. UPDATE: Many tips… Continue reading Photo Tip #35 (revisited) | Windows Clipboard – now with history
The moment this Boomer learned to love the Millennial generation
Millennials get some bad press. The whiny snowflake persona, if true, would be incredibly annoying. Fortunately, I get to work with many of them and know better. As a generation, Millennials been good sports with all our ribbing for years and eventually came up with one of the greatest subtle comebacks of all time, Okay,… Continue reading The moment this Boomer learned to love the Millennial generation
Unsolicited advice #1: Destressing during election season
Do negative political attack ads stress you out? Not me. They make me smile. And in 48 seconds, they can do the same for you. During this scene from the show “Leverage” (S3E16), the young hacker Hardison creates a political ad to help overthrow the government of San Lorenzo: “I did an image and language… Continue reading Unsolicited advice #1: Destressing during election season
Photo Tip #49 | Perception is everything
Why “Black lives matter?! I think all lives matter” is 100% true and 100% wrong
I hear people talk past each other every day. We can fix this. Let me back up and explain my perspective. My mom is from Mexico and I have some African ancestry on both sides (also Jewish, Polynesian, and Pakistani). I grew up brown and blessed in the Deep South in the 1960's. I'm not… Continue reading Why “Black lives matter?! I think all lives matter” is 100% true and 100% wrong
Photo Tip #48 | Learn the slash commands in Teams
So, who do we root for now?
I have a teammate who loves baseball. He's a regular season ticket holder for the Twins and just cancelled his baseball-related vacation days. Bummer. With all the suffering in the world, it's sad when yet another simple and distracting joy is cancelled. Plus, I miss that wonderful feeling when my team wins. So... I need… Continue reading So, who do we root for now?
COVID-19, jalapeños, and llamas
My art is instructional design – the process of helping people learn. People use all types of tricks to help learn and practice good advice. Sayings like "starve a cold, feed a fever... or is it the other way around?" don't seem to help much. Singing the "Happy Birthday" song twice while washing your hands… Continue reading COVID-19, jalapeños, and llamas
‘Sinfully delicious’?
I don't have many pet peeves but the ones I have are big and hairy with scary teeth. One such peeve, for example, is the phrase sinfully delicious. Variations of these sadly misguided words have filled shows and commercials for years: This dessert is so good... it's sinful. Pththth. I'm no theologian but I am… Continue reading ‘Sinfully delicious’?
Photo Tip #47 | Sort Outlook mail with Delete and Backspace
Don’t overthink your mail sorting strategy. Most mail should be answered quickly, archived, or deleted. You know that the Delete key will delete your mail – but the nearby Backspace key will move mail to the Archive folder that you configure. Just put one finger on each key and start clearing that Inbox.
Photo Tip #46 | Quick, I need an emoji (or a kaomoji)!
Microsoft culture in 10 seconds
In 2011, Microsoft ran a microfilm contest where contestants attempted to capture our culture in a 10-second film. Most entries highlighted the many positive qualities of Microsoft life. Here's the flip side. Do other companies struggle with this? https://www.youtube.com/watch?v=jgV7K1QpS3Y
Curmudgeonville Quote #03
In addition to Curmudgeonville, we have a group called Pollyannaville. It's a happy place that brings about a little balance – perhaps like Whooville does to Mount Crumpit. Some of the best and hopeful news gets shared there. But it's never as popular as Curmudgeonville. Why? I think Mr. Tolkien found the answer when describing… Continue reading Curmudgeonville Quote #03
Photo Tip #45 | Real life feature requests?
Photo Tip #44 | Change line spacing quickly
Photo Tip #43 | Another reason for some non-screen time
Curmudgeonville Quote #02
What is quotable (to you)?
Did you ever go looking for a favorite movie quote online — a quote that's already become part of your family lexicon — only to find that nobody else quotes it?! Oy. Friends and family and workmates latch onto certain movie quotes that may or may not capture popular attention. "I'm the king of the… Continue reading What is quotable (to you)?
Photo Tip #42 | Avoid “Where’s the other dollar?” questions
Consider this. Most of our fire drills start when we’re chasing down the wrong question. For example: “How can we make an unnecessary process more efficient?” If you’re struggling with an emotionally-charged and apparently unsolvable question, step back and ask yourself if you’re looking for the OTHER DOLLAR.
Photo Tip #41 | Learn about visual storytelling
Some of the greatest visual storytellers on the planet have created a free course on storytelling. This Pixar course on Khan Academy is kicked off by my hero, Pete Doctor. No matter what your job, I guarantee that the ability to tell a good story (pitch, scenario, etc.) is an important part of your success.… Continue reading Photo Tip #41 | Learn about visual storytelling
Photo Tip #40 | Bad analogies are like bad analogies
Curmudgeonville Quote #01
Photo Tip #39 | How to mute Outlook distractions
This one changed my work life. I used to close Outlook to focus — but then I’d need to reference an email or my calendar. So I’d open Outlook for a quick peek and… BAM, five urgent mails and the end of my focus time. This way is better. The Work Offline toggle temporarily disconnects… Continue reading Photo Tip #39 | How to mute Outlook distractions
Crying at the movies
Sadly, I was raised in a generation where men were expected not to cry, including at the movies. Okay, technically, boys were allowed to cry at exactly two movies: Old Yeller and Brian's Song. I never saw Brian's Song but boy I did cry at Old Yeller. I remember sitting in the back seat of… Continue reading Crying at the movies
Photo Tip #38 | Let Windows type for you
So I sprained my wrist last week wrestling blue sharks in the North Atlantic — or cleaning the garage, I forget which. But anyway, the point is that it was very difficult to type. I figured out different ways to use speech-to-text in various apps, but there is one keyboard shortcut that seems to work… Continue reading Photo Tip #38 | Let Windows type for you
Photo Tip #37 | Movies are the tribal stories of our generation
As educators and communicators, it is important to remember that certain movies and movie quotes have gone beyond linguistic decorations to become part of the fabric of our language. I group movie quotes into three categories: I. Culturally iconic quotes that everyone is expected to know. These are so pervasive that many are actually misquotes… Continue reading Photo Tip #37 | Movies are the tribal stories of our generation
Photo Tip #36 | Visual misinformation (and a puzzle!)
My mom lives on the US east coast and I live on the west coast. When she called to tell me about an upcoming supermoon, I knew that she would see it rise three hours before me – just like she sees sunrises and sunsets three hours before me. But during the total solar eclipse,… Continue reading Photo Tip #36 | Visual misinformation (and a puzzle!)
Photo Tip #34 | Good editors are a godsend
Photo Tip #33 | Outlook Calendar understands you
Photo Tip # 32 | Proposal for a new word
Photo Tip #31 | Pause for deep thought
Looking back over the years, my favorite work moments resulted when I took the time to pause, look at the big picture, and think deeply. Bill Gates famously set aside a week for such thoughts in his Think Week. I hate to admit this but most of the time I don’t pause; I just skim… Continue reading Photo Tip #31 | Pause for deep thought
Photo Tip #30 | Close the loop
Microsoft has started a remarkable cultural transformation under Satya Nadella. For too many years, our Achilles' Heel was failing to "close the loop". We would build heaps of world-class parts, check off a box, and then rush off to build some more parts. Perhaps the greatest change is that our culture is beginning to value… Continue reading Photo Tip #30 | Close the loop
Photo Tip #29 | The epitome of your art
To me, Calvin & Hobbes is a wonderful example of taking one art form (comics) and exploring every way to reach the epitome of its elements (writing, art, and humor). For example, Bill Watterson captured the movement of his characters in a way that we can easily imagine through simple static drawings. Animator Adam Brown… Continue reading Photo Tip #29 | The epitome of your art
Blog | The Desilu Factor
My phone doesn't take a week to boot it. My TV doesn't crash when I mute it. I miss ASCII text, and my floppy drive. I wish VIC-20 was still alive... - Three Dead Trolls (Every OS Sucks, 2000) I love technology. Yet there is a strangely intangible quality that is lacking in almost every… Continue reading Blog | The Desilu Factor
Photo Tip #27 | Technological innovations don’t arrive in the expected order
Picture yourself in a busy airport. The year is 1969. Newspapers announce that we "landed a man on the Moon and returned him safely to the Earth". Older people in the airport still remember man's first heavier-than-air flight at Kitty Hawk. Imagine that – from Orville & Wilbur to Neil & Buzz in 66 years… Continue reading Photo Tip #27 | Technological innovations don’t arrive in the expected order
Photo Tip #26 | Stats can illuminate or obscure truth
Doodle | Pangaea Moving Co.
Photo Tip #25 | Don’t believe every product rumour you hear
Photo Tip #24 | Don’t worry about Skynet yet
Photo Tip #23 | Don’t just fix features
Photo Tip #22 | Never bury the lede
The "lede" is the opening and most important sentence or paragraph of a news article (or email or poster or story or letter). Most of us write beautiful ledes and then bury them somewhere in the second or third paragraph. For some reason, the 1967 concert poster below has always reminded me of this helpful… Continue reading Photo Tip #22 | Never bury the lede
Photo Tip #21 | Always tell the truth
Doodle | Rockytana says never forget your roots
Photo Tip #20 | How to mine gold from stupid ideas
I made this short sample video for an informal 3-minute-or-less pitch competition at Microsoft called "Presentation Idol". It tells the story of Encarta Encyclopedia, Joshua L. Cowen, toy trains, and lighted flower pots and has helped me many many times. When smart people say something that appears stupid on the surface, look a little deeper...… Continue reading Photo Tip #20 | How to mine gold from stupid ideas
Photo Tip #19 | Anthromorphize bad ideas
Photo Tip #18 | PowerPoint is a legit image editor
Today’s Photo Tip is just a reminder. Although PowerPoint will never compete in the Photoshop space, it has many powerful features that can take you all the way from silly idea to silly image in less than five minutes (and yeah, it works for less-silly prototyping too). For example, the following snarky movie poster only… Continue reading Photo Tip #18 | PowerPoint is a legit image editor
Photo Tip #17 | A project’s traction is as important as it’s velocity
Photo Tip #16 | How to search within a website
Doodle | Quality is everything and testers are rock stars
Photo Tip #15 | How to view system performance graphically
Photo Tip #14 | How to type common phrases quickly
Photo Tip #13 | Don’t be a Goofus
One effective model of visual illustration comes from the old Goofus and Gallant cartoons in the children’s magazine, Highlights. The human brain loves to compare similar items and derive meaning from the delta. Before and After is a similar model. Obviously, you don’t need to use two cartoon boys for your training purposes, but I… Continue reading Photo Tip #13 | Don’t be a Goofus
Photo Tip #12 | How to open Task Manager (left-handed)
Photo Tip #11 | How to visualize time zones
Have you ever tried to schedule a meeting across several time zones? “Oops, sorry, I thought that was 2*pm* for you.” There are some excellent web-based tools like http://worldtimebuddy.com that allow you to line up multiple time zones and explore different meeting times.
Blog | The one AI setting we really need
Most of the time, we want our machines to be smart. Like when I put popcorn in the microwave for 23 minutes. “Duh, kitchen machine… you KNOW what I meant!” But other times, we want machines to simply do what we ask. “Hey phone machine… stop auto-correcting my friends with non-Anglo names into food items!”… Continue reading Blog | The one AI setting we really need
Photo Tip #10 | Memorize something today. Anything.
Photo Tip #9 | How to copy the full path to a file on a share
Photo Tip #8 | Please don’t do this
Yes, I’ve done this. You’ve done this. But now it’s reaching epidemic proportions that are clogging our communication channels and further degrading our collective signal-to-noise ratio. There’s something about the volume and urgency of long email threads that inspire us to chime in without actually reading them. As feline philosopher Hobbes once noted, “Maybe we… Continue reading Photo Tip #8 | Please don’t do this
Photo Tip #7 | Another way to launch Cortana
Photo Tip #6 | How to toggle text case
Quote of the day | Originality
When I see a great quote, I often smile, nod – maybe even quote it a few times, and then gradually forget it. But this quote keeps coming to mind in a myriad of daily applications. I’m not an artist but I’ve had the privilege of having artist friends my whole life. One such friend… Continue reading Quote of the day | Originality
Photo Tip #5 | How to copy text from a Kindle book
Have you ever tried to copy a favorite quote from one of your Kindle books only to end up retyping the whole thing? Here is a simple and totally unintuitive workaround: Highlight text in the Kindle readerGo to https://read.amazon.com/kp/notebookCopy the text from your book’s highlights Three old books with the titles: "Kindle Reader: highlight text",… Continue reading Photo Tip #5 | How to copy text from a Kindle book
Photo Tip #3 | How to move the active window
Photo Tip #2 | The Office keyboard shortcut for… everything
Today’s Photo Tip is a real-life superpower. Can you tap and release the ALT key without looking? If not, learn to. Just slide either thumb off the spacebar. Then find one keyboard shortcut for anything that you do frequently in Office. Want to insert a time stamp? Try tapping ALT (and release), N, D. Pull… Continue reading Photo Tip #2 | The Office keyboard shortcut for… everything
Photo Tip #1 | Fight the tyranny of the urgent
"We live in constant tension between the urgent and the important. The problem is that the important task rarely must be done today or even this week. …but the urgent tasks call for instant action – endless demands pressure every hour and day. … The momentary appeal of these tasks seems irresistible and important, and… Continue reading Photo Tip #1 | Fight the tyranny of the urgent

























































































