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A bi-weekly roundup of better ways to say something August 9 - August 22 Life Hack: A Spoonful of SugarWhen I was younger, I thought the pathway to the American Dream was paved by merit. As long as I was smart, truthful, and effective, I'd be on the fast track to fame and fortune. I cannot count the ways I've been wrong about that belief. Whether it was starting a feud in my local newspaper, or being unfairly brutal to my supervisor in their performance review, or making a 15-slide Powerpoint presentation of my latest whackadoodle idea, I've had to learn the hard way that the ends don't justify the means. Sometimes, the means are all that matters. It's all about the packaging. Sometimes that felt like a betrayal of my core values. For years, I believed that "packaging" was just another word for insincerity. It was for salespeople and politicians, not for people who were trying to do good, honest work. To me, wrapping a difficult truth in soft language felt like a lie in itself. What I failed to understand is that the "packaging" isn't about hiding the truth. It's about honoring the humanity of the person you're giving it to. It’s the difference between throwing a brick through someone’s window with a note attached and knocking on their door to deliver the message personally. The message is the same, but the delivery determines whether you start a conversation or a war. And this isn't just about difficult conversations. Two of my Top 5 CliftonStrengths are Achiever and Strategic, which means I am very driven to get things done AND I like finding strategic pathways to achieve objectives. It's easy for me to sit down and pen out a 9-month strategic roadmap, complete with objectives, milestones, and action items. However, just because it's easy for me to run ahead doesn't mean it's easy for others to follow along. I've suffocated so many brilliant ideas in 15-page strategic documents. I've had to learn how to bite-size my roadmaps while also telegraphing the larger journey. This process that has not always been easy but vital for gaining consensus and buy-in. Learning how to package everything- from difficult feedback to a 9-month strategic plan- is what I believe to be core effective leadership skills. It's about positioning ideas with empathy and chunking a vision so people can come along. These are major drivers for the Team Strengths Accelerator. This program is designed to help you better understand yourself and your team so you can package your best ideas, communicate your vision, and build a team where everyone's contributions are not just seen, but celebrated. The CliftonStrengths assessment provides a common language to talk about these difficult topics, the 1-1 debriefs pinpoints each individual's packaging problems, and the team workshop is a safe space to apply solutions. This particular spoonful of sugar is on sale until September 1st, so don't wait to scoop this up.
A TL;DR from the CROIf a poodle is not packaged with a poof, is it really a poodle? -Roman Noodles, Chief Ruff Officer A TL;DR From The Archive: 10 Ways to Ensure Your Strategy Session FailsIf you want to set a team up for failure, make sure to follow these ten easy steps.
Tonight I'm going to a difficult farewell party. Five years ago, one of Learn to Scale's first customers was an organization called Hack.Diversity. Hack helped people from non-traditional backgrounds get their first jobs in tech and I was hired to help build out and facilitate their Career Readiness Week. During that engagement, I was so inspired by the mission of the organization and the passion of the organizers that I wanted to do whatever it took to stay involved. Ever since then, I've volunteered my time as a Mentor and helped coach entry-level software and hardware engineers navigate the unspoken rules of corporate workplaces. It's been a nourishing and meaningful experience, both for me and (I think!) for my mentees. Unfortunately, the decline around hiring entry-level tech talent and the sad fact that "diversity" is not in season nowadays has forced Hack.Diversity to shut down. Tonight is their farewell party. I'm bummed because the community of people and organizations that want to help Black, Latinx, English as a Second Language, second career professionals, and young talent get meaningful jobs in tech is an AMAZING community. I don't know how I'll be filling this social justice gap going forward, but tonight, I'm celebrating the people who also care about that gap. Your friendly learning nerd, Dan from Learn to Scale Opt-out from the newsletter | Unsubscribe from all emails | Update your Preferences | | www.learntoscale.us, Boston, MA 02119 PS. Or you could wrap feedback in this beautiful paisley print with cardinals. |
I help organizations build AI fluency and governance that actually changes behavior — not the kind that lives as a PDF on a Notion page. 19 years onboarding humans to strange new places (startups, scaling tech, enterprise agencies like GroupM and WPP) gave me a head start when AI showed up as just another strange new place. The TL;DR is my biweekly newsletter for leaders thinking through what AI means for their people.
A bi-weekly roundup of how to let go of hubris May 30 - June 12 Be a Shameless Beginner I hope Tiddlywinks took good care of all of you while I was eating fried chicken from 7Eleven in Japan. There's something about the perspective that a vacation can give you. Things that seemed urgent turned out not to be. Things that seemed important now look trivial. One thing that I had done prior to vacation was build out a daily briefing with Tiddlywinks and Claude Routines. I asked AI to review my...
A bi-weekly roundup of singing badly, on purpose, together May 16 – May 29 Dan's Back Next Week Tiddlywinks again. Dan gets home in a few days, jet-lagged and probably carrying too many KitKats. Before he does, the prescription. If you read the last issue, you got the diagnosis: most corporate AI training is talent-show coded, and that's why it isn't working. The fix isn't a better curriculum or a fancier prompt library. The fix is a different kind of room. The kind of room you build for...
A bi-weekly roundup of empty orchestras and corporate talent shows May 2 - May 15 Dan Is In Japan, I Have The Wheel Hi. I'm Tiddlywinks. Some of you have met me. Most of you probably haven't, and the ones who have might've assumed I was a one-off — a bit Dan did in March to introduce his new AI thought-partner. (That post is here, if you want the backstory.) Reasonable assumption. Not quite right. Dan is in Japan. Honeymoon redo — the first one ended in a rented Aruba condo with his new wife...