Four signs you need a fractional eng leader: Your CTO is still writing code. No one's thinking about career ladders. Cross-functional comms are a disaster. You keep saying, "We'll deal with it when we hire a VP." Those problems don't pause, they compound into a mess. A fractional VP bridges the gap.
My latest newsletter is about the messy middle — of careers, teams, and life. Fixing meetings, ADHD in midlife, stalled teams, and yes, reality TV. None of us are static. We're all figuring it out in real time. No judgment.
open.substack.com/pub/seasoned...
Most people think facilitators teach or help groups discuss things. True, but only part of it. The details people don't consciously notice are often the ones that shape how the day lands. That's experience intelligence. This HBR piece speaks to my soul: hbr.org/2026/02/disn...
If your team had an offsite recently, pause for a second. Did you accomplish what you needed to? Are follow-ups moving forward or dying in a shared doc? What lasting decision came out of it? That's the difference between an offsite that mattered and one that just felt productive.
Before I led teams, I worked in large-scale food production. First at summer camp, then a college dorm. At camp, we fed 600 people 3x a day for a month. It's where I learned important leadership lessons I still carry: mentorship shows up unexpectedly, ownership gets real fast, and chaos can be fun.
Leaders love a good framework, but off-the-shelf training rarely solves the problem. You hired your people for their specific traits and expertise, why would a one-size-fits-all method unlock what they're capable of? Start with what you want to accomplish, then design around the people in the room.
Just wrapped 3 AI workshops: nonprofit leaders, engineering VPs, Chiefs of Staff. 600+ registrations. Real work. Real results. Real "holy shit, this works" moments. Most people use 10% of what AI can do. I can fix that. If you're thinking about bringing a custom workshop to your team, let's talk.
The Passover seder is the ultimate facilitation model!
Storytelling, songs, symbolic foods. All structured around these three questions:
How do you want people to feel?
What do you want them to know?
What do you want them to do?
Always bring the agenda back to what you’re trying to accomplish.
Walkshop is a leadership retreat built around multi-day hiking, challenging and connecting leaders in ways a conference room never will. I'm facilitating November's trip in Patagonia (on my bucket list!).
Sold out, but join the waitlist so you don't miss another one: www.walkshop.io/argentina2026
Most meetings are a waste of time. We sit through thousands, then start leading them, and assume we'll figure it out. That's like running a 10K because you've watched others do it. The bar is on the floor. I don't accept it. If your meetings feel like a tax on morale, I can help reset them.
The networking question we all know: "So, what do you do?"
In case you've been searching for something like this, here's a refresher on the workshops I run: half- or full-day. Customized. Interactive. Leave with an action plan, not just notes.
More info here: daydreamsinruby.com/workshops/
Honored to be published on one of my favorite topics: MEETINGS. We're all in them, run them, attend them and mostly, hate on them. Check out my piece on why your meetings are failing and what to do about it. Huge thank you to Dreamers and Doers! Full article: www.fastcompany.com/91503434/her...
I planned half our team offsite on the flight there. I KNOW. It landed well, but I knew what it COULD have been. Planning week-of isn't a failure of caring, it's a signal you're at capacity. Sometimes the most valuable thing isn't knowing what to do. It's having someone else do it.
#TeamOffsites
My daughter: "Grippy socks = guaranteed fun." Somewhere along the way, we decided strategic can't also be joyful. But after years of designing offsites and workshops: fun isn't fluff. It's fuel. Energy drives outcomes, not the other way around. Where are YOUR grippy sock moments?
Last chance! AI for Chiefs of Staff this Wed 12-1p ET. Exec briefings, decision memos, stakeholder comms, meeting prep, and the "can you pull this together by EOD" requests. Hands-on, 60 minutes. Bring a real task. Join the waitlist if you want in (or to join a future session): luma.com/f57mylkh
"My work is so context-dependent, I'm not sure AI can actually help." Sound familiar?
You bring a real task. We work on it together. Real practice, not lectures or demos. You leave with something you made, not just ideas.
AI for Chiefs of Staff — Wed March 18, 12-1p ET: luma.com/f57mylkh
This month's input stream has been…intense: leadership, sustainability, moral courage. Newsletter recs include a new doc, two binge-worthy shows and a kids' podcast. Because managing the heavy stuff means protecting the light stuff. Check it out here: seasonedleadership.substack.com/p/the-art-of...
Sometimes you just need to have fun with AI. I prompted: "A leadership team at an offsite, but as if they're in a Dr. Seuss book." Hilarious, but also a good reminder: people remember what made them feel something, and that’s not fluff when you’re trying to create alignment and decisions.
Honored and excited to be heading out tomorrow to NTEN's annual conference in Detroit to speak about AI!
Who will I see there?
Most exec leaders default to two extremes with team offsites: mandate everything or mandate nothing.
The move most execs miss: define overarching outcomes, not agendas.
Every team leaves with clarity. How they get there? Up to them.
Read more on the blog: daydreamsinruby.com/blog/2026-02...
The AI adoption bottleneck isn't tools. It's behavior change. Most orgs have a few power users, some skeptics and a LOT stuck in 'I kinda use it' territory. Adoption happens when you meet people where they're at and give them time + space to practice. The goal: get them to their next 'aha' moment.
March 4, 12:30-1:30p ET: AI for Engineering Leaders.
Last few spots—grab one if you want in!
We're covering roadmaps, stakeholder comms, 1:1s, and the leadership work that quietly eats your calendar.
60 min, hands-on. Bring a real challenge from your work. luma.com/0cp5gemo
Engineering leaders encourage their teams to use AI, but their OWN leadership work? Still staring at a blank screen.
Next week's workshop, come practice with YOUR real work.
AI for Engineering Leaders - Wed, March 4th 12:30-1:30p ET
luma.com/0cp5gemo
What would you bring? Drop it below!
Chief of Staff might be the most AI-ready role and the least talked about in AI training.
You're already synthesizing info, managing context, translating between teams. AI was built for this work.
Free workshop Mar 18, 12-1p ET. Real examples, zero generic tips.
Register here: luma.com/f57mylkh
Honored to be speaking THIS WEEK at the Jewish Digital Summit sharing my remote manager's playbook.
I've been managing remote and hybrid teams for 16 years (yes, SIXTEEN) so this topic is near and dear to me.
It's virtual, so there's still time to grab your tickets! Hope to see you there :-)
AI for Nonprofit Leaders: Practical Applications Without the Hype luma.com/735c9ntf
AI for Engineering Leaders: Practical Applications Beyond the Code luma.com/0cp5gemo
AI for Chiefs of Staff: Working Smarter in the Most Context-Heavy Role luma.com/f57mylkh
Three free AI workshops coming up, each designed for a specific role. Real, hands-on sessions where you work on challenges from your actual job.
📍Nonprofit Leaders Feb 24, 11:30a ET
📍Engineering Leaders Mar 4, 12:30p ET
📍Chiefs of Staff Mar 18, 12p ET
Grab your spot now. Reg links in comments.
I saw this and immediately took a picture. #obsessed
A little free TARDIS library!! (littlefreelibrary.org)
I debated a deeper post... but at the end of the day? It brought me joy. And we could all use those mini-moments amidst the chaos. When something makes you smile, pause and appreciate it.
Skip levels are one of the most underused tools in a leader's toolkit (IMHO).
The trick? A few good questions ready so you're not stuck when someone says "things are good." And always close the loop. If you hear themes, share what you're taking away.
More here: daydreamsinruby.com/blog/2026-02...
Wall-to-wall meetings? AI will help you with everything in between: roadmaps, stakeholder updates, performance convos. Join my free workshop: AI for Engineering Leaders - Beyond the Code
60 min, hands-on, for VPEs, CTOs, Directors
Wed, March 4th | 12:30–1:30p ET
Register: luma.com/0cp5gemo
