If you lead multiple engineering teams, offsite quality varies wildly based on each manager's bandwidth. One fix: use the same external facilitator across teams. Department priorities get woven into each offsite, quality is consistently high, and one person holds context across teams.

Next week I'm co-hosting the first ever Fractional Women's Summit. We have amazing speakers and tracks, but what I'm most excited about is what we've built in between. Friction-free moments designed to get people into real, substantive conversation. Ping me for an invite.

I think there’s a leadership lesson somewhere in this picture.

I have strong opinions about how conferences miss the mark on connection. The Fractional Women's Summit is doing things differently. Offering the opportunity to share the room with others building something great, with real and creative ways to actually engage with one another. DM for more info.

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 :-)

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

Most facilitators are just expensive meeting organizers who keep you on time, make everyone feel heard, but won't push for hard decisions. Result? Fuzzy priorities, unclear owners, same tensions repeat. You need someone who surfaces real friction, builds agendas around decisions and follows through.

We're getting smarter about how we connect. This month's reading list covers skip-levels that actually work, coordination that doesn't waste time and why we're craving in-person connection in an AI-everything world. Plus, I'll be speaking at both NTEN and Jewish Digital Summit soon! bit.ly/4kFKhUL

People keep asking about AI and engineering teams. Should we force it? Why aren't people using it? Here's the thing: AI isn't magic, but it can be magical. The goal isn't adoption for adoption's sake, it's helping people work smarter. Dig into what's holding them back. AI adoption takes time.

Most AI workshops: everyone nods, two weeks later...still haven't used it. That's why AI for Nonprofit Leaders is different: hands-on practice with your actual work. Bring a grant, report, donor comm. We work on it together. You leave with something you can use. Feb 24, 11:30a ET luma.com/735c9ntf

Most retreats don't feel right. High-performing women don't need inspiration. They need the right room. Extraordinary Machines is real conversations at your level. Strategic. Curated on purpose. No yoga. No keynotes. Just the room you're looking for. Interested? docs.google.com/forms/d/e/1F...

Planning your offsite around "Did people have a good time?" instead of "What's different in 6 months?" You're designing a nice experience, not a strategic one. Ask instead: What conversations are we avoiding? What decisions keep getting deferred? Read more here: daydreamsinruby.com/blog/2026-01...

Most nonprofit leaders aren’t asking, “Should we use AI?” They’re asking: “Which AI tools should we be using and how exactly do they work?” In this free workshop built for leaders, we'll work through real applications. AI for Nonprofit Leaders Feb 24 | 11:30a-12:30p ET luma.com/735c9ntf

Only 26% of tech workers see their managers as highly effective (Lenny's Newsletter surveyed 8,000+ tech workers). Most managers are trying—they just lack support. Offsites are one place this shows up, where "more of the same" reinforces ineffectiveness. Want offsites that land? Let's talk.

Snow storm week at our house = living room fort building. What got me: same blankets and cushions we've always had, but my kids have never built the same fort twice in 7 years. It's a good reminder that the best outcomes come from reimagining for NOW, not defaulting to what worked last time.

Poll time! Offsites aren’t just “nice-to-have.” They’re often a reset preventing alignment drift and slow decisions from compounding. How often does your team do an offsite? A) Quarterly B) Twice a year C) Annually D) We don't do offsites Curious what's standard and what’s driving your answer?

You know that meeting that should've been an email, or better yet, just an FYI on a decision? We're so eager to be inclusive that we forget: sometimes you should just decide! When? When it's not up for debate, when you're going in circles, or when everyone's had their say - just make the call.

I'm so excited about my new website and logo! For two years I've been explaining what I do: "It's facilitation but not the kind you're thinking of." Now I finally have a digital space and logo that SHOW how this work is different. Check it out: www.daydreamsinruby.com #Facilitation #Consulting

Time for a fun post! I'm so excited about my new instant print camera (like a Polaroid, but fancier and cooler!) and will definitely be snapping photos during my upcoming workshops and offsites 📸 Check out my short video about it over on LinkedIn! www.linkedin.com/posts/apmcmi...

What a fun surprise! Thank you Dreamers & Doers for spotlighting Parent Driven Development and the conversations that remind parents they’re not alone. Check out the article here: www.dreamersdoers.com/leading-visi... and give the podcast a listen if you get a chance: www.parentdrivendevelopment.com

Part 3 of my reorg series is all about individual contributors - the group most often overlooked. How you can actually help your team process it. People need time to figure out what it means for them. Check it out: daydreamsinruby.com/blog/2026-01... #Leadership #OrganizationalChange #Management

Are we in our “over-engineering” era? We take simple ideas and heap more process onto them, becoming one more job to manage. I'm always asking: How can we streamline this? Are we the one who has to do it? How can we empower or delegate instead of being a bottleneck? open.substack.com/pub/seasoned...