Missing my kids this week but don't worry, I have the creepy 3d printed child-sized person they made to keep me company.

It's summer camp drop-off day so basically I’m a mess. Sleepaway camp is good for them, but I'm nervous. Meanwhile, as a busy working mom I have a lot planned. That intense craving to be mama bear AND the person who knows she’s so much more than a mom and loves reclaiming those parts of herself too.

"Can't we just promote someone internally?" Maybe! But do they already know how to build a roadmap, design interviews, coach managers? If not, that's a reason to bridge the gap while they grow into it. Fractional support handles what needs doing now and mentors your person so they're ready later.

Today I found a single glove in this pile. (Yes. This pile.) This is the school lost and found. Hundreds of items, no system, no labels, sloped into one heap that everyone walks past because where would you even start. And I found the glove. Honestly? Unstoppable now. Send me your hardest problems.

A lot of CEOs are convinced AI is the solution. And honestly? It might be. But there's a big gap between "AI is the answer" and actually getting there. The answer isn't to resist AI. It's to stay honest about what it actually takes, and flexible because the ground is still shifting.

I've been running a lot of AI workshops lately and I love it. People walk in overwhelmed, skeptical or spooked, then they get hands-on and the switch flips: “ooo, ok, NOW I get it." Most people don't need more AI info. They need one small, successful loop with a real task. Fear turns into curiosity.

The most common reaction to bringing in a facilitator for team offsites: "I'll never get budget approved." Your leadership team doesn't think twice about spending this money. The key is making the business case and if you're not sure how to do that for your specific manager, I'm happy to help.

We spend so much energy designing perfect systems for people, and then people go and be human. This month's newsletter is about what happens when we stop fighting that and start designing for it instead. Read here: seasonedleadership.substack.com/p/rethinking...

We've got minimal weeks left before we all hit summer brain. So consider this your reminder: if you've been noticing places where your engineering team could be working together better, now's the time to talk about it. Not after the summer scatter. Now, while people are still in the room.

A vast majority of the women I know are in a book club. (I'm in two, with VERY different vibes.) So here's my question: are you in one? And if so, what makes it worth showing up for? Feel free to drop a great book yours has read recently, too.

One of my favorite offsite sessions flips how strategy usually lands. Instead of a slide deck and passive absorption, people actually interact with it. Break it into themes, add questions you've been hearing then let groups add answers, thoughts, and things they're curious about. It hits different.

A colleague said something that stuck with me: we don't think twice about bringing in a facilitator for leadership gatherings. Why don't we think the same way about team offsites? If one team walks away thinking "that was worthwhile," imagine every team having that experience.

So honored to be featured in this piece on female founder advice, full of gems on what no one warns you about when starting a business. Thank you WeRule and Dreamers & Doers! Check it out: we-rule.com/blog/female-...

That moment when you’ve accidentally planned too few breaks and pushed the group a little too far.

Every conference has AI front and center, and most of it assumes your team is further along than they are. What actually moves the needle: a day designed for where your team is today, with multiple entry points so no one is bored and no one is lost. These teams are seeing 50%+ adoption rates.

Back in March I spoke to folks in the nonprofit tech space about AI — such a fun conversation in a space so different than the startup tech scene. I also joined @tonymart.bsky.social on #NonprofitRadio to talk all things AI for nonprofits. Give it a listen! tony.ma/NonprofitRad...

You believe in bringing your teams together. You're just not sure the time is being used as well as it could be. Because the stakes shouldn't just be "did people enjoy it?" The stakes are: did anything change after everyone went home? Did you leave with real decisions and clear owners?

Last week's inaugural Fractional Women's Summit was everything we dreamed. Incredible women sharing mind-shifting information. A true sense of camaraderie and support. Where women actually engaged with one another in meaningful ways, and walked away thinking "wow, that day FLEW by.”

If you're both a real participant AND the facilitator in your leadership meetings, those roles are in direct conflict. What changes the game: a facilitator with zero stake in the outcome. No history with the issue. No side in the debate. I run the room so you can stay in the conversation.

In a world obsessed with efficiency, this month's links are a reminder that the things that matter most still require a human in the room. Check it out here: seasonedleadership.substack.com/p/ai-ificati...

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.