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...

My holiday break highlight? Making family vision boards. After convincing them last year, it turns out they loved it and asked ME to do it again. Applauding myself as both a mom and a facilitator because if you can get your family into something, you can pretty much get anyone into anything.

I finally reached my breaking point. The "let's always call the mom first" or, more often, "let's only call the mom" thing. So frustrating, and we deal with this all the time. Watch my video on LinkedIn to find out what I did. www.linkedin.com/posts/apmcmi...

"Everything is important" is a prioritization problem. When everything's a priority, nothing is. Prioritizing well means really talking through trade-offs. Then saying no, even to good things. As you plan for 2026, make a list of what to stop doing or delay. That's where real prioritization happens.

There's a loneliness epidemic at work. People on teams for years who don't know much about each other. Work doesn’t need to be entertaining and we’re not camp counselors, but people who have fun and enjoy their peers do better work. It's not about playtime, it’s about helping people connect.

The flip side of AI nobody wants to talk about? AI can't read nuance like humans, can't build relationships, can't handle truly novel situations, and definitely can't replace institutional knowledge teams build over years. Orgs getting AI right are using it to augment their teams, not replace them.

Now is the time to think about setting your team up for success for the new year. A great place to start is recognizing unsuccessful patterns to learn from them and not repeat the same mistakes. Here are the top 5 mistakes I see orgs make over and over. open.substack.com/pub/seasoned...

Most orgs miss out on big time savings because they don't know how AI actually helps. Teams doing this well identify specific repetitive tasks and experiment until it works (meeting summaries, data cleanup, etc). So, if you're saying “I could be using my time in so many better ways," start there.

New to fractional work in tech? I want to help! I'm hosting a week-long AMA on Filament where aspiring and early-stage fractional professionals can ask me ANYthing about building a successful fractional business + brand. No stupid questions! Sign up here: form.typeform.com/to/UlG0lH3B

I'm on the SUPER conference circuit! From JFNA's General Assembly to NATA to present an AI workshop for nonprofits AND today presenting remotely at JS Nation on facilitating technical conversations! Why? Because I want to help people accomplish their work better in tangible, actionable ways.

I had a fun chat with my 7 year old about how I approach teams and staffing different projects. She goes “this is such a hard problem to solve!” She's right. It's a complex puzzle where every piece affects multiple others. How do we staff for headcount AND project success and individual growth?

November highlights are here! You'll find questions to consider as you’re making and planning for changes, plus some cool products and a few great articles worth reading. seasonedleadership.substack.com/p/whats-your...

It’s that time again…performance review time! Need some helpful tips? Look for my performance review posts here: daydreamsinruby.com/blog/

Yes, friends. It’s the end of October. Time to get your team organized for 2026. When I go into an organization, I look for 2 things: What is everyone saying and what isn't being said? So, what issues are your team avoiding? And how will you tackle them in a positive way to move the group forward?

Feedback I received during a training: "You're facilitating around something instead of through it." I was avoiding the real tension rather than helping the group work through it. True facilitation creates the right container for groups to navigate complex challenges together. #Facilitation

I've been busy... Chiefx in NYC, The Linux Foundation’s JSConf and Chiefx in DC. Women are claiming our multi-hyphenate identities as strategists, educators, fractional executives, fixers, all at the same time. We re-imagine, create, and impact positive change and forward momentum.

So far October has been a SPRINT, but I'm in it for the marathon. This month's highlights include a post on post-reorgs from me, a few great book recommendations, and blog highlights from other great thought leaders. Give it a read here: seasonedleadership.substack.com/p/sprinting-...

Yesterday's post was about what to do as a leader of a new business area post-reorg. Today we look from the other perspective. What happens when you’re a manager reporting to a new senior leader? Read my recs here: 5 things every manager should do after a reorg daydreamsinruby.com/blog/2025-10...

Reorgs… There’s no escaping them, there’s just getting really good at figuring out what to do when they happen. Here's what I often see, what you should do, and what I hope I see more of. Read on for tips to setting a strong foundation for moving forward. daydreamsinruby.com/blog/2025-08...

Great leaders know: it’s the people who define culture & do the work. Yet we often underinvest in them. Workshops, trainings & offsites give space for learning, connection & fun—without the pile of work waiting after vacation.

Recipe for an offsite 4.5 tablespoons strategic planning or reviewing of the plan 2 cups celebration 2 cups learning A heavy pour of mindfully curated and planned togetherness A dash of manufactured magic 1 cup clear outcomes and next steps

Last call for Extraordinary Machines apps! Deadline - Oct 6 + $500 “procrastinator discount." You’ll walk away with: • Strategic insights to use right away • A network that actually responds • Upgraded leadership toolkit • Clarity on what’s next shorturl.at/G6OhL

In preschool, my daughter played “someone’s missing”—one hid, the rest guessed who was missing. How often do we hide instead of allowing ourselves to be seen? Extraordinary Machines helps women step out, connect & leave with real takeaways. Apps close Oct 1. Link in comments, DMs open.

open.substack.com/pub/seasoned... Check out this months newsletter!

Part 3 company offsite concerns: We’ve always gotten good feedback, why change? Good is relative. Most teams haven't experienced a great offsite. A great offsite shifts team dynamics, speeds up decisions & creates momentum that lasts or years. You’re investing the time & money; why settle for good?

Part 2 of common tech company offsite concerns: “A facilitator isn’t in our budget.” But with flights, hotels, meals, and lost work time—you’re already investing big. A facilitator ensures that investment pays off. The real question: what value are you leaving on the table without one?

Kicking off a 3 part series to cover common concerns for planning offsites & bringing in a facilitator: Part 1: We want people to connect not spend our time in formal sessions Great facilitation marries content sessions & team bonding to create frameworks for real conversation to sustain remote work

The first deadline for Extraordinary Machines is tomorrow. This is a room for women in leadership who want real systems, not just good vibes. If you are looking for honest strategy and smart company, this might be it. Apply here: daydreamsinruby.com/retreat/ #WomenInLeadership #FallRetreat

There is a moment, right before fall really kicks in, where you can still set the tone. I wrote about that window and what it might look like to use it well. Read here: open.substack.com/pub/seasoned... #Leadership #WorkCulture