Allison Serfin’s Together Tour: Issue #114

May 22, 2025

Together Friends,

Together Tour: Allison Serafin

Today’s Tour feature, Allison Serafin, the Chief Strategy and Development Officer for Building Hope, an organization that focuses on charter school finances and real estate, is a longtime friend of The Together Team. Fun fact: I knew Allison back when she was an amazing teacher working on my summer staff for Teach For America’s training institutes in the early 2000s.

Delivered with Allison’s signature direct nature and wry sense of humor, I have learned so much about Togetherness from her over the years. Whether she’s juggling her three giant beautiful dogs, traveling often to support folks in financing school real estate, creating a life serving as her elderly parents’ main caretaker, or posting about AI prompts on LinkedIn, she’s keeping it Together. I know we can all learn from Allison’s wisdom!

First off, tell me about Hearth, this wild and beautiful digital calendar.

I purchased Hearth because after I moved with my parents (aka my 80-year-old roommates) to South Carolina, I needed to synch my Google calendar, work travel, and other calendar accounts to one visual device. We include all of my flights, meal planning, veterinarian appointments, and medical appointments so my parents can see it at a glance. They do not drive, and having this shared calendar helps us coordinate, allows them to maintain independence, and lets them see when I’m available. It really helps us avoid decision-making friction when we are scheduling appointments for them, and cues if one of us can get a head start on preparing dinner. (Editor’s Note: My own family uses the Skylight,  though I personally find it to be too small, and we also like the Echo Show. The NY Times just reviewed the Hearth here.)

As we get older, it can be brutally hard to surrender independence. As you age, the smaller your world gets and you live vicariously through those you love and care about. The more my parents can be connected to my world, it improves their quality of life, since they don’t get to go out often. Our shared calendar gives them a porthole into my world.

Speaking of frictionless, I was fascinated by your recent post about using AI for weekends. Say more!

After a busy week of work and caregiving, I do not want to spend my whole weekend planning – hence my recurring Friday AI prompt. I was already searching for more weekly opportunities to get my parents and I out of the house, and I needed things ADA-friendly. I was also looking for AI to help with some of the life admin, such as meal planning and more. The automation of knowing what we can read, watch, visit, and eat has saved me so much time – and added a lot of joy! (Editor’s note: Adding this trick to my toolkit!)

And while we are on the topic of generative AI, say more about using it for meal planning!

My parents are not big fans of takeout, they don’t like leftovers, and don’t like eating the same thing daily. I want meal prep that takes less than 30 minutes and contains a lot of protein and a vegetable. I use ChatGPT to help me plan.

And what about for you personally? What tools do you use to stay Together?

As someone who has ADHD and has tried alllll the things, I need to have as few tools as possible. These are mine:

  • Google Calendar – I live by my calendar and meetings, all-day notes, reminders, and anything else that takes time goes there. I also get a lot of invitations to events that don’t link to a calendar hold, so I use a text-to-ICS app, which uses AI to extract event details from a text or email and convert it to a calendar file, so I can instantly add the event to my calendar.
  • AnyList – for grocery shopping we all use AnyList. We share a family account, and my mom and I use it. She’s better with tech than my dad, so when she remembers we’re low on something, she adds it to AnyList and I’ll see it when I’m at the store.
  • Granola – I’ve tried every app out there for notetaking and they all have their own pros and cons. I often have back-to-back meetings, and Granola is designed for that kind of schedule. It is $10 / month, and it runs in the background. It doesn’t have a bot and isn’t meant to be a stenographer, but it offers a transcript, summary notes, next steps and action items, and builds into my calendar. Granola creates a frictionless experience, where I can get follow up communications out quickly. Relationships are built through nurturing and attentive follow up, so I don’t want to get to the end of the week without hitting my action steps. Granola also eases the cognitive lift so that I’m not spending my time wordsmithing, and I can do work that moves strategy and helps the client.

(Editor’s Note: Allison kindly showed us the three step process she uses.)

Step 1: The Granola app captures basic notes from Zoom meetings (and a simple transcript).

: Step 2: Allison pastes the transcript into the chat with tailored prompt for email follow up.

Step 3: Granola drafts a personal follow up, which Allison copies to Gmail and sends.

And with all of your travel. . . how do you stay organized on the road?

I have tech with me at all times. I use a device called Plaud, credit to John Ripka who showed me this tool, which I put on the table at conferences to record conversations. I’m not capturing conversations to record people, but for my own learning style and IEP accommodation. At the end of a long day, Plaud allows me to have a transcription of the day, and allows me to follow up via suggested action items based on the transcription and summary.  Click the video below to see how Allison uses Plaud!

Watch Allison explain how she uses Plaud!

Thanks, Allison, for giving us a window into your world, how you serve as an attentive caregiver for your parents, and an excellent dog mom! I learned SO much in our conversation.

As Maycember marches on in full force (and I’m not mad about it because I’m throwing a grad party for our senior, and prom dress shopping is fun!), consider if there is anything you can automate, and as always, anything you can push off or cancel. I had a non-urgent medical procedure scheduled that I just bumped out until fall to give me a little room in a very busy six-week period.

  • Are your Google docs getting out of hand? You can now create tabs within your Google docs to make them easier to organize and quickly find the information you need.
  • How do you get ready for a big event? Sometimes you’ve got to get yourself in the zone. And if Beyonce can have a warm-up ritual, so can I.
  • With summer approaching, some seasonal projects can be daunting. Whether it’s end-of-year close out or onboarding new staff, try my tried-and-true staging technique to break down big tasks.