Long Story Short
Being seen and heard matters, always. AND having a system that makes sure you’re appreciating everyone you work with matters just as much. Jessica Eastman Stewart makes it doable: meeting openings, a rhythm you can keep, and the details that make it land. We built Jessica’s Appreciation Toolkit if you want to start this week.
A few years ago, I started doing a writing group called Unmute with Ann Randolph. Ann had built this incredible set of rules for it.
The structure was this: there’s a space where you can share your writing, where you give two people feedback, and then you get feedback from two people. And you can only give feedback on what was working. You can name the lines. You can point at a detail, a piece of dialogue, any of those sorts of pieces, but they have to be the things that are working – the strengths.
When I started, I was like, Oh, I’ll have to be constructive. So I’d say things like — I’d love to hear more about this. When you started this, it got me intrigued, I can’t wait to see where it goes. And if you had added these things, I would love it even more.
And then I started getting the feedback that other people were getting. The cadence. The piece of dialogue. All the pieces.
And I was like, Oh my god. This is magical. There was no “And if you had added xyz I would have loved it more.” It was all about strengths. And I realized that I learned JUST as much from strengths-only feedback.
I’ll be the first one to say you absolutely need constructive engagement and edits and all of those things. Ann would say you get almost everything you need from the strengths alone — and that when you’re starting, in the first few rounds, all you need to work on is what’s working.
I just really, really, really love that. And I started taking it into how I parent, into how I work, into all the different pieces.
I think about it now every time someone tells me they’re not feeling appreciated at work. Because I wonder how much of being appreciated is really just about being seen and being heard and being known for what is working, which is the core thing I think we all want. And I wonder if not being appreciated is when you start to feel unseen, and overworked, and underpaid, and unclear — because you genuinely don’t know what’s going well and what’s not.
Feeling seen and heard is the most fundamental, right, and beautiful thing that can happen in the world. I don’t want to pretend that workplaces are always wonderful, or that just appreciating someone solves all things. AND the idea of starting from a place of what’s working — highlighting it, feeling gratitude, telling someone this, THIS is great — especially if you can be specific? What a beautiful gift for the person. What a beautiful gift for you, in showing up.
The Person who Has an “Appreciation System”
Jessica Eastman Stewart has spent her career figuring out how to make places great to work. She taught in Oakland, did professional development at Teach For America, and spent over a decade building GO Public Schools before passing the torch in 2021. These days she leads workshops and retreats and coaches executives on how they show up for their teams.
“What I had loved the whole time was making a great place to work and building systems that allowed us to do good work and support people really well. And so these days that’s what I try to do — help people have easier lives at work and build organizations that are fun to work at and do good work.”
Appreciation is at the core of what she does to make a great place to work, and when she said it has to happen at least once every seven days, which stopped me in my tracks.
I was like,What? I hope I’m doing that in parenting. But at work? I’m not sure that I am.
The seven days came from Gallup research she found early as a manager — the survey item asking whether you’ve received recognition or praise for good work in the last seven days.
“I remember as a new manager reading that and not being surprised about the appreciation piece, but being surprised at the frequency piece. I was like, every week. Wow, that’s a lot.”
What she did when she heard that was to build the system, so that appreciation wasn’t just something she aspired to, or something that happened sometimes, or with certain people. It became a practice.
“I’m a systems person. I see things in systems. I’m always creating systems. And so to me, when I have a problem to solve, I’m going to try to systematize it.”
The Key Takeaway
Appreciation matters — there is more evidence behind that than anything else we could do to make a workplace somewhere people want to work and do good things.
It doesn’t solve all the things that make our work world hard. AND making appreciation a practice that happens on a regular cadence goes a long way toward building a world folks want to live in.
Before the steps
We’re not pretending this solves all things. Appreciation is not a replacement for fair wages or healthy workplace practices. And I want to go further than compensation and time off, because the list is so much longer than that.
Feeling overworked. A manager who doesn’t have real space to manage. A leader who changes direction constantly. Fewer and fewer resources, and the stress and pressure that come with that. Underlying technology systems that don’t work. The capitalist structures we’re all operating inside of. The list goes on and on and on.
None of that gets solved by appreciation, and we are not trying to pull the wool over anyone’s eyes.
Things are hard right now, especially because so much of the hard stuff is out of our control. AND things feel better and turn out better when we latch onto what we CAN do, and then do that well.
This is one of those things.
Whatever seat you’re in, whatever’s going on around you, you don’t need permission, a budget line, or a title to start appreciating the people around you.
“Almost anybody can try this with some ideas and get a little better at it. It’s hard to mess up.” — Jessica
Jessica’s Appreciation Practice
If you’re a “just give me the tools, I’m ready to start” kind of person (aka Helia’s COO, Libby), we built Jessica’s Appreciation Toolkit that includes her notes system, the Round of Appreciation, and her full session plan.
If you’re a “tell me why each piece works” kind of person (a Jess), read on:
- Step 1 — Build the rhythm
- Step 2 — Know your people
- Step 3 — Say the specific thing
How Jessica’s appreciation practice works
Step 1: Build the rhythm
Seven days goes by fast — fast enough that it doesn’t happen on memory alone. But the number isn’t really the point. The real question is not Did I hit seven days, it’s How long has it actually been since I last appreciated someone? Most of us are going a month without noticing.
A rhythm is what closes that gap. Here’s what Jessica does, sorted by how often it comes around.
| How often | The practices | What it takes |
| Daily | #kudos channel — a Slack channel or Google Space where people post the moment they think of it The small window — Jessica uses unexpected few minutes, before a meeting or waiting on the kettle, to send a voice note or quick email | Set the channel up once, then reply to what people post — a channel nobody responds in dies in about three weeks. The small window is 2–3 minutes, no occasion required. |
| Weekly | Standing appreciation slot on the team meeting agenda. Jessica loves this for teams of five to nine. A line in your own planning ritual — who am I appreciating this week? | 5 minutes on the agenda. Name it, and don’t skip it. 1 minute, wherever you already set up your week. |
| Monthly, or when something closes | A line on your project and event checklists asking how the people who did this are being recognized The Round of Appreciation — everyone writes their name on a page, papers pass around the circle to music, everyone writes a note to whoever’s name is in front of them | Add the checklist line once and it happens every time. The Round is 10–15 minutes at the end of a meeting. Full run-of-show is in the toolkit. |
| Occasional | Totem — a card game Jessica brought to team happy hours as an ED. Everyone assigns each other positive animals and characteristics, and everyone says something good about everyone. A micro-bonus system, if you have budget — every employee gets a small amount to send thank-you gifts to colleagues, say $100 a quarter sent in $25 pieces | 20–30 minutes. Commercially available card game, not a Jessica or Helia product. The micro-bonus system is an organizational decision and real money. |
| Once or twice a year | A full team session on appreciation — Jessica’s plan is in the toolkit, and it runs in about 30 minutes without books | 30–60 minutes at a retreat or all-staff |
Pick one daily and one weekly, and put the weekly one somewhere it doesn’t rely on you remembering.
Step 2: Know your people
Here’s the reason to write any of this down, and it’s the thing from our conversation I haven’t stopped thinking about:
“There are employees that I’ve had that just — I would work with them in every lifetime after this again. And then there are other folks for whom I like working with them but we might not have that same exact chemistry. So I might need a little bit of system to help me make sure that I’m not leaving them out of feeling really appreciated for what they do.”
Gut check: are the people you appreciate most often also the people you most enjoy?
I counted, and I did not love my answer.
To solve this, Jessica keeps a private Google doc of everyone she manages or works closely with. Names, and under each one, bullets of whatever she’s learned about them. Nickname in college. Grew up outside Chicago. Really likes cured meats. Really liked Power Rangers as a kid.
Then she uses it. A work anniversary. A birthday. A big project closing for the person who likes cured meats.
She also designs icebreaker questions specifically to collect this. During the pandemic, she asked her team about their favorite childhood cereal, and a box of Fruity Pebbles showed up at someone’s door. She asks about celebration food, which is how a colleague who got into grad school ended up with a steak and steak sauce on his porch the next morning. And she writes down Starbucks orders by sneaking a peek at the sticker on a colleague’s cup mid-meeting.
“It’s fun to be able to show up and be like, Well, that was a hard day yesterday, wasn’t it? I got your vanilla latte with oat milk.“
There’s also the how. Different people want appreciation to arrive differently. Words. Time. Gifts. Someone jumping into the work alongside them. Someone whose thing is quality time will feel it when you keep your one-on-ones, and feel the absence when you don’t. Jessica uses The 5 Languages of Appreciation in the Workplace and its quiz with teams for exactly this.
Just because gifts is one of the people on your team, and bringing them their favorite Snickers bar might be a really excellent move, doesn’t mean that you shouldn’t say in the meeting, Hey, you did a really great job last week. Say the thing!
Step 3: Say the specific thing
Here’s what a solid appreciation looks like: “Great job on the budget!”
This is what a great appreciation looks like: “You did such a great job getting everybody’s feedback on the budget and then laying it out really clearly so that the board could ask their questions and understand it and then vote on it with a lot of confidence. And you got it done by the deadline without everybody scrambling at the last minute.”
If you only have the brain space for the solid version, say it! That’s still solid, and it builds the muscle. But as you get deeper in your appreciation practice, taking the extra 2-3 minutes to make your appreciation extra specific will pay dividends in employee morale and overall culture.
Appreciation almost always wants to live out loud. A Slack channel. A team meeting. An email where you copy their manager. A space you’re both already in. A gift you send. Think about who’s receiving it and what would normalize this for your team — and then do it out loud.
Critique generally belongs behind closed doors. But appreciation? How wonderful that we get to share it!
The added bonus here is that when people feel generally recognized by all of this out loud appreciation, the constructive feedback they receive when they need to improve lands the way it was meant to. They don’t hear it as “Oh I’m a failure at everything” because you’ve built this foundation of appreciation. They hear it more as you saying what Adam Grant commonly says — I’m giving you this feedback because I have high expectations and I know you can meet them.
When to do this Yourself vs Bring Someone in
You can start most of this this week. Add the meeting slot, start the notes doc, send the voice note.
And how lovely would it be to give your whole team a session where everyone leaves with the ways to do this — not just you. That’s worth bringing Jessica in for. So is:
- You’re a new manager jumping in, or taking on a team for the first time
- You’re stepping into a place where the culture is tricky and you want somewhere to start
- Your team is distributed enough that “add it to the agenda” isn’t quite the answer
- Appreciation has been tried here before and it went flat, and you want to understand why
If You Want Help
Jessica Eastman Stewart leads workshops and retreats on project management, appreciation, team culture, and creates public group cohorts for those who want to get more organized and effective in their leadership. Her most-requested topics include Appreciation Matters for Your Team Culture, Implementing Asana, Managing Up, Down, and Laterally at Work, How to Plan Your Week, and Getting Your Email Under Control. She runs 50–75 sessions a year for groups of 15 to 200+ and would love to design a great experience with you for your people.
She’s a good fit if:
- You want a session designed and facilitated for your team, not a deck handed to you
- Your staff is running more projects than people, and nobody’s quite sure who owns what
- You want recognition built into the meetings you already run, instead of one more initiative
- You’d like a thought partner on making work less stressful for the people who work for you
Connect with Jessica!
Try it Yourself
Jessica’s Appreciation Toolkit
- Know Your People — Jessica’s system for tracking what matters to each person you work with
- The Round of Appreciation — the full run-of-show for a 15-minute activity, with her printable and playlist
- Jessica’s Appreciation Session — her complete session plan, including the 30-minute no-book version
Questions to Sit With
- Who did I appreciate in the last week? How long has it actually been since I said something to each person on my team?
- What’s one appreciation I’ve been meaning to give and haven’t said out loud yet?
- Where in my week does an appreciation rhythm actually fit — a meeting, a planning ritual, a Slack channel?
- What do I know about how each person on my team likes to be recognized?
Not sure Jessica‘s the right fit? Talk to Helia directly!
This article comes from a coffee chat with Jessica in August 2026. These conversations form the heart of the Helia Library — because we’ve learned the most from doing and from talking with other doers willing to share their wisdom. We don’t need to start from blank pages or do everything alone.
As always, take what’s helpful, leave what’s not, and make it your own.
About Jessica
Jessica Eastman Stewart grew up mostly outside the US and was the first person in her family to go to college. She applied to Teach For America, saw that Oakland had a Black cowboy parade, decided that sounded like the kind of place she’d like to be, and moved to a city she’d never visited. She spent a decade building GO Public Schools before handing it off, and now runs Joyfully Managed Life, helping people build organizations that are impactful and fun to work at.
Work with Jessica
