As part of our follow-up series from Running Remote 2025, held this April in Austin, we’re spotlighting the sessions that created the biggest buzz. Building on our pre-event interviews and live content, this blog dives into real-world strategies shared by remote leadership veterans.
In this rapid-fire session, top remote leaders from HubSpot, Block, dbt Labs, LTSE, Kendor, Float, Upwork, Atlassian, Doist & Coursera delivered bite-sized, practical insights on keeping teams engaged, connected, and productive in distributed environments. Each speaker shared their most actionable lesson in 60 seconds or less—making this one of the most dynamic and idea-packed panels of the event.
Now, let’s jump into the fast-paced wisdom from this powerhouse panel of seasoned remote leaders.
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Watch the Full Session Below
This session features a rapid-fire format, with each remote leader sharing their most actionable tip for building team engagement in distributed environments.
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Key Takeaways from the Rapid-fire Bites Session
🚀 Keep rituals consistent. Daily stand-ups, weekly wins, and quarterly retros create rhythm and connection across time zones.
🎯 Clarity over control. High-performing remote teams rely on outcome-driven alignment—not micromanagement.
🪞 Feedback fuels engagement. Create intentional spaces for honest feedback loops that build trust and ownership.
🌐 Asynchronous ≠ disconnected. Smart tooling and cultural norms keep async communication just as human and high-impact.
🌟 Recognition matters. From Slack shoutouts to video kudos, consistent recognition drives morale more than perks ever will.
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Quote Highlights
🔹Jessica “JJ” Reeder (start: 00:00:06)
“If people don’t feel good about the work that they’re doing in the day-to-day, there is no off-site that will be transformative enough to fix that.”
🔹 Leigh Staub (start: 00:02:35)
“If you want to improve engagement, don’t just add more stuff. Start by removing what’s slowing people down.”
🔹 Georgie Roberts (start: 00:04:47)
“At the heart of that is curiosity.”
🔹 Chase Warrington (start: 00:06:56)
“We simultaneously increased engagement, ambition, and output by bringing everyone inside the strategic planning process.”
🔹 Julie Armendariz (start: 00:09:31)
“Oftentimes, engagement is about those small, consistent moments where we just show that we care.”
🔹 Meaghan Williams (start: 00:12:09)
“Your engagement efforts don’t have to be loud, they don’t have to be large-scale. They just have to be real and rooted in the places that people already call home.”
🔹 Mark Cruth (start: 00:14:30)
“User manuals enable us to help our people not just know what they do, but how they work.”
🔹 Tiffiney Fort (start: 00:16:44)
“The medium is as important as the messages that they’re giving.”
🔹 Adora Ikwuemesi (start: 00:19:40)
“Be connected by design, not by accident.”
🔹 Sarah Walker (start: 00:23:23)
“We value things more when we’ve had a hand in creating them.”
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Panel Reflections (post-event)
We followed up with a few of the speakers from the session to go deeper on key takeaways. Here’s what they shared:
What’s one engagement ritual your team would never give up?
Georgia Roberts (Director of Operations @ Float.com) – Our annual meetup. It’s a misconception that remote team members don’t know each other or don’t want to spend time together; at Float, it’s quite the opposite. We rely heavily on our relationships to collaborate effectively across more than 20 countries. Our meetup is a vital part of this dynamic and is one of our most valued perks.
Leigh Staub (Sr. Manager, Distributed Experience @ dbt Labs) – Our revamped QBR process. We share an async doc that recaps progress, roadblocks, and key metrics tied to our core strategies and initiatives. Then we come together for a live session that includes a silent read, individual reflection, and group discussion. Shifting to this format has been a game changer – it helps the team see the full scope of our work, spot opportunities to collaborate, and feel more connected to our strategy and goals.
Sarah Walker (Chief People Officer and interim COO @ Long-Term Stock Exchange (LTSE)) While this isn’t necessarily something we do team-wide, this is something that I do as a leader with my team: I start every meeting asking my team if they have any clearings of vibes – what are they coming into the meeting with that could be a distraction, a fresh insight, a personal or professional concern or celebration, etc. that helps to get it out on the table to ensure the team can focus (or optimize) as needed.
How do you ensure async feedback doesn’t get lost or misinterpreted?
Georgia Roberts (Float.com):
a. Not all feedback should be shared async and this requires good judgment. If it’s sensitive, I wouldn’t share it async unless I know the receiver’s style well.
b. Choose the medium and environment carefully. If it’s a difficult conversation, don’t do it in front of others. If it’s simple and light feedback needed quickly to move something forward, I love a voicenote or a quick Loom.
c. Spend more of your own time crafting your message and preparing your delivery to avoid miscommunication and wasting the receiver’s time. You don’t need to reinvent the wheel for remote feedback (use any common feedback models like Situation/Behaviour/Impact or What/So What/Now What for e.g.). Remote feedback and in-person feedback are the same in that they both require good intent and clear delivery.
Leigh Staub (dbt Labs)- It starts with strong relationships and clear norms. Trust makes async feedback more effective. We’re intentional about matching the message to the medium – sometimes that means a Slack voice note, a quick Loom, a follow-up in a 1:1, or starting with sync depending on the type of feedback. We also rely on communication norms (like Slack emoji reactions and response expectations) to close the loop and make sure feedback is seen, understood, and acted on.
Sarah Walker (LTSE) – At LTSE, we are big users of slack and Asana (shoutout to Asana who is an LTSE listed company). We try to work out in the open (aka put updates in channels and projects, versus DMs), so that folks stay informed of what’s happening in the business and across working groups. This saves a ton of side chatter, and swirling that can happen when teams don’t receive the right information at the right time. Subsequently, for feedback that might be directed toward an individual, we go the old fashioned route – pick up the phone (or a slack huddle) and call the person directly. It can be a tough muscle to build, especially acknowledging multi-general approaches to communication, however we model this from the top down. If you have an issue, concern, etc. and you happen to vent to somebody else about it, we re-direct each other to the person to facilitate the feedback.
What’s a common mistake remote leaders make when trying to improve team culture?
Georgia Roberts (Float.com):
- Trying to replicate in-office experiences rather than designing for remote.
- Culture ≠ events. An easy trap to fall into is trying to solve cultural problems with ‘fun events’. This can translate to leaders asking their team for more of their time, but not addressing the behaviours and values required to build a good culture.
Leigh Staub (dbt Labs)- Adding more stuff. The better move is to level up what already exists. Culture isn’t just how people feel – it’s how the team works. Reinforce it through the way you run meetings, give recognition, set priorities, and make decisions. Culture becomes more tangible when it’s baked into daily operations, not just celebrated in one-off programs that don’t address deeper issues.
Sarah Walker (LTSE) – Assuming they have to do everything that their employees request/ask for. I’ve seen it time and time again, where team engagement goes down – a survey goes out to employees, and a long list of requests/ideas come in. Immediately the manager (or HRBP) begins to action on these items, worried that if they don’t change/implement they’ll lose engagement even further. Instead, try this – tell your team up front, we can’t implement everything, but we want to throw spaghetti at the wall, and then we’ll prioritize items that will have the biggest impact, fit with our culture and strategy, and fit within the budget. Encourage outside of the box thinking, and reassure them that not all ideas will be incorporated. This way you get fresh ideas without the obligation and overwhelm of doing it all (and possibly not doing it well).
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🔁 From Theory to Practice
Want more insights like these? Visit the Running Remote Library to watch every session from the 2025 event—plus a treasure trove of talks from previous years. It’s all free, all on demand, and packed with inspiration from remote-first leaders.
➡️ Which of these tips hit home for you? Share your team’s favorite engagement ritual or tag someone who leads with empathy and clarity. Which of these tips hit home for you? Share your team’s favorite engagement ritual or tag someone who leads with empathy and clarity.
➡️ Keep exploring the best of Running Remote 2025. The conversation—and the innovation—continue.
