Developing a Remote Onboarding Process

Hiring good people is just the start. Onboarding well is the key to keeping them. The truth about weak onboarding: ↳ It costs you 2-3x more in the long run ↳ Creates unnecessary imposter syndrome ↳ Breeds preventable mistakes ↳ Kills momentum before it starts What strong onboarding actually looks like: 1. Structured First 90 Days • Clear milestones and wins • Regular check-in rhythm • Progressive responsibility increase 2. Support System That Works • Dedicated mentor assignments • Cross-team introductions • "Stupid question" channels 3. Resources Ready Day 1 • Updated documentation • Tool access pre-configured • Team processes explained 4. Learning Built Into The Schedule • Protected learning blocks • Practice environments • Feedback loops Stop expecting people to "figure it out." Start investing in their success. The best companies know: A slow start beats a false start. What was your best (or worst) onboarding experience? ♻ Share if you believe in better onboarding

Wade Foster is the co-founder and CEO of Zapier, an automation business that raised only $1M and was most recently valued at $5 billion. In this episode, Wade and I discuss why Zapier barely raised any money and unpack their strategy for growing profitably. Wade shares lessons from building one of the first remote-only companies in tech, including key tips for hiring, onboarding, building a great management team, and much more. Some of my favorite takeaways from a true first-principles thinker: 5 Tips for Effective Remote Work… 1. Remote work requires companies to be more explicit than in-person work. Document rules of engagement, operating principles, accountability, naming conventions, and more. 2. Play with adding in non-work related conversations to virtual meetings. Zapier has an “unplugged” section of their Friday check-ins where employees share something they did outside of work with a photo. 3. People often dwell on whether in-person get-togethers should be more strategy oriented, versus more team/fun-oriented. It almost doesn’t matter what form they take, just getting people together makes a huge difference. If you really want to figure out what’s working, survey employees about their experience and ask them how to make it better next time. 4. When onboarding, share a deep sense of purpose, mission, and culture. Zapier starts people in batches and has a dedicated slack channel for every onboarding cohort that joins (#crew-<datejoined>). This allows new employees to move through the organization together with a sense of tight-knit community. 5. Slack can make it difficult to interpret the level of severity of any given idea or issue particularly when it comes from the senior most folks in the org. Use a naming convention to give people context and set expectations. These are Zapier’s (borrowed from Hubspot) #fyi = I’m just putting this out there for your information, take it or leave it #suggestion = I have an idea, but I haven’t looked into it deeply #recommendation = I have evidence or expertise on this, please consider it #plea - please for the love of God (a mandate) “Don’t Hire Until it Hurts”  The main thing a company spends money on is people. Zapier adopted a “don’t hire ‘til it hurts” philosophy so that when any given person was brought on, they knew exactly what they would do. In their case, constraints helped keep things simpler at the early stage (pre-product-market fit). Finding Product-Market Fit  Wade recalls one of his earliest interactions at Zapier with a customer that was struggling to use an early version of the product. It took 30 minutes to talk the customer through setting up a Zap and certainly wasn’t smooth, but when it worked, the user was blown away. It immediately addressed something that the customer hated doing manually. Despite the then janky customer experience, the customer insisted on paying Zapier. “When you have to ask [if you’ve found PMF], you kind of know the answer.”

I’ve onboarded remote hires across time zones, continents, and cultures. And here’s what I’ve learned: Remote onboarding doesn’t ⭐fail⭐ because of location. It fails because of assumptions. Assuming someone will “just speak up.” Assuming they’ll know what success looks like. Assuming they feel like they belong. Without hallway chats or shadowing, remote employees miss all the informal context that makes onboarding feel human—not just functional. Here’s how I’ve made it work: 💬 Over-communicate expectations and priorities 🎥 Use video, even for 15-minute check-ins 📅 Create a rhythm of connection—1:1s, team intros, buddy syncs ☕ Encourage informal conversations (yes, even virtual coffee chats) Remote doesn’t have to mean disconnected. In fact, with the right systems, it can feel even more inclusive. It took me many years of learning the hard way to build this out. And I’d like to share it with you, no strings attached. (see link in comments) That’s why I built these practices right in our Manager Onboarding Kit—to help leaders support their teams with intention, no matter where they are.

Let’s get real; those chats around the water cooler were never that great. There’s a reason why this photo looks like a generic stock photo—this situation is fictionalized. While people may have shared casual stories about the weather or the latest movies around the water cooler, deep relationships were never built there. Remote and hybrid work is criticized for a perceived inability to build culture. If people aren’t talking about their weekends in the break room, the thinking goes, how can we build a cohesive team? In reality, those surface-level conversations don’t do much to build a strong culture, and they certainly aren’t more important because they happen in person. In fact, Gallup research shows only 20% of fully in-office employees feel connected to their company’s culture, slightly below the rate of hybrid employees. What people need more than serendipitous chit-chat is focused, intentional moments of connection - and you don’t need an office building for those. Instead, managers can adopt a few strategies to create connections in hybrid/remote (or in-person) settings that build cohesiveness, decrease feelings of isolation, and boost morale. Good examples are outlined in @Rising Team’s new Guide to Maximizing Hybrid Work Success, including strategies like: 🛠️Dedicate time to build understanding:  Activities that foster authentic understanding are essential for maintaining connection in hybrid environments. While happy hours may be fun, learning about people’s workplace preferences, like how they like to be appreciated and how they prefer to receive feedback, go a lot further towards building strong relationships. 🔗Create micro-connections:  Quick, intentional check-ins about work and life can do much more than casual conversations. Try asking, “How do you like to be supported on a hard day?” or “What is something you’re proud of outside of work?” instead of small talk about weekend plans. Questions like these enhance trust and understanding. 👥Maximize in-person time:  When your team does meet in person, focus on activities that the research shows benefit from face-to-face interaction, like brainstorming or collaborative projects. These in-person moments should strengthen virtual connections and keep the team aligned on shared goals. Find the full list of examples by downloading our free Guide: https://lnkd.in/g9ditxXA Building a strong team culture isn’t about casual in-office encounters—it’s about fostering intentional connections that have real impact. Whether through meaningful check-ins or focused team activities, managers have the tools to create a cohesive, engaged team in any environment. Hybrid and remote work aren’t obstacles to culture-building—they’re opportunities to redefine it. #HybridWork #RemoteLeadership  — This is the final post in my series on maximizing success in remote work. Check out my LinkedIn channel for past posts on best practices for leading hybrid/remote teams.

How do I build a 12-month roadmap for a recruit using their production and my company playbook? Let me share a quick story. One of the leaders I coached was struggling to onboard a new hire effectively. They had great potential but didn’t quite understand how they fit into the big picture. As they dove into the role, the rookie felt lost and overwhelmed, leading to a few early missteps. We worked together on a solution. Instead of just assigning tasks based on numbers and quotas, we flipped the script. We created a detailed 12-month roadmap aligning their production goals with our company playbook. This wasn’t just about selling; it was about grasping our vision and understanding how their contributions would make an impact. Here’s how you can do the same: Start by identifying key production milestones for the recruit, breaking them down into manageable quarterly goals. For each quarter, align these objectives with specific elements of your playbook — training modules, key projects, or team collaboration opportunities. Ensure that each milestone has clear, actionable steps and reasons behind them, so the recruit knows not just what to do but why it matters. Also, keep communication open. Regular check-ins will help you both stay aligned and pivot if necessary. This framework works because it transforms the onboarding experience from a transactional series of tasks into a collaborative journey. When recruits see how their efforts support a greater vision, they’re not just going through the motions; they’re genuinely invested in the success of the team and the company. A meaningful onboarding process can set the stage for long-term engagement and high performance. Let’s make sure our new hires feel they belong and can see the roadmap to their success right from the start.

My remote hires (probably) ramp faster than yours. Here's why: Most remote onboarding means a calendar packed with Zoom meetings and endless Slacks from strangers. No real connection. No clear priorities. No clue how tall anyone actually is. It can feel isolating, especially when you’re new and eager to prove yourself. That’s why I take a different approach at UserEvidence. I meet every new hire in person during their first week. Wherever they live, on their home turf. Every time, it leads to the same outcome: faster ramp-up, stronger confidence, and immediate momentum. I’ve improved this process three times now, cutting out fluff and getting feedback from every person to make it even better for the next hire. They each get a beast of a Notion page that covers: - Key people to meet (and why those meetings matter) - Important docs and links to review right away - A roadmap for their first 30, 60, and 90 days, clearly outlining expectations and where I need them to take ownership From day one, new hires have full visibility into what's working, what's not, and where our biggest opportunities lie. They don't have to hunt for information, either. It’s all there for them: board decks, old marketing roadmaps, past OKRs, and a clear breakdown of the agencies and freelancers we partner with (plus their “superpowers” and how to best work with them). By the end of week one, we’ve already had honest and vulnerable conversations about: - How we can best work together  - Our working styles and weird work quirks to be aware of (we all have them) - What success looks like in their role - Where they want to grow and how I can help We also make time for fun and get to know each other outside of work. Like our upbringing, favorite life stories, and who we are as humans. Work matters, but who you work with matters even more. Building trust right out of the gate makes everything easier.

Coinbase had the best onboarding process I have ever experienced. Unfortunately, in most legal teams, onboarding is treated like an afterthought. Some docs on a shared drive, a few meetings, and then you’re on your own. No wonder most new hires spend their first quarter (or more!) just figuring out which processes to follow, where to find the right templates and the right people to ask questions. That’s why Coinbase’s process stuck with me. In a remote first company, they managed to bring newcomers up to speed in 2 weeks. → Videos that explained the different functions in the company → A list of critical Slack channels that introduced people to ongoing projects → Quizzes to reinforce what you learned → 1:1 intros with relevant folks so you knew who to go to for what So here’s a tactical list for Legal Ops teams building onboarding programs: 1. Share org charts and key tools. 2. Assign a legal team buddy to answer questions informally. 3. Record a Loom video explaining where to find SOPs, playbooks, and templates. 4. Host intro calls with key cross functional partners (Sales, Finance, Procurement etc). 5. Set up learning modules explaining internal processes. 6. Add new hires to relevant Slack channels and explain their purpose. 7. Schedule recurring 1:1s in the first month for feedback and support. 8. Use quizzes or checklists to make learning fun and track progress. Shout out to L.J. Brock and Emilie Choi at Coinbase - yours is one of the best onboarding processes I’ve seen. Would love for legal teams to learn from it too. What’s one thing that has helped with onboarding in your legal team? #LegalOps #LegalLeadership #Onboarding #LegalTech #ScalingLegal

Remote work is killing company culture, but it doesn’t have to be that way. I'm 2 years into founding Platter and this is still something I'm figuring out. With team members all over the world (USA, Canada, South Africa, Argentina, Philippines, Costa Rica, Brazil, Croatia) and everyone communicating over Slack/Zoom - building a strong culture has been difficult. However, one strategy has proven incredibly effective for me and could benefit your company too: A "Working With Me' document. A team member (shoutout Elliot Roazen) recommended this, and it’s now a key part of our onboarding process. The document asks employees questions like: ➝ What motivates me? ➝ What exhausts me? ➝ How to best give me feedback?  ➝ What parts of a project am I best at? Just reading this doc about others expedites the learning curve. Normally you'd learn these things from in-person hallway conversations, but remote work doesn't allow for that. I can say with full confidence—the difference it's made at Platter has been significant. Want access to the full "Working With Me" template for you and your team? Shoot me a DM or comment "DOC" below for a copy!

Head of Leadership Development at a mid-size tech company: We did a lot of research as we revamped our program, and the top reason programs fail is that they're not tied to business priorities. Me: So what did you do? Head of LD: We honed in on the number one strategy for establishing business context - social interaction She then broke down SEVEN tactics she uses to drive social interaction: 1/ She ensures manager buy-in BEFORE the program. Both for the participant's workload and for their commitment to help the participant grow. 2/ She asks a manager to kick off each program. The manager shares context via on-the-job examples & stories. 3/ She has manager check-in conversations to prep managers for conversations with participants. 4/ She facilitates paired conversations about application exercises & reflections. 5/ Participants go through exercises with their teams. They practice applying what they learned. Then they reflect as a team on how it went. 6/ She hosts live wrap-up calls after each session. Peers share feedback, experiences, and examples. Senior execs tie learnings to business priorities. 7/ She hosts a peer learning network on Slack. People share challenges and examples. And they can look back at those shared by previous cohorts. ___ THE TAKEAWAY Social interaction is the "is your computer plugged in?" of leadership development. If you're not seeing the results you want, facilitate more interaction, and better interaction. You'll immediately drive real-time feedback and on-the-job application. And as managers get involved, you'll build up a culture of teaching, sharing, and learning. ___ P.S., Follow me, Kevin Kruse, for more leadership development posts like this one. ___ #leadershipdevelopment

Starting a new job while remote can suck. Imagine your first day: You get your laptop and login info. Set up all the software and benefits. Lovely HR folks onboard you but it’s all going through the process. You don’t actually meet your teammates though or learn about your work until later. That would feel kinda lonely, eh? 😔 Imagine a different first day: 👋Your manager posted an intro message in the company new hires channel (at Slack, we call this #yay). 📮People from different teams message you offering to chat or welcoming you to the company! ☕️You have virtual coffee invites already. I joined Slack in April 2020. Remote. Didn’t meet anyone IRL for over a year! Yet, I felt welcome and included because Slack’s leadership is very intentional about curating the culture (David Ard Robby Kwok would directly welcome people!) People from across the company DMed me. To my slack colleagues reading this, this might feel obvious. However, a lot of companies are still figuring out hybrid culture - across time zones, cultures and borders 🌎🌏🌍 Today, I try to carry on the torch. Every Monday, I message the new hires in our #yay channel. On lighter weeks, I do 15 min coffee chats. For the ones in NYC, we coordinate office days. We might be in completely different parts of the company and never work together, but that’s also an opportunity to learn something new. It might be just one message or meeting for you, but it can make a HUGE difference in someone’s onboarding experience. So, carry the torch - go make someone’s first day amazing 🔥