Onboarding Programs for Remote Workers

I was embarrassed when we onboarded new hires. I don't have fancy collateral. No welcome videos. No searchable database. Just a bunch of Google Docs. (And a lot of my time) When I hired our first employee, I gave them these docs as part of their onboarding. I apologized that I didn’t have something fancier for them. Mentioned how we're a start-up with limited resources. But they told me they were amazed at the level of detail. And they wished they had something like that in their previous jobs. They came from a big company so my first thought was: "There's no way that's true." "They are probably used to more robust onboarding." But then our 2nd hire said the same thing. Then the 3rd. And so on. Even people outside my company applauded our process. My key takeaways: ➟ Many companies don't prioritize onboarding properly. ➟ You don't need flashy tools to set up new hires for success. Just provide the right information in a clear, organized way. Important elements of good onboarding: • Clear documentation covering roles, expectations, processes • A structured timeline for taking in information • Assigning a mentor to provide guidance • Scheduled check-ins to address questions It’s easy to assume more complexity means better onboarding. But from my experience, the basics done right go a long way. What do you think makes for an effective onboarding experience? Share below ⬇ ---- P.S. If this resonated with you, ♻ reshare to your network

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.

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.

Stop “welcoming” new hires. Give them a win in 30 days instead. When I first hired 8 years back, I thought the best onboarding was all about making new hires feel at home. I was wrong. New hires actually struggle with: → Understanding the business and their role. → Aligning with company culture and expectations. → Getting that first “win” to build momentum. → Building relationships with colleagues. I’ve now completely changed our onboarding process. The only goal is to get new hires to their “first win” fast. Instead of generic training, we work backward from their first big achievement. Here’s the framework: Step 1: Define the “first win” (within 30 days) Every new hire gets a specific, meaningful milestone. 1. It should be important enough that not doing it has a business impact. 2. Something that pushes them but is achievable with team collaboration. 3. It should give them real insight into how we operate. Our new Demand Gen Marketer’s first win was securing Market Development Funds (MDF) from a partner. To do this, they had to: - Work with our internal team. - Engage with a partner manager. - Propose a campaign relevant to both companies. This wasn’t just a task (it was a meaningful contribution). Step 2: Provide context (without overloading them) Most onboarding programs drown new hires in endless presentations. We limit training to what they need for their first win. 1. A 45-minute deep dive on the company’s journey, priorities, and challenges. 2. Targeted learning on only what’s relevant for their milestone. 3. Hands-on guidance instead of passive training. For the Demand Gen hire, we focused on: - Who the partner manager was and their priorities. - How the partnership worked. - What MDF campaigns typically get approved. Step 3: Align them with our work culture Culture isn't learned in a handbook. It’s experienced. Every new hire is paired with a mentor to guide them through: → Quality Standards → What "good" looks like in our company. → Processes & Tools → How we work and collaborate. → Feedback Loops → How we review, iterate, and improve. The result? New hires achieve something meaningful within their first month. They feel pride, momentum, and confidence (not just onboarding fatigue). Great onboarding isn’t about information. It’s about impact. 💡 How do you set up new hires for success?

After collaborating with over 1,000 Virtual Assistants (VAs) at HelpFlow, we’ve uncovered the core ingredients to building a reliable and high-performing remote workforce. Here’s what our journey taught us—lessons too valuable not to share with founders, HR leaders, and remote team managers: - Prioritize Process, Not Just People: While hiring for culture fit is critical, airtight processes are the backbone of reliability. Well-documented SOPs make onboarding seamless and safeguard against disruptions. - Communication Cadence is Everything: Daily standups and weekly deep dives ensure clarity and accountability. Structured check-ins foster rapport, prevent isolation, and quickly surface roadblocks before they escalate. - Feedback Loops Drive Growth: Constant feedback (both ways) empowers VAs to achieve more and feel genuinely invested. We learned that transparent performance metrics and frequent recognition help VAs and managers align on growth targets. Invest in Tools AND Trust - Technology enables efficiency, but trust cements loyalty. Secure collaboration platforms paired with transparent leadership build long-term dedication far beyond what a tech stack can offer. These lessons didn’t come easy. They were forged through trial, error, and a genuine commitment to people and process. Curious about leveling up your remote workforce? What’s the #1 challenge you face in managing remote teams? Let’s share insights below!

I’ve spent 300+ hours coaching PMM through onboarding. Here is the most important tip I have: Build your 30/60/90 day plan backwards. 👇 Most PMMs' onboarding plans start with a to-do list: --> Meet with cross-functional teams --> Review past launches --> Read docs The problem with this approach is that you never feel like you’re doing enough, and everything seems equally important. You also have no real sense of how long things will take. It makes it nearly impossible to prioritize your time or align expectations with your manager. When I coach PMMs through onboarding, I tell them to build it BACKWARDS. Start at day 90 and determine, by then: – What do you want to have delivered? – What do you need to have learned? – Who needs to know and trust you? Then work backwards and chunk it down. One of my clients just joined as the first PMM at a 50-person startup. In her second week, she was already getting requests for: -> Improving the ICP and messaging -> Updating the sales enablement decks -> Building a launch strategy 😬 As you can imagine she was pretty stressed and needed a good way to set the right expectations and also plan her work. So we built a new plan, working backwards from day 90, which included: ✅ 3 streams: deliver/learn/meet ✅ Tied each project to an outcome, not just a task ✅ Chunked out each project into smaller milestones ✅ Treated learning as a deliverable, so her ramp time was visible She used that plan to align with her manager, which not only set clear expectations but also showed she could think strategically and take initiative from day one. If you’re onboarding in a startup, remember the key is not to add more, but to work backwards, and then clearly communicate that to set the right expectations. Let me know how I can help. 💪 #productmarketing #newjob #coaching #strategy

🧭 You Hired Someone, Now What? A New Manager’s Guide to Not Screwing It Up Hiring someone is just the start. What you do next determines whether they succeed, struggle, or quietly disengage. Here are 10 ways to get onboarding right from day one: 1️⃣ Start Before Their First Day Send a welcome message. Confirm logistics. Set expectations. 💬 Silence = anxiety. A simple “We’re excited to have you” builds early trust. 2️⃣ Have a Real Onboarding Plan HR does the paperwork. You handle integration. 🗺️ Create a 30-60-90 day roadmap with key projects and success markers. 3️⃣ Make Introductions with Intention Don’t rely on chance meetings. Schedule 1:1s with key players. 🤝 Explain why each intro matters, relationships are early currency. 4️⃣ Clarify Expectations Immediately Define what “great” looks like. Be explicit about goals and norms. 🔍 Most people don’t fail from lack of skill, they fail from unclear expectations. 5️⃣ Stay Present Without Micromanaging New hires don’t need a shadow or a ghost, they need you. 📆 Check in often. Offer context, listen to questions, and share what’s working. 6️⃣ Give Feedback in Week One Yes, week one. Start early with praise and coaching. 🗣️ Early feedback builds confidence and prevents bad habits. 7️⃣ Ensure They Have the Right Tools No access? No progress. 🔐 Get systems, passwords, project files, and tools ready before day one. 8️⃣ Protect Them from Chaos (Temporarily) Every company has mess. Don’t throw them into it right away. 🛡️ Let them build confidence first, then guide them through the noise. 9️⃣ Ask for Feedback About You “How can I support you better?” builds trust faster than any pep talk. 🧠 It also sets the tone for open communication from day one. 🔟 Be the Reason They Stay People don’t quit jobs, they quit managers. ❤️ Show up. Be human. Onboarding is leadership. ✅ Bottom Line: Hiring is only half the job. Great managers don’t just add people to the team, they build trust, clarity, and momentum from day one. 💬 What’s one thing a past manager did during your first week that made a big impact? 👉 Follow Ricardo Cuellar for more people-first leadership advice. 📬 Want more like this? Subscribe to my newsletter, link in bio!

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 🔥

We spend months interviewing to find the “perfect” CSM… and then set them up to fail. Here’s the reality I see too often: ❗ New hires are thrown customers after 1–2 weeks. ❗ Product training is rushed or nonexistent. ❗ SOPs are thin, outdated, or missing. ❗ Leaders don’t invest the time to set expectations or coach. ❗ And then KPIs are handed down that even seasoned CSMs struggle to hit. The issue isn’t the talent, it’s the lack of enablement. But here’s the good news: you don’t need a dedicated L&D team or endless resources to onboard well. You need intention. A simple enablement plan for new CSMs (even with limited resources): 1️⃣ Onboarding Buddy - Pair new hires with an experienced CSM for shadowing, Q&A, and feedback. 2️⃣ 30-60-90 Plan - Outline clear goals and expectations for their first 3 months. (Focus on learning before doing.) 3️⃣ Product Deep Dives - Host weekly “lunch and learns” where Product, CS, or Support walks through one feature in detail. Have them shadow customer onboarding or watch recordings. 4️⃣ Playbook Starter Pack - Even if you don’t have full SOPs, document 3–5 repeatable workflows (renewals, QBR prep, escalation handling). 5️⃣ Mock Meetings – Run practice customer calls internally before they ever face a real customer. 6️⃣ Leader Time - Block weekly 1:1s focused not just on performance but on coaching, context, and confidence-building. These aren’t heavy lifts, they’re discipline and focus. If you want your CSMs to succeed (and your customers to stay), stop spending all your energy on hiring the “perfect” candidate and start spending more on enabling them once they walk through the door.

What’s the #1 cause of frustration and friction you encounter as an organizational leader? We believe the answer centers on “unmet expectations.” We have observed a common 4-step cycle when companies hire new employees and begin setting expectations. The cycle goes like this: Step 1: Hope. After a new hire, the supervisor is hopeful the new employee will fulfill their assigned role perfectly, and the employee is excited about their new job. Step 2: Unclear expectations. Rarely does the supervisor take the time to engage the new employee and deliver a clear duty description with roles and responsibilities. Despite not delivering clear expectations, the supervisor is sure that the employee understands their expectation of “ABC” but often the employee has a very different picture of the expectations and believes their job entails “XYZ” Thus, they quickly transition to the next step. Step 3: Frustration. The supervisor grumbles, “My darn employee won’t do their job!” While the employee complains, “My boss is a toxic leader!” This leads to a critical decision in Step 4. Step 4: Fire/Quit/Tolerate. The supervisor fires the employee. The employee quits. Or they maintain the work relationship, but the team suffers due to suboptimal performance. A healthy 4-step cycle looks like this: Step 1: Hope. This remains the same. Step 2: Clear Expectations. The supervisor sits down with the employee and gets to know them during onboarding. They both share their backgrounds, hobbies, families, goals, and strengths/weaknesses. The supervisor asks, “What are your expectations of me as your supervisor?” The supervisor creates an environment of caring engagement and open communication. Only when this is complete, does the supervisor clearly lay out the expectations for the employee in the form of 1) Company Values 2) Required Skills 3) Roles and Responsibilities 4) Goals/Key Performance Indicators. Step 3: Review Standards. The supervisor regularly sits down with the employee and reviews these agreed upon standards. The supervisor praises the employee for areas of compliance, holds them accountable for areas of non-compliance, and helps the employee solve problems and develop in their role. Step 4: Conform or Leave. The supervisor is on a firm foundation and the employee chooses to either conform to the clear standards or leave the team. This healthy cycle is vital to solving two critical aspects of organizational leadership. The first is building culture. The values the supervisor describes to the employee are the desired cultural values of the company. Relaying the importance of these at the outset and routinely reinforcing them is essential to building the company’s desired culture. The second aspect is holding people accountable. The clear initial discussion and following one-on-ones minimize emotions from the equation and make holding someone accountable a much easier and feasible endeavor. Looking for more leadership development? Message me!