Onboarding Remote Workers With Limited Resources

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

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 ❗ SOPs are thin, outdated, or missing.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.

I once onboarded myself alone in an office on my first day. But that wasn't actually the worst onboarding I've ever had... The worst was when I was placed in front of a computer in a packed office and asked to watch 8 hours of training videos. Everyone worked around me, and hardly anyone spoke to me. I felt awkward if I tried to engage, and I was mostly bored, overwhelmed, and deeply uncomfortable. In the first scenario, I was at a startup. The rest of the team was out chasing a huge opportunity, and it made total sense that they couldn’t be there in person. What they did do was send welcome emails, offer support, and check in throughout the day. I felt included, even though I was technically on my own. That warm environment made all the difference. Given the choice, I’d rather have a flexible, scrappy first day with heart than a hyper-structured experience that feels cold. Now, I support early teams building onboarding that actually works. The kind that keeps new hires and builds trust fast, but also doesn’t overcomplicate things for teams that are already stretched thin. Here’s my go-to approach: ✨ Have a plan for Day 1, Week 1, and Month 1 ✨ Schedule and keep consistent check-ins with their manager (ask every time: what’s working, what’s not, and what support do you need?) ✨ Set up a listening tour so they can meet teammates and understand the bigger picture ✨ Send swag or a welcome package alongside their equipment. For remote teams, this matters more than you think to build belonging! I’ve seen beautifully built onboarding cohorts with full team activities and custom learning tracks. That’s wonderful, and when you get to that level, go for it! But for small teams, it’s about what’s both realistic and meaningful. What are your favorite onboarding practices that early teams can implement? I would love to hear other creative ideas!