Setting Expectations For Remote Workers From Day One

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

Every struggling new hire carries “baggage” from their last job. They just need a reset, not a rejection. A new hire once froze in a meeting when I asked for their thoughts. Later, he admitted, "In my last job, only managers spoke. I wasn’t sure if I should." That’s when I realized you’re not just hiring a person. You’re hiring their past workplace norms too. I now use a 3-phase framework to spot, reset, and reinforce workplace norms early. Phase 1: Surface the hidden sensitivities New hires won’t tell you what’s confusing. They’ll just hesitate. I try to uncover what they assume is “normal.” I look for clues: 🔍 Do they wait for permission instead of taking initiative? 🔍 Do they avoid pushing back in discussions? 🔍 Are they hesitant to ask for feedback? You can do this with an easy expectation reset exercise in onboarding: 1. "At your last job, how did decisions get made?" 2. "How was feedback typically given?" 3. "What was considered ‘overstepping’?" Their answers reveal hidden mismatches between their old playbook and your culture. Phase 2: Reset & align Don’t assume new hires will "figure it out". Make things explicit. I set clear norms: 1. Here, we challenge ideas openly, regardless of role. 2. We give real-time feedback—don’t wait for formal reviews. 3. Speed matters more than waiting for perfection. For this, use “Culture in Action” moments. → Instead of just telling them, model it in real time. → If they hesitate to push back, directly invite them to challenge something. → If they overthink feedback, normalize quick iteration—not perfection. Phase 3: Reinforce through real work Old habits don’t vanish. They resurface under stress. The real test is how they act when things get tough. Create intentional pressure moments: 1. Put them in decision-making roles early. 2. Assign them a project where feedback loops are fast. 3. Push them to own a meeting or initiative. Post-action debriefs help here: “I noticed you held back in that discussion—what was going through your mind?” This helps them reflect & adjust quickly, instead of carrying misaligned habits forward. Most onboarding processes focus on training skills. But resetting unspoken norms is just as critical (if not more). A struggling new hire isn’t always a bad fit. Sometimes, they’re just following the wrong playbook. What’s a past habit you had to unlearn in a new job?

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.

🧭 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!

Stop expecting new hires to "hit the ground running." It's a recipe for failure. Instead, create an environment where they can thrive from day one. Here's your 10-step guide to onboarding for productivity: 1. Open communication: Create safe spaces for questions and feedback 2. Clear expectations: Define roles, goals, and KPIs upfront 3. Mentor assignment: Pair new hires with experienced team members 4. Comprehensive plan: Map out the first 30, 60, and 90 days 5. Celebrate early wins: Build confidence through recognition 6. Continuous feedback: Regular check-ins to address concerns 7. Work-life balance: Show you value their well-being from the start 8. Realistic timelines: Set achievable milestones for steady progress 9. Regular check-ins: Schedule weekly 1:1s to track progress 10. Patience: Remember, everyone learns at their own pace The result? • Faster ramp-up times • Higher employee engagement • Improved retention rates • Increased overall productivity Remember: Investing in your new hires' success is investing in your company's future. By 2025, the most successful companies will be those that prioritize productivity through effective onboarding and continuous development. What's your best onboarding tip? Share below! ♻️ Repost to help your network create better onboarding experiences! Follow for more insights on building high-performing teams and driving organizational success.