Engaging Employees in Onboarding Training Programs

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?

When I was 24, I built the recruitment department for a billion-dollar hedge fund hiring traders from MIT and Caltech . Here’s how I got the smartest kids in the world to work for me: 1/ Go where they are I wasn’t just recruiting. I was selling a completely different world to engineers and mathematicians. To meet them where they were, I’d sponsor coding competitions and poker bot games. After the event, I’d take the winners to a fancy dinner in a limo. It was about showing them that I understood their skills and how valuable they were. A handful of these dinners turned into some of my best hires ever. 2/ Choreograph the experience Recruiting isn’t just interviews. It’s a performance. For Superdays, I obsessed over every detail: • Hotel proximity • Welcome notes in their rooms • Goody bags on check-in These small touches set the stage for something unforgettable. Even the social events were choreographed…. I matched candidates with the right people—like pairing a cerebral candidate with my head of algorithmic trading. This helps because: 3/ Intentionality ensures the right person lands at the right place. At GrowthAssistant for example, I interviewed a DMA for a client. Talking to her I realized she would be a killer EA for another client, so I asked her and got them started. She’s been there 2 years now. 4/ Thoughtful transitions Our 6-week onboarding program was a game-changer. Classroom time, simulations, and small group projects gave hires the confidence to excel. We even designed sessions to teach managing up and navigating office culture. By the time recruits walked into the office, they already felt at home. And I brought this with me: At GrowthAssistant I am extra careful because these are remote GAs working from thousands of miles away. I get them integrated into the client’s slack, team activities, and prep onboarding plans that make them feel like part of the team. 5/ Build bonds The magic of onboarding wasn’t just the training; it was the cohort experience. We planned group projects, simulations, and activities that created strong peer bonds. When people feel connected to their team, they’re not just joining a job—they’re joining a community. Years later, many of these cohorts still keep in touch, and some have gone on to epic careers. This also led to incredible bonds with my GrowthAssistant team in the Philippines… 2 years ago, Raffy joined as a part-time video design GA. Last fall when she became a lawyer she wrote me one of the most thoughtful emails I’ve received for supporting her in her journey. These experiences and connections are everything.

A good onboarding plan conveys: People - Who do you need to know Personalities - How to collaborate well Process - How to do stuff Policies - What the rules are Politics - What the unwritten rules are Think about format. How should you best convey this information? How should it be referenced or reinforced? Self-paced resources? One-on-one convos? Group trainings? A combo? It's going to be different based on the role, what you need them to know, and when. And WHEN. What information must be conveyed immediately vs later? If later, how do you ensure "later" doesn't become "never?" When I was still leading teams, my go-to onboarding template was: 1️⃣ Pre-scheduling 1:1s with key stakeholders in the role, prioritized and spread out over the first 14-30 days. No agendas, just get to know you's. 2️⃣ Pre-scheduling 1:1 role-related chats with process/policy/outcome stakeholders. These stakeholders were strongly requested (required, if poss) to create a 1-2 guide for the new hire to have as a reference. The new hire was expected to read the reference BEFORE the meeting and come with questions. It's meant to be more of a conversation than a training. 3️⃣ Creating (if needed) a role wiki that tracks with the JD, naming stakeholders and linking to recommended tools/docs 4️⃣ Making sure the team has updated their "User Manuals," documents that explain their roles, a bit about their personalities, and working style. These manuals include the sections "When I'm At My Best" and "When I'm At My Worst" so preferences and quirks are explicit, instead of discovered slowly by accident. 5️⃣ Scheduling 2x weekly hour-long 1:1s for the first month, staggering down in frequency and duration as needed into the appropriate cadence for their role and growth trajectory. Sounds like a lot, but it's worth it to make sure you get the best out of someone. So many downstream problems and costs can be avoided with decent onboarding, and it doesn't have to be high-tech.