Top Onboarding Mistakes That Drive Agents Away

✨ Executive Summary (TL;DR)

Most brokerages lose agents not because of bad culture or poor splits—but because of a broken onboarding process. In this guide, Stu Hill of MNKY Agency reveals the top onboarding mistakes that silently sabotage agent retention. From overwhelming new hires to skipping mentorship, these missteps cost you talent and revenue. Learn how to fix them and build a retention-first onboarding experience.

✅ Key Takeaways

• Onboarding is a 90-day journey, not a one-day event.
• Personalization is key—tailor onboarding to each agent’s experience level.
• Avoid information overload by phasing training and tools.
• Culture and mentorship are just as important as systems and sales.
• Use automation to streamline onboarding without losing the human touch.
• Regular feedback loops help you improve and retain more agents.

🎙️ Ask Stu: Real Talk for Real Brokers

Over the years, I’ve had hundreds of conversations with brokers, team leaders, and recruiters who are all asking the same thing: “How do I keep agents from walking out the back door?” That’s why I created Ask Stu—a space where I answer the real questions I get every day, straight up, no fluff.

As a side note, if you’re looking to recruit real estate agents check out my recently published: Ultimate Guide to Real Estate Agent Recruitment in 2025. It’s packed full of ideas and resources to help you with recruiting real estate agents to your brokerage or team.

Anyway, Each answer below includes a detailed breakdown and a (forthcoming as I haven’t finished recording them yet) video where I walk you through the strategy, just like I would if we were sitting down over coffee. Whether you’re onboarding your first agent or your hundredth, these are the insights that move the needle.

Why Onboarding Is the Hidden Key to Agent Retention

Let’s be real—most brokerages don’t have a retention problem. They have an onboarding problem disguised as a retention problem.

You can offer the best splits, the flashiest tech stack, and the most beautiful office in town, but if your onboarding process is broken, agents won’t stick around long enough to care. First impressions matter. And in real estate, onboarding is your first—and best—chance to prove that joining your brokerage was the right move.

At MNKY Agency, we’ve worked with hundreds of brokerages across North America, and we’ve seen the same patterns repeat: agents leave not because they’re unmotivated, but because they feel lost, unsupported, or overwhelmed from day one.

Avoid These Real Estate Onboarding Mistakes to Boost Agent Retention

1. Treating Onboarding as a One-Time Event

One of the biggest mistakes I see brokerages make is thinking onboarding ends after the first day—or maybe the first week if they’re feeling generous. They hand over a stack of paperwork, give a quick tour of the office (or a login to the CRM), and then expect agents to hit the ground running.

That’s not onboarding. That’s orientation.

At MNKY Agency, we coach brokerages to think of real estate agent onboarding as a 90-day runway—a structured, strategic process that sets agents up for long-term success. Why 90 days? Because that’s the window where agents decide if they’ve made the right move. It’s also when they’re most vulnerable to second-guessing, burnout, or jumping ship if they feel unsupported.

A proper onboarding journey should include:

• Week 1: Systems access, introductions, and quick wins.
• Weeks 2–4: Training on tools, marketing, and lead gen.
• Month 2: Goal setting, accountability, and early production.
• Month 3: Deeper coaching, performance reviews, and integration into the culture.

When you treat onboarding as a one-time event, you’re not just missing an opportunity—you’re actively increasing your churn rate. But when you treat it as a journey, you build loyalty, confidence, and momentum.

2. Lack of Personalization

Let’s face it—no two agents are the same. So why do so many brokerages onboard them like they are?

One of the fastest ways to lose a new recruit is to drop them into a generic onboarding flow that doesn’t reflect their background, goals, or experience level. A brand-new licensee needs hand-holding, foundational training, and confidence-building. A seasoned agent switching brokerages? They need fast-track integration, tech alignment, and a clear value proposition.

At MNKY Agency, we always say: “Personalization isn’t a luxury—it’s a retention strategy.”

Here’s how to personalize onboarding without overcomplicating it:

• Segment your onboarding tracks: Create different flows for new agents, experienced agents, and team leaders.
• Ask the right questions upfront: What are their goals? What’s their learning style? What do they want from your brokerage?
• Customize the first 30 days: Align training, mentorship, and milestones with their unique needs.

When agents feel like you “get” them from day one, they’re far more likely to stay, engage, and produce.

3. Overwhelming Agents with Information

You’ve seen it. Day one hits, and the new agent is handed a login to the CRM, a stack of marketing materials, a 50-page onboarding manual, and a calendar full of training sessions. By the end of the week, they’re drowning in logins, acronyms, and unanswered questions.

This is one of the most common—and most damaging—onboarding mistakes: information overload.

At MNKY Agency, we coach brokerages to think of onboarding like a drip campaign, not a firehose. The goal isn’t to show agents everything—it’s to show them the right things at the right time.

Here’s how to fix it:

• Phase your onboarding: Break it into weekly modules or milestones. Start with essentials (email, CRM, compliance), then layer in marketing, lead gen, and advanced tools.
• Use microlearning: Short, focused videos or checklists are easier to digest than hour-long webinars.
• Prioritize action over theory: Give agents quick wins they can implement immediately—like setting up their email signature or launching their first social post.

When agents feel overwhelmed, they disengage. But when they feel empowered, they take action—and that’s what drives retention.

4. Ignoring Culture and Community

You can teach someone how to use a CRM. You can train them on scripts and systems. But you can’t fake culture—and if you ignore it during onboarding, you’re missing the glue that keeps agents loyal.

Too many brokerages treat onboarding like a tech tutorial. They focus on tools, compliance, and checklists, but skip the human side of the business. And that’s a huge mistake.

At MNKY Agency, we’ve seen it time and again: agents who feel connected to a community are far more likely to stay, even when things get tough. Culture isn’t just a vibe—it’s a retention strategy.

Here’s how to build it into onboarding:

• Introduce agents to your mission and values early and often.
• Create opportunities for connection—team lunches, welcome calls, Slack channels, or virtual coffee chats.
• Celebrate small wins publicly. Recognition builds belonging.
• Assign a culture ambassador or buddy who helps new agents integrate socially, not just professionally.

When agents feel like they’re part of something bigger than themselves, they’re not just working for a brokerage—they’re building a career with a community.

5. No Clear Success Metrics

Imagine starting a new job and having no idea what success looks like. No benchmarks. No targets. No feedback. Just vibes.

That’s the reality for a lot of agents during onboarding—and it’s a major reason they disengage or leave.

At MNKY Agency, we always say: “If you don’t define success, don’t be surprised when agents don’t succeed.” New agents crave clarity. They want to know what’s expected of them, how they’ll be measured, and what milestones they should be hitting in their first 30, 60, and 90 days.

Here’s how to fix it:

• Set clear, realistic goals for each phase of onboarding—like completing training modules, booking listing appointments, or building a pipeline.
• Use scorecards or dashboards to track progress and give agents a sense of momentum.
• Celebrate early wins—even small ones. Recognition builds confidence and reinforces the right behaviors.

When agents know what success looks like, they’re more likely to chase it—and stick around long enough to achieve it.

6. Failing to Assign a Mentor or Buddy

Real estate can be a lonely business—especially for new agents walking into a brokerage where everyone already knows the ropes. If you’re not assigning a mentor, coach, or onboarding buddy, you’re leaving your agents to figure it out alone. And that’s a fast track to frustration and turnover.

At MNKY Agency, we’ve seen the power of peer support firsthand. Agents who are paired with a mentor or buddy during onboarding are more confident, more productive, and more likely to stay. Why? Because they have someone to lean on, ask questions, and model success.

Here’s how to make it work:

• Assign a mentor or buddy on day one—ideally someone who’s been through your onboarding process and embodies your culture.
• Set expectations for both parties. This isn’t just a coffee chat—it’s a structured relationship with regular check-ins.
• Incentivize mentorship. Recognize and reward agents who help others succeed.

Mentorship isn’t just about training—it’s about belonging. And when agents feel like they belong, they stay.

7. Not Leveraging Automation

Let’s be honest—manual onboarding is a productivity killer. It’s inconsistent, time-consuming, and prone to human error. Worse, it creates a disjointed experience for your agents. One agent gets a welcome email. Another doesn’t. One gets access to the CRM on day one. Another waits a week.

That’s not just inefficient—it’s a retention risk.

At MNKY Agency, we help brokerages implement automated onboarding systems that deliver a consistent, high-touch experience at scale. The goal isn’t to remove the human element—it’s to free up your team to focus on the parts of onboarding that actually require a human touch.

Here’s how to do it:

• Use onboarding software or a project management tool like Trello, Asana, or Monday.com to track tasks and progress. I’m not paid by them, but I personally like to use Asana.
• Automate email sequences that drip out training, reminders, and resources over the first 30–90 days.
• Create templated workflows for different agent types (new, experienced, team leaders) so nothing falls through the cracks.

Automation doesn’t replace connection—it supports it. And when agents feel like nothing is missed, they feel like everything matters.

8. Skipping Feedback Loops

You can’t improve what you don’t measure—and that includes your onboarding process.

One of the most overlooked mistakes brokerages make is failing to ask agents how onboarding is going. They assume silence means satisfaction, when in reality, it often means confusion, frustration, or disengagement.

At MNKY Agency, we encourage every brokerage we work with to build feedback into the onboarding experience—not as an afterthought, but as a core component.

Here’s how to do it right:

• Schedule regular check-ins at 7, 30, 60, and 90 days. Ask what’s working, what’s missing, and what could be better.
• Use quick surveys to gather insights anonymously. You’ll often get more honest feedback this way.
• Act on what you hear. If multiple agents say your CRM training is confusing, fix it. If they love your mentorship program, double down.

Feedback isn’t just about improving onboarding—it’s about showing agents that their voice matters. And when people feel heard, they stay.

Conclusion: These Onboarding Mistakes Will Kill Agent Retention

If you’re losing agents faster than you’re recruiting them, it’s time to stop blaming the market, your comp plan, or your CRM—and start looking at your onboarding.

Because here’s the truth: onboarding is retention.

It’s your first real opportunity to deliver on the promises you made during recruitment. It’s where agents decide if they’re in the right place, with the right people, doing the right work. And if you get it wrong, no amount of tech or training will keep them around.

But if you get it right? You don’t just retain agents—you empower them to thrive, produce, and become advocates for your brand.

At MNKY Agency, we help brokerages build onboarding systems that do exactly that. If you’re ready to stop the churn and start building a team that sticks, let’s talk.

FAQs About Onboarding Mistakes

If you’re serious about improving agent retention through better onboarding, you’re not alone. Below are some of the most frequently asked questions we hear from brokers and team leaders we work with at MNKY Agency. These answers will help you fine-tune your onboarding process and avoid the costly mistakes that drive agents away.