Training New Hires: A No-BS System That Actually Works

Why Most New Hire Training Fails

I've hired hundreds of people across my companies. Most founders and managers screw up training the same way: they dump information on new hires for two weeks, then throw them in the deep end and hope they figure it out.

That's not training. That's hazing.

The result? New hires take 90-120 days to get productive, burn through your patience, or quit before they ever contribute. I've lost good people this way early on. Now I get new sales reps closing deals in their first 30 days using a system I'll walk you through here.

The difference isn't how much you teach them. It's when you teach them, what you prioritize, and how you build confidence through quick wins instead of overwhelming them with your entire playbook on day one.

Here's the brutal truth: most new hire training fails because managers confuse information transfer with skill building. They think if they show someone a process once, the person should be able to execute it. That's not how humans learn. We learn through repetition, feedback, and real-world application under pressure.

The Real Cost of Bad Training

Before I walk you through what works, let's talk about what bad training actually costs you. Because most founders don't do the math.

Let's say you hire a sales rep at $60,000 base salary. That's $5,000 per month in fixed costs before benefits, taxes, or tools. If they take four months to become productive instead of one month, you've burned $15,000 in salary while getting zero return.

But it's worse than that. You're also paying for their software licenses, maybe their phone bill, their CRM seat. Add another $500 per month minimum. You're into the opportunity cost too - every deal they didn't close because they weren't trained properly is revenue you'll never recover.

Then there's your time. If you're spending two hours per day helping a poorly trained employee instead of 15 minutes per day with a well-trained one, that's 7.5 hours per week of your time wasted. Multiple that across multiple hires and you're spending half your week babysitting instead of growing your business.

The worst part? If they quit after six months because they never felt confident in the role, you get to do it all over again. Recruiting costs, training costs, opportunity costs - the whole cycle repeats.

I've calculated that a bad hire who quits after six months costs me roughly $45,000 when you factor in everything. A good training system that gets them productive in 30 days instead of 90 pays for itself with one hire.

The Difference Between Onboarding and Training

Most people use these terms interchangeably. They're not the same thing, and confusing them is why most new hire programs suck.

Onboarding is about integration. It's getting someone set up with payroll, introducing them to the team, explaining company culture, showing them where the bathroom is. It's the administrative and social layer of bringing someone into your organization.

Training is about capability. It's teaching someone the specific skills and processes they need to do their actual job. It's tactical, measurable, and directly tied to performance.

Both matter, but they serve different purposes. I've seen companies spend two weeks on onboarding - company history presentations, meet-and-greets with every department, tours of the office - and then give someone a 30-minute crash course on their actual job responsibilities. That's backwards.

I front-load training and spread out onboarding. Day one, you're learning how to do your job. Week two, we'll talk about company values and introduce you to other departments. Because if you can't do the work, you won't be here long enough for the culture stuff to matter anyway.

Here's what most founders miss: onboarding is paperwork and company culture, but training is where you actually make money. When I built my cold email team, I learned this the hard way. My lead generators needed to hit 200 relevant leads per day, my cold email managers needed to send 200 emails daily with campaign optimizations, and my appointment setters had to handle up to 300 email responses per day. Those aren't aspirational numbers-those are the benchmarks that separated teams generating millions from teams that flamed out in 90 days.

The 30-Day Onboarding Framework

Here's the structure that's worked for me across multiple businesses. Three phases, each with a specific goal.

Week 1: Tools and First Actions

Don't start with company history or your mission statement. Nobody cares yet. Start with what they'll do every single day.

Day one, get them logged into every tool they'll use. CRM, email platform, lead database, communication tools. If you're running outbound, that means your email sending platform like Instantly or Smartlead, your lead sourcing setup, and your CRM.

Then have them send their first cold email. Not in three days. Day one. You write it with them, they send it from their account, and suddenly they've done the actual job on their first day. That psychological shift matters more than you think.

Give them one task to complete each day this week. Send 10 cold emails. Make 20 cold calls. Book one meeting (with you playing the prospect if needed). The goal isn't volume yet. It's familiarity and removing the fear of the activity.

This week is also when you have them shadow your best performers. Don't just have them sit there listening to calls passively. Give them a scorecard. Have them track what objections come up, what language the rep uses, how they structure the conversation. Active observation beats passive listening every time.

By the end of week one, your new hire should have sent at least 50 cold emails, made 50 cold calls, and sat through 10+ live sales conversations. They won't be good yet. That's fine. They're building the muscle memory and desensitizing themselves to rejection.

Week 2: Process and Repetition

Now they understand the motions. Week two is about teaching them your specific process. Not best practices from some blog post. Your actual methodology that makes you money.

If you run a sales agency, this is where you show them your prospecting system. How you build lists, where you source leads, how you qualify them before outreach. I use this B2B lead database for most of my prospecting, so new hires learn the filters, the export process, and how to validate data before loading it into sequences.

If you're prospecting local businesses, you might use a Google Maps scraper to pull lead data. If you're going after ecommerce stores, there are specific tools for that. The point is showing them exactly where leads come from and how to process them systematically.

This is also when you introduce your scripts, templates, and frameworks. But don't just send them a Google Doc. Roleplay with them. Have them pitch you. Record it. Play it back. This is uncomfortable, but it compresses months of learning into days.

I have a discovery call framework I've used to close thousands of deals. New hires don't just read it - they practice it out loud until they can run a discovery call in their sleep.

Week two is also when you assign them a mentor or buddy if you have one available. Someone who's been there 90+ days and remembers what it's like to be new. Peer learning cuts your training time in half.

The buddy system works because new hires will ask their peer questions they're afraid to ask you. They don't want to look stupid in front of the boss, but they'll ask their buddy the same question five times if they need to. Make sure the buddy gets recognized for this - either compensate them for it or factor it into their performance reviews.

Week 3-4: Quota and Accountability

By week three, training wheels come off. They have a real quota now. Not your A-player quota, but a simplified version focused on activities, not just results.

For an outbound sales rep, that might look like: 100 cold emails sent per day, 30 cold calls per day, 2 discovery calls booked per week minimum. You're measuring behavior, not just outcomes, because outcomes take time but behavior is immediate.

Daily check-ins matter here. Not long meetings - five-minute standups where they report what they did yesterday, what they're doing today, and what's blocking them. You solve problems in real-time instead of letting new hires spin their wheels for days.

This is also when you start introducing complexity. Advanced objection handling. Deal structures. Pricing conversations. But only after they've proven they can execute the basics.

By the end of week four, your new hire should be operating mostly independently. They're hitting activity metrics without you reminding them. They're booking meetings on their own. They might not have closed a deal yet, but they're clearly on the path.

If they're not hitting activity metrics by the end of week four, you have a problem. Either they're not capable, not motivated, or your training system has a gap. You need to diagnose which one fast.

The Biggest Mistake: Teaching Everything at Once

I see founders do this constantly. They want new hires to understand the full business context, every product feature, all the edge cases, the entire sales process from prospecting to close.

So they create a 40-page onboarding doc and a week of training videos. The new hire watches it all, retains maybe 20%, and still has no idea what to actually do on day eight.

Here's the truth: people learn by doing, not by watching. Your job isn't to transfer all your knowledge into their brain. It's to get them taking the right actions as fast as possible, then layer in knowledge as they encounter real situations.

When a new sales rep runs into an objection they can't handle, that's when you teach objection handling. When they book a call with a prospect who asks about pricing, that's when you teach your pricing framework. Context makes information stick. Dump it on them upfront and it evaporates.

This is called just-in-time training, and it's how the best companies operate. You teach people what they need right when they need it, not three weeks before they'll use it. The brain doesn't retain information that has no immediate application.

I structure my training materials in modules that correspond to real situations. There's a module on handling the "we don't have budget" objection. There's a module on what to do when a prospect ghosts after the demo. There's a module on closing techniques. New hires access them when they encounter that situation, not before.

I go into detail on this in the video:

What to Document (and What to Skip)

You do need documentation. But most companies document the wrong things.

Skip the mission statement, the company values, the history deck. New hires don't need that to do their job. Document the repeatable processes they'll execute daily.

Here's what I keep in every new hire playbook:

• Step-by-step workflow for their core task (prospecting, outreach, discovery calls, etc.)
• Screenshots and video walkthroughs of every tool they'll use
• Scripts and templates with annotations explaining why each part works
• FAQs for the 10 most common objections or questions they'll encounter
• Who to ask for help with specific problems

Keep it under 15 pages. If you can't explain someone's job in 15 pages, your process is too complicated or you haven't clarified what they actually need to know versus nice-to-know.

I use Trainual for this now. It's built specifically for process documentation and makes it easy to update as your systems evolve. New hires can check off sections as they complete them, and you can see exactly where people get stuck.

The documentation should live somewhere accessible. Not buried in Google Drive where nobody can find it. Not locked in someone's head. In a centralized knowledge base where any new hire can search for what they need and find it in 30 seconds.

I also keep a running FAQ document that gets updated every time a new hire asks a question. If one person asked it, others will too. Document the answer once and you never have to answer it again.

The Role of Live Training vs Self-Serve

You can't automate everything. Some things require live coaching.

Here's how I split it: anything that's pure information transfer gets documented. Tool logins, process steps, where to find resources - that's all self-serve. Watch the video, read the doc, check the box.

Anything that requires judgment or interpersonal skill gets live training. Cold calling tonality, how to read a prospect's engagement level, when to push for the close versus nurture longer - you can't learn that from a PDF.

I run live group training sessions weekly where I'll dissect actual deals, calls, and emails. New hires see how I think through problems in real-time. That's worth more than any training manual.

If you're scaling fast and need a more structured approach to this, I walk through the full methodology inside Galadon Gold where we've helped agencies build onboarding systems that cut ramp time in half.

The other benefit of live training is you can adapt on the fly. If I'm teaching objection handling and I notice someone's struggling with a specific concept, I can slow down and drill deeper right there. You can't do that with a pre-recorded video.

But here's the key: record your live sessions. The first time you teach something, do it live. Then take that recording, clean it up, and turn it into your self-serve module for future hires. You get the best of both worlds - the adaptability of live training with the scalability of recorded content.

Training for Different Roles: Sales vs Operations vs Marketing

The 30-day framework I outlined works for sales roles because that's what I've hired most. But the principles apply across different functions - you just adjust the specifics.

For operations or admin roles, week one is still about tools and first actions. But instead of sending cold emails, maybe they're processing their first customer support ticket or setting up their first client account. The goal is the same: real work on day one, not theoretical training.

For marketing roles, week one might be writing their first piece of content or setting up their first ad campaign (even if it's a small test). By week two, they're learning your content strategy, brand voice, and marketing frameworks. By week three, they're running campaigns independently with you reviewing their work.

The pattern holds: start with action, layer in process, remove training wheels and add accountability. The specific activities change based on the role, but the structure stays the same.

One thing that doesn't change: every role needs measurable outputs. For sales, it's calls made and meetings booked. For marketing, it's content published and campaigns launched. For operations, it's tickets closed and accounts set up. If you can't measure what someone's doing in their first 30 days, you can't manage their training effectively.

For sales roles, I have a specific philosophy: your closer should be hitting 10-25% close rate from cold leads and 80% from warm marketing qualified leads. If they're not hitting those numbers after proper training, you have a training problem or a hiring problem. One client came to me after their first implementation of my system-they hit $50k in new business after just one hour of applying the concepts. That's not magic, that's what happens when you train people on a system that actually works instead of generic sales theory.

The First Deal Matters More Than You Think

Nothing builds confidence like closing your first deal. Everything before that is theoretical.

This is why I focus on getting new sales hires a win in their first 30 days. Not their biggest deal. Not their ideal customer. Just a win. Even if it's a small client or a low-ticket offer, that first close proves to them they can do this job.

You might need to rig this a bit. Give them warmer leads. Let them close an inbound prospect. Have them shadow you on a call and let them deliver the close. Whatever it takes to get them that first win fast.

After that first win, their confidence and competence compound. Before it, they're fragile. One of the best investments you can make in new hire training is engineering early success.

I've seen new reps who struggled for three weeks suddenly transform after their first close. It clicks. They realize they can actually do this. Then they close two more deals that week because their energy and confidence are completely different.

The opposite is also true. A rep who goes two months without closing anything starts to believe they can't do the job. Even if they're doing everything right and just got unlucky with timing, that psychological damage is hard to reverse.

So I stack the deck early. The first few leads I give a new rep are the warmest, most qualified prospects I have. I'm not trying to test them - I'm trying to build them up. The hard leads can come later after they've proven to themselves they can close.

Testing and Feedback Loops

You can't manage what you don't measure. I track specific metrics for every new hire:

• Days to first outreach activity
• Days to first meeting booked
• Days to first deal closed
• Activity metrics (emails sent, calls made, meetings completed)
• Quality metrics (email response rate, call connection rate, show rate)

Every Friday, I review these with new hires. We celebrate what's working and troubleshoot what isn't. The feedback loop is tight - weekly, not monthly - so they course-correct fast.

I also have them self-assess. What went well this week? What didn't? What do you need help with? Often they'll identify their own gaps before you do, and self-identified problems get solved faster than problems you point out.

The weekly review is structured. We don't just have a casual conversation. I pull up their dashboard, we look at the numbers together, and we identify the one thing they're going to focus on improving next week. Not five things. One thing.

If their email response rate is low, we're workshopping their email copy. If their call connection rate is low, we're looking at their calling times and strategies. If their show rate is low, we're improving their confirmation and reminder process. One focus area per week means they actually make progress instead of trying to fix everything at once and fixing nothing.

Creating a Skills Progression Path

New hires need to see what good looks like and understand the path to get there. I break skills down into levels and make it explicit.

For a sales role, it might look like this:

Level 1 (Weeks 1-4): Can execute the basic prospecting and outreach process. Hits activity metrics consistently. Books meetings with qualified prospects.

Level 2 (Months 2-3): Runs effective discovery calls. Handles common objections. Closes small to mid-sized deals. Starts to develop their own style within the framework.

Level 3 (Months 4-6): Consistently hits or exceeds quota. Handles complex objections and deal structures. Mentors newer reps. Contributes ideas for improving the process.

Level 4 (6+ months): Top performer. Closes large, complex deals. Develops new prospecting strategies. May move into a senior or lead role.

Making this explicit does two things. First, it shows new hires they're on a journey, not just thrown into the deep end permanently. Second, it gives you a framework for deciding what to teach when. Level 1 skills get taught in onboarding. Level 2 skills come after they've mastered Level 1. And so on.

This also helps with retention. People leave when they feel stuck. Showing them the path forward keeps them motivated even when they're struggling early on.

When to Invest in Training vs When to Cut Loose

Not everyone makes it. I've learned to spot the warning signs early.

If someone isn't hitting basic activity metrics by week three, that's a red flag. I'm not talking about results yet - I'm talking about effort. If they can't send 100 emails a day when you've given them the list, the tool, and the templates, that's a motivation issue, not a training issue.

Coaching fixes skill gaps. It doesn't fix effort gaps. I'll invest heavily in someone who's trying hard but struggling with technique. I'll cut loose someone who isn't putting in the work, no matter how much potential they have.

The worst thing you can do is drag out a bad hire. I give people 60 days to show they can do the job. If they're not on track by day 60, I move on. Every week you keep them beyond that is a week you're not hiring someone better.

Here are the signals I watch for that tell me someone isn't going to make it:

• They consistently miss activity metrics despite having the time and resources
• They don't ask questions when they're stuck (either too proud or too disengaged)
• They make the same mistake repeatedly without adjusting
• They blame external factors (bad leads, bad timing, bad luck) instead of taking ownership
• They avoid the hard parts of the job (prospecting, cold calling, following up)

On the flip side, here's what tells me someone's going to be great even if they're struggling early:

• They hit their activity numbers even when results aren't coming yet
• They ask specific questions that show they're thinking deeply about the work
• They take feedback and implement it immediately
• They stay positive and persistent through rejection
• They take initiative to improve without being told

The activity metrics piece is critical. I can teach someone to write better emails or handle objections more smoothly. I can't teach someone to show up and do the work. That's either in them or it isn't.

I'll be blunt: if someone can't locate 200 quality leads per day after you've trained them properly, don't waste time retraining-hire somebody else. I've hired lead generators from developing economies where thousands of people have been doing this for decades, and here's the thing: if they need extensive training on the basics, they're not the right hire. Your time is better spent finding someone who's already been trained by companies like Salesforce, Cisco, or Oracle. You can find these people on platforms like Upwork, and they're ready to go out of the box.

Building a Training System That Scales

When you're hiring one person every few months, you can wing it. When you're hiring one person every week, you need a system.

Here's what that looks like operationally:

Standardize your start date. I onboard new hires on the first Monday of every month. That way I can batch training sessions and have new hires go through together. Cohort-based onboarding is way more efficient than one-off training.

Assign a training owner. As soon as you have more than five people, someone needs to own onboarding. This can't be a side project for your top sales rep. It's a full-time job once you're at scale.

Record everything once. Every training session I run live, I record. Then I don't have to teach it again. New hires watch the recording, then we do a live Q&A to answer specific questions. Cuts my training time by 70%.

Create a certification process. Before someone graduates from training, they have to pass specific tests. Roleplay a discovery call successfully. Send a cold email that meets our quality bar. Make 50 cold calls and book at least one meeting. Certifications ensure minimum quality before they're fully ramped.

I also built a 7-figure agency blueprint that includes the full hiring and training system I've used to scale multiple companies. It's free and covers everything from writing job posts to building comp plans.

The certification piece is non-negotiable at scale. You can't have people graduating from training who haven't proven they can do the basics. It creates a quality floor that protects your brand and your customers.

When someone fails a certification, they don't move forward. They get remedial training on that specific skill and re-test. If they fail twice, that's usually a sign they're not going to make it and you should cut your losses.

The Tools That Make Training Easier

You don't need a huge tech stack, but a few tools make a massive difference.

For process documentation, I already mentioned Trainual. It's purpose-built for this and way better than Google Docs.

For call recording and review, I use whatever's built into our CRM or meeting platform. The key is actually reviewing calls with new hires, not just recording them. I'll pick one call per week, watch it with them, and coach them on what to improve.

For async video training, Descript makes it stupid simple to record, edit, and share training videos. I record my screen while I do a task, add some narration, and publish it for new hires to watch.

For project management and task tracking during onboarding, Monday.com keeps everything organized. Each new hire gets a board with every task they need to complete in their first 30 days. I can see at a glance who's on track and who's falling behind.

For lead data and prospecting, having clean, organized data makes training easier. If new hires are fighting with messy spreadsheets or broken contact info, they spend their first weeks frustrated instead of learning. Tools like email finders or phone lookup tools keep the data clean so new hires focus on the selling, not the data cleanup.

If you're dealing with email deliverability issues during training, use an email validation tool to clean your lists before new hires send from them. Nothing kills a new rep's confidence faster than high bounce rates on their first campaigns.

Training Remote Hires vs In-Person

I've done both. Remote training is harder, but not impossible.

The biggest difference is you can't rely on osmosis. In an office, new hires overhear conversations, watch how people work, and absorb culture naturally. Remote, you have to be way more intentional.

I overcompensate with communication. Daily check-ins, weekly one-on-ones, constant Slack contact. I also pair remote new hires with someone who's been there longer for the first 30 days. They can ping that person with dumb questions without feeling like they're bothering the boss.

I also do more live training sessions for remote hires. When everyone's in an office, you can walk over and answer a question in 30 seconds. Remote, you need to schedule more structured teaching time.

The upside of remote training? It forces you to document everything, which makes your process better for everyone. You can't hand-wave through a process when you have to write it down or record it.

One tactical thing that helps with remote training: I use StreamYard for live training sessions because it makes recording and streaming dead simple. New hires can watch live or catch the replay, and the quality is way better than Zoom recordings.

Screen sharing is also more important for remote training. I can't look over someone's shoulder and say "click that button," so I have them share their screen and I walk them through processes in real-time. It takes longer but ensures they're actually learning the tools correctly.

The Psychology of New Hire Confidence

Training isn't just about skills. It's about building confidence. A skilled person who doesn't believe in themselves will underperform. A moderately skilled person with high confidence will outperform.

Confidence comes from three places: competence (knowing you can do something), social proof (seeing others succeed), and early wins (proving to yourself you can do it).

That's why the structure matters. Week one gives them competence through repetition. Having them shadow successful reps gives them social proof - they see it's possible. Engineering an early win gives them proof they can do it too.

I'm also very careful about how I give feedback early on. In the first two weeks, I'm 80% positive reinforcement and 20% constructive criticism. Not because I'm coddling them, but because their confidence is fragile and I need them to believe they can do this before I start picking apart everything they're doing wrong.

By week three, the ratio shifts to 50/50. By week four, I'm giving them the unfiltered truth because they're ready to hear it and act on it without spiraling.

I also celebrate small wins publicly. When a new hire books their first meeting, I announce it in Slack. When they close their first deal, the whole team knows. Public recognition accelerates confidence building.

New hire confidence comes from early wins, period. One agency owner I worked with went from $10.5k in monthly sales to $20-25k the following month after implementing my cold email system. That psychological shift-from "I hope this works" to "I know this works because I've seen it work"-is what separates confident closers from order-takers. Build your training system to get them a win in the first 30 days, even if it's a small one.

Common Training Mistakes I See Founders Make

I've made most of these mistakes myself, so I can spot them easily when I consult with other founders.

Mistake 1: Assuming things are obvious. Just because you've done something 1,000 times doesn't mean it's intuitive to someone doing it for the first time. Explain everything, even the stuff you think is basic.

Mistake 2: Not checking for understanding. Asking "does this make sense?" is useless. People will nod and say yes even when they're confused. Instead, say "show me how you would do this" or "explain this back to me in your own words." That's how you find gaps.

Mistake 3: Training for perfection instead of progress. New hires don't need to be perfect. They need to be good enough to start creating value. You can refine their skills over time. Holding them back until they're perfect means they never actually start.

Mistake 4: Ignoring personality and learning styles. Some people learn by reading. Some learn by watching. Some learn by doing. If you only train one way, you'll lose people who learn differently. I try to cover all three - written docs, video walkthroughs, and hands-on practice.

Mistake 5: Forgetting to train on soft skills. Everyone focuses on hard skills - how to use the CRM, how to write an email. But soft skills matter just as much. How to ask for help. How to manage your time. How to stay motivated through rejection. These things separate good hires from great ones.

Mistake 6: Training and forgetting. Training doesn't end after 30 days. It's ongoing. The best companies have continuous learning built into their culture. Weekly training sessions, monthly skill-building workshops, quarterly deep dives on advanced topics.

How to Handle Different Learning Speeds

Not everyone ramps at the same pace. Some people get it in two weeks. Others need six weeks. That doesn't necessarily mean the slow learners are bad hires.

I track two things separately: learning speed and ceiling. Learning speed is how fast they pick things up. Ceiling is how good they can ultimately become.

I've hired people who were slow to ramp but became top performers after six months. I've also hired people who looked amazing in their first month and then plateaued hard.

The key is identifying whether someone's slow because they're being thorough and careful (good) or because they're not capable (bad). Thorough learners ask detailed questions and take good notes. Incapable learners make the same mistakes repeatedly without learning from them.

If someone's a slow learner but showing progress, I give them extra time. Maybe they need eight weeks instead of four to be fully ramped. That's fine. The investment pays off if they become a strong performer.

If someone's slow and not showing progress - they're making the same mistakes, not implementing feedback, not asking questions - I cut them loose earlier rather than later.

Training for Culture, Not Just Skills

Skills are useless if someone doesn't fit your culture. And culture isn't just about whether people are nice to each other. It's about how you operate.

In my companies, the culture is high output, high autonomy, and high accountability. I don't micromanage, but I expect people to own their numbers. That cultural fit matters as much as whether someone can write a cold email.

So I train for culture as much as skills. I explain our communication norms - how we give feedback, how we run meetings, how we handle conflict. I model the behavior I want to see. I call out when someone does something that fits the culture and when they do something that doesn't.

If someone's a great performer but a cultural mismatch, they won't last. They'll get frustrated with how we operate or make everyone else miserable. Better to figure that out in the first 30 days than six months in.

One way I test for cultural fit during training: I give new hires problems to solve independently. Do they take initiative or wait for detailed instructions? Do they figure it out or give up? Do they ask smart questions or expect to be spoon-fed? That tells me more about cultural fit than any interview question.

Building a Training Library Over Time

The first time you train someone on a topic, it takes forever. You're figuring out what to say, how to say it, what examples to use. The second time is faster because you've done it before. By the tenth time, you should have it down to a system.

That's when you document it. Record a video. Write the guide. Build the template. Now you never have to train that topic from scratch again.

Over time, you build a library of training materials that covers every aspect of the job. New hires can self-serve on 80% of their questions, and you only need to step in for the complex stuff.

I started with nothing. Every time I trained someone on something, I documented it. Five years later, I have a training library that covers everything from setting up your email signature to negotiating complex enterprise deals. New training managers use it. New hires reference it constantly. It's one of the most valuable assets in my business.

The key is making documentation part of your training process from day one. Don't wait until you have time to document things properly - you never will. Document as you go, even if it's rough. You can clean it up later.

Measuring Training ROI

Training costs money. Time, resources, potentially external trainers or tools. You should know if it's working.

I measure training ROI in three ways:

Time to productivity. How long does it take a new hire to generate more value than they cost? If I cut that from 90 days to 30 days, I've saved two months of salary with no return. Multiply that across multiple hires and the savings are massive.

Retention rate. What percentage of new hires are still here after six months? After a year? Poor training leads to high turnover. Good training means people stay longer, which saves recruiting and training costs on their replacements.

Performance metrics. Are people who went through your training program hitting quota? How do they compare to people who didn't go through formal training (if you have that data from before you built the system)?

For me, the ROI on building a real training system was obvious within three months. My time-to-first-deal dropped from 60 days to 25 days average. My 90-day retention went from 60% to 85%. The system paid for itself many times over.

Here's how I measure training ROI: Can your team follow up without spamming? Do they know that if a prospect shows interest in a $50,000 product, you chase them down until you get a yes or no-even if it takes months or years? I used to get paid thousands to teach this exact process because most founders train their people on theory, not on the behaviors that actually generate revenue. My teams have generated hundreds of millions using these systems, and it all comes down to training people on the specific actions that move deals forward, not vague "best practices."

Advanced Training: Ongoing Development Beyond Onboarding

The 30-day onboarding is just the beginning. The best companies have continuous learning built into how they operate.

I run weekly training sessions where we workshop real problems. Someone's stuck on a deal? We brainstorm as a team. Someone discovered a new prospecting tactic that's working? They teach everyone else. Someone closed a huge deal? We break down exactly how they did it.

These sessions serve double duty. They're training for the team and continuing education for people who have been around a while. Even my top performers learn new things in these sessions.

I also encourage people to train themselves. I'll pay for courses, books, conferences - anything that makes them better at their job. The ROI on education is insane. A $500 course that helps someone close one extra deal per month pays for itself immediately.

Some companies do lunch-and-learns where someone presents on a topic over lunch. Some do monthly skill-building workshops. Some bring in external trainers quarterly. The specific format doesn't matter. What matters is that learning never stops.

When to Hire a Dedicated Trainer

At some point, if you're growing fast, you need someone whose only job is training new hires.

I hit that point around 15 employees when I was hiring 2-3 people per month. I couldn't keep up with training that many people while running the business. So I promoted my best sales rep into a training manager role.

Big mistake. Just because someone's good at sales doesn't mean they're good at teaching sales. He lasted three months in the role before we both agreed it wasn't working and he went back to selling.

The second time, I hired someone who had training experience specifically. Former teacher, actually. She wasn't the best salesperson I'd ever seen, but she was excellent at breaking down complex processes into simple steps and coaching people through them. She's still running training five years later.

The profile for a great trainer is different from a great performer. You want someone who's patient, organized, good at explaining things multiple ways, and energized by helping others succeed. If those traits happen to overlap with top performance, great. But don't assume they do.

Training in High-Growth vs Steady-State

Training needs change based on your growth stage.

If you're in high-growth mode, hiring multiple people per month, you need standardized, scalable systems. Cohort-based onboarding, recorded training modules, certification processes. You don't have time to customize training for each individual.

If you're in steady-state, hiring occasionally to replace attrition or add capacity, you can afford to be more flexible. More one-on-one coaching, more customized training paths, more time spent on individual development.

I've been in both modes. High-growth training is all about efficiency and consistency. Steady-state training is about depth and personalization. Both work - you just need to know which mode you're in and build accordingly.

Final Thoughts

Training new hires is where most companies leak money. You pay someone for 60-90 days while they learn, and if they quit or fail, you've lit that cash on fire.

The system I've outlined here isn't complicated. It's just structured. Teach less upfront, focus on action over information, engineer early wins, and measure everything.

The goal isn't to transfer everything you know. It's to get someone productive as fast as possible, then layer in knowledge as they grow. Do that, and you'll cut your ramp time in half and lose fewer good people to bad onboarding.

Most founders know their training sucks. They just don't prioritize fixing it because it feels like a long-term project with no immediate payoff. But if you're hiring regularly, better training is one of the highest-ROI investments you can make. It pays back within one or two hires and keeps paying back forever.

Start small. Pick one thing from this article and implement it this week. Document your core process. Record your next training session. Set clear 30-day goals for your next hire. Small improvements compound into massive advantages over time.