5 Ways Managers Kill Your Plans to Scale (Without Realizing It) [Webinar Recording]
5 Ways Managers Kill Your Plans to Scale (Without Realizing It)
[Video Recording]
[Video Recording]
[Research Report]
Scale revenue-driving behaviors with Gong Enable. Turn every rep into a top performer with enablement powered by real customer conversations. Gong uses conversation data to pinpoint winning behaviors and drive data-backed behavior change across your revenue team.
Check out their guide, ROI of sales enablement: Using AI to prove business impact, to tie enablement initiatives to growth.
How do you build a top-performing sales team? Short answer: Skills. Confidence. Coaching.
Every sales team has a few all-star reps. The ones who just get it and crush it. The question is, how do you clone that kind of success?
Here’s the truth: some people are born with drive, curiosity, and that inner fire to win. But top-performing sellers aren’t just born, they’re developed. They learn the skills, build the confidence, and have managers who coach them along the way. The good news? Every bit of that can be taught.
If your reps are struggling to find the right contacts, freezing up when someone actually answers the phone, or taking forever to ramp, it’s not a talent problem. It’s a skills and confidence problem.
So, whether you’re building a team from scratch or helping seasoned sellers hit the next level, here’s how to turn potential into performance.
Before you can grow a high-performing sales team, you have to figure out what’s slowing reps down. For most, it starts with confidence. New sellers don’t know the language yet, feel unsure about the tools, and get stuck just trying to figure out who to call.
Here’s what sales leaders say are the top challenges:
And even when they do reach the right people, getting them to engage (and knowing what to say next) isn’t always natural.
Confidence doesn’t just appear. It’s built, one conversation, one small win at a time.
New hire sales training often tries to do too much. But what sellers need most in their first few weeks is confidence, the kind that comes from actually knowing what to do and say in real situations.
Skip the deep dives into quoting systems or pricing battles. In the beginning, focus on the basics that make up 90% of their day:
That’s the heart of just-in-time sales training. Teach what reps need for their first 30 days, not their first 300.
Tip: When new reps leave training feeling confident, they come back hungry for more. That’s how you build a learning culture and ramp faster.
READ: 8 Sales Rep Onboarding Best Practices
One of the most effective coaching tools out there is the Pause Game. It’s simple and powerful:
This exercise pulls reps out of their own heads and into the customer’s world. It builds active recall, which science shows is five times more effective than passive learning.
The game teaches reps when to apply knowledge, not just what to say. That small shift in awareness can shave weeks off ramp time.
Tip: It’s not just about knowledge. It’s about retrieval. Helping reps recognize when to use the right skill is what separates good from great.
READ: Sales Training Techniques: Telling vs. Teaching
Reps can’t succeed without the right tools and the know-how to use them at the right moment.
To set your team up for success:
Digital Sales Rooms (DSRs) are must-have sales tools. These microsites let sellers organize resources, track buyer engagement, and keep deals moving with mutual action plans and real-time visibility.
Tip: Tools like DSRs don’t just help reps. They make it easier for buyers to stay informed and move deals forward. That’s a win-win.
If you want to keep your top reps, you have to do more than teach them how to sell. You have to show them what’s next.
Reps are motivated by success stories, recognition, and growth. So give them that:
Coaching plays a massive role here. Too many managers run 1:1s, review pipeline, and put out fires, but never actually coach.
That’s why developing your managers matters. Coaching certifications give them a repeatable system to build skills, boost confidence, and grow their people.
Tip: If managers don’t know how to coach, reps don’t improve. Equip your frontline leaders to develop people, not just push deals.
READ: Tips for Enablement Leaders to Increase Sales Coaching Focus
Let’s be real. Most reps are buried under too many tools and use none of them well. The average tech stack is a juggling act, not a system.
Keep it simple. Your learning, content, and call-intelligence tools should actually talk to each other so managers can move fast, coach smarter, and see what’s working.
Manager dashboards should show trends, not snapshots; who’s improving, who’s stuck, and where to step in.
And here’s the kicker: about 90% of what managers say in a 1:1 is forgotten within a week. Real learning sticks when it’s reinforced, coached, and repeated until it becomes a habit.
READ: The Secret to Scaling Sales Team Revenue: Your Managers
This article is based on insights shared during a Sales Shot webinar featuring Lauren Bailey and Devyn Blume, Sr. AE at Allego. Watch the full session here.
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Sales is changing fast. AI is accelerating everything, buyers are harder to impress, and mediocre selling is getting exposed.
That’s the bad news.
The good news is also simple: the teams that win are going to be the ones who get clear, get current, and double down on human skills that actually move deals forward.
Here are the trends I’m seeing, and the practical moves to make right now if you want a strong year.
We’re living in the noisiest time in history. Tools. Tactics. Hot takes. EVERYONE SHOUTING (😉).
If you wait for clarity, you’ll be waiting forever.
Set your own clarity:
Then act like you mean it. Put it on your calendar. Build your plan around it. Stop drifting.
AI will absolutely wipe out a lot of low-level tasks. Anything that looks like copying, pasting, summarizing, basic research, first drafts, list building, and “good enough” outreach is getting automated fast.
So here’s the play:
If you’re a rep, AI can help you research, organize, and prep.
If you’re a frontline manager, AI can help you spot trends, clean up pipeline signals, and prep for better coaching conversations.
If you’re a sales or revenue leader, AI can help you scale what’s working, identify risk earlier, and make better growth decisions without losing visibility into the human side of performance.
If you’re in enablement, AI can help you reinforce consistency in skills and training, but it should not define what “good” looks like.
READ: The Ultimate AI Toolkit for Sales & Enablement Leaders
As marketing and automation go further “digital,” the moment a buyer finally talks to a human matters more than ever.
Which means sales has to feel less like a pitch and more like a helpful consultation.
If your selling is still built on:
You’re going to feel the shift.
The bar is rising. Thank God.
AI has made outbound louder. Not better. Louder.
So prospecting wins this year when it’s:
Practical upgrades:
And yes, pick up the phone. Calls are weirdly becoming a differentiator again because fewer people are doing them at all, or well.
READ: Best AI Tools, Tips, And Prompts For Sales Prospecting
Buyers do not want to be pitched at. They want to feel understood quickly.
Your edge is better discovery:
A simple standard: if the buyer can’t clearly explain the problem and the stakes after talking to you, your discovery wasn’t discovery. It was a tour.
READ: 4 Steps to Asking Better Sales Discovery Call Questions
The era of the 45-minute “power demo” is fading.
Teams are moving toward:
If your demo is still a feature parade, you’re doing product theater, not selling.
Make demos:
Ghosting isn’t new. Buyers disappearing mid-deal is basically a sport now.
One of the simplest skills that helps is call bridging: setting up the next step while you still have them, with clarity and agreement, so follow-up isn’t chasing.
Quick example language:
It’s not pushy. It’s professional.
READ: Call Bridging 101: Paving the Way for a Follow-up Sales Call
More teams are leaning on AI for forecasting. That’s a win.
But AI can’t save you from messy inputs.
If your CRM stages are fuzzy and everyone has their own definition of “qualified,” you’ll still get bad forecasts. They’ll just arrive faster.
Team move to make:
Most organizations spend way more on tools than training.
Tools are coming. Skills are what will separate teams.
If you’re a leader or enablement:
People don’t change from watching. They change from doing.
READ: The Secret to Scaling Sales Team Revenue: Your Managers
If you’re a rep
Put these blocks on your calendar weekly:
If you’re a manager
Protect your calendar or you’ll burn out:
If you’re a sales or revenue leader
Scale without losing control:
If you’re in enablement
Speed is the name of the game:
READ: 8 Sales Enablement Best Practices to Partner with Revenue Leaders
This year is going to reward the people who stay current, build real skill, and show up as humans.
Use AI to get faster. Use your people to get better.
And please, for the love of all things, don’t let a robot set the standard for your customer conversations.
[Research Report]
When I became the Global Head of Enablement at SAP, I was given one monumental task: launch outbound virtual sales training FAST.
I had no team.
No curriculum.
And a deadline that did not care.
In four weeks, 37 reps were scheduled to sit in a classroom in Barcelona. And I had nothing. No content. No internal resources. No time to build it all from scratch.
So I did what most enablement leaders in that situation do. I started shopping for sales training.
What I found was the same thing you still see everywhere today. A standard two day workshop. One version for Sales 101. One for Sales 201. One for managers. One for leaders. A little pre-work, maybe a little post-work, but essentially a one-size-fits all experience that was not designed for our motion or our customers.
When I asked vendors for customized sales training, I paid an extra ten thousand dollars and got two role plays printed on paper and shoved into the back of the workbook.
That was the “customization.”
It was not just frustrating. It was unusable. I did not want a vendor. I needed a partner. I needed content that actually fit our inside sales training reality and that my team could reuse, adapt, and build on, not a one time event.
That experience stuck with me. It shaped how I think about sales training, and it is a big reason I am on a mission to make customizable sales training the norm instead of the exception.
DOWNLOAD: Sales Training Vendor Partner Checklist
If you have ever sat through generic sales training, you already know why it fails.
Most programs are built for delivery efficiency, not real world application. They are designed so a trainer can fly in, deliver the same deck to a different audience, and fly out again.
On paper, it looks like this:
In reality, this creates three big problems.
Reps and managers are busy and overloaded. The human brain is always scanning for reasons not to change. The second they hear an example that does not match their buyers or their sales cycle, they check out.
“This is for field sellers.”
“Our buyers are nothing like that.”
“This feels like theory, not inside sales training.”
Even great ideas die if the rep has to translate them alone. When training is generic, you are asking each seller to figure out how to apply it to their role, their accounts, and their conversations. A few high performers will do it. Most will not.
We know from learning science that people forget the majority of what they hear in class within days if they are not actively recalling and using it. If there are no real calls, no role specific activities, and no coaching built around the new skills, the investment evaporates fast.
That is why truly customizable sales training matters. Not because it sounds fancy, but because relevance is what keeps reps engaged long enough to try something new, and trying is the first step toward results.
If you run enablement or revenue, you are caught in a familiar trap.
But you also run into the reality:
But the tradeoffs are real:
Enablement leaders live in that tension. You want the speed and quality that comes from buying, but you also need the control and customization that comes from building.
Revenue leaders feel it from a different angle. They see the price tag and ask if this sales training will move pipeline, conversion, and quota attainment. The answer depends almost entirely on whether the content feels relevant enough to use and simple enough to apply quickly.
That is the heart of the build vs. buy dilemma. It’s not about training for training’s sake. It’s about behavior change, time to impact, and whether the organization will actually adopt what you invest in.
This is where customized sales training and modular sales training become a strategic lever, not a “nice to have.”
For enablement leaders, customizable sales training means:
For revenue leaders, inside sales training that is truly customized means:
At its best, sales training is not a one time event. It is a system that combines short, tactical learning, manager coaching, live call practice, and reinforcement activities over time.
Generic content cannot support that system. Customizable sales training can.
DOWNLOAD: What Best-in-Class Sales Training Looks Like Checklist
This is exactly the gap we’re filling at Factor 8.
Instead of a single, fixed workshop, our inside sales training is built from more than 40 mini modules that we mix and match based on real data about your team. We start with an assessment. We listen to calls, review metrics, talk with leaders and reps, and identify where deals stall and where confidence breaks down.
From there, we design a custom enablement plan that often includes different paths for different roles. A BDR, an AE, and a manager should not all sit through the same day and hope to extract what they need. Each role gets the skills and scenarios that match their reality.
Customization shows up in the delivery too. The decks do not talk about “selling ice to Eskimos.” They use your buyers, your stories, your competitive landscape. Activities, role plays, and even customer logos are built around your sales motion. Reps often bring real calls into the room. We give feedback on actual conversations, not hypotheticals.
We also use a blended learning model that puts application at the center. Reps take short eLearning first to learn the core concepts. Then they complete customized homework that applies those concepts to their world, for example writing their own intros or value statements. When they come to the live workshop, they are already working from their own talk tracks and we coach them up from there.
After class, we keep going. Reps and managers come back together for accountability sessions where we review recorded calls, give next level feedback, and layer in more advanced tips. Managers then meet with us separately so we can calibrate what “good” sounds like and make sure they are reinforcing the skills in one on ones, huddles, and team meetings.
That is customized sales training in practice. It is inside sales training that is specific to your world, built to be used, and supported by your managers, not just a trainer.
Now here is where the model really shifts for enablement.
We heard the same thing from leaders again and again. They loved the training. They loved the outcomes. And they wanted more control. They wanted to keep building on the content with their own voice, their own products, and their own expertise.
So we created the All Access Sales Training License.
With All Access, you still get the full Factor 8 experience, including the assessment, the modular curriculum, and our trainers. But you also get the editable soft copies of our workshops and materials, along with train-the-trainer support and LMS ready files.
That means:
In plain terms, we help you solve the build vs. buy dilemma.
You get the speed, expertise, and credibility of buying outside sales training. You get the control, flexibility, and ownership of building your own. And your reps get inside sales training that finally feels like it was made for them.
If you are tired of choosing between generic workshops and year long build outs, this is the middle ground. Customized sales training that is modular, practical, and actually yours to keep.
Contact us today to learn about our customizable virtual sales training programs
available for reps (and managers).
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