You’re Not Crazy: What Women in Corporate America Need to Know About Promotions, Politics, and Power [Webinar]
Meet the Speakers
Culture + Engagement
How to Build a Top-Performing Sales Team: Skills, Confidence & Tools That Actually Work
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.
Getting Started: What’s Holding Sellers Back?
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:
- Fear of the phone
- Low business acumen
- Poor time management
- Struggling to find the right contacts
- Stalled or ghosted deals
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.
Build Confidence from Day 1 by Training These Skills
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:
- Leaving voicemails that get a callback
- Knowing what to say when someone actually answers
- Keeping prospects on the line
- Handling “Who the heck are you with?”
- Finding the right people and getting them to engage
- Delivering your value prop with confidence
- Capturing key contacts on the call
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
The Confidence Hack That Cuts Ramp Time in Half
One of the most effective coaching tools out there is the Pause Game. It’s simple and powerful:
- Play any recorded call (it doesn’t even have to be their own)
- Pause every 10 seconds
- Ask two questions:
- What’s the customer thinking right now?
- What would you do next?
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
Give Reps the Right Tools (At the Right Time)
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:
- Give them pre-built lead lists to avoid “blank page” syndrome
- Equip them with Sales Navigator and ZoomInfo to enrich contacts quickly
- Push microlearning tied to performance gaps (like call intros or value props)
- Create call libraries and show reels of top reps in action
- Run timed CRM drills during training to build speed and multitasking skills
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.
Retention, Career Paths, and Coaching the Coaches
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:
- Share real win stories across the team to celebrate success and boost morale
- Create safe spaces for loss stories to promote learning and vulnerability
- Build clear career paths from BDR to AE to manager, with skills mapped at every level
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
Just-In-Time Training, Simplified Tech, and Manager Reinforcement
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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State of Sales [Webinar Recording]
The State of Sales
[Video Recording]
Top Sales Trends, Challenges & AI Tools You Need to Know [Webinar Recording]
Top Sales Trends, Challenges & AI Tools You Need to Know
[Video Recording]
Meet the Speakers
Lauren Bailey
Founder
Factor 8 | #GirlsClub | Legacy
Jessica Fryback
Sales Development Manager
Dun & Bradstreet
Katie Grant
Vice President of Customer Growth
Teton
Fiona Simpson
Sr. Enablement Business Partner
Boomi
The Secret to Scaling Sales Team Revenue: Your Managers
What’s the most overlooked factor in sales growth? Your frontline sales managers.
They influence every deal, every rep, every forecast, and yet about 60% of new managers report they never received training when they stepped into leadership.
Let’s stop looking past the obvious. Your frontline managers are the secret to scaling sales growth.
If you want more reps hitting quota, more deals converting, stronger forecasts, and less burnout across the board, it starts with your managers. Not your tech stack. Not your latest AI tool. Not another rep enablement platform (though these are important and we love them, check out our friends at Allego).
I’ve worked with thousands of sales teams and here’s the hard truth. Most companies are investing in everything except the role that has the biggest impact on team performance and revenue growth.
And when we flip that, the results are massive. We’re talking 20 to 47% increases in rep conversion rates. And we didn’t even touch the rep. Just by developing their manager.
So if you’re planning for growth, keep reading. Because managers aren’t a bottleneck. They’re your biggest growth engine.
1. Managers Bring Consistency (and That’s What Scales)
Change is part of growth. Reps switch teams. Territories shift. Comp plans evolve. But in the middle of it all, your frontline managers keep the team focused, engaged, and aligned.
That only works when they’re supported.
Too often, every manager ends up running their own playbook. Not because they want to, but because they’ve never been shown what “good” looks like. And even when you have playbooks, they don’t get translated into everyday actions and team rhythms.
Here’s where the cracks usually show up:
- Hiring: Everyone’s looking for different things. Even with a profile in place, managers need support identifying what good sounds like in an interview.
- Performance management: Breaking down a big quota into measurable KPIs isn’t intuitive. And very few new managers have been trained to do it.
- Rep engagement: Some managers meet weekly. Some meet monthly. Some skip 1:1s entirely. Most spend time reviewing pipeline, not developing skills or coaching.
- Pipeline hygiene: Definitions for deal stages vary across teams. That makes forecasts unreliable and coaching hard to scale.
Consistency is what turns momentum into real, scalable growth. And it starts at the manager level.
Give them the tools to:
- Hire with confidence using a shared rubric
- Set goals and track KPIs that actually drive performance
- Run a standard meeting cadence that blends coaching, performance, and career conversations
- Clean up pipeline processes so everyone’s speaking the same language
Even tenured managers benefit from this kind of clarity. One enterprise team we worked with had over 10 years of management experience and still walked away from this training saying, “I wish I’d had this years ago.”
2. Great Managers Build People, Not Just Pipelines
Most sales managers were promoted from rep roles. And as reps, their entire world revolved around winning. So when things get tough, what do they fall back on?
Closing the deal.
They hop on the call. They take over the demo. They second-voice the close. It’s not bad intentions, they’re just doing what worked for them. But when a manager becomes the deal hero, the team stops learning.
And that’s when reps leave.
- They leave when they don’t feel developed
- They leave when they’re not hitting quota
- They leave when they don’t have a strong relationship with their manager
The revolving door hurts growth. Every open seat is lost pipeline. Every green rep takes months to ramp. Every exit chips away at morale.
What helps? Redefining the manager role and giving your leaders a new toolkit.
- Help them shift from deal-doer to rep-developer
- Give them interaction frameworks like COACHN so coaching doesn’t feel like guesswork
- Recognize managers for building people, not just saving quarters
Because a manager who builds skill, confidence, and trust is someone who retains reps, not replaces them.
READ: Build Your Sales Manager Cadence (& Save Time and Stress)
3. Coaching Is a Skill, and It Can Be Learned
We all love to say coaching is the silver bullet. And it is. But only when it’s done well.
Real coaching moves the needle on performance, confidence, and retention. But too often, what we call “coaching” is just a pipeline review in disguise.
If you’ve ever listened in and heard:
- The manager doing all the talking
- A rep leaving with three disjointed to-dos
- A session that feels more like a performance review than a development convo
Then chances are, your managers need support here.
The most common trap? The Mini-me. That’s the manager who coaches every rep to be a version of themselves. It works for the one or two reps with the same style. Everyone else gets frustrated, disengaged, or overlooked.
Good coaching is consistent, rep-centered, and rooted in skill development, not deal rescue.
That’s why we don’t treat coaching like a one-hour workshop. It’s now a six-hour, three-part course here at Factor 8. Because shifting behavior and building confidence takes time. And when it clicks, reps perform. They stay. And they grow.
READ: The Best Sales Coaching Questions Ever
If You’re Skipping Manager Development, You’re Skipping the Scale
Let’s be honest. The biggest miss isn’t the manager. It’s us.
We’ve skipped the basics. We assume managers will figure it out because we did. We prioritize tech over training. We fix people problems with process or platform investments.
But if you want more reps to hit quota, you don’t need a new tool (yet). You need stronger conversations first.
That comes from skilled, supported, confident managers.
Most reps today get a sliver of what they need in onboarding. Then they’re tossed five tools and a quota. They’re still learning the basics. And the person who owns the rest?
Their manager.
So let’s invest in them. Train them. Coach them. Give them a framework, a cadence, and a community. Make development part of the rhythm, not a one-time event.
Because your reps aren’t going to grow if your managers aren’t growing too.
Managers are the secret to scalable revenue growth. Let’s stop hoping they figure it out, and start helping them knock it out of the park.
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How to Improve the Relationship Between Sales Reps and Managers
With all the economic uncertainty out there, it’s tough to find and keep good reps right now. Data from HubSpot indicates that sales rep turnover is around 35% (even in an economic downturn, attrition is shockingly high).
So how do you keep your star players around? Well, according to our Sales Team Retention Research Project study, the top reason both reps and managers stay with a company is ongoing training and development opportunities to help them succeed in their roles.
In my opinion, the key to a solid rep-manager is: both sides support each other to develop and grow. Here are some tips to put it into action to improve the sales rep-manager relationship.
What should managers do to retain their reps?
READ: How to Hire and Retain Sales Reps
1. Create coaching opportunities outside the normal flow
A lot of managers wait until the pipeline call or the forecast call to coach. While those meetings add value, they focus on specific outcomes. Where reps often struggle is investing in skills that they can apply to a variety of situations, like negotiation and price anchoring. Spend 30-60 minutes with your reps to work on these skills, and you’ll start seeing more engagement from them. As a general rule, newer or underperforming reps should be coached once per week and tenured or high-performing reps should be coached once per month.
2. Create an explicit growth template
Reps can’t grow if they don’t know what their growth path is supposed to look like. This means you need to actually document the basic competencies and objectives you expect. Then monitor rep improvement on a weekly, monthly, and quarterly basis—not just during an annual 360-review.
READ: Increase Sales Coaching Frequency
3. Don’t be hypocritical
People have a strong B.S.-meter. They know when you’re faking them out. So if you’re going to expect things from them, you better make sure you’re holding yourself to the same standards.
This doesn’t mean you need to be “macho” or push bravado all the time. You’re going to make mistakes, just like anyone. But set the example of always striving to be better, holding yourself to a high standard, and fixing problems when they arise.
4. Drive deeper engagement
The more engaged your reps are at work, the more they’ll stick around. So make sure their work stretches them and helps them grow. Provide opportunities for them to push themselves without setting them up to fail.
When appropriate, let them provide input on the direction and growth of the product and company. They have valuable insights that you can use. Plus, it helps them feel included.
5. Stay hungry and humble
Even though you’re in a management position, there’s always the opportunity to learn more. Don’t rest on your laurels. Stay hungry, and always look for ways to learn, grow, and improve.
DOWNLOAD: Tips for Retaining The New Generation of Sales
6. Don’t expect your people to always copy you
Don’t fall for “mini-me” syndrome. Just because you have a great process for selling doesn’t mean it’s the best for everyone. Instead, think about how effective reps are in driving results and meeting quotas, and focus on helping them close gaps and reach those goals faster. There can be an openness in process and style, while at the same time consistency in results.
7. Seize on little opportunities to build human connections
Managers can do a lot to show reps that they care about them not only as sales machines, but as individuals. And these don’t take a lot of extra time.
Especially in virtual environments, reps hear from their managers only to discuss forecasts, or when there’s a problem. Find other ways to connect with them as well, even if it’s just to talk about how they’re doing on a personal level.
What can reps do to build a better relationship with their managers?
1. Be solution-oriented
Don’t come with problems and no solutions. Be a solution-oriented thinker. It helps show the manager that you’re taking ownership of a problem, rather than force them to handle every little thing that comes up.
2. Be coachable
The opposite of coachability is “I already know everything.” Know what you know, but also know what you don’t know. And be open to learning and growing. It’s really hard for a manager to support a rep who thinks they know everything.
READ: 10 Tips for Sales Success from a High Performer
3. Don’t blame the leads
We all hear it all the time: If only the leads were better… Strike that phrase from your vocabulary! Stop blaming outside sources for your problems. Find a way to make the most of what you already have.
4. Get comfortable with ambiguity
Things aren’t always going to be straightforward, especially at different stages of companies. Can you execute when the answer isn’t fully defined? Are you willing to put the answer together yourself? If so, your manager will love you for it.
5. Always be curious
No one knows everything. There’s always a chance to learn, grow, and evolve. While your manager should be open to your own style, don’t assume that your way works best. Learn from others, and find a way to implement those learnings in your own unique way.
Final thoughts on the ultimate rep-manager relationship
The key to a good rep-manager relationship is this: support each other, hold each other accountable, and focus on growth. If you do that, you’ll build a solid foundation that makes both parties hesitant to leave the organization. Happy selling!
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Overcoming Sales Call Reluctance
Let’s dive deep into a phenomenon that’s rearing its head in the world of sales: call reluctance. Having chatted with senior sales leaders this month, it’s clear this isn’t just an isolated challenge; it’s a widespread issue. But why is it happening, and more importantly, how do we tackle it?
DOWNLOAD: 20 Value-Add Reasons to Call Your Customers
The Reason for Sales Call Reluctance
When you have reps dodging calls and taking refuge behind emails or DMs, you’re witnessing call reluctance in action. So, why are our once-confident reps hesitating? A few reasons…
The COVID Comfort Zone: The pandemic changed buying patterns. Many sellers shifted to a laid-back, order-taking mode. Now, as the world returns to some semblance of its pre-pandemic self, we need to dust off our sales hats and get back into the game.
A Crisis of Confidence: A few factors are at play here:
- The lack of immediate success can chip away at confidence and motivation.
- The absence of a clear purpose or compelling reason for calling.
- The pandemic brought easy sales, which meant we didn’t flex those traditional sales muscles. Now, they’re feeling a bit stiff.
Demoralized Frontline Leaders: These folks are the backbone of our teams. When they’re down, the whole ship can veer off course.
READ: Sales Is A Confidence Sport
Rebuilding Rep Confidence to Overcome Sales Call Reluctance
So, how do we turn the tide? How do we help reps build confidence and get back on the phones?
Rediscover the ‘Why’: Tap into what truly drives our reps and managers. Align their goals and motivations with their roles and rewards. It’s all about the personal connection.
Celebrate Small Wins: Start small. Take, for instance, a client of mine: once struggling with a mere 100 dials a month across a team, they shifted focus to small victories. Now? They’re rocking 90 discovery calls a week!
Skill Refresher: It’s time to retrain and remind our reps about the art of tactical sales. Equip them with the tools they need to navigate this new landscape.
Invest in Your Leaders: Here’s the golden nugget: support your frontline sales managers. I can’t emphasize this enough. Whether it’s training, resources, or just a chat over coffee, check in with them. And hey, if you’re looking for training, I might know someone. 😉 But jokes aside, these leaders are pivotal. Ensure they have the right support, tools, and motivation to steer the ship.
READ: Why You Need Training for Sales Managers
Best Practices to Remember
Embrace Technology: Virtual sales tools aren’t just about tracking; they can offer insights, refine strategies, and enhance client relationships.
Regular Check-ins: In the world of virtual sales, regular team check-ins can bridge the gap, ensuring everyone’s aligned and motivated.
Client Engagement: Beyond the sale, focus on building and nurturing relationships. Virtual doesn’t mean impersonal.
The sales landscape is ever-evolving, and while challenges like call reluctance arise, with the right strategies and support, we can not only overcome them but thrive. It’s about reconnection, retraining, and relentless support.
Do your reps need help overcoming sales call reluctance?
Contact us today to learn about our customizable virtual sales rep training programs
to help rebuild rep phone confidence.