Ultimate guide to successful sales coaching in 2026

From delivering winning doses of inspiration, to transforming rookies into all-stars, coaches are a key component of any winning team—and not just in sports.

In the world of modern B2B sales, coaches (managers) are just as essential to ensuring reps have the sales skills they need to close deals with confidence.

We’ve teamed up with leading sales training and service providers Sandler Training, Challenger, and Corporate Visions to share everything you and your go-to-market team need to build a sales coaching programme that drives impact.

Workato’s go-to-market team leverages Highspot’s AI sales coaching and training tools to improve rep readiness and help each seller better engage active opportunities.

What is sales coaching?

Sales coaching is the process of evaluating and mentoring a salesperson one-on-one and through the use of AI-powered tools to strengthen sales performance and drive consistent sales success. An effective sales coaching programme led by go-to-market leaders and managers helps reps self-diagnose deficiencies, enabling these sellers to take greater ownership of their work and improve their outcomes to deliver a memorable B2B sales experience that fully addresses prospects’ pain points and needs.

Why is sales coaching important?

You adopted a proven sales methodology to provide a framework and guardrails for reps that informs their day-to-day outreach and prospecting efforts. So, why add strategic coaching into the mix? The simple answer is, “Because it works.”

“When you ask reps what most enables them to achieve their success metrics, more often than not, they’ll say it’s implementing and applying learnings via training and coaching interactions with an experienced mentor,” said Challenger Senior VP of Marketing and Business Development Spencer Wixom.

Yet despite touting the benefits of sales coaching strategies, very few companies have a formal investment in place. Coaching is often approached on an ad-hoc basis—a new BDR asking a tenured one for advice, for instance.

These discussions are useful, but programmatic coaching distributes its benefits to a broader audience: the salesperson, sales manager, and buyer:

• Sales reps are coached in a way that provides the space needed to address their deficiencies (skill gaps) in core competencies. The process of self-discovery is difficult to achieve in group settings like team meetings, where some reps may hesitate to publicly share failures or top sellers may dominate the conversation.
• Sales managers get the targeted support that coaching provides ensures that no team members slip through the cracks during more general training. As a result, sales managers should see better outcomes across the entire sales cycle, stronger working relationships with their direct reports, and higher retention and team morale.
• Buyers receive better, more consultative vendor engagements from highly capable sellers—something every lead who has suffered through a terrible sales call knows is invaluable. New and experienced reps alike leverage the valuable insights gleaned for coaching sessions to get on the same page as prospects.

All three of these stakeholders on either side of the account-based selling coin only realise these advantages, though, when AI sales coaching is incorporated into your existing programmes, since it fills in gaps in manager-led coaching.

“Effective training and coaching are top concerns for organisations, as they’re often difficult to scale,” according to Highspot’s State of Sales Enablement Report 2025. “Increasingly, teams are augmenting traditional training and coaching with AI and securing new impact on topline metrics.”

Benefits of sales coaching: How AI helps sales leaders guide their teams

Those are the macro pros of sales coaching activities. At a more micro level, sales coaching effectiveness is amplified (a lot) with AI, as the tech:

• Helps managers coach effectively without burning hours in admin hell: Instead of manually reviewing call recordings or CRM notes, AI serves up targeted insights that highlight where reps are crushing it or could use help. It’s like having an always-on coaching analyst on each sales call.
• Brings a personalised coaching touch to every rep, every day: Whether you’ve got a sales team of new hires and veteran sellers, AI tailors development cues based on real deal activity. That means better conversations, sharper skills, and less of the one-size-fits-none playbook.
• Keeps coaching tied to real-world sales activity and impact: By connecting with daily sales activities like emails, calls, and CRM updates, AI sales tools give coaching more teeth. It’s not just, “Try harder.” It’s, “Here’s what worked in your last two wins—let’s do more of that.”
• Helps reps enhance their own performance, even between check-ins: With embedded feedback loops and just-in-time learning, reps get smarter fast, without waiting for a pipeline review. That autonomy builds confidence, strengthens execution, and aids their career development.
• Uncovers what your top reps are doing—and scales it to the whole team: Artificial intelligence for sales teams connects the dots between behaviour, buyer engagement, and revenue growth, turning what used to be anecdotal into a repeatable, more impactful and effective sales coaching technique. That’s how teams go from scattered success to strategic consistency.
• Motivates reps with data-driven praise, not guesswork or gut feel: Smart coaching conversations—grounded in insights from plays, collateral, and messaging developed by sales enablement that’s shared by reps—help sales managers celebrate what works and inspire effort as needed.

One of the ‘right’ tools with AI-powered capabilities that many sales managers use today to support their reps’ education efforts is AI sales role play tool, like the one offered in our agentic platform for today’s go-to-market teams.

“When your reps use AI role play, you get a clearer picture of what’s working and where you’re building the most momentum,” Highspot’s 5 Ways to Win with AI Role Play Guide. “Are your reps practicing new messaging? Are they preparing ahead of key meetings? Which scenarios are they using most, and when?”

It’s these signals that “show where your team is building skills, where initiatives are landing, and where reps are investing the most time,” per the guide.

Tactical sales coaching tips to empower reps and improve performance

There are many different coaching techniques you can use to put these activities into play, so follow the advice and insights below to get an idea of how you can create a more structured coaching plan that supports your B2B sales process.

Self-diagnose through discovery

Coaches who regularly review rep data and observe activities will typically be aware of a problem before a rep. During this first stage, it’s important to guide a rep to self-diagnose an issue by asking targeted questions, such as:

• What would you like to explore today?
• What went well about a customer engagement?
• What could be done differently?
• What are the benefits of changing?
• What are the consequences of not changing?

Just focus on the behaviour changes and skillsets you hope to see members of your sales organisation adopt, like remembering to log notes in Salesforce. An effective coaching process is one that gets your entire team to self-evaluate daily.

Plan for the future state of selling

Once opportunities for improvement have been identified, it’s time to discuss what the future state will look like. Again, your job is to guide the discussion, not dominate it. Ask questions like:

• What does good look like in this scenario?
• What will it take to get there?
• What will stop you from achieving this state?
• How can I help you achieve this state?

These questions allow the rep to explore their own potential and encourage them to take ownership of changes without fear of failure or punishment.

Create a concrete action plan

Next, work with your rep to create a plan of action. Write out the steps the rep will need to take to achieve their desired future state. These include:

• A few immediate actions to facilitate change: Start with 1–2 simple shifts they can apply this week—something low-effort that builds confidence quickly and shows you’re in this together.
• A timeline for progress check-ins: Map out specific moments to review progress, adjust course, and stay aligned, ideally anchored to deals already in motion, not just the calendar.
• An expected date of goal completion: Choose a deadline that’s ambitious but achievable, based on deal cycles or team milestones, and tie it to something meaningful for the rep.
• A support plan for deal or skill application: Outline how you’ll help them apply coaching to real opportunities, whether through call-recording review, role rehearsal, or shared prep work.

Put your action plan documentation in a shared location, like your enterprise content management system where you store other sales play, content, and messaging docs. You’ll want to revisit this record to check on progress down the line.

Support and energise your sales professionals

Once you’ve determined your action plan, take a moment to step back and listen to what your rep needs from you to be successful. Now is the time to offer encouragement and positive feedback. Ask your rep questions like:

• Is there anything in our discussion today that I can clarify further?
• How do you feel about the steps we’ve outlined in this coaching plan?
• Are there other important topics you’d like us to talk through today?
• What support would be most helpful for you in the next few weeks?

Keep in mind that your goal is to encourage behaviour change that leads to more deals getting across the finish line. Feedback, especially when negative, is difficult to receive. The more encouraging and supportive you can be during 1:1 sessions, the more effective coaching will be for you.

Follow up with each rep regularly

In the following coaching sessions, use your action plan as a guide to assess progress and make changes as needed. Check in with questions such as:

• How are things going since we started working on this coaching plan?
• Do you feel like you’re making steady progress toward your next goal?
• What new challenges or blockers have come up since our last session?
• What adjustments should we consider making to improve your progress?

Work together to review progress, offering additional feedback and encouragement as you go. Once the rep had effectively adjusted behaviours, reward them with praise and by sharing their best practices with other team members.

What successful sales coaching looks like in action: Examples to inspire

Coaches walk a delicate line. You must be firm enough to shift behaviour while open enough to help reps feel comfortable discussing shortcomings. Most managers aren’t born knowing how to do this. But just as a great rep is taught how to sell, anyone can become a good coach. They just have to learn how.

“Too much of sales management is telling sales professionals what to do as opposed to letting salespeople do their own self discovery and learning,” said Sandler Training Head of Global Strategy and Growth Damon Jones.

“By investing in training your sales coaches often, you can foster good behaviour and better outcomes from the start,” according to Damon.

A formal sales coaching programme should therefore develop and certify managers with advanced coaching skills before they engage with reps. By the end of their training, a great sales coach should understand how to:

• Ask the right questions to prompt self-discovery of issues
• Use data and observation to identify performance gaps in reps
• Create an environment that fosters open, honest conversation
• Motivate and incentivise individuals to improve team culture
• Give sellers the direction to have impactful customer interactions

You may notice a pattern here: It’s essential to act early, often, and with empathy to connect with your reps. At its core, that’s all great sales coaching really is.

Sandler Training Global Head of Content Mike Montague, summed it up nicely.

“There are no bad salespeople, only bad coaches,” said Mike. “It’s the coach’s job to understand what a rep needs in order to be successful—and deliver it.”

How to measure sales coaching effectiveness: KPIs to track early and often

Corporate Visions Chief Strategy Officer Tim Riesterer said it best when he explained that the primary goal of sales coaching today is simply “ensuring reps have the ability to articulate value at every stage of the B2B buying journey.”

With this in mind, measuring certain key performance indicators tied to the GTM performance and developmental growth of each BDR and SDR can help you gauge where reps are growing and improving and what requires further attention.

Specifically, it’s ideal to track KPIs like:

Sales performance metrics: Tie your seller and deal coaching to field results and ROI

To measure the impact of coaching via rep effectiveness, track metrics including:

• Percentage of reps who meet or exceed sales quota attainment targets
• Individual deal size and profitability across key product or service lines
• Individual rates of retention and renewal over a defined time period
• Individual size and frequency of upsells tied to coaching-driven tactics

Performance data like the above examples can reveal deficiencies in individual rep behaviour and allow you to remedy them with point solutions.

“Evaluating managers based on the percentage of team members who hit revenue-growth targets as opposed to the team average against target ensures that the activities of high-performers don’t obscure the core performers who may be in need of coaching help,” said Spencer.

Check on progress tied to these sales performance metrics often to proactively support reps before they—and the company’s bottom line—miss their mark.

Observational activity metrics: Monitor reps’ sales calls and other engagement activities

In addition to looking at salespeople as a reflection of coaching, you can track what’s described as ‘downward feedback,’ which is how directors and second-line managers observe a frontline manager’s coaching behaviours.

Understanding whether or not prescribed sales coaching guidance has been followed by specific reps and the sales organisation at large has two benefits:

1. It helps business leaders in GTM and RevOps understand the impact of their sales coaching programmes. If nobody adopts guidance, it’s probably not very useful.
2. When a coach’s team fails to meet sales goals, a go-to-market director can determine whether or not the coach followed their own guidance accordingly in 1:1s.

And if a manager’s coaching plan still defaults to old habits instead of applying the new approach, you’ll be able to catch that early, address the gap directly, and avoid wasting another month hoping for different rep-related outcomes.

Culture metrics: Track the sales team members’ morale to ensure they remain motivated

Finally, you can measure markers tied to your team’s sales culture to determine the effectiveness of your coaching efforts. These kinds of metrics include:

• Percentage of reps who voluntarily leave within a rolling 12-month span
• Number of reps promoted into leadership roles within the sales org
• Reps’ satisfaction with their role, manager, and company environment
• Frequency of manager recognition for strong rep performance in-team
• Employee Net Promoter Score (eNPS) tracked quarterly or biannually

This is vital data that reveals the personal nature of the coaching relationship.

Bad sales coaches can make or break a salesperson’s experience at a company. If high performers are leaving for other opportunities, this intel will let you know if a coach was to blame. Conversely, if previously low performers are now being promoted, a really good sales coach can likely take credit.

Together, measuring these data points provides a holistic view into the ability of coaches to drive revenue, motivate their team, and grow the business.

Best practices for sales coaching: Techniques every manager should use

No two sales coaching programmes look exactly alike. But ask any B2B GTM manager with a thriving L&D strategy today, and they’ll tell you they abide closely by these proven strategic coaching tips and tricks. to elevate reps’ performance.

Which sales coaching platforms do high-performing go-to-market teams use today?

High-performing teams combine agentic GTM platforms like Highspot, which offers native AI sales coaching tools like AI role play and AI sales agents that help train reps based on real-world selling scenarios and offer real-time deal intelligence and next-best actions, with CRM and buyer engagement tools.

Together, these technologies support seller preparation, buyer follow-up, and structured deal conversations that help managers guide reps consistently.

How can artificial intelligence help me and other sales managers improve our coaching?

Cutting-edge AI sales tools like Highspot support managers by reviewing calls, messages, and deal progress at scale. Insights highlight patterns across rep execution, helping managers prepare focused conversations, prioritise development areas, and spend time guiding sellers rather than compiling notes manually.

What are the first steps to building an effective sales coaching programme from scratch?

Start by defining your sales coaching goals tied to BDR and SDR development, deal quality, and buyer experience. Establish a repeatable meeting cadence, prepare question frameworks, document agreed plans, and listen closely so reps drive discovery and ownership during sessions and gain role-based autonomy.

How do successful B2B sales managers track their coaching effectiveness today?

Strong managers review seller outcomes like quota attainment, deal value trends, renewals, and expansion growth. They pair those metrics with observation of manager follow-through during one-to-one sessions, creating visibility into whether coaching guidance translates into improved seller execution.

How can sales managers coach their sales reps to overcome objections from buyers?

Managers coach objection handling by reviewing recent buyer conversations, identifying repeated themes, and practicing alternative responses together. Sales reps refine language through repetition and reflection, building stronger buyer alignment during discovery, negotiation, and late-stage discussions.