Sales Coaching: 10 Straightforward Tips That Work

Good sales coaching can unlock serious revenue potential. In fact, effective coaching can increase sales performance by 8%, according to a study by Gartner . But many sales managers find coaching difficult to master, especially in remote environments or when asked to do more with fewer resources.

If you’re struggling to effectively coach your sales team, don’t despair — I’ve struggled too. I went seven weeks without closing my first deal when I started out. Thirteen years later, I teach sales professionals how to develop the right skills, habits, and mindset required for sustained success.

My sales coaching tips are easy to implement (with many of the tools already at your disposal) and effective for both in-person and remote teams. So, if you want to give your reps the support they need to close more deals, here’s how to get started.

• What is sales coaching?
• What does a sales coach do?
• Benefits of sales coaching
• How to coach and develop your sales team
• 10 sales coaching techniques
• Examples of sales coaching
• How to measure sales coaching effectiveness
• Sales-coaching tools you should be using

Sales coaching refers to the training, tools, resources, and support sales managers give to sales teams to improve their skills and hit revenue targets.

This coaching can be done in house or with an external sales coach. In-house coaching typically involves a member of your sales or enablement team working with reps to improve performance. An external sales coach is usually hired to help build a long-term playbook for sales teams with field-tested strategies.

A sales coach works directly with sales teams to improve how they handle sales calls, objections, and common challenges. A coach may also provide tactical advice for how they should structure their day, manage their time, stay organized, and develop the right mindset for selling.

In addition to team sessions — which can happen in person or online — a coach may also work with reps one on one. When an individual sales rep is underperforming and needs extra attention, a coach may review recorded sales calls to identify areas for improvement. Sometimes, the coach will even shadow individuals on sales calls to see how they handle themselves in real time.

For example, say a rep has a low close rate, but plenty of promising leads in the sales pipeline. A coach will privately meet with them and diagnose the exact constraints they are running into. The diagnosis may reveal poor discovery skills, ineffective multithreading skills, or more. This allows the sales coach to tailor very specific coaching to help them improve their results immediately.

During my years of sales coaching, I’ve found that many reps feel like their companies don’t provide enough support or resources for them to be successful — only 26% of reps say that they receive one-on-one coaching weekly, according to the State of Sales report.

Many times, they’re told “it’s a numbers game” or “work harder,” but aren’t given any tools to improve. These people don’t want to just grind their way to the top — they want to actually develop their skills and get better results.

Sales leaders are undoubtedly busy managing daily operations, which can sometimes make consistent support hard to provide. However, investing in your team’s skills and knowledge is a sign of good sales leadership. If you have the resources, hiring an external coach who can dive deeper into your team’s obstacles and suggest specific things to work on is beneficial.

Some of the key benefits of sales coaching include:

• Personalized attention: One-on-one support for reps who may be struggling is crucial.
• Improved retention rates: Investing in your team’s success shows that you want them to thrive.
• Collaboration: Your team becomes aligned on best practices, sales approaches, and skill sets — allowing them and you to meet your goals.

In addition to the required technical skills and product knowledge, top salespeople must also possess certain soft skills — active listening, emotional intelligence, and self-awareness, to name a few. These can take time to develop. Buyers want to work with someone who understands them and who can actually solve their problem. Great sellers must first understand the needs of the customer to do this. And this is where coaching can make a difference.

So, where should you start?

First, look at your sales data. Pretty quickly, you’ll get an idea of the areas you need to improve. Talk with your team and ask about how they’re currently addressing challenges. You can do this as a group, individually, or both. This is an opportunity for you to understand where they’re struggling and why. Then, you can share insights from your own sales experience, discuss sales techniques, and create a plan for improvement.

Next, decide what goals you want reps to meet, a realistic timeframe in which they can accomplish them, and a plan for making it happen. You can create team goals as well as individual ones. Be sure to measure their progress — something easily done with sales dashboards and incentive programs — and stay consistent with coaching to see results. If weekly, one-on-one training sessions are stretching you thin, technology solutions (such as AI-generated insights) can help you do more with less.

Hiring an outside sales coach to review strategy and offer feedback to your team is a long-term investment in increasing your win rate. But if you want to improve your team’s performance right away, these sales coaching strategies are a great place to start.

1. Focus on rep wellbeing

Many sellers (70%) say that they struggle with mental health, according to the 2024 State of Mental Health in Sales report. Burnout, an “always on” work ethic, and isolation can affect your reps’ mental health — and impact their sales performance.

You can alleviate this in a couple of ways. First, create boundaries for your team. Set clear work hours and urge reps not to schedule sales or internal calls outside of these hours. Also, be clear about when reps should be checking internal messages and when they can sign off.

Lori Richardson , founder of sales training company, Score More Sales, advises managers to address this head-on by asking reps about their wellbeing during weekly one-on-ones. “I like to ask open-ended questions about the past week,” she said. “Questions like, ‘How did it go?’ and ‘What was it like?’ are good first steps. Then, you need to listen.”

When the rep is done sharing their reflection, Richardson suggests restating the main points to ensure you’re on the same page. If necessary, ask for clarity so you fully understand what’s affecting their state of mind. Also, she urges: Don’t judge. The level of comfort required for sharing in these scenarios can only exist if you don’t jump to judgment.

2. Build trust with authentic stories

For sales coaching to work, sales managers must earn reps’ trust. This allows the individual to be open about performance challenges. The best way to start is by sharing personal and professional stories.

These anecdotes should be authentic, revealing fault and weakness as much as success. There are two goals here: Support reps with relatable stories so they know they’re not struggling alone, and let them know there are ways to address and overcome challenges.

For example, a seasoned manager might share details about their first failed sales call as a cautionary tale, highlighting poor preparation, aggressive posturing, and lack of empathy during the conversation. This would be followed by steps the manager took to fix these mistakes, like call rehearsing and early-stage research into the prospect’s background, business, position, and pain points.

3. Record and review sales calls

Once upon a time, sales reps learned by shadowing tenured salespeople. While this is still done, it’s inefficient and often untenable for virtual sales teams.

To give sales reps the guidance and coaching they need to improve sales calls, deploy an intuitive conversation recording and analysis tool like Conversation Insights (ECI). You can analyze sales call conversations, track keywords to identify market trends, and share successful calls to help coach existing reps and accelerate onboarding for new reps. Curate both “best of” and “what not to do” examples so reps have a sense of where the guide rails are.

4. Encourage self-evaluation

During post-call debriefs, skill assessments, or routine coaching during one-on-ones, it’s critical to have the salesperson self-evaluate. As a sales manager, you may only be with the rep one or two days a month. Given this disconnect, the goal is to encourage the sales rep to evaluate their own performance and build self-improvement goals around these observations.

There are two important components to this. First, avoid jumping directly into feedback during your interactions. Relax and take a step back. Let the sales rep self-evaluate.

Second, be ready to prompt your reps with open-ended questions to help guide their self-evaluation. Consider questions like:

• What were your big wins over the last week/quarter?
• What were your biggest challenges and where did they come from?
• How did you address obstacles to sales closings?
• What have you learned about both your wins and losses?
• What happened during recent calls that didn’t go as well as you’d like? What would you do differently next time?

Reps who can assess what they do well and where they can improve ultimately become more self-aware. Self-awareness is the gateway to self-confidence, which can help lead to more consistent sales.

5. Let your reps set their own goals

Immediate improvement is great to see, but you really want to focus on long-term results. In my experience, reps who participate in a comprehensive coaching program typically see higher gains than those who don’t. This falls in line with self-evaluation. Effective sales coaches don’t set focus areas for their salespeople; they let reps set this for themselves.

During your one-on-ones, see if there’s an important area each rep wants to focus on and go with their suggestion (recommending adjustments as needed to ensure their goals align with those of the company). This creates a stronger desire to improve, as it’s the rep who is making the commitment. Less effective managers will pick improvement goals for their reps, then wonder why they don’t get buy-in.

For instance, a rep who identifies a tendency to be overly chatty in sales calls might set a goal to listen more. To help, they could record their calls and review the listen-to-talk ratio. Based on their findings, they could set a clear goal metric and timeline — for example, achieve a 60/40 listen-to-talk ratio in four weeks.

However, Richardson does have one note of caution. “Reps don’t have all the answers. Each seller has strengths and gaps,” she said. “A strong manager can identify those strengths and gaps, and help reps fill in the missing pieces.”

6. Focus on one improvement at a time

For sales coaching to be effective, work with the rep to improve one area at a time instead of multiple areas simultaneously. With the former, you see acute focus and measurable progress. With the latter, you end up with frustrated, stalled-out reps pulled in too many directions.

Here’s an example: Let’s say your rep is struggling with sales call openings. They let their nerves get the best of them and fumble through rehearsed intros. Over the course of a year, encourage them to practice different kinds of openings with other reps. Review their calls and offer insight. Ask them to regularly assess their comfort level with call openings during one-on-ones. Over time, you will see their focus pay off.

7. Ask each rep to create an action plan

Open questioning during one-on-ones creates an environment where a sales rep can surface methods to achieve their goals. To make this concrete, have the sales rep write out a plan of action that incorporates these methods. This plan should outline achievable steps to a desired goal with a clearly defined timeline. Be sure you upload it to your CRM as an attachment or use a tool like Slack to create a collaborative document editable by both manager and rep. Have reps create the plan after early-quarter one-on-ones and check in monthly to gauge progress (more on that in the next step).

Here’s what a basic action plan might look like:

Main goal: Complete 10 sales calls during the last week of the quarter

Steps:

• Week 1: Identify 20-25 prospects
• Week 2: Make qualifying calls
• Week 3: Conduct needs analysis (discovery) calls, prune list, and schedule sales calls with top sales prospects
• Week 4: Lead sales calls and close deals

The power of putting pen to paper here is twofold. First, it forces the sales rep to think through their plan of action. Second, it crystallizes their thinking and cements their commitment to action.

8. Hold your rep accountable

As businessman Louis Gerstner, Jr. wrote in “Who Says Elephants Can’t Dance? “, “people respect what you inspect.” The effective manager understands that once the plan of action is in place, their role as coach is to hold the sales rep accountable for following through on their commitments. To support them, a manager should ask questions during one-on-ones such as:

• What measurable progress have you made this week/quarter?
• What challenges are you facing?
• How do you plan to overcome these challenges?

You can also review rep activity in your CRM. This is especially easy if you have a platform that combines automatic activity logging, easy pipeline inspection, and task lists with reminders. If you need to follow up, don’t schedule another meeting. Instead, send your rep a quick note via email or a messaging tool like Slack to level-set.

9. Offer professional development opportunities

According to a study by LinkedIn, seven in 10 people say learning improves their sense of connection to their organization. When companies make an effort to feed their employees’ growth, it’s a win-win. Productivity increases and employees are engaged in their work.

Book clubs, seminars, internal training sessions, and courses are all great development opportunities. If tuition reimbursement or sponsorship is possible, articulate this up front so reps know about all available options.

Richardson adds podcasts to the list. “Get all of your salespeople together to talk about a podcast episode that ties into sales,” she said. “Take notes, pull key takeaways and action items, and share a meeting summary the next day with the group. I love that kind of peer engagement. It’s so much better than watching a dull training video.”

10. Set up time to share failures — and celebrations

In my experience, failure can be a valuable learning opportunity. But as Richardson points out, a lot of coaches rescue their reps before they can learn from mistakes: “Instead of letting them fail, they try to save an opportunity,” she said. “But that’s not scalable and doesn’t build confidence in the rep.”

Instead, give your reps the freedom to make mistakes and offer them guidance to grow through their failures. Set up a safe space where reps can share their mistakes and learnings with the larger team — then encourage each rep to toss those mistakes on a metaphorical bonfire so they can move on.

By embracing failure as a learning opportunity, you also minimize the likelihood of repeating the same mistakes. Encourage your reps to document the circumstances that led to a missed opportunity or lost deal. Review calls to pinpoint where conversations go awry. Study failure, and you might be surprised by the insights that emerge.

Also — and equally as important — make space for celebrating big wins. This cements best practices and offers positive reinforcement , which motivates reps to work harder to hit (or exceed) quota.

When I coach salespeople, I don’t focus on immediate results because learning the necessary skills takes time. Instead, I focus on developing the fundamentals using frameworks, like active recall and spaced repetition, to build long-term muscle memory. With regular practice, your approach will start to become second nature — natural and authentic.

It’s the same in sports. Once you have the fundamentals down, it’s much easier to adjust and develop your own style. You don’t get to the Olympics the first time you step on a tennis court. Gold-medal winners put in countless hours of practice, perfecting their skills.

There are a few different ways to approach sales coaching. Usually, it’s a combination of different methods. Here are a few examples:

Online training portal models: These are short, instructional videos of every need-to-know sales process. They’re effective because they’re digestible enough that sales reps can come back and revisit them anytime they need a quick brush up. And every time you rewatch a module, it hits a little bit differently depending on what you’re working on. You typically learn something new that you may have missed the first time around. Topics include things like: how to make cold calls and write cold emails, how to run discovery, and how to move a deal to close.

Frameworks: Templates for common sales frameworks are available online and can be downloaded and customized based on your goals. For example, if you want to work on handling objections, a framework can help you get started. It provides an outline you can learn from, including how to prep before speaking to the prospect — and what to do when obstacles arise. There are common patterns in sales, and frameworks can help you recognize them and prepare for any situation.

Asset reviews: After reviewing a rep’s performance, a sales coach may outline strategies for success and offer personalized feedback based on their unique challenges.

Shadowing and role playing: A coach may shadow a rep on their sales calls — or listen to past recordings — and offer expert feedback and strategies for improvement. Coaches can also facilitate role-playing exercises to evaluate how effectively a rep applies a sales strategy and critique areas they could improve.

Follow-up support: Finally, a sales coach may offer additional or ongoing coaching support over Slack, phone calls, and email — whatever form of communication that the rep prefers.

To know if coaching is effective, you need to compare sales performance metrics before and after. Tracking metrics helps you identify where you’ve improved — and what could use more attention.

Some of the metrics you should look at include:

• Number of sales: Data points that represent an individual or team’s performance
• Amount of revenue: The income generated from sales
• Average deal size: The average amount of money a client spends on your product or service
• Conversion rate: The number of leads that are converted into sales divided by the number of qualified leads
• Sales cycle length: The total number of days it takes for a deal to close divided by the total number of closed deals.

Don’t expect immediate results. After implementing a coaching plan, the initial assessment period should last between one and two months. That gives enough time to gather feedback and notice behavioral changes or attitude shifts in the sales team.

The long-term effect of sales coaching becomes evident after six months to a year. If the coaching is effective, you should see more closed deals, revenue growth, and improved performance among your team.

A coach can also assess team and individual progress and provide sales managers with feedback. Through shadowing and observation, coaches will have a good sense of how much reps’ sales techniques have improved (or not) and be able to offer a detailed assessment.

Some 75% of sales professionals have confidence in their sales organization’s ability to re-skill their reps. However, sales managers need the right tools and resources to coach their team effectively. In addition to personalized sales coaching, I recommend implementing some of the following tools:

• Sales cadences (in Sales Cloud): Help your sellers customize their workflows with AI recommendations and step-by-step instructions for how to prospect. This can help them gain confidence and consistency when conducting sales activities.
• Einstein conversation insights: Improve your team’s performance with coachable moments based on customer interactions, trends, and more. Call summaries are a great tool to pinpoint specific areas for improvement and what’s working well.
• Sales performance management: Empower your reps to close deals faster with real-time visibility into commission trends, performance data, and personalized analytics. By outlining goals and highlighting progress, you can hold your team accountable and celebrate wins.
• SPIFF programs: Improve departmental alignment and boost your reps’ confidence with achievable compensation plans optimized for revenue growth.
• Slack: Use communication tools to check in with individual reps or your whole team anytime, anywhere. Creating an atmosphere that encourages regular communication can help reps feel empowered to ask questions, get help, or seek advice.

The results of coaching won’t happen overnight. It takes dedication, a desire to improve, and the right tools and time to develop good habits. There are many resources available for sales leaders interested in developing their coaching. But when my clients ask, “What’s the one thing I can do to help my sales team develop their skills?” I tell them that it almost always comes down to habits. Most salespeople have ineffective habits. But they can overcome this with coaching, discipline, time, and a dedicated routine for success.