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10 Effective Sales Coaching Tips That Work

Lead with empathy, build trust with your team, and learn to cultivate your sales reps to keep them engaged and selling. This is what effective sales coaching looks like now.

One-on-one sales coaching
Effective sales coaching balances empathy with metrics-guided goal-setting for maximum impact. [Hugh Sitton/Stocksy]

World-renowned sales coach Timothy Gallwey has captivated CEOs, entrepreneurs, and business leaders for decades. How? With one simple idea: “[Sales] coaching is [the key to] unlocking a person’s potential. It is helping them to learn rather than teaching them.”

The bad news is that many sales managers find coaching a difficult skill to master – especially in an environment where reps are increasingly remote. The problem is twofold:

1. Sales management teams, led by chief revenue officers (CROs) and VPs of Sales, do not always know how to model coaching effectively. As one in-depth study in the Harvard Business Review pointed out, many sales leaders think they’re coaching when they’re actually just telling employees what to do.

2. Many frontline sales managers said they lack the confidence they need to support their team, thanks in part to lack of training. 

Can you relate to this?

If you’re not getting the support you need to effectively coach your sales team, don’t despair. These 10 sales coaching tips are effective for both in-person and remote teams.

1. Focus on rep wellbeing

A survey by the Sales Health Alliance unveiled a startling statistic: two in five sales reps struggle with mental health – double that of the general workforce. One of the biggest reasons is the shift to remote work environments, pushing sales reps to change routines while still hitting quotas. Add in the isolation inherent in virtual selling and you have a formula for serious mental and emotional strain.

Many sales leaders think they’re coaching when they’re actually just telling employees what to do.

Lori Richardson, founder of sales training company Score More Sales, advises managers to address this head-on. She recommends 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. It also builds a two-way relationship via shared experiences. 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. Use a conversation intelligence tool to 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 master sales calls, deploy a conversation intelligence tool like Einstein Conversation Insights (ECI). You can analyze sales call conversations, track keywords to identify market trends, and share successful calls to help reps with ongoing training. Curate both “best of” and “what not to do” examples so reps have a sense of where the guide rails are.

Effective sales coaches don’t determine focus for their reps. If there’s an important area the rep decides to focus on, go with their suggestion.

Luxury travel company Inspirato does this well. They recently rolled out ECI for their reps and use insights from sales calls in pipeline reviews, weekly team meetings, and ad hoc discussions to highlight big wins and key training opportunities. 

Ben Shoff, senior manager of sales enablement at Inspirato, said it’s been a game-changer: “Our reps now have the ability to say, ‘This person closed 10 deals last month, so I’m going to listen to their calls.’ And they’re finding little nuggets they can use in their own sales calls. Before this, we had no formal process … we just listened to reps on the phone around the office.”

4. Encourage self-evaluation

When doing post-call debriefs or skill assessments – or just 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 critical 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?

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 

This falls in line with self-evaluation. Effective sales coaches don’t determine focus for their reps. If there’s an important area the rep decides to focus on, go with their suggestion. 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 than they talk. To help, they could record their calls and review the listen/talk ratio. Based on industry benchmarks, they could set a clear goal metric and timeline – a 60/40 listen/talk ratio in four weeks, for example. 

Richardson does have one note of caution, however. “Reps don’t have all the answers. Some things they have to learn from managers or others in the company.” This applies to goal-setting as much as day-to-day sales, she said. Managers need to coach reps on the alignment of personal, professional, and business goals and ensure they’re achievable, measurable, and impactful.

Sales rep setting goals with a manager
Let your reps set their own goals.

6. Focus on one improvement at a time

For sales coaching to be effective, you need to 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 questions create an environment where a sales rep can think through focus and change, and help them 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 Salesforce Anywhere to create a CRM-based collaborative document editable by both the manager and the rep. 

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

  • Main goal: Complete 10 sales calls during the last week of the holiday season
  • 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 prospects
    • Week 4: Lead sales calls and close deals

The power of putting pen to paper here is twofold. First, the sales rep needs 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 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 platform to level-set.  

9. Create boundaries

Achieving goals is difficult for sales reps, especially virtual ones who suffer from a constant barrage of emails, text messages, phone calls, and video calls. 

Avoid this confusion by creating 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.

When boundaries are in place, reps do a better job of allocating time for goal-focused work.

10. Offer professional development opportunities

According to a study by LinkedIn, 94% of employees would stay at a company longer if it invested in their career. 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 upfront 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 engagement. It’s so much better than watching a dull training video.”

Next steps for sales coaching

Successful sales coaching requires daily interaction with your team, ongoing training, and regular feedback. Follow the best practices above and you can help improve your sales reps’ performance. Remember: coaching is the key to driving sales performance.

Steven Rosen, founder of sales management training company STAR Results, contributed to this article.

Keri Brooke is the Senior Vice President of Sales Cloud Marketing. She has more than 20 years of experience in the enterprise software and cloud technology sector as a strategic thinker and leader. She came to Salesforce from a series of startups. She's led multiple product marketing teams, including Einstein Analytics and Quip.

More by Keri

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