Podcast: How American Express Builds Long-Term Selling Skills


Episode summary

In this re-airing of an episode of Ready Set Sell, Hannah interviews Jeffrey D. Hatchell, an accomplished author and the Vice President of U.S. Sales Enablement & Global Leadership at American Express. With extensive experience as both a sales leader and a performance coach, Jeffrey brings valuable insights to the table. He is also the author of the highly regarded book, The Inspired Career, which focuses on inspirational leadership. Currently, Jeffrey leads a sales enablement organization dedicated to equipping salespeople and their leaders with the necessary skills to enhance their effectiveness with customers and prospects.

During their conversation, Hannah and Jeffrey delve into the concept of leading an inspired career. They explore how sales professionals can develop a deeper awareness of their own potential and discuss practical steps individuals can take to improve their leadership abilities. Jeffrey emphasizes the significance of transforming followers into leaders and cultivating leaders who can drive positive change within their organizations. He also sheds light on his role as an advocate for the Black community in the business world.

Overall, this engaging episode provides valuable insights into the pursuit of an inspired career, the importance of self-awareness for sales professionals, and the initiation of leadership skill enhancement. Furthermore, it highlights Jeffrey’s commitment to empowering individuals and fostering positive change within the business community, particularly in support of the Black community.

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Deal Coaching vs. Skill Coaching: What’s the Difference? (It’s Big and it Impacts Revenue)

Managing your sales team involves a lot of responsibilities: from initial onboarding for new hires, to ongoing training and coaching, to regular performance assessments.

Both deal coaching and skill coaching are strategic techniques for guiding sales reps, each with its own goals and procedures. Effective coaching can improve win rates by 27% or more — but which approach will help you hit that potential? 

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Win rate improvement with effective coaching

Say you are an experienced rock climber, and you’re teaching a newbie the basics. In this scenario:


Deal coaching

Skill coaching

Deal coaching would be teaching this person exactly how to tackle the formation in front of them. You go through each foothold and each hand placement so they know exactly what lies ahead of them.

Skill coaching would involve going over a foothold that lies ahead, but also providing different scenarios you may encounter in the future and how to approach them.


Sales managers typically coach sellers through individual deals. While that’s important, skill coaching is imperative to building a coaching culture and preparing sellers for consistent quota attainment. Continue reading to discover the distinctions between the two and which will be more lucrative for your organization.

Deal coaching: Working through the pipeline

Deal coaching focuses on buyers and what resources are needed to engage them and move them further along the sales funnel. While typically unstructured, these sessions help reps work through specific deals in their pipeline for more immediate impact.

The goal of deal coaching is to remove stalled or unqualified deals, adjust effort toward real opportunities, and strategize how to tackle those opportunities. In deal coaching sessions, managers ask questions like:

  • What is this buyer’s business need?
  • What unique value does our solution bring to this buyer?
  • Who are the decision-makers?
  • What objections (if any) have there been thus far?
  • Who are we competing against for this buyer’s business?

By answering these questions together, manager and rep can together come up with the best plan of attack, determining what content and approach will be most relevant and drive the deal to close. And while this method may improve a single interaction with a buyer, its benefits tend to be temporary.

Skill coaching: Polishing the competencies that matter most

Skill coaching, on the other hand, focuses on the sellers themselves. Rather than walking through individual deals, its objective is to develop the knowledge and behaviors most critical to success. These may differ from one organization to another, but the following are the most common skills we see amongst top-performing salespeople:

Assessing tasks and prioritizing them

Capturing buyers’ attention and keeping them engaged throughout the sales cycle

Effectively express the business value to address buyer needs

Tuning into buyer challenges to adequately address them

Managing and mitigating buyer hesitation and/or doubts

Understanding customer pain points and how your solution helps to solve them


Skill coaching is an ongoing effort, promoting professional development, learning reinforcement, and evaluation. To contribute to their team’s growth, managers can send them to a class or seminar or assign them a book to read. Managers also assess reps’ training completion and performance for further insight into knowledge and skill improvement. Leveraging data, managers are empowered to have more personalized and relevant one-on-one coaching sessions with their reps.

Which coaching style drives results?

Managers have limited time with each rep, and coaching conversations often become deal reviews — with only 5% of time being spent giving useful feedback on next steps.

Deal coaching is advantageous in the short term; for instance, when a buyer has an immediate need or request. In this case, giving the rep training materials will not help; you’ve got to offer specific and timely advice that helps the seller quickly and competently resolve the problem.

But the most effective sales coaching should identify individual areas for improvement for each rep, then provide content and regular guidance to develop skills – in other words, skill coaching.

If you are teaching someone to rock climb, you need to prepare them for more than just what is in front of them. Teaching and mastering the basics will ensure they can tackle more difficult walls and structures in the future.

It’s a longer game, but working on the high-level abilities that lead to success pays off. Coaching sellers through skill gaps better positions them down the road so they’re able to navigate deals more effectively and, ultimately, close them.

Managers who use skill coaching also stand to be trusted mentors to the members of their teams. Investing time and effort into building a seller’s personal and professional growth earns their respect and loyalty.

Digital tools for successful skill coaching

While deal coaching has its benefits for short-term needs, skill coaching delivers results that generate long-term revenue growth. Using data to inform one-on-one sessions, providing the right learning content at the right time, and ultimately cultivating the behaviors and knowledge of top-performing sellers, your team will achieve peak productivity and revenue growth.

With data at the heart of skill coaching, leadership needs the right tools to administer learning materials and track both individual completion and performance. A revenue productivity platform automates onboarding and training so managers can focus on what’s important: giving sales reps what they need to reach success.

Mindtickle enables front-line sales managers to collaborate with sales reps to close knowledge gaps and achieve higher quota attainment. Kickstart a culture of coaching with tools that make sales readiness a reality for your team.

This post originally published in March 2021 and was updated in July 2023. 

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4 AI Sales Tools That Will Help Your Sales Team Close More Deals

A 2021 study by Gartner found that 88% of CSOs have already invested in, or are considering investing in AI tools and technologies for their sales teams. If your team isn’t already using AI tools, they risk being left behind. Your competitors are already using AI to optimize their processes, work more efficiently, and equip their reps with more information ahead of any sales interaction.

Sales teams use AI tools in different ways, like:

  • Improving lead prioritization based on sales interactions
  • Analyzing data from customer conversations
  • Personalizing rep training and coaching recommendations based on live sales interactions

AI tools will help your salespeople and front-line managers find the important and actionable insights within the avalanche of data that modern sales generate. Here are some of the tools that can help you sift through and actually use this data and insights.

  • Mindtickle

Many sales organizations know the 80-20 rule all too well: the all-too-frequent situation where 80% of the revenue is driven by 20% of their reps. But when one of your top performers leaves, that can cause a major headache (and revenue shortfall) for sales departments. Instead of continuing to hope that their top reps don’t leave, forward-thinking companies turn to Mindtickle. Our platform empowers sales reps to achieve a continuous state of sales excellence by using its tools and processes to increase reps’ knowledge and improve their performance. With Mindtickle, you can correlate competencies with revenue outcomes, helping you focus on the individualized knowledge, skills, and behaviors that help your reps win deals.

Mindtickle uses AI to analyze all sales interactions, from customer calls to emails, to assess reps’ performance at each stage in the sales process. Then it uses that data to provide AI-driven coaching and training recommendations that are personalized to each rep. These recommendations, exercises, and activities help to raise the performance level across your whole sales team so all agents can become top performers and achieve sales readiness.

An AI-powered sales readiness platform like Mindtickle offers sales leaders (and their teams) many benefits that have a positive impact on the rest of the organization:

  • Managers automatically get better visibility into their reps’ performance, including specific areas for improvement so they can prioritize coaching where it will have the biggest impact.
  • It creates a team culture of continuous improvement, as reps receive training and coaching recommendations on an ongoing basis, not just once a quarter in your sales kickoff.
  • It raises the team performance standards, which leads to improved close rates, as reps are better able to manage complex or high-value sales interactions.

A platform like Mindtickle helps your sales team close more deals by ensuring all your reps are ready for their upcoming sales calls, equipped with the skills, knowledge, and best-practice behaviors to perform at their best.

  • Rollio

Incomplete data in your CRM makes it impossible for sales leaders to monitor the progress of leads through the sales funnel or know when their reps are facing challenges and need support. Tools like Rollio make it easier for teams to update records in the CRM after every customer interaction to improve the quantity and quality of your CRM data.

Rollio connects with Salesforce and uses AI to enable sales reps to interact with their CRM like they’re speaking to a person. For example, agents can ask Rollio to update a prospect record in Salesforce using conversational language, for example, “Update my opportunity with Mindtickle. Add a pricing conversation as a next step, and push the close date back one month.” Rollio’s AI will interpret their instructions and update the record accordingly. This speeds up data entry, so your customer records are more up-to-date and contain more information about sales interactions compared with updating records manually.

An AI-driven tool like Rollio benefits sales reps and managers by:

  • Reducing time spent on data entry, so reps can spend their time on higher-impact sales interactions instead
  • Improving the quality and quantity of data in your CRM, so reps and managers have access to all the relevant data for prioritizing leads and follow-up sales activities
  • Giving sales leaders an easy way to get updates about their team’s activities

More complete data in your CRM helps sales professionals close more deals, as they have the full context available for their next interaction with a prospect. For example, reps can personalize follow-up messages based on their conversation, and managers can more easily support agents when CRM data suggests a deal is moving toward closed/lost.

  • Conversica

Forrester found that sales reps spend only 23% of their time on core sales activities. Tools like Conversica enable sales organizations to increase their team productivity (in terms of touchpoints and follow-ups) without hiring more reps and increasing their headcount.

Conversica provides sales teams with an AI assistant to automatically follow up with leads via chatbot, email, or SMS. It helps increase the number of touchpoints leads have with your company by automating low-value acknowledgment messages while enabling your reps to focus on higher-value sales interactions. In addition, Conversica uses conversational AI to speed up response times and scale up your team’s productivity without needing additional team members to do so.

  • For sales teams, this means:
    They can automate lead follow-up, so prospects hear back from you sooner
  • Leads are kept warm and engaged between interactions with real members of your team
    Sales cycles may accelerate due to an increased number of touchpoints in the process
  • Reps have more time to personalize their interactions with customers, as low-value acknowledgment-style interactions are handled automatically

AI tools like Conversica, which provide sales teams with a virtual assistant, help them close more deals by spending more time personalizing their messages and less time on routine prospect interactions.

  • Troops

If sales leaders don’t know how prospects are progressing through their sales funnel, it becomes difficult (or almost impossible) to accurately plan team resources or prioritize upcoming sales interactions. A revenue communication tool like Troops gives sales teams — both reps and managers — ongoing visibility into your team’s performance by surfacing and sharing relevant updates from your CRM.

Troops connects your CRM with messaging apps your team uses all the time through integrations with Slack and Microsoft Teams. It automatically delivers notifications in your messaging tools to provide your team with insights, updates, or reminders about deals in their pipeline. It also notifies you in real-time when anything happens that will have a significant impact on revenue — such as a deal that’s marked closed/won or closed/lost.

It offers several benefits for sales organizations:

  • Sales leaders get a better overview of deal flow and rep performance
  • Improved pipeline visibility means managers can improve the accuracy of their sales forecasting
  • You can leverage team expertise to move deals forward, as all updates are visible to your whole team

AI tools that give your sales leaders better pipeline visibility help sales teams close more deals by making it easier for managers to support more complex customer interactions. Managers are more aware of ongoing sales conversations and the potential roadblocks and can support their team where needed.

AI sales tools will empower your team — not replace them

Many sales teams still have a lingering fear that AI sales tools will replace them and steal their jobs. Or they worry the AI will become a data dump, giving their teams piles of data with no context to help them draw actionable insights.

But AI technology actually empowers and enables your sales team — it helps them do their jobs better and gives them the data and insights they need to help them close more deals. There are lots of different ways AI can support sales teams, so if you’re ready to add artificial intelligence into your department’s toolkit, check out our Buyer’s Guide to Conversation Intelligence Solutions.

This post was originally published in March 2022 and was updated in July 2023. 

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