Training ≠ Coaching: What the Old Playbook Gets Wrong

The traditional playbook for training front-line teams (Sales & Customer Success) is pretty cut and dry: recommend a selection of classic books (Never Split the Difference, The Psychology of Selling), hold Sales Kickoff sessions (SKOs) with external speakers, have managers run 1:1 call reviews, etc.

While these methods are usually considered tried and true, there are a few challenges that they don’t address:

  1. People forget quickly: SKOs are great for initially engaging your Sales team and cultivating excitement, but these sessions often see a return to normal within 90 days. There’s even a name for this phenomenon called the Ebbinghaus Forgetting Curve, which demonstrates that people usually only retain about 20% of the content in the long term.
  2. Training ≠ Coaching: Front-line team development often focuses on training employees, educating them on product/market knowledge. Strategies like creating a curriculum and giving recommended reading are great ways to train front-line employees and give them the knowledge they need to be successful. However, coaching is equally important for developing front-line employees’ skills. Skills are different from knowledge in that they’re used in time-sensitive, high-pressure situations. For example, being able to flawlessly run a meeting or execute a live negotiation requires skills, not just knowledge. Skills are developed not through training, but through coaching. Coaching your front-line employees is similar to how you would coach a sports team — practice, practice, practice. Traditional methods for front-line teams often don’t incorporate enough opportunities for practice. A quote from Connor on the importance of practice:
“Your team needs to practice, because if you’re not practicing with them, they’re practicing on customers.”

A 5-Step Playbook for Developing Knowledge & Skills in Front-Line Employees

1. Start with A Clear Map

The essential foundation for developing knowledge and skills in your front-line teams is outlining exactly what members need to be successful, rather than assuming implied “general Sales skills.” At Clearbit, Connor designed the concept of Skills Trees. A Skills Tree is a visual representation of the skills that a front-line rep must master in order to grow in their role. For example, the Skills Tree for SDRs is divided into “Prospecting Skills” and “Having a Conversation.” Within each category, there are ~10 skills a rep needs to achieve mastery.

2. Focus on Adoption

Once you communicate to the team what skills they need, you have to also give them the tools to master them. For front-line teams, that means practice, practice, practice. For example, the Sales team at Clubhouse has mock call sessions twice a week. The team is broken down into groups of 3 to 5 and each person in a group is given the role of the customer, the salesperson, and the coach. The groups then rotate who plays each role and get the opportunity to practice rapid-fire mock calls.

3. Build Manager Skills

Managers are the main coaches of a front-line team, and there are distinct skills managers need to be able to lead their team successfully. The primary skills a manager needs to hone are the ability to execute an effective 1:1, a team call review, and a practice session. In Connor’s experience, coaching in groups rather than 1:1 is orders of magnitude more effective. At Clubhouse, team members submit calls to the manager every week; the manager then comes to the team meeting with snippets of the calls to review and get group feedback on.

4. Create Comfort & Encourage Engagement

The key to making this practice exercise successful is to make everyone feel comfortable enough in the space to participate. A few tactics Connor uses to encourage engagement:

  • Managers and executives go first: The first round of these call feedback sessions should be for managers and executives. By observing their leadership making mistakes and having the opportunity to give upward feedback, front-line employees realize that it’s normal and acceptable to make mistakes and therefore are more primed to participate in the future.
  • Self Feedback: Before the group gives a team member feedback on her call, the team member does a self-reflection first. By allowing members the opportunity to give themselves feedback, they often end up addressing a majority of the issues before anyone else does.
  • Celebrate Participation: It can be really difficult to receive public feedback. So during these practice sessions, Connor notes that it’s incredibly important to celebrate members that participate even through small gestures like giving them a round of applause before they begin their call review.
  • Measure and Track success: Alongside the Skills Tree, Connor developed the concept of Levels Keys. A Levels Key helps reps and their managers measure success, and gauge what level of mastery a rep has reached. Levels Keys are great for navigating employee reviews and potential promotion discussions.


Level 1: Communicate the skill and explain how it should work
Level 2: Demonstrate the skill during roleplay and other off-call interactions


Level 3: Execute the skill 1–2 times per week with some issues
Level 4: Execute the skill 80% of the time, expected with minor issues
Level 5: Execute the skills 80% of the time, expected with no flaws


Level 6: Teach the skills to others
Level 7: Coach others practice and develop the skills

5. Hire for the System

Once you clearly map the skills needed to be successful on your team, you can build them into the new hire interviewing process. Similar to the Levels Key, Clubhouse scores candidates on levels of mastery for each skill they’re hiring for. The interviewer judges the candidate on their question-based selling, where do they fall on the leveling system, what their existing skills are, and how that maps to the skills needed for the organization.

Bonus Hiring Tip: Testing for Coachability

Another practice Clubhouse uses in the interview process is that they have the candidate run through a mock sales call — but in a slightly unique manner. In order to test for coachability — one of Connor’s most important traits to hire for — the interviewer will provide feedback to the candidate, give them ~30 minutes to incorporate it into their language, and then have the candidate re-do the sales call. The level to which the candidate is able (and more importantly eager to) incorporate the feedback that was given, the more coachable they’ll likely be if hired.