How to Build a Sales Coaching Culture | SBI Podcast
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Sales organizations constantly look for ways to scale success, and the frontline manager serves as the ultimate force multiplier for the entire team. Companies frequently promote great sellers into management roles and provide them with minimal training. These new leaders often find themselves buried in administrative work, and they spend their days simply putting out fires to close deals. Organizations must equip these managers with a clear operating rhythm to establish a true coaching culture.
In this podcast episode, I spoke with Mark McWatters, Vice President of Sales at Ambition. We discussed the process of turning administrative managers into highly effective coaches. Mark shared his insights on establishing structured routines, and we explored the best ways to leverage performance data to drive team success.
1. Establish a Consistent Operating Rhythm
During our conversation, Mark highlighted a fundamental flaw in how companies treat new sales leaders. Organizations frequently promote their best sellers into management roles, and they simply put them through a basic two-day training course before expecting them to lead. These new managers are expected to drive results immediately, and they often end up feeling lost in administrative tasks. We must start obsessing over our frontline managers because they act as the true force multiplier for the entire sales team.
To fix this issue, leaders must establish a consistent operating rhythm. Success in sales management is not rocket science. Teams require a defined schedule of weekly one-on-one meetings alongside bi-weekly skill-based coaching sessions. Everyone must also agree on a regular time for the routine forecast call. Once these core pillars are set, managers need to clearly define exactly what should live within each of these conversations. Setting this clear expectation allows the manager to be much more strategic in helping the team. The operating rhythm gives everyone a predictable beat to march to, and it effectively reduces the feeling of micromanagement.
What frontline managers need to do:
- Define the schedule
Set specific times for weekly one-on-ones, routine skill coaching, and forecast calls - Document the process
Create clear expectations around the specific topics covered in each meeting type to keep the team focused and aligned
2. Empower Rep-Led Coaching Conversations
Once you establish that operating rhythm, the actual coaching conversations must be rep-led. Mark explained that managers often make the mistake of walking into a one-on-one meeting and simply handing out a list of directives. This top-down approach turns the session into a weekly beating, and it fails to build real capability within the seller. The salesperson must absolutely drive the agenda. They should come to the meeting prepared to share their current focus areas, recent struggles, and specific highlights from the previous week.
This active participation forces the representative to process their own development needs. As a leader, you want your team members to own the outcome of these discussions. The rep brings their own challenges to the table, and the manager gains the perfect opportunity to respond and gently guide them toward a solution. We can now pair this rep-led approach with actual conversational intelligence data from our AI tools. Managers no longer have to guess what went wrong on a call, and they can use concrete insights to make the coaching session incredibly productive.
What frontline managers need to do:
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- Shift the agenda
Require salespeople to bring their own updates, answers, and challenges to the weekly meetings - Guide the discussion
Use the representative's input and concrete data to facilitate a productive problem-solving session that allows the seller to own the outcome
- Shift the agenda
3. Use AI to Reduce Administrative Tasks
Mark and I explored the rapidly changing landscape of artificial intelligence (AI) in sales. As a sales leader, you handle a massive amount of administrative work daily. You spend countless hours looking at different systems and reviewing historical data to prepare for a simple one-on-one meeting. AI tools truly excel at these mundane tasks, and they can easily synthesize this information to save you valuable time.
Most managers only have about five minutes to prepare for a coaching conversation. Platforms like Ambition analyze performance metrics alongside historical coaching context to generate a comprehensive pre-read in just one minute. We can confidently offload pipeline checking and basic CRM updates to these intelligent systems. Leaders then gain the freedom to focus entirely on human skills like active listening, relationship building, and team motivation. These uniquely human traits remain highly essential because artificial intelligence still struggles with complex creativity.
What sales leaders need to do:
- Offload routine tasks
Assign data synthesis and CRM hygiene tracking directly to AI platforms - Focus on human connection
Use your saved time to double down on team motivation and active listening
4. Revive the Lost Art of Encouragement
Mark brought up a powerful point about how we motivate our teams. Encouragement is unfortunately becoming a lost art in sales leadership. Many people mistakenly associate it with soft cheering or blindly celebrating losses. Real encouragement involves telling your team that you genuinely want them to win, and you must actively show them your shared commitment to that goal.
When a representative successfully sets a meeting with a key decision-maker, we need to celebrate that specific milestone. The event might not be a closed deal just yet, and we still recognize that key step to build positive momentum. You create a lasting culture change by marrying this genuine encouragement with clear accountability. This powerful combination ultimately drives incredible results for the entire organization.
What sales leaders need to do:
- Celebrate leading indicators
Recognize key steps like setting a meeting at power to build consistent positive habits - Combine support with accountability
Pair your encouragement with clear performance expectations to drive meaningful culture change
🎧 Listen to the Full Conversation
Mark McWatters and Ray Makela discuss the process of elevating frontline managers into highly effective coaches. The conversation revolves around how sales organizations can build a strong operating rhythm and leverage data to drive massive team success.