"Not everyone knows how to coach. Being good at something doesn't mean you're gonna be able to pass the knowledge on in an effective way."
This hard truth shared by Jackelyn Skudra, VP of Sales at Xello, during SellMeThisPen podcast hits at the core of why so many sales managers struggle with coaching their teams effectively. Despite their own success in sales, they often fail to transfer those skills to their reps during one-on-ones in a way that creates real improvement.
In this article, we'll explore a proven framework for effective coaching during one-on-one based on insights from a seasoned sales leader with over 20 years of experience transforming high-performing sales teams. We'll break down the common mistakes most managers make and provide you with an actionable 5-step framework that will enhace your coaching sessions.
Sales managers face a challenging reality: the skills that made them successful sales reps are not the same skills needed to be effective coaches. As Jackelyn points out, many managers default to ineffective coaching methods simply because they haven't been taught how to coach properly.
If you recognize any of these approaches in your coaching style, it's time to reconsider:
So what's the alternative? Let's explore Jackelyn's 5-step framework for one-on-ones that helped her deliver results.
The coaching process begins before the actual coaching session. Instead of immediately sharing your observations about a call, ask the rep to:
This approach instantly changes the dynamic from manager-directed criticism to self-directed improvement. As Jackelyn explains, this puts the rep in the driver's seat of their own development journey.
Once you're in the coaching session, resist the urge to tell the rep what they did wrong or how to fix it. Instead, use targeted questions to guide their thinking:
Questions are the secret weapon in effective AI sales coaching. They accomplish several things that direct instruction cannot: help reps self-discover improvements, build problem-solving skills, create deeper learning through personal insight and develop autonomy rather than dependency.
"When a rep arrives at a solution themselves, they're much more likely to implement it effectively," Jackelyn shares. "It becomes their own insight rather than just following orders."
Rather than attempting to fix everything at once:
By focusing on one theme at a time, you create manageable change that actually sticks. This approach ensures that improvements build on each other over time, rather than creating a scattered, ineffective development path.
Knowledge without application has no value. After identifying an area for improvement and discussing strategies, the critical next step is creating clear accountability:
"After we've done a coaching session, I tell them: The next time you apply it, share that recording with me. I want to see it in action."
This simple request transforms theoretical coaching into practical improvement. It creates:
Without this step, even the best coaching insights often remain unused. With it, you create a culture of constant skill development and application.
The final step in the framework is measuring improvement. Effective coaching should produce measurable results in:
Jackelyn recommends focusing on one metric at a time that directly relates to the skill being developed. This creates clarity around whether the coaching is actually working.
Beyond the 5-step framework, Jackelyn shared perhaps the most surprising insight of all:
"You have to admit that you're not the expert."
This counter-intuitive approach—showing vulnerability as a manager—creates the psychological safety needed for genuine development. By acknowledging that you're there to help reps develop a different mindset and skillset, but that you don't have all the answers, you create space for collaborative growth.
Sales coaching doesn't have to be a mysterious art form or a dreaded obligation. With Jackelyn's 5-step framework, it becomes a structured, effective process that empowers both managers and reps.
The key is shifting from telling to asking, from overwhelming to focusing, and from theoretical to practical. When combined with appropriate vulnerability and consistent accountability, this approach creates the conditions for continuous improvement and sales excellence.
Start by implementing just one element of this framework in your next coaching session. Watch how it changes the dynamic and opens new possibilities for growth within your team.
In this episode of SellMeThisPen Podcast, Michael and Jackelyn dive deep into effective sales coaching techniques, exploring how managers can transform their approach from dictating solutions to guiding self-discovery. They discuss common coaching mistakes and share practical frameworks for helping sales reps develop through focused improvement, accountability, and measurement.
Jackelyn Skudra is the VP of Sales at Xello with over 20 years of experience in sales leadership. Known for transforming sales teams through effective coaching methods, she brings practical insights from her successful career developing high-performing sales professionals through structured coaching approaches.
