Picture this: every time sales reps walk into a coaching session, their stomach drops. They know what's coming - a dissection of everything they did wrong on that last call, followed by a lecture about what they should have done instead. Sound like an experience you wouldn’t wish for anyone?
Here's the uncomfortable truth: quite often sales coaching feel exactly like this for reps. Leaders jump straight to feedback without listening, turning what should be growth opportunities into dreaded interrogations. But what if there was a better way?
Kieran Smith, Senior Director of Enablement at TechnologyAdvice, has cracked the code on effective coaching with a simple yet powerful approach. With over a decade of experience in sales leadership, Kieran revealed a framework that transforms coaching from a one-way feedback session into a collaborative conversation that actually drives improvement.
In this article, we'll explore Kieran's 4-question framework that turns coaching sessions from something reps dread into sessions they actually look forward to.
Before diving into the solution, let's acknowledge the elephant in the room. Traditional sales coaching often follows a predictable pattern: the manager does most of the talking, points out what went wrong, and tells the rep what they should do differently next time. This approach has several fundamental flaws.
First, it creates a defensive mindset. When reps know they're about to be critiqued, they naturally become defensive rather than receptive to learning. Second, it assumes the manager has all the insights while the rep has none. This overlooks the fact that the rep was actually in the conversation and may have picked up on nuances the manager missed from listening to a recording.
Most importantly, traditional coaching doesn't create ownership. When solutions are handed down from above, reps are less likely to internalize and implement them. They become passive recipients of advice rather than active participants.
Kieran's approach starts with a fundamental redefinition of coaching itself. As he puts it:
"My definition of coaching is a human interaction that is led by questions that influences future performance."
This definition is crucial because it shifts the focus from what happened to what could happen. Coaching isn't just feedback on past performance – it's guiding someone to improve future performance through thoughtful questions.
This question-led approach works because it:
The beauty of this framework is that it works whether you're coaching a top performer looking to get even better or helping a struggling rep find their footing.
Let's break down Kieran's four essential questions that transform coaching sessions from dreaded meetings into powerful growth conversations.
This opening question is deceptively simple but incredibly powerful. Instead of launching into your analysis, you start by listening to theirs. This approach immediately creates psychological safety and shows that you value their perspective.
Why this question works so well:
The key here is to listen completely before responding. Don't interrupt, don't jump in with corrections, and don't start formulating your response while they're talking. Give them the space to fully express their thoughts about the call or meeting.
After hearing their initial thoughts, this follow-up question provides a concrete baseline for the conversation. As Kieran notes,
"That number they give is fairly arbitrary, but it helps to understand where they would place themselves."
This scaling question serves several important purposes:
Don't get too caught up in whether their self-assessment is "accurate" by your standards. The number itself isn't as important as what it represents – their honest assessment of their performance.
This is where the magic happens. Instead of telling them what to improve, you're asking them to identify the path forward. As Kieran explains:
"If that was a 6, what would it take to take that from a 6 to a 7?"
The brilliance of this improvement question lies in its psychology:
This question transforms the rep from a passive recipient of feedback into an active problem-solver. They're not just hearing what you think they should do – they're figuring out what they think would work best.
Sometimes, despite your best questioning efforts, the rep might not arrive at the insight you believe would be most helpful. This is where Kieran's fourth question comes in. As he acknowledges:
"Sometimes you can't question your way out of it. Sometimes you have to give an answer as a coach."
This question works because it allows you to introduce new perspectives while still maintaining the collaborative tone of the conversation. You're not commanding or demanding – you're suggesting and exploring.
Use this approach when:
The key is framing your suggestion as a question rather than a statement. Instead of saying "You should try this," you're asking "Have you thought about this?" This subtle difference maintains their ownership of the decision while providing the guidance they need.
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The success of this 4-question framework isn't just about the questions themselves – it's about the mindset behind them. Great coaching isn't about having all the answers; it's about asking the right questions.
This approach works because it fundamentally changes the dynamic of the coaching relationship. Instead of a teacher-student relationship where knowledge flows one way, you create a collaborative partnership focused on mutual discovery and growth.
The framework builds trust through active listening, makes coaching collaborative rather than hierarchical, creates ownership of solutions in the rep's mind, and respects their perspective and insights. When reps feel heard and valued, they're much more likely to be open to growth and change.
While human coaching conversations are irreplaceable, modern technology can enhance and support this question-based approach. AI sales coaching platforms like SellMeThisPen AI can provide reps with additional practice opportunities and real-time feedback that complements human coaching sessions.
The combination of thoughtful human coaching and AI-powered practice creates a comprehensive development environment. Reps can practice scenarios, receive immediate feedback, and then bring their insights and questions to human coaching sessions for deeper exploration.
Effective sales coaching isn't about having all the answers – it's about asking the right questions. Kieran Smith's 4-question framework transforms coaching from a dreaded feedback session into a collaborative conversation that drives real improvement.
By starting with "How do you think that went?" you create psychological safety and show that you value their perspective. Following up with a scaling question provides a concrete baseline for improvement discussions. Asking "What would make it one point better?" empowers reps to create their own action plans. And finally, offering suggestions through questions maintains collaboration while providing necessary guidance.
The next time you sit down for a coaching session, resist the urge to jump straight to feedback. Instead, start with a question, listen completely, and watch how the conversation transforms. Your reps will thank you for it, and your results will show the difference.
In this episode of SellMeThisPen Podcast, Michael and Kieran dive deep into what makes coaching sessions truly effective. They explore why traditional feedback-heavy approaches often backfire and how a question-based framework can transform these conversations into powerful growth opportunities that reps actually look forward to.
Kieran Smith is the Senior Director of Enablement at TechnologyAdvice with over a decade of experience in sales leadership. He's passionate about aligning go-to-market teams to accelerate growth and performance, and has developed practical frameworks that turn coaching from a dreaded task into a collaborative partnership focused on future success.
