May 11, 2025 | Read online
The One Question That Will Transform Your 1:1s
by Kevin 'KD' Dorsey
All right, let’s talk about the one question that’s sabotaging your one-on-ones and holding your reps back. I’m talking about the classic “How can I help you?” that every well-meaning manager asks. But here’s the thing, y’all - this question is actually breeding learned helplessness, stifling problem-solving skills, and creating a dangerous dependency on the manager.
I’ve spent years leading sales teams and crafting coaching frameworks, and I’m telling you, we need to flip the script. Instead of asking “How can I help?”, start asking “What challenges are you facing?” This small change is going to transform your reps from passive recipients waiting for solutions into proactive problem-solvers taking ownership. It fundamentally changes the dynamics of empowerment and accountability.
So let’s dive into why this one shift is so powerful and how it can revolutionize your one-on-ones and take your team’s performance to the next level.
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"How can I help?” Breeds Learned Helplessness
Now, I know “How can I help?” seems like the supportive thing to ask, but it’s actually conditioning your reps to just dump their problems on you and give up responsibility. This leads to a decline in motivation and problem-solving abilities - it’s called learned helplessness. Research by Seligman way back in 1972 showed that when people repeatedly face situations where they feel they have no control, they eventually stop trying to change things, even when they can.
This is poison for a sales team. Reps who don’t build those crucial problem-solving muscles are less likely to innovate, adapt, and overcome obstacles on their own. Instead, they just wait for the manager to swoop in and save the day, and that’s not sustainable or scalable, y’all.
"What Challenges Are You Facing?” Forces Ownership
So here’s what we’re going to do instead. We’re not going to point out what’s not working. We’re going to ask, “What challenges are you facing?”. This puts the onus on the reps to identify and articulate the obstacles themselves. They have to start thinking through potential solutions, and that encourages a mindset of personal accountability and agency.
Reps have to take the first step instead of waiting for you to solve their problems. This shift in responsibility fosters a culture of ownership and self-reliance. When you ask reps to pinpoint their challenges, they engage in critical thinking and problem-solving. This approach empowers them and prepares them to handle future challenges on their own.
Benefits of This Reframing
Notice how we’re framing this - we’re not asking how we can help. We’re asking what challenges they’re running into. This is about identifying the issues, not solving them just yet. This subtle but powerful change develops reps’ critical thinking, problem-solving abilities, and decision-making skills, and that leads to better sales performance.
When reps take the first crack at identifying and addressing their challenges, they build self-sufficiency and resourcefulness over time. You, as the manager, can coach more effectively, focusing on guiding reps through their thought processes rather than providing ready-made solutions. This not only enhances the reps’ skills but also frees up your time and bandwidth from playing Solver-in-Chief.
Plus, this approach aligns with the principles of effective coaching. By encouraging reps to take ownership of their challenges, you foster a growth mindset within your teams. This mindset shift is crucial for long-term success because it promotes continuous learning and improvement.
Conclusion
So let’s recap the subtle but powerful impact of this one small change. By simply shifting the question from “How can I help you?” to “What challenges are you facing?”, you transform your one-on-ones and your reps’ mindsets. This empowers reps to take ownership of their challenges, fosters critical thinking and problem-solving skills, and ultimately leads to better sales performance.
I want you to try this approach in your next one-on-one meetings and see the difference for yourself. Empower your reps through this reframing, and watch as they become more self-reliant, resourceful, and effective. This one small change can have a profound impact on your team’s growth and success. Let’s go!
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