Cutting Deep: How Uncomfortable Questions Lead To Real Solutions

If the consultant you’ve hired to solve your big challenges isn’t making you shift in your seats and feel a little uncomfortable at times, then they aren’t doing their job. 

Big challenges are usually a result of small issues adding up over time and never being properly resolved. And, to solve those problems, you need to dig into all of those issues and understand why they happened in the first place.


I was meeting with an engineering client a few weeks ago doing just that. They came to me with what they thought was the one problem they needed to solve. 

I started asking some tough, uncomfortable questions not because I enjoy making my clients shift in their seats but because they were questions that needed to be asked. And no one on the team was asking them.


“Do we know the revenue lost from this problem?”


“It sounds like that solution was a band-aid and cost you quite a bit of money. Is that correct?”


After both questions, the room was quiet for a few moments. And then response that usually comes with questions like these:


“Woah, Sam, you’re cutting deep.”


Yes, I do cut deep especially when we’ve got big challenges that are leaking money. Again, asking uncomfortable questions is not about causing distress for the sake of it. It’s about steering the dialogue toward the heart of the matter, bypassing surface-level symptoms and addressing the underlying issues head-on.

Why does cutting deep pay off? Because it catalyzes meaningful change. It propels us beyond the realm of quick fixes and temporary solutions, towards sustainable strategies that tackle root causes. Here's why it matters:

Uncovering Hidden Costs

Band-aid solutions come with a hidden price tag. They may offer temporary relief, but they rarely address the core issue. Since a band-aid solution doesn’t solve the real problem, the issues tend to come up again months down the line and can sometimes have an even bigger price tag by then. By digging deep and asking the tough questions, we expose the true cost of inefficiencies and ineffective practices. Whether it's lost revenue, wasted resources, or damaged reputation, understanding the full extent of the problem is the first step towards effective resolution.

Nurturing Growth Through Feedback

If you’re used to band-aid solutions then it likely means that your team is also used to never really navigating conflict and giving tough feedback to each other. Feedback is a catalyst for growth, both at an individual and organizational level. Yet, delivering candid feedback isn't always easy. It requires courage to confront shortcomings, admit to our own shortcomings, and provide constructive criticism to move forward. However, by embracing transparency and openness, we create an environment where improvement thrives. Cutting deep with feedback isn't about tearing down egos; it's about fostering a culture of continuous learning and development.

Root Out Your Crappy Processes 

Crappy processes are like weeds in a garden—they stifle growth and hinder productivity. Ignoring them or patching them up with makeshift solutions only prolongs the pain. Cutting deep involves a willingness to challenge the status quo, dismantle outdated practices, and embrace innovation. It's about streamlining workflows, optimizing efficiency, and paving the way for sustainable success.


If you’re ready to get your team asking the tough questions and find real, effective, profitable solutions, then book your free Business Transformation Strategy Call today. Don’t shy away from discomfort, embrace it because that’s where the key to progress and success lies. 

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