In a recent LinkedIn post, Tobi Oluwole discusses a strategic approach to scaling a coaching business, highlighting the transformative power of asking the right questions rather than focusing on perceived impossibilities. Oluwole shares the journey of a founder he began working with this year, who aimed to grow his business from $250,000 to $750,000 within a single year to enable his parents’ retirement. This founder had been stagnant at a similar revenue level for over three years.
Instead of dwelling on the difficulty of such an ambitious goal, Oluwole explains that their focus shifted to a series of targeted questions designed to unlock growth. These key inquiries aimed to address critical areas of the business.
“How do we increase the lead flow with better content & paid ads?”
Strategic Questioning as a Growth Catalyst
Oluwole emphasizes that the initial step was not to provide answers, but to facilitate a process of discovery through potent questions. He outlines several pivotal questions that were central to their strategy:
- How do we increase the lead flow with better content & paid ads?
- Who is the ideal client for the offer and what makes them so ideal?
- How do we boost the life time value of each customer to $25k/year?
- How do we delegate 80% of his role and focus on what he does best?
These questions, as Tobi Oluwole points out, are designed to dissect the core components of a scalable business: lead generation, client definition, customer lifetime value, and operational efficiency through delegation.
Overcoming Pricing Fears and Achieving Tangible Results
A significant hurdle for the founder, according to Oluwole’s account, was the fear of customer pushback on new pricing structures. This is a common anxiety for service-based businesses looking to increase their rates.
“His biggest fear was that customers would push back on the new pricing.”
However, Oluwole’s post reveals that by addressing the value proposition and the ideal client profile more effectively, this fear proved to be unfounded. The strategy paid off rapidly. In just the first 45 days of implementing their revised approach, the founder successfully closed $160,000 in new revenue.
The Mindset Shift: Growth Through Action
Tobi Oluwole uses this case study to underscore a broader principle about achieving ambitious goals. He argues that the key lies in understanding the ‘cost’ of achieving a goal, which includes not just financial investment but also strategic effort and a willingness to overcome internal barriers.
“Every goal is possible if you understand what it costs to get it.”
Furthermore, Oluwole challenges the common self-limiting belief of not being qualified enough to pursue big objectives. He advocates for a proactive mindset where growth is a direct result of taking on challenges that push individuals beyond their current capabilities.
“You grow by doing things that you aren’t qualified to do yet.”
This perspective, shared by Tobi Oluwole on LinkedIn, offers a powerful framework for entrepreneurs and business leaders looking to break through plateaus and achieve significant growth by focusing on strategic inquiry and embracing challenges.
📝 About This Content
This article is based on insights shared by Tobi Oluwole on LinkedIn.
📅 Originally posted on September 3, 2026 | View original post on LinkedIn →