Selling your business is the most difficult event during a business owner’s journey. Period. After 25 years advising business owners, I have developed a deep conviction in the phrase that during ownership transition “the soft stuff is the hard stuff.”
Historically, something has always been thought to disrupt companies, from the printing press to machinery to Excel, and now AI. Every day, I log into LinkedIn or other social media and see new content about AI. Some are inspiring, some educational, but there are also warning AI will replace the whole workforce.
This quote resonates with me: “Work on the business, not in the business.”. For me, part of working on the business is making myself more resilient, healthy and happy so that I can make the investments in the rest of the business. If I’m not stable, energized and able to bounce back from challenges, then how am I supposed to work on the rest of the business?
Big Deal Excitement Can Blind Us. Imagine you have a massive deal in the pipeline. This is it, it is your ticket to the big time. You’re excited, as you should be. But is the deal a good deal or not? Sometimes our excitement lends us rose-tinted glasses; glasses that blind us to agree to terms or be overly optimistic for performance. We once experienced a client engagement where our excitement blinded us, which caused us to lose meaningful money, something we didn’t anticipate due to several terms within the deal.
Most mid-market companies track the obvious metrics such as revenue, margins, utilization rates. But when we dig into their operations, we consistently find that the data they’re watching isn’t telling them where to actually focus their attention. They’re measuring outcomes instead of the inputs that drive those outcomes. The result is that even strong operators end up reacting to lagging indicators instead of managing the levers that actually move them.But there’s one question that still trips up even seasoned professionals:
Multiple rocket stages are an apt metaphor for exploring the free scaling aspects of small teams. As the number of small teams expands in the first stage, it reaches a tipping point around 7 to 9 teams where a second stage forms, requiring another small team of up to 7 to 9 team members to govern and manage the other teams. The second stage allows the professional services firm to scale to around 100 employees. To scale to around 1000 employees, a third stage of another small team is necessary to govern and manage the earlier two stages of small teams of small teams. These stages can be added iteratively so long as small teams can collaborate effectively with an overarching shared purpose with minimal friction. This is the fractal nature of layering small teams in a free scaling structure.
You’re scaling the firm. You are no longer the Chief Rainmaker who is winning every deal. You have salespeople now who are generating leads and closing deals. But let’s be honest about what happens when a deal is stuck. When the client objects to the price, deliverables or compares you to the competition.
One of our core beliefs at Tenzing is that deep, authentic conversations have the power to drive business forward. Over the years, we’ve found that sharing stories—especially those of fellow Experts, Operators, and Practitioners—has not only enriched our community but also helped strengthen our brand and attract new clients.
Every founder experiences the exhilarating rush of building something new. However, this initial energy often gives way to overwhelm as daily operations become overbearing. This article shares the journey of a Collective 54 member who met this juncture and found a path forward. Names and specific details are omitted to focus on universal lessons that echo the struggles many others face.
As I’ve spoken with more members of Collective54 about their Go-To-Market strategy, there is a common theme. Their primary Buyers, their Heroes, are typically C-level executives, but rarely the CEO. This is true of professional services generally, as CFOs, COOs, CIOs and CHROs dominate the landscape of Buyers. Proserv firms vary in their capability to engage and stay relevant with CEOs. If you are wondering how effective your team is at engaging CEOs, there are two leading indicators to look for.