“If you don’t know where you’re going, any road will take you there”
– Lewis Carroll
Everyone has a sense of what “good” looks like. But that sense is often shaped by personal experience, not objective standards. If you have never worked in a high performing, scaled organization, your expectations may be too low. Founders who have not operated inside large enterprises may lack exposure to best-in-class practices. And while many entrepreneurs avoid corporate environments to preserve their independence, that choice can limit their understanding of what excellence truly requires.
Improvement over last year is not the same as success. If last year’s performance was poor and this year it is slightly better, that is still not good. Without external benchmarks and objective data, incremental progress can be mistaken for achievement.
Data Defines Reality
Metrics aren’t just for reporting – they’re revealing. They are the foundation for clarity and accountability. Data reveals whether you are improving, stagnating, or falling behind. Data—especially well-defined metrics—is the only way to objectively assess performance and if you’re on track to meet your quarterly or yearly goals. Without data, you are navigating without a compass. Senior leaders must build a data-driven foundation early. It is not optional. It is the cost of entry for effective leadership. You can either invest the time to build this foundation now or pay the price later in missed targets, poor decisions, and lost opportunities.
Working On the Business, Not Just In It
Entrepreneurs often find themselves consumed by the day-to-day demands of running a company. They are focused on acquiring customers, managing cash flow, and resolving operational issues. This is the essence of working in the business. It is necessary, but it is not sufficient.
To build something enduring, leaders must also work on the business. This means stepping back to define the long-term vision, align resources with strategic goals, and build the systems that will support sustainable growth.

It requires asking fundamental questions. Are you building a legacy business that will outlast you, or are you positioning for a strategic exit in the next few years? Is your company designed to scale, or is it optimized for short-term wins?
Working on the business is not a luxury. It is a leadership imperative. It involves setting the direction, designing the roadmap, and ensuring that every operational decision supports a broader strategic objective.
Lewis Carroll captured this challenge perfectly in Alice in Wonderland when he wrote, “If you don’t know where you’re going, any road will take you there.” Without a clear destination, even the most energetic execution can lead to wasted effort. You might get lucky and exit at a premium, but more often, the absence of strategic clarity results in stalled growth, investor pressure, and missed opportunities. Worse still, it can erode the trust of early supporters—friends, family, and employees—who believed in your vision.
Senior leaders must carve out time to work on the business. It is the only way to ensure that the company is not just surviving but building toward something meaningful.
What Investors Expect
Institutional investors do not invest in potential alone. They invest in roadmaps. They want to see a clear, data-backed plan. They want to see a credible team with a track record of execution. They want to see a scalable model with measurable milestones.
Early-stage investors may buy into vision. Later-stage investors demand proof. Metrics, milestones, and trusted operators matter more than charisma. Even when a venture capital firm is excited about your idea, they will look for validation from people they trust. These are individuals who have built companies before and can vouch for your ability to do the same.
A compelling story is not enough. Execution is everything.
Preparing for Exit
When potential buyers evaluate your business, they are typically focused on three critical factors:

Let us take these one at a time.
Valuation expectations must be grounded in market reality. If your asking price is disconnected from what the market will bear, even the best investment bankers will hesitate to represent you. Serious buyers will not engage. In one case, a private equity firm reviewed a company seeking an eighty-million-dollar valuation based on a four-times revenue multiple. During due diligence, it became clear that the business was not scalable. The founder held all the customer relationships, the CEO—his spouse—had no audited financials, and growth had stalled. The deal collapsed.
Emotional readiness is just as important as financial readiness. If you are rolling over equity or staying on the board, you need to be clear about what comes next. There is a saying: you do not retire from something; you retire to something. Whether your next chapter involves launching a new venture, engaging in philanthropy, or spending more time on personal pursuits, you need a plan for the Monday after you sell your business on Friday.
Buyers also want continuity. They typically expect the existing management team to stay in place for at least three to twelve months. While they may upgrade finance and sales leadership over time, they need a stable foundation to build on. After the founder exits, it is common for buyers to bring in a new chief financial officer, implement standardized reporting tools, and establish consistent key performance indicators. They often enhance the sales and marketing strategy as well, which may include replacing the chief revenue officer if necessary.
The bottom line is this: a successful exit requires more than a compelling valuation. It demands emotional clarity, operational readiness, and a leadership team that can carry the business forward.
Final Thought
This article is the beginning of a broader conversation. In the coming weeks, we will explore how to translate that definition of “good” into measurable outcomes. Upcoming articles in this series will focus on:
- How to identify the right metrics that truly reflect business performance
- The difference between metrics and KPIs, and why that distinction matters
- How to design OKRs that align teams, drive accountability, and accelerate growth
Each piece will offer practical guidance for senior leaders who want to lead with clarity, make better decisions, and build organizations that outperform.
The journey to excellence starts with knowing what to measure. Let’s go there together.
Turning Vision into Measurable Results
We help you align strategy, goals and performance, so you can lead with clarity and confidence.
Mark Dailey
Newport LLC
✉ Mark.Dailey@newportllc.com
📞 Phone: (203) 424-0433
💻 www.newportllc.com
Janet Bumstead
Enroot Strategies LLC
✉ jbumstead@enrootstrategies.com
📞 Phone: (914) 420-8805
💻 www.enrootstrategies.com
About the Authors
Mark Dailey is a Partner at Newport LLC and President of the Connecticut Chapter of the National Association of Corporate Directors (NACD). With over 20 years of experience, he advises boards and executive teams on strategy execution, performance management, and data-driven decision-making. Mark specializes in turning metrics into meaningful action—helping organizations align goals, governance, and results. Learn more at newportllc.com.
Janet Bumstead, founder of Enroot Strategies and a RevOps strategist with over 20 years of experience helping organizations grow through data, analytics, and technology. She partners with leadership teams to align strategy, scale infrastructure, and activate growth with the right people, tools and systems. Janet also teaches courses in consumer insights, data analysis, professional sales and sales leadership as an Adjunct Professor. Learn more at enrootstrategies.com.
A collaboration between Newport LLC and Enroot Strategies, LLC.
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