Why Real Planning Starts with Real Numbers
(and a Reality Check on “Happy Ears”)
Let’s get one thing straight: not all forecasts are created equal. Some are rooted in solid data. Others? They’re little more than wishful thinking in a PowerPoint deck. That’s where planning can go off the rails—when optimism replaces evidence.
It starts with vision. You need a clear picture of what success looks like next quarter—and next year. A strong revenue strategy isn’t just helpful; it’s essential. It guides decisions, aligns teams, and keeps everyone rowing in the same direction.
If you’ve already built your budget, great. If not, don’t panic—it’s not too late to create a plan that drives growth.
Start with revenue. Always. It’s the foundation of your financial strategy, and everything else—expenses, hiring, investments—flows from there. Your CFO and Head of Sales should work together to define a realistic revenue target.
Revenue First: The Foundation of Your Plan
Before you start mapping out expenses, product launches, or hiring plans, zero in on one thing first: revenue. It’s the North Star of your entire strategy. Everything else—budgets, headcount, investments—flows from that single point. That’s why your CFO and Head of Sales need to be in lockstep, aligning on a revenue target that’s built from the ground up—not plucked from the sky.
Start by asking each salesperson or team to forecast their quarterly revenue. But don’t take those numbers at face value. Salespeople are wired for optimism—it’s part of what makes them great. They hear “maybe” and log it as “closed-won.” That’s what we call “happy ears.”
So, apply a reality filter. Take those forecasts and trim them by 10–20% to account for the natural optimism baked in. It’s not about being cynical—it’s about being ready for what’s real.
Learn from the Past: What Worked, What Didn’t
Before you plan forward, take a moment to look back. Last year’s performance holds valuable clues—if you’re willing to dig into the data. What fueled your growth? What fizzled out? The goal isn’t just to spot failures—it’s to double down on what worked.
If a particular product, campaign, or customer segment drove strong results, lean into it. Success leaves a trail—follow it.

Every flop has a root cause. And while the details vary, most failures fall into one of three buckets:
- Bad idea: Some ideas are doomed from the Take Enron, for example—a spectacularly bad idea wrapped in accounting fraud. The fallout? The company collapsed, 32 individuals were charged, and 8 went to jail. Or consider Blockbuster, which famously passed on buying Netflix for just $50 million in 2010. That decision didn’t just age poorly—it helped write Blockbuster’s obituary.
- Poor execution: Even good ideas can fail if they’re poorly executed. Boeing’s 737 Max is a case in point. Software flaws and a rushed certification process led to two fatal crashes, grounding the fleet and damaging the company’s reputation for years.
- Bad timing: Sometimes, the idea is solid—but the market isn’t Pets.com launched during the dot-com bubble with a catchy sock puppet and a broken business model. With unsustainable logistics and no clear path to profitability, it burned through $300 million and folded in under two years. Lehman Brothers? Another timing disaster—caught holding toxic assets when the financial crisis hit, triggering a global meltdown.
The takeaway? Whether it’s a flawed idea, poor execution, or just bad timing, the real value lies in understanding why things went wrong. That insight is what fuels smarter, more resilient strategies going forward.
And you don’t need a headline-making collapse to learn a lesson. Sometimes it’s the quiet missteps— ignoring market signals, stretching your team too thin, or launching before you’re ready—that quietly derail your goals.
The key is honesty. Be clear-eyed about what worked, what didn’t, and why. Then turn those lessons into a sharper, more focused plan for what’s next.
Focus on What Sells: The 80/20 Rule in Action

Not all products are created equal. The Pareto Principle tells us that 20% of your offerings likely drive 80% of your revenue. Double down on what works. Don’t be afraid to sunset underperformers.
A strong product roadmap includes both enhancements and innovations. What’s launching next quarter? What’s in the pipeline for next year? A good product manager should have answers—and a plan.
And don’t forget to grow smarter, not just bigger. Increasing your average order value (AOV) by targeting larger customers or expanding into new markets can move the needle without adding complexity.
Set SMART Goals: Because Hope Isn’t a Strategy
Accountability isn’t just important—it’s non-negotiable. And our preferred methodology for holding people accountable is through SMART goals. Why? Because they bring structure, clarity, and focus to your strategy.

- S – Specific: “Increase revenue by 5% next quarter” and “Increase revenue by 15% by next year” is actionable. “Do better” is not.
- M – Measurable: Your CRM should be able to generate real-time reports and dashboards by individual and There are no gray areas in measurement—progress should be visible, trackable, and unambiguous.
- A – Achievable: Ambition is Delusion is not. There is no reason to double your sales within a year if it’s not achievable. Robert Browning sums it up as “but a man’s reach should exceed his grasp, or what’s a heaven for?”
- R – Relevant: Many businesses fall into the trap of tracking too many KPIs and metrics, creating noise instead of clarity. Focus on the few that truly move the needle—those that directly impact performance and outcomes.
- T – Timebound: Once again, make it achievable. Aiming for a 100% customer retention rate might sound impressive, but for most businesses, it’s simply not A 90% retention rate, on the other hand, is both ambitious and attainable. And remember—deadlines matter. They turn good intentions into real results.
You can also use frameworks like RACI to define roles and responsibilities, but SMART goals are what keep teams aligned, focused, and accountable.
We’ll explore KPIs and OKRs in greater depth in Chapter 7, but for now, remember: clear goals are the foundation of follow-through—and SMART goals are how we get there.
Final Thoughts: Plan with Purpose
Strategic planning isn’t about guessing—it’s about grounding your vision and following through. That means:
- Using data to set realistic revenue targets
- Learning from past wins and failures to refine your approach
- Prioritizing high-impact products that drive real results
- Holding your team accountable with clear, measurable goals that align with your strategy
When everyone knows what they’re aiming for—and how success will be measured—execution becomes focused, intentional, and far more effective.
The best time to plan was yesterday. The second-best time? Right now. Just make sure you leave the “happy ears” at the door.
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.
© Newport LLC 2025 and © Enroot Strategies, LLC 2025. All rights reserved.