You’ll eventually hit a wall if you’re running a sales organization—or wearing multiple hats as founder, CEO, and sales manager. That wall is often invisible until growth stalls, key deals slip through the cracks, or your top salesperson burns out. So, what’s the next move? It’s not more hustle. It’s assessment.
A sales assessment isn’t about checking boxes. It’s about understanding where you are, how you operate, and what’s holding you back. Too many small business leaders assume they’re doing fine because revenue is growing or the team is hitting their quotas. But are you growing at the rate your market allows? Are your sales activities aligned with your long-term goals? Are you building a repeatable system, or are you just getting lucky?
Let’s get tactical. A sales plan isn’t just a revenue target. It’s your go-to-market strategy. It defines your audience, your message, and your motion. It answers why you’re talking to those prospects and what value you’re bringing to them. Without a plan, you’re reacting instead of executing. You’re chasing leads instead of building a pipeline.
If you’re a small company—perhaps under $30 million in revenue—and selling into a national market, chances are your market potential is hundreds of millions, maybe billions. That means your market share is a rounding error, which means there’s room to grow. The question is: Are you operating in a way that allows you to capture that growth?
Even if you’re running lean, you should benchmark your performance against top-tier organizations. Not because you’re competing with them directly, but because they set the standard. What are they doing that you’re not? Where are they more efficient? How do they structure their teams? You’re leaving money on the table if you’re not asking those questions.
Sales performance isn’t just about effort. It’s about alignment. Your sales process, messaging, and team structure need to work together. If you’re still founder-led on sales, you perform two roles: seller and sales manager. That’s not sustainable. You need to start thinking about what you want others to do, not just what you do now.
That shift—from doing to leading—requires clarity. Where do you want your company to be in five years? If your goal is to exit, do you have the infrastructure to support that? If you want to scale, are your processes scalable? If you’re still doing all the selling, how will your business evolve when you’re no longer in the room?
The timeline matters. If you aim to sell in five years, the systems to support that sale must be in place at least two years before. Buyers want proof that the business runs without you. That means sales need to be predictable, measurable, and transferable. You can’t hand over a Rolodex; you must hand over a system.
Even if you’re not planning to sell, you may want to step back from day-to-day selling. That requires building a team that can handle discovery, demos, and deal scoping without you. Your role becomes strategic—showing up at the right time to close or build executive alignment. That’s how enterprise sales work. And that’s how you have a scalable sales organization.
Let’s not pretend that stepping back means stepping away. CEOs meet with customers even in billion-dollar companies—not to pitch but to align on vision, strategy, and partnership. If you’re the founder, your presence still matters. But it should be intentional, not reactive. You’re there to reinforce value, not to create it from scratch.
Salespeople need to think the same way. If you’re not improving your process, you’re falling behind. The market doesn’t wait, and your competitors don’t stop. If you’re not assessing, you’re assuming, and assumptions in sales are expensive.
Your clients measure your value, not you. If your process is outdated or inconsistent, they’ll feel it—even if you don’t. That’s why assessment matters. It’s not about internal validation. It’s about external relevance.
Think about your last few discovery calls. Were they about your product? Or did they help the client think differently? The best sales conversations create clarity. They challenge assumptions. They move the client forward. You can’t do that if your process is stuck in neutral.
Assessment starts with questions—not just about sales metrics but about outcomes. What do you want your team to do better? What does success look like in six months? What’s getting in the way? Too often, companies skip this step. They jump to training or tools without understanding the root issue.
Your team may lack a defined process, your Ideal Client Profile (ICP) may be too vague, or your messaging may not resonate. You won’t know until you dissect what’s working and what’s not. That’s the role of assessment. It’s diagnostic, strategic, and necessary.
If you’re managing a sales team, you must ask: How consistent are we? How coachable is our process? Can someone new step in and succeed? If the answer is no, you don’t have a system. You have a few high performers and a lot of risk.
Consistency is what clients respond to. They want to know what to expect. You’re creating doubt if your sales experience varies wildly depending on who they talk to. And doubt kills deals.
Complacency is a quiet killer. It shows up when things are “fine,” such as when revenue is steady, and no one’s asking hard questions. But your competitors are still moving, and the market is still evolving. If you’re standing still, you’re already behind.
That’s why assessment isn’t a one-time project. It’s a discipline, just like pipeline reviews or forecast calls. It’s a regular check-in on your strategy, execution, and results. It’s how you stay sharp.
Let’s consider the founder who wants to stop doing early-stage sales but still wants to close deals. This is common and solvable, but it requires a structure. You need a team that can qualify, provide a demo, and provide scope. You need enablement that supports that team. And you need a clear handoff point where the leaders step in to close.
That’s not theory. That’s execution. It’s how enterprise sales teams operate. It’s how startups scale. And it’s how you move from sales operator to sales leader.
The same logic applies whether you’re at $2 million or $200 million. The numbers change, but the fundamentals don’t. You still need to prove ROI, drive outcomes, and align your sales process with how your buyers buy.
If your pricing has a few extra zeros, the expectations rise. But so does the opportunity. That’s why value clarity matters. You’re competing on price if you can’t articulate why your solution is a better investment than the alternative. And that’s not a game you want to play.
Every customer has a choice. Every dollar they spend with you is a dollar they’re not spending elsewhere. Your job is to make that trade-off obvious. Your sales process should help you do that. If it doesn’t, it’s time to reassess.
This isn’t about perfection. It’s about progress. Mistakes happen. But inaction is worse. If you know your system is broken—or nonexistent—and you do nothing, that’s a choice. And it’s costing you.
The best sales organizations don’t just sell. They adapt, evolve, and learn. That starts with asking better questions—not just about your clients but about yourself. What are we doing? Why are we doing it? And how can we do it better?
If your answers are fuzzy, that’s your signal. Don’t panic, but pause, assess, and adjust. That’s how you build a sales system that scales.
If you’re not sure where to start, start with your goals. Where do you want to be in three years? What needs to happen this quarter to move in that direction? What’s getting in the way? Then, look at your process. Is it aligned with those goals? Is it documented? Is it repeatable?
If you’re a CEO, ask yourself: Could someone else step into my role and drive sales? If not, what would need to be true for that to happen? That’s your roadmap. That’s your future.
Business-to-business sales isn’t magic. It’s math, process, and people. But without a system, you’re relying on talent and luck. And that’s not enough.
So assess. Get clear. Build something that works without you. That’s how real growth happens. That’s how you create value. And that’s how you win.
If you need help thinking through it, I’m here. Let’s talk. If you just want to jump to the head of the line, you can take my 20-question sales assessment here.
Here are immediate action steps for sales leaders to implement today:
- Conduct a Comprehensive Sales Assessment: Evaluate your current sales processes and strategies. Are they aligned with your long-term goals? Identify gaps and areas for improvement. This assessment should focus on revenue and the sustainability and scalability of your sales system. Use this evaluation to redefine your go-to-market strategy, ensuring your messaging and target audience are well-defined and effective.
- Define and Document Your Sales Process: If it isn’t clearly outlined and repeatable, dedicate time today to document it. Ensure that every team member understands their role within this process. A well-documented sales process will help new team members succeed faster and provide a consistent customer experience, reducing the risk of deals slipping through the cracks due to inconsistency.
- Benchmark Against Top-Tier Organizations: Research and analyze the strategies of leading organizations in your industry. Identify what they do differently and where they excel. Use these insights to set new standards for your team. This benchmarking will help you identify areas where you can increase efficiency and competitiveness, potentially unlocking new growth opportunities.
- Shift from Tactical to Strategic Leadership: If you’re still heavily involved in day-to-day sales, start transitioning to a more strategic role. Identify tasks you can delegate and build a team capable of handling initial sales stages independently. Focus on strategic initiatives, such as creating executive relationships and aligning your team’s activities with broader company goals. This shift will enable you to scale your operations and position your company for long-term success.
Implementing these actionable steps today will transform your sales organization into a more efficient, scalable, and strategically aligned entity.
