The honest reason most founders struggle to close deals and how starting with a real sales plan does
We hear it over and over again from new businesses and startups: they have a product that works, customers who’ve said it’s great. The founders are constantly on calls, following up, hustling.
And yet, deals are still stalling.
You might get an A for effort in school, but in the real world effort isn’t enough. And, often, it’s not even the main problem. In our experience, founders lose deals not because they’re lazy, but because they were never formally trained in sales and don’t know how to build the foundation for successful sales: a sales plan. Instead, they are improvising a new approach every single time and hoping that through huge outputs, they’ll land enough deals to make their company profitable. The problem in their minds is marketing/lead generation and not their sales process.
The beginning of any sales process has to be creating a sales plan. It’s not just a guide for how to run your sales, it’s a game-changer that improves every conversation you have, shifting your sales process from hope to knowing exactly what to do in every situation.
This guide will walk you through what a sales plan is, why you need one, and how to think through the questions that matter most. If you’re building a sales program for the first time these are the questions to sit with before you generate a single email or script. Answer them honestly, and everything downstream gets easier.
What Is a Sales Plan?
A sales plan is a documented system that answers three questions: who you’re selling to, what you’re going to say, and how you’re going to manage deals from first contact to close.
That’s it.
The problem is that most founders mistake a sales plan for a business plan, or for a playbook, or for a pipeline tracker. They’re all part of your sales process documentation, but they’re not the same thing.
A sales plan is the strategic layer: your ICP, your positioning, your competitive stance, your deal process, your proof points. It’s the thinking that makes everything else consistent. This is what you should be putting into your intake form when signing up for DealMentor, and the reason why so many founders hate this step is that they don’t have a living document with this information to copy and paste.
A sales playbook is the tactical layer: the scripts, the objection handlers, the cold call frameworks. It lives inside the plan. (If you want to go deep on building a playbook specifically, we’ve covered how to build a sales playbook in 15 minutes, which is a separate read worth your time.)
Sales planning is the process of building both, and keeping them updated as your market changes, your ICP sharpens, and your deals teach you what’s actually working.
Most founders skip this entirely. This guide is about why skipping this foundation step cripples your sales potential – and how to fix it.
Why Founders Skip Sales Planning (And Pay For It)
Most founders skip sales planning because it feels like busy work, something that makes you look like you are working, but doesn’t contribute any real value. Or they think they can skip immediately to the playbook. Or they’ll get to the sales planning once they reach their first 100 customers and are looking to scale.
What would happen if you built a house without a foundation?
Sure, you can get it up and running, but soon it’s going to start to fall apart.
Your sales plan is the foundation of your sales. If you skip this step, you probably won’t be targeting the right buyers, each meeting will have a different strategy, you won’t understand which conversions went well or why, and you’ll end up wasting time on people who will never buy from you.
And ultimately, you are failing to build perhaps the most important part of your business – the one that generates revenue and lets you keep operating.
A sales plan is the difference between a founder who has a great idea, and hopefully it will succeed, and a founder who is planning for success because he’s operating with the same clarity a CRO brings.
What’s your takeaway at this point? You don’t need to hire a CRO – you need to think like one.
Here are the questions you need to ask yourself to build a sales plan for your business.
The Foundation: What Are You Actually Selling?
This sounds obvious, but it’s almost never as clear as founders think.
When you’re asked what you sell, the wrong answer is your product. The right answer is the outcome your buyer gets, and specifically, the pain it removes.
Push yourself here. Don’t write “we help companies improve their sales process.” Write: “We stop founders from walking into calls unprepared and watching deals die because they didn’t know what to say.”
The more specific you are, the more the buyer can see the value they would get from working with you, buying your product – giving you their money!
Ask yourself:
- What does a bad week look like for your buyer right now?
- What are they Googling at 11pm that you could help with?
- What would they say to a colleague the morning after using your product for the first time?
Your value proposition should sound like relief, not features.
Know Your Buyer Before You Know Your Pitch
Most founders think about their ICP (ideal customer profile) as a demographic: industry, company size, revenue range. These details matter, but they’re just that – details.
A great ICP tells you why someone buys, not just who they are.
Think in tiers. Not every customer is equal, and you shouldn’t treat them like they are. Your Tier 1 buyer is the one who closes fastest, pays the most, and gets the most value. That’s your target. Everyone else is secondary until you’ve built a machine to close Tier 1 consistently.
Think in triggers. The best buyers don’t buy because your product exists; they buy because something happened.
A new VP of Sales just joined. They missed Q2. A key rep quit. A competitor started eating their lunch.
These trigger events are the moments when urgency is real and your solution becomes obvious. When you know what those moments are, you know when to reach out and exactly what to say.
Ask yourself:
- Who is (or would be) your absolute best current customer and what made them the easiest to close?
- What changed in their world right before they came to you?
- What’s the cost of them doing nothing in words they would use?
- Where do they spend time before they’d ever find you?
The goal is to describe your ideal buyer so specifically that your mom could go find ten of them on LinkedIn.
The Competitive Reality: You’re Always Being Compared
Your prospect is never evaluating you in a vacuum. They’re comparing you to something, and you need to compare yourself to that something as well, especially “doing nothing” and “just using ChatGPT.”
The founders who lose on competitive deals usually do so because they never made the comparison explicit, they haven’t already crafted out how they should respond to why they are better than the status quo, or the cost of turning to AI instead.
Know their weaknesses, not in a petty way, but in a factual one. What does your approach do that theirs doesn’t? Where does the alternative break down at scale, or for a specific buyer type, or at a specific stage?
Know the “status quo” argument. In many cases, your biggest competitor isn’t another vendor – it’s inertia. The prospect who says “we’re not ready yet” is choosing to stay where they are. What does staying where they are actually cost them? That number needs to be part of your conversation.
Ask yourself:
- If a prospect said, “We’re already using [competitor X],” what would you say word-for-word?
- What have your prospects tried before that didn’t work? Why didn’t it work?
- What makes you the right fit specifically for your Tier 1 buyer, even if you’re not right for everyone?
Objections Are Information, Not Obstacles
Every objection your buyer raises tells you something about where they are in the decision, what they’re afraid of, and what they still don’t understand.
Most founders treat objections as attacks. “Too expensive” becomes a negotiation. “I need to think about it” becomes a follow-up spiral. “We’re already using something” becomes a dead end.
None of these have to be dead ends. But you have to know what each one actually means.
“Too expensive” usually means: I don’t see enough value yet, or I’m not the right decision-maker. “Need to think about it” usually means: I’m interested but I don’t feel urgency, and I have concerns I haven’t told you. “We have something” usually means: I’m not ready to disrupt what’s working, even a little.
Before your next call, write down the five objections you hear most. Then, for each one, write: what does this actually mean? What would a great response sound like, not a rebuttal, but a response that opens a real conversation?
What if you don’t have any customers yet? Then brainstorm. Think about it from your ICP’s perscpective – why do you think they are most likely to say no?
That exercise alone is worth more than any script. It’s also one of the core inputs your sales plan needs to be complete.
Ask yourself:
- What are the real top five objections in your deals right now?
- Which ones are stalls and which are genuine concerns?
- What’s the one objection you’ve never figured out how to handle well?
Deal Management: The Part of Sales Planning Most Founders Ignore
You’ve had a great call. They’re interested. They said they’d get back to you. And then… nothing.
This is one of the most common and most solvable problems in early-stage sales and it almost always comes back to the same root cause: the deal was real to you but optional to them.
There was no compelling event. No internal deadline. No cost attached to waiting.
Every deal you carry forward needs a clear answer to: why would they buy now, and not in three months? If you can’t answer that, the deal isn’t as strong as it feels.
Deal management isn’t just tracking. It’s making daily decisions about where your time and energy go. A good sales plan includes a deal management framework: which deals get attention today, and exactly what to do next on each one. Otherwise, every morning you’re left guessing why you aren’t hearing back and closing deals.
In DealMentor v2.0, this is what My Deals is built for. Today’s CRO Priorities ranks your open deals every morning and gives you the single most important next move on each one. It’s the part of a sales plan most founders never actually build, and the part that pays off every single day.
Ask yourself:
- What’s the next concrete action for each open deal – not “follow up,” but what specifically?
- What would have to be true for this deal to close in the next 30 days?
- Are you waiting on them, or are they waiting on you?
What is a Sales Motion and Why Should I Care?
There’s a question that often gets skipped in sales planning: how do I actually sell?
Not “what do I sell” but the mechanics of how you are generating leads, usually referred to as your company’s sales motion. Your sales motion answers how are you primarily generating leads: Outbound? Inbound? Referrals? Cold email? LinkedIn? Events?
Your sales motion shapes your playbook, your daily workflow, your outreach strategy, and your pipeline velocity. A referral-driven business has completely different levers than a cold outbound business. And a founder trying to apply outbound tactics to a referral-led business, or vice versa, will always feel like they’re pushing against something.
Be honest about how customers actually come to you today. Then ask whether that motion is working fast enough. If not, what’s the highest-leverage channel to add?
What if you don’t have any customers yet? This is one of the toughest parts of sales for people who have never done sales before. DealMentor 2.0 has a new feature where it suggests which channels you should be on for lead generation. Try it out and then continue with the exercise questions below.
Ask yourself:
- How did your last five customers actually find you or get introduced to you?
- Where do the buyers you want spend time: LinkedIn, industry communities, events, referral networks?
- What’s your current process from first contact to closed deal? Where does it break down?
Proof Is the Part of Your Sales Plan You’re Not Using Enough
Every founder knows they need testimonials. Almost no founder uses them well.
Proof isn’t just a quote on your website. It’s something you weave into the conversation at the exact moment the buyer is asking themselves: can I trust this?
That moment usually comes right after they’ve told you their pain and you’ve told them what you do. When you can bring an example of a situation similar to theirs, and how you successfully solved it, that gets them deeper into the conversion funnel.
Specificity is everything here. “A customer cut their sales cycle by 30%” is useful. “A two-person SaaS team in the same situation you’re in closed their first enterprise deal within 60 days of building their sales plan” is a story that sells itself.
What if you don’t have any customers yet? This isn’t your first job. Think of examples previously in your career where you were able to help customers in similar situations. As the founder, you are the “reason to believe” in your company – show your leads how you’ve succeeded in the past, and they’ll believe in your ability to help them now.
Ask yourself:
- What’s the one outcome a customer has gotten that would make your ideal buyer sit up straighter?
- Who are your two or three best current customers, and would they talk to a prospect?
- What specific proof point speaks directly to the “too expensive” or “I’m not sure it works for companies like mine” objection?
What a Sales Plan Template Actually Looks Like in Practice
Most sales plan templates you’ll find online give you a structure to fill in. They are forms you might get if you signed up for a workshop on how to build a sales plan. They ask the right questions, but they don’t help you fill out the answers.
A real sales plan template isn’t a standardized questionnaire – it’s a set of answered questions. The quality of the plan you develop from these questions depends on the quality of the thinking that went into it. (much like the DealMentor intake form).
Here’s the complete set of questions your sales plan needs to answer. If any of these are fuzzy, that’s where to focus first.
Your product and market:
- What’s the specific, felt outcome your product delivers?
- What does a bad week look like for your buyer right now?
- What’s the cost of them doing nothing for another six months?
Your ideal customer:
- Who is your Tier 1 buyer in detail, not just what company type?
- What trigger event usually precedes a purchase?
- Where do they spend time before they find you?
Your competition:
- What are you up against? List both your top 5 competitors and the status quo.
- What’s your honest answer to “we’re already using [X]”?
- Where do competitors fall short for your specific buyer?
Your deal management:
- What are your top five objections and what does each one really mean?
- What compelling event exists in each of your open deals right now?
- What’s the next concrete step on each deal – word for word?
Your sales motion:
- How do buyers find you, and is it fast enough?
- What’s your primary outreach channel, and is it generating enough pipeline?
- Where does your current process consistently break down?
Your proof:
- What’s your strongest specific proof point?
- Which customers would speak to a prospect?
- What outcome story speaks directly to your most common objection?
What Sales Planning Looks Like When It’s Working
A founder with a real sales plan starts every morning knowing which deals need attention today and exactly what move to make on each one. They walk into every call with a guide – opening words, discovery questions, likely objections, closing move – tailored to the specific person they’re talking to. They have a framework for every stage of the deal, so when something unexpected happens, they have a format and formula to rely on, not improv and prayers.
They don’t wing it. Not because they’re rigid, but because with a plan they already know 99% of what the lead is going to say, and they already know how to respond to it. By removing the anxiety of not knowing what to do next, they can be confident, assertively moving the deal down the pipeline, instead of passively waiting for sales to happen
That’s what sales planning actually does for you: it gives you the foundation to be your best on every call, not just the good days.
Ready to Build Your Sales Plan?
You don’t have to answer all of these from memory or figure them out alone.
DealMentor v2.0 was built to take exactly these inputs, your product, your buyers, your competitors, your proof, and turn them into a complete sales program: a playbook, an ICP and targeting guide, outreach sequences across six channels, objection responses, and a daily workflow that includes deal management built in.
The thinking still has to come from you. The founders who get the most from the platform are the ones who’ve sat with these questions before they fill in a single field. This guide gives you the questions. DealMentor builds the plan.
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DealMentor is a Virtual CRO platform built by veteran sales leaders. DealMentor v2.0 gives founders and sales teams the guidance of an experienced CRO — built into their daily workflow, starting at $149/month.