How Entrepreneurs Generate Leads and Close Deals: 17 Tips
Successful lead generation and deal closing require strategic approaches. We asked industry experts to share one piece of advice they would give to entrepreneurs who are struggling to make sales — and the strategies they’ve found effective for generating leads and closing deals. Discover actionable tips for enhancing your sales process, building meaningful customer relationships, and promoting sustainable business growth.
- Offer Value Before Asking for Sales
- Narrow Your Focus to Specific Customer Niches
- Pursue Quality Conversations Over High Volume
- Build Trust Before Attempting to Close Deals
- Target the Right Audience with Relevant Offers
- Sell Transformation Instead of Product Features
- Position Your Solution Within Customer Stories
- Recognize When Your Marketing Strategy Needs Change
- Solve Real Problems Through Authentic Partnerships
- Establish Credibility Before Pursuing Deals
- Stop Selling and Start Understanding Customer Needs
- Focus Locally for Your First Breakthrough
- Ask for Help Instead of Delivering Pitches
- Diagnose Customer Problems Before Proposing Solutions
- Create Genuine Connections Rather Than Transactions
- Prioritize Speed in Your Customer Response
- Back Your Product with Strong Guarantees
Offer Value Before Asking for Sales
When I was struggling to make sales early on, I realized my biggest mistake was trying to sell too soon instead of building trust first. What really turned things around was focusing on relationships by offering free value through insights, quick audits, or personalized recommendations before pitching anything.
For lead generation, I leaned heavily on LinkedIn and email outreach with a personal touch using real conversations instead of templates. Once I started listening more and selling less, closing deals became much easier. My advice is to stop chasing transactions and start building connections because sales will follow naturally.
Narrow Your Focus to Specific Customer Niches
If you’re struggling to make sales, the single most important shift I’d recommend is to stop trying to appeal to everyone and instead go deep into a specific niche. When we first started, we were trying to be helpful to every type of agency under the sun. It made our messaging vague and our outreach inconsistent. The real momentum came when we narrowed our focus to creative, PR, and digital agencies and got crystal clear on the types of new business problems they faced. That clarity gave us the ability to speak directly to their pain points in a way that felt personal rather than generic.
As for generating leads, the most effective strategy for us has been building tailored outreach programs that feel relevant and considered rather than templated. We’re not chasing hundreds of leads with one message. Instead, we’re approaching a much smaller number with something that actually shows we’ve done our homework. That includes referencing their recent work, understanding the sectors they’re targeting, or speaking to something their founder has said publicly. The aim is to create conversations that feel like a good fit on both sides rather than trying to convince someone into a meeting.
Closing deals tends to be less about persuasion and more about qualification. We’ve had better results by not trying to convince someone they need us but instead spending more time figuring out if we’re actually the right partner for them. That shift in mindset builds trust and usually accelerates the sales process. If I had to sum it up, I’d say go narrower than feels comfortable, do the unscalable things in your outreach, and spend more time listening than pitching.
Pursue Quality Conversations Over High Volume
After almost two decades in sales and business development, my biggest piece of advice is this: stop chasing volume and start focusing on genuine conversations.
Too many entrepreneurs fall into the trap of thinking more emails, more ads, or more activity will automatically lead to more sales. In reality, people buy from people who listen, understand their challenges, and offer something relevant, not just whoever shouts the loudest.
The most effective strategy I’ve found for generating leads and closing deals is consistent, human-led outreach. That means doing the groundwork, i.e., identifying your ideal customer profile, crafting a message that resonates, and following up with purpose.
I’ve built an entire business around this principle. We use structured outreach to open doors, but it’s the quality of the conversation that converts. When your team approaches every lead as a relationship, not a transaction, that’s when sales become predictable and sustainable.
Build Trust Before Attempting to Close Deals
If you’re struggling to make sales, chances are you’re trying to sell before you’ve built trust. People don’t buy from a pitch; they buy from clarity and confidence in the value you bring. My advice: stop focusing on closing deals and start focusing on solving problems. When you truly understand your customer’s pain points and can clearly demonstrate how your solution makes their life easier, sales follow naturally.
For lead generation, I’ve found success with a three-pronged approach: consistent content creation so people can discover you, direct outreach so you’re not passively waiting for leads, and showcasing proof of results so prospects see your credibility. Case studies, testimonials, and even quick wins shared on LinkedIn all serve as powerful trust builders. Once you’ve established trust and demonstrated proof, the conversation transforms from convincing to collaborative decision-making. That’s when deals actually close.
Target the Right Audience with Relevant Offers
If I had to give one piece of advice to entrepreneurs struggling to make sales, it would be this: stop trying to sell to everyone, and instead double down on the right audience with the right offer.
1. Narrow Your Focus on the Right Audience
A common mistake is casting the net too wide. When you try to appeal to everyone, your messaging ends up bland and forgettable. I’ve seen sales turn around quickly when entrepreneurs define a sharp ideal customer profile (ICP) — who they are, what problem keeps them up at night, and how your solution directly solves that.
For example, when I helped a SaaS client reposition from “helping all small businesses” to focusing specifically on e-commerce brands struggling with cart abandonment, their lead-to-close ratio jumped by over 35% because every message suddenly felt hyper-relevant.
2. Use Value-First Lead Generation
People don’t want to be sold to, but they love being helped. Strategies that work:
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Content with clear ROI: Guides, calculators, or case studies showing how you solve their exact pain.
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Micro-offers: Low-barrier “entry points” (free audits, webinars, mini-consults) that build trust and allow a natural transition to the sale.
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Social proof: Testimonials, before-and-after case studies, and data-backed stories that reduce skepticism.
Sell Transformation Instead of Product Features
The single most important piece of advice I would give to entrepreneurs struggling to make sales is to immediately stop selling features and start selling transformation. Entrepreneurs often get too close to their product — like our camp management software — and focus on listing every feature it has. However, customers only care about one thing: solving their most painful, expensive problem. Instead of saying, “Our software has online forms and email automation,” you must articulate the transformation: “We eliminate 90% of your administrative burden, turning hours of chaotic paperwork into minutes of automated camp registration, allowing you to focus on the campers, not the clipboard.”
For generating leads and closing deals in our specific market, we’ve found two strategies highly effective. First, for lead generation, we use problem-centric, educational content marketing. We don’t write about our product; we write about the common struggles of camp directors (e.g., “The 5 Biggest Mistakes in Camp Scheduling,” or “How to Increase Early-Bird Registrations”). This content attracts the right leads actively searching for solutions. Second, for closing deals, we leverage a high-value, low-risk conversion path tied to our pricing model. Since our camp management software is pay-as-you-go, our closing strategy is simply: “Try us for free, process your next five camp registrations with zero commitment, and only pay a transaction fee if it works.” This strategy eliminates the final financial hurdle, making the decision to switch almost effortless for the customer.
Position Your Solution Within Customer Stories
One piece of advice I’d give to entrepreneurs struggling with sales is to stop selling and start connecting. People don’t buy from logos; they buy from humans. Focus less on pushing your product and more on understanding your customer’s pain points, motivations, and daily frustrations. When you position your solution as part of their story, sales naturally follow.
In my experience, effective lead generation and deal-closing come down to three key strategies:
First, leverage storytelling and social proof. Share real stories through customer testimonials, behind-the-scenes insights, or your brand’s purpose. Authentic content builds trust, and trust converts.
Second, build a system, not just a sales pitch. Combine inbound methods, such as content marketing and SEO, with outbound approaches, including personalized outreach and partnerships. Every interaction should guide prospects toward a simple next step.
Third, follow up with purpose. Most deals close during follow-up, not initial conversations. Be proactive and consistent while adding value in your communications. Offer insights, not just reminders.
Ultimately, sales happen when your audience feels seen, understood, and supported, not sold to.
Recognize When Your Marketing Strategy Needs Change
One piece of advice I’d give to entrepreneurs struggling to make sales is to recognize when your go-to-market strategy has stopped working. Early on, I grew my company to $500k ARR almost entirely through cold outreach. But despite that traction, we were only seeing about 1,000 unique site visits per month. The truth was, no one really knew we existed. That strategy got us off the ground, but it wasn’t going to scale and our revenue flat-lined.
Last July, we started posting educational content on LinkedIn, and in January we expanded to Instagram. Since then, our audience has grown to 175,000 followers on LinkedIn and 100,000 on Instagram. The impact has been dramatic. In September alone, we saw 21,000 unique site visits, and we’ve built a steady pipeline of inbound leads from employers who already understand and trust our brand before we even speak.
We are an AI-powered hiring platform that helps companies find and hire vetted early-career talent who are ready to hit the ground running. Shifting to an education-first approach didn’t just drive awareness, it positioned us as thought leaders in early-career hiring and unlocked a new level of growth we couldn’t reach through cold outreach alone.
Solve Real Problems Through Authentic Partnerships
For entrepreneurs struggling to make sales, my top advice is to deeply understand your customer’s true needs and pain points — not just what you think they want. Sales aren’t about pushing a product but about solving real problems with solutions that resonate. When your message connects authentically to what matters most to your prospects, the sales process becomes less about persuasion and more about partnership.
Effective strategies for generating leads start with building trust through valuable content and consistent outreach. Share insights that demonstrate your expertise and help prospects before they buy. I’ve found that leveraging networks with warm introductions, hosting webinars to address specific challenges, and active engagement on platforms like LinkedIn create meaningful opportunities. Listening actively during conversations allows you to tailor your pitch precisely to each prospect’s situation, which significantly increases closing rates.
Above all, persistence combined with genuine connection wins the day. Sales is often a numbers game, but success comes from thoughtful, respectful follow-up and showing that you truly care about helping clients achieve their goals. When you approach sales as a service to others rather than a transaction, you unlock leads and close deals more naturally and sustainably.
Establish Credibility Before Pursuing Deals
One piece of advice I’d give entrepreneurs struggling to make sales is to focus on building trust and credibility before pushing a deal. In my experience with government contracts, rushing the pitch or overpromising often backfires; relationships, reputation, and reliability matter far more than flashy marketing.
Effective strategies I’ve found include deeply understanding client needs, demonstrating consistent expertise, and leveraging long-term relationships. This meant thoroughly reviewing bid documents, maintaining a flawless compliance record, and consistently delivering on past commitments. Word-of-mouth, repeat contracts, and institutional trust became our most powerful lead generators, often more effective than advertising or cold outreach.
Another critical element is structured follow-ups and transparent communication. Keeping clients informed, explaining challenges, and offering practical solutions builds confidence and positions you as a partner rather than just a vendor. In sales, patience and reliability often convert more deals than urgency or pressure tactics.
Stop Selling and Start Understanding Customer Needs
When entrepreneurs struggle with sales, it’s usually not due to a lack of effort but a lack of alignment between what they offer and what the customer truly values. My biggest advice is to stop “selling” and start “understanding.” Spend time learning your customer’s challenges, industry language, and decision-making patterns. At Tecknotrove, many of our best leads have come from conversations where we simply listened. Understanding a client’s safety challenges or productivity goals often opens the door to offering the right simulation solution.
Another strategy that’s been effective is leveraging proof of concept. Rather than pitching a full-scale product, we often demonstrate a small, high-impact simulation that addresses one critical problem. This approach builds trust and shortens the sales cycle because clients can visualize real-world value before committing.
Finally, consistency in follow-ups is key. People often underestimate the power of persistence combined with genuine curiosity, and that’s what turns a lead into a long-term partner.
Focus Locally for Your First Breakthrough
As a public relations consultant and business developer, there’s one piece of advice I give to entrepreneurs who are struggling with sales: for a while, focus as locally as possible. They should join local business associations and attend their networking events, collaborate with other local business owners, and attend trade shows and pitching events. Additionally, entrepreneurs should introduce themselves to local business journalists. More often than not, startups go national or enter multiple markets right away. However, the first business opportunity is often from someone you met in person and were able to make a real impression on. From there, entrepreneurs can leverage testimonials and recommendations.
Ask for Help Instead of Delivering Pitches
Ask your prospects for help instead of trying to sell them something. People love giving advice, and having that conversation will help you more than spending days on your sales script. When you approach with genuine curiosity rather than a pitch, resistance disappears and real dialogue starts.
I’ve seen this work when asking clients for honest feedback on what we’re building rather than launching into our standard pitch. They’ll often tell you exactly what’s missing, what actually matters to them, and where competitors fall short. Those conversations turn into sales more often than polished presentations ever did. People trust you when you’re willing to listen and learn from them first, not just talk at them.
Diagnose Customer Problems Before Proposing Solutions
If you’re struggling to make sales, stop selling and start solving.
Most entrepreneurs focus on pitching their product, when they should be diagnosing their customer’s problem. The moment you shift from, “Here’s what we do,” to, “Here’s how we can help you grow,” conversations turn into conversions.
We’ve found education-driven lead generation incredibly powerful — sharing insights, case studies, and actionable tips that position us as partners, not vendors.
Once trust is built, closing the deal isn’t a push — it’s a natural next step. People buy clarity and confidence, not pressure.
Create Genuine Connections Rather Than Transactions
My key advice is: focus on building relationships, not just transactions. Sales thrive when you create genuine connections and identify your customer’s core needs. I’ve found that actively listening to customers and positioning your product or service as the right solution makes a huge difference.
To generate leads, I recommend targeting a more specific audience and concentrating efforts on high-value prospects. Use platforms like LinkedIn and industry-specific forums to connect personally with prospective customers. Once you’ve got their attention, provide meaningful insights to spark interest.
When it comes to closing deals, follow-through matters. Regular follow-ups, addressing concerns directly, and ensuring you meet expectations will differentiate you. Remember, building a relationship doesn’t end after the sale; keeping the conversation going leads to repeat business and referrals.
Prioritize Speed in Your Customer Response
One piece of advice I’d share, that works incredibly well for us, is SPEED. Get back to people as fast as possible, and you’ll be in front of the majority. In this day and age, people aren’t keen to wait for days, they want minutes, so engineer your business for speed where possible. Whether that’s email, phone, whatever, make it REAL and make it FAST.
Strategies for leads and deals: we work on daily “content and connection.” Always working on useful content, whether that’s written, tools, or video, and then as a team we are connecting with people as much as we can. In person, LinkedIn, Facebook — whatever — we know that the more content we create, and the more real connections we achieve, the more and better leads we get.
Back Your Product with Strong Guarantees
If you’re struggling to make sales, don’t just tell people your product is good. Prove it by backing it. We build our tools in the USA and offer 90-day returns and a lifetime warranty. That’s our way of putting skin in the game. If we’re asking someone to bet on us, we should be willing to bet on ourselves first.
