30-Day Authentic Connection and Sales Mindset Course
If we're all going to eat, someone's got to sell. -- Ken Griffin, CEO of Citadel
Day 1: Embracing Sales as Human Connection
Sales is fundamentally about people. Whether you’re a startup founder pitching your vision, a freelancer seeking clients, or an introvert building a network, remember that selling is not about tricking someone into a transaction – it’s about making a genuine human connection. In fact, the ability to build authentic relationships and understand others’ needs remains the foundation of successful sales. We are all involved in “selling” in some form in our daily lives, because at its core, selling means persuading or moving others. As author Daniel Pink notes, “we are all in the sales business” – no matter our profession – as part of our work (and life) involves convincing or influencing others through exchange.
Today’s Action: Begin a journal for this course. Write down what “sales” means to you right now and any words or feelings you associate with it (e.g. excited, nervous, helpful, pushy). Also list a couple of everyday situations (at home, work, or social life) where you had to persuade or influence someone – this is selling in daily life. Recognizing that sales is human and happens daily will set a positive tone for the month.
Day 2: Everyone Sells, Every Day
Selling isn’t confined to business or sales jobs – it’s a life skill. Think about it: when you convinced a friend to try a new restaurant or negotiated your salary, you were selling an idea or yourself. Realizing this helps demystify sales. It means you already have some sales experience to build on! For example, teachers sell students on the value of learning, and project managers sell team members on timelines. If you broaden the definition, everyone is selling something in everyday life.
Importantly, approach these daily “sales” as opportunities to form authentic connections. People respond best when they feel understood, not manipulated. Today, observe one interaction – perhaps asking a colleague for help or persuading your child to do homework – and note how being empathetic or listening made a difference. Jot down in your journal what tactics worked (or didn’t). This will heighten your awareness that positive influence is a part of life, not a dirty trick.
Today’s Action: Pick one non-business interaction from your day where you had to persuade someone or propose an idea. Write a short reflection on how you approached it. Did you focus on the other person’s needs or just your own goal? What was the outcome? This exercise reinforces the idea that sales = everyday communication. Over time, you’ll start approaching these situations with more intention and care for the human connection.
Day 3: Self-Awareness – Your Attitude Toward Sales
Before building new sales habits, let’s understand where you’re starting from. Many people (especially first-time salespeople or introverts) carry preconceptions about sales – some think it’s “sleazy” or feel they’re just not cut out for it. To grow, you must become aware of these beliefs. Self-awareness is the first step in changing any mindset. How do you feel about selling yourself or your product? Do you cringe at the thought of “pitching,” or worry about rejection? Write these feelings down.
Acknowledge any negative stereotypes you might hold. Perhaps you recall pushy telemarketers or spammy sales tactics – no wonder “sales” gets a bad name. But also think of times you enjoyed being sold to – maybe a salesperson took the time to understand your needs and you left grateful for their help. Noticing your emotions and experiences will help you pinpoint what you want to do differently. Remember, sales success starts with managing your own mindset and emotions. Salespeople with high self-awareness can regulate negative feelings and stay positive, which helps them build better customer experiences.
Today’s Action: In your journal, answer: “When I think of a salesperson, I think of….” and “My biggest fear/hesitation about selling is….” Be honest. Then, list one or two positive qualities you believe an ideal salesperson should have (e.g. honesty, helpfulness). This contrast will highlight gaps between old stereotypes and the authentic approach we’ll cultivate. Simply becoming aware of these thoughts is progress toward a healthier sales mindset.
Day 4: Shifting Negative Sales Stereotypes
It’s time to challenge and change those negative sales stereotypes. If you’ve felt that “selling is sleazy or tacky,” know that you’re not alone – and that this feeling largely comes from old-school, pushy sales tactics that you don’t have to follow. You can sell with integrity, aligned to your core values, and still be successful. Today, reframe your perspective: Think of selling as an exchange of value between two people. In a good exchange, both sides benefit. The customer’s problem is solved, and you gain a client or income – a win-win. There’s nothing disingenuous about that when done honestly.
Next, identify any internal “limiting beliefs.” For example, do you secretly believe “I’m too introverted to sell” or “People will think I’m annoying”? Challenge those beliefs. In truth, introverts can be excellent at sales by leveraging listening and empathy, and most people appreciate genuine recommendations when it helps them. Replace negative assumptions with positive truths: e.g. “Sales is about helping, not bothering.” By consciously flipping the script, you’ll start dismantling the mental barriers that have held you back.
Today’s Action: Take one negative belief or stereotype you uncovered on Day 3 (for instance, “salespeople are pushy” or “customers hate being sold to”) and reframe it in a positive light. Write the new belief in your journal. For example: “Persistent doesn’t mean pushy – if I truly believe in my solution, it’s worth following up to help the customer,” or “Customers actually appreciate it when someone takes the time to understand and solve their problem.” Read your new belief out loud. Keep these reframes handy – they’ll become mantras to reinforce your new mindset whenever doubt creeps in.
Day 5: Reframing Sales – Serving, Not Pushing
Now that you’re breaking old stereotypes, let’s cement the most important mindset shift of this course: selling is serving. At its heart, selling is simply the act of helping someone solve a problem or fulfill a need. You’re not taking from them; you’re giving them something of value in exchange for value. Reframe your thinking to “Selling is solving a problem for my customer. Selling is serving them in the best way possible.”. When you truly believe this, your tone and approach change from “I need to convince them” to “I need to understand them and help them.” This shift is powerful – it turns anxiety into enthusiasm and builds trust.
Also, consider why you sell what you sell. If you’re a founder, perhaps you created your product to improve lives or make work easier. If you’re a freelancer, maybe you offer your services because you genuinely enjoy helping clients succeed. When you connect with this deeper purpose, selling starts to feel like an act of sharing something good, not an imposition. Customers can sense this sincerity. Remember the advice: focus on solving problems, not selling – the best sales conversations feel like collaborative problem-solving, not a pressured pitch.
Today’s Action: Think of a product, service, or idea you truly love because of how it helps you or others (it could even be something you personally experienced as a customer). Write a short note about why you’re grateful for it. Example: “I’m thankful for my project management app because it reduced my stress and saved me hours each week.” Now, reflect: when you sell, you’re aiming to create that same kind of positive impact for someone else. Jot down how your product or service (or personal skill) helps others – list at least 3 specific benefits or problems it solves. This exercise reinforces the mindset that selling is a form of serving and improving someone’s life.
Day 6: Knowing Your Why and Value
Reflecting on why you sell and whom you serve can deepen your sense of purpose and motivation. Knowing the deeper reason “why it matters” helps align your sales efforts with your values, making your approach more authentic and resilient. For example, a startup founder might realize they sell their product because they genuinely believe it will improve lives, or a freelancer might remember that their services save clients time and stress. Additionally, reframing selling as solving a problem for clients and serving them best can reinforce that sense of purpose.
Today, clarify your personal “Why” – the driving purpose behind your work or business. Ask yourself: What motivates me to do this? How does what I offer serve others or fulfill a passion of mine? When you connect sales activities to a meaningful purpose, it’s easier to stay motivated and confident. Also identify your unique value: What makes you or your product valuable? It could be your expertise, your approach, or a specific benefit you deliver. Understanding this gives you confidence because you know what you’re offering is worthwhile.
Knowing your “why” will also carry you through tough days. If rejection or obstacles happen, remembering the purpose (e.g. “I’m helping small businesses thrive with my software” or “I’m earning freedom for my family”) will keep you resilient. It transforms sales from a grind into a mission.
Today’s Action: Write a “Why Statement” for yourself. For example: “I connect with clients to [your impact] because [your deeper reason].” It might be, “I build websites for local businesses because I love helping entrepreneurs succeed online,” or “I sell eco-friendly products because I care about sustainability and want to make it easy for others to live green.” Also list 3 things that make your offering valuable or different (your “value propositions”). Save this page in your journal and revisit it whenever you need a boost of confidence or direction.
Day 7: Authenticity Builds Confidence
Introverts often shine in sales by leveraging strengths like listening and empathy to build deep, meaningful connections. Embracing your authentic personality—whether introverted or extroverted—can increase confidence and trust with customers.
One of the greatest assets in connecting with others is authenticity. People can tell when you’re being genuine versus using a fake “sales persona.” The good news is you don’t have to be an extraverted, smooth-talking pitcher to excel in sales. You just have to be you – with sincere intent to help. Lean into your natural style. If you’re an introvert, leverage your thoughtful nature, calm presence, and ability to listen (qualities many clients actually prefer in a salesperson). If you’re more extroverted, use your energy to engage and enthuse customers, but remember to listen too.
Authenticity breeds confidence because you’re not acting or lying; you’re aligned with your values. It also breeds trust: customers trust those who are real and transparent. Research shows that authenticity is a must-have in modern sales – customers crave honesty and can sense insincerity quickly. So give yourself permission to drop the gimmicks and be honest. For example, if you don’t know an answer, say so and promise to find out, rather than bluff. If you genuinely believe in your product, let that passion show. When you operate with integrity and authenticity, you stand out and make others feel at ease.
Today’s Action: Recall a time when being your genuine self paid off in connecting with someone (maybe you weren’t trying to impress, and it led to a meaningful conversation or opportunity). Write about that in your journal. Next, jot down any ways you might have been hiding your true self in professional settings (for instance, using jargon you’re not comfortable with, or mimicking a “salesy” tone you heard elsewhere). How can you instead approach your next conversation more authentically? Commit to one authentic behavior (like admitting if you need clarification, or sharing a sincere personal anecdote) in your next sales interaction. Notice how it feels – most find it empowering and confidence-boosting to be genuine.
Day 8: Practicing Empathy
Empathy – the ability to understand and share someone else’s feelings or perspective – is a superpower in building connections and selling. When you practice empathy, you put yourself in the other person’s shoes. This helps you grasp their true needs, concerns, and hopes. Empathy is what turns a superficial sales pitch into a meaningful conversation. It’s also key to the idea of “selling is serving,” because to serve someone you must first understand them.
Start small: in your next conversation, really tune in to the other person. What might they be feeling or worried about? Notice not just their words, but tone and body language if in person. If a prospect seems anxious about cost, an empathetic response might be, “I sense that budget is a big concern for you.” This shows you get it, and it builds trust. In fact, empathy and active listening often go hand in hand to create trust quickly. When the other person feels heard and understood, they lower their guard – now you’re two humans collaborating, rather than a seller and a target in opposition.
Empathy also helps introverts and those new to sales, as it plays to being observant and thoughtful. Many top salespeople mention that showing genuine care for the customer’s situation sets them apart. Remember, “People don’t buy from companies, they buy from people they trust,” and demonstrating empathy is how you earn that trust.
Today’s Action: Do an empathy exercise. Think of a current client or someone you’re trying to “sell” an idea to. Write down at least 3 questions or statements from their perspective, like “What if this doesn’t work for me?” or “I need to look good to my boss by choosing the right solution,” or “I’m overwhelmed with options.” Then, for each, write a compassionate response or reassurance. For example: “I understand you need confidence that this will work – how about we do a small pilot project first?” Practicing this will prepare you to respond empathetically in real conversations.
Day 9: Active Listening – Hearing the Need
Listening is often cited as the most important communication skill in sales, and for good reason. When you actively listen, you aren’t just waiting for your turn to speak – you’re fully concentrating on what the other person is saying and signaling that you value their input. This builds tremendous trust. In fact, active listening builds trust, and trust is the foundation of every successful relationship in sales. By listening more than you talk, you uncover the real needs and concerns of your potential customer.
To practice active listening, start with these basics: maintain eye contact (or attentive posture on phone/video), nod or give small verbal cues (“I see,” “Got it”), and don’t interrupt. After the person finishes, reflect back what you heard: “So, if I understand, your main concern is X, and you’re also looking for Y, did I get that right?” This reflection shows you truly paid attention and allows them to correct anything. It’s okay to pause and digest what they said – you don’t need to jump in immediately with a solution or pitch. Often, the act of letting a customer fully express themselves is more impressive to them than any spiel you could deliver.
Active listening can be challenging if you’re nervous or excited about your product – you might feel an urge to rush in with advice. But trust that listening first will make anything you say later far more relevant and welcome. Listen for emotions and subtext, not just facts. If a client offhandedly mentions a bad past experience, that’s a clue to handle that area with extra care. Listening will give you ammunition to tailor your approach precisely.
Today’s Action: Practice pure listening in a conversation (professional or personal). For at least 5 minutes, focus only on asking questions and summarizing the other person’s points without inserting your own story or pitch. In your journal, note what you learned that you wouldn’t have if you had been speaking. Also note if the person’s demeanor changed – often, you’ll find they become more relaxed and open when they realize you’re truly listening. This is a habit to build every day: talk less, listen more.
Day 10: Asking Powerful Questions
Sales (and any influence) isn’t about having all the right answers – it’s about asking the right questions. Powerful questions unlock conversations, uncover needs, and engage the other person in finding solutions with you. By asking thoughtful, open-ended questions, you invite the customer to talk about their situation and feelings, which both gives you valuable insight and makes them feel valued. As one sales principle states, people are more persuaded by what they themselves say and conclude than by what you tell them. Good questions lead them to those conclusions.
What makes a question powerful? It should be open-ended (cannot be answered by just “yes” or “no”), and it should be about the person or their needs. Examples: “Can you tell me about the biggest challenge you’re facing with X?”; “How would an ideal solution look for you?”; “Why is this important to you at this time?” These encourage detailed responses. Also, asking “why” (tactfully) can get to motivation: “Why is solving this now a priority?” – this might reveal their deeper drive (e.g. they need to save time to spend with family, or they have a KPI to hit this quarter).
Don’t pepper someone with a laundry list of questions like an interrogation. Instead, have a conversation, where each question builds on what they’ve shared. Active listening from Day 9 sets you up to ask relevant follow-up questions: “You mentioned X, could you elaborate on that?” or “How is that currently affecting your business/day?” Remember, questions also show your expertise when done right – they can make the person reflect on issues they hadn’t considered. It positions you as a problem-solver.
Today’s Action: Prepare a list of 5 open-ended questions related to whatever you’re selling or proposing, which you can use in your next conversation. Use the classic starters: Who, What, When, Where, Why, How. For example: “What do you wish you could improve about…?” “How are you handling… currently?” Now practice by actually asking at least one of these questions in a real conversation today (even if it’s a casual context like asking a colleague about their work challenges). Listen to the answer fully. Later, jot down in your journal which question sparked the most engaging discussion and why you think it worked. This will refine your questioning skills.
Day 11: Building Rapport and Trust
Rapport is that comfortable vibe or connection you establish with another person, and it is golden in sales and networking. When you have rapport, conversations flow easier, there’s mutual understanding, and trust forms naturally. Trust is the currency of sales – people buy from people they trust. So how do you build rapport? Start by finding common ground and showing genuine interest. This could be as simple as noticing you share an interest (“I see you’re a baseball fan too”) or as meaningful as aligning on values (“Our company also prioritizes sustainability – that’s something I really care about personally.”).
Be friendly but sincere. Use the person’s name, smile if appropriate, and engage in a bit of human-to-human talk (weather, weekend plans, a compliment about something you genuinely appreciate about them or their business). Small talk isn’t pointless – it’s a trust lubricant, as long as it’s respectful and not forced. However, building rapport is more than chit-chat; it’s about showing you care. One effective method is to acknowledge something they’ve said earlier: “You mentioned earlier that you value reliability in a partner – I want to assure you…” This shows you listen (tying back to active listening) and respect what matters to them.
Consistency and reliability also build trust. If you say you’ll send them info tomorrow, do it. Each kept promise, however small, cements trust. Conversely, one broken commitment can undermine rapport quickly. Remember that first impressions matter: coming across as composed, courteous, and prepared in your initial meetings lays the groundwork for rapport. But even if it doesn’t click immediately, don’t worry – rapport can grow over multiple interactions by continually demonstrating empathy, honesty, and value.
Today’s Action: Think of two ways you can establish or improve rapport with a current or prospective client. One might be personalization – e.g., start your next email with “I hope your daughter’s first semester at college is going well” (if they’ve mentioned their family), demonstrating you remember personal details. Another might be shared experience – e.g., “I also struggled with scaling my business, which is why I’m passionate about this solution.” Write down your two ideas. Next time you interact with that person, consciously apply at least one and note the reaction. Over time, these small rapport-building efforts create a strong bond of trust.
Day 12: Telling Your Story
Humans are storytelling creatures. Facts and figures are important, but it’s stories that stick in our minds and touch our emotions. In sales and building connections, learning to share your story – and your customers’ success stories – can make your message far more compelling than a dry pitch. Storytelling doesn’t mean rambling on about yourself; it means using narrative to illustrate a point in a relatable way. For example, instead of saying “Our product is easy to use,” you could tell a quick anecdote: “One of our clients, a self-proclaimed ‘tech novice,’ set it up in 10 minutes and said it saved her two hours a day – she spent that extra time with her kids.” That story paints a picture and highlights a benefit emotionally.
Your personal founder/freelancer story is powerful too. Why did you start your business or career? What challenge did you see or experience that led you here? Sharing this in a concise way can build authenticity and trust. It shows you have a personal connection to what you’re offering – you’re not just selling for the sake of it. It can be as simple as: “Back when I was [describe problem scenario], I realized how much time was wasted, and I became determined to create a better way. That’s why I’m passionate about offering this service to others in that situation.” Such narratives signal your genuine passion and relatability.
Also encourage your satisfied customers to share their stories (testimonials or case studies). These serve as social proof and help future clients see themselves in those stories. When you frame a sales conversation as “Let’s write your success story next”, it positions you as a partner in their journey, not just a vendor. Storytelling essentially helps to reframe selling from a cold transaction to a human experience of sharing and solving together.
Today’s Action: Draft a short version of your personal story related to what you’re selling. Use a simple structure: The Challenge (what problem or need existed), The Turning Point (how you discovered a solution or decided to help others), and The Resolution (the positive outcome now, and how you bring that to clients). Keep it to a paragraph. Practice saying it out loud in a conversational tone. Also, write down one customer success story you could tell (even if it’s hypothetical for now: e.g., “Imagine a client who...”). Having these stories at the ready will enrich your conversations.
Day 13: Communicating Value with Confidence
By now, you’ve honed listening and questioning, which means you understand your customer better – now you must clearly communicate how you can help them. This is where you articulate your value proposition confidently. Communicating value is not bragging or being pushy; it’s educating the other person on how you can solve their problem or improve their situation. If you’ve done the previous steps, you can frame your offering directly in terms of the needs the customer expressed. For instance: “Earlier you mentioned struggling to keep track of tasks; what I offer can give you an organized dashboard so nothing falls through the cracks.” This ties their need to your solution.
Confidence is key here. If you sound unsure about your own product or service, how can they feel sure? Confidence doesn’t mean overhyping or pretending you’re perfect; it means speaking clearly about the benefits and believing in the worth of what you’re offering. One way to boost confidence is by remembering the positive outcomes you’ve seen or the preparation you’ve done (recall the value list from Day 6 and the stories from Day 12). Also, use simple, jargon-free language. You don’t need fancy terms to impress; in fact, speaking plainly about benefits often shows more confidence and clarity. For example, instead of “Our solution optimizes financial outcomes,” say “Our solution will help increase your sales by tracking leads better, which means more revenue for you.” Be direct.
If you notice yourself feeling nervous when it’s time to talk about your solution, take a breath and remember: you’re helping, not begging. Adopting a mindset that “I have something valuable and I’m here to see if it’s a fit for you” can psychologically switch you from a posture of neediness to one of offering. Practice your key points, but stay flexible to adjust based on what the customer cares about. When you communicate with conviction and focus on the value to them, you’ll come across as both confident and client-centered.
Today’s Action: Write a short pitch (3-5 sentences) that describes what you do in terms of the value or outcomes it provides, and practice saying it out loud confidently. For example: “I help busy professionals regain 5-10 hours a week by organizing their schedules and tasks, so they can focus on what really matters.” Adjust the wording until it feels natural and strong. Then, if possible, use this pitch on a friend or colleague and ask for feedback: Did it sound confident? Did they grasp the value? Note any improvements in your journal. Each time you articulate your value, it will strengthen your confidence and clarity.
Day 14: Mid-Course Reflection
Congratulations on reaching the midway point! Two weeks of consistent effort is no small feat. Today, we’ll pause to reflect on your journey so far. Reflection consolidates learning and builds self-awareness, ensuring that new habits truly stick.
Look back through your journal entries from Days 1–13. What patterns do you see in your thoughts or experiences? Perhaps you notice that initially you felt very anxious about reaching out to people, but by Day 10 you felt excitement after asking good questions. Maybe you see your attitude towards “sales” shifting from aversion to curiosity or even enthusiasm. Acknowledge those changes – that’s progress! Also note any challenges: Did you struggle with certain exercises, like listening without speaking or writing your personal story? These might be areas to focus a bit more on in the coming days.
Take stock of any external results too. Have you noticed any difference in how others respond to you? Even small wins count – maybe a usually quiet prospect opened up more because you listened, or you had a networking chat that felt easier than before. Celebrate those wins. Reflection is also a time to adjust if needed: Is there any daily exercise you skipped or want to redo? For instance, if you feel your “why statement” (Day 6) could be stronger, this is a great time to refine it.
Today’s Action: On a fresh page of your journal, write a short mid-course summary for yourself. You can use prompts like: “So far, I’ve learned that I…”; “The hardest part has been…”; “The most significant change in my mindset or behavior has been…”; “Going forward, I want to focus more on…”. Also list 2-3 accomplishments from the last two weeks that you’re proud of (e.g., “had my first sales call without freezing up” or “changed my view of sales to see it as helping”). Finally, write one commitment for the next two weeks – maybe “I will speak up and make an offer when I see I can help” or “I will reach out to one new contact each weekday.” This reflection will boost your confidence and clarify your aims for the second half of the course.
Day 15: Identifying Needs and Pain Points
Entering the second half of our journey, we pivot more into practical selling techniques – but always grounded in empathy and service. Today’s focus: how to effectively identify the needs or pain points of the person you’re trying to help. In any sales or persuasive situation, if you don’t accurately understand what the other person truly needs or what problem they want solved, your chances of helping (and closing a deal) drop dramatically. That’s why the listening and questioning skills you built are so critical – they are the tools to uncover needs.
When conversing with a prospect or client, listen for explicit statements of need (“We’re looking to improve X”) but also watch for implicit clues. Sometimes people won’t state a need outright because they assume it’s unsolvable, or they haven’t fully articulated it even to themselves. They might say, “We’ve tried everything and growth has plateaued,” which hints at an underlying need for a fresh approach or guidance. A good approach is to ask probing questions that get to the root of the issue: “What do you think is causing that plateau?” or “If you could wave a magic wand, what’s the one thing you’d fix immediately?” Such questions encourage them to reveal the core pain point.
Also, distinguish between surface wants and deeper needs. A client might say, “I think we need a new website,” but their deeper need is “we need more customers/sales” – the website is just a presumed solution. If you identify the deeper need (more customers), you might realize a website is part of it, but also SEO or marketing might be needed. This allows you to address the real problem more holistically (and maybe offer more value). People feel truly understood when you can articulate their problem even better than they can. They might say, “Yes! That’s exactly what we’re struggling with.” That’s when they know you “get it,” and trust soars.
Today’s Action: Take one person or client you’re working with (or a hypothetical one if none currently) and do a needs discovery brainstorm. Write down what you think their obvious needs are, then push yourself to ask “why is that important?” for each need to find a deeper level. For example: Need: “improve online presence.” Why? “to reach more customers online.” Why is that important? “their current sales are declining in physical stores. ” Now the pain point is clearer: declining sales and the need to reach new customers. This exercise trains you to peel back layers. In your next conversation, try asking “why” or “tell me more about that” to uncover deeper needs. Document any insights in your journal.
Day 16: Presenting Solutions (Not Just Products)
Once you understand a person’s needs and pain points, you can position what you’re offering as a solution – not just a product or service for its own sake. This is a big distinction. People don’t buy a product; they buy what that product will do for them. They don’t purchase consulting hours; they invest in the outcome or relief those hours will produce. So, when you present your solution, frame it 100% in terms of how it addresses the needs you uncovered. Use the customer’s own language where possible: “You mentioned your team wastes hours tracking tasks via email – this tool will centralize all tasks in one dashboard, eliminating those email chains and saving those hours.” Now you’re explicitly connecting the dots between their pain and your answer.
Keep the focus on benefits and outcomes rather than features. A feature is a fact about your offering (e.g., “24/7 support line”); a benefit is what it means for the customer (“peace of mind knowing help is available any time”). People often remember feelings and outcomes more than technical details. To practice this, for every feature of your service, state “which means…” and complete the sentence with the benefit. For example: “I offer a one-month trial (feature), which means you can test it in your workflow risk-free to be sure it truly meets your needs (benefit).” This way, even when describing features, you immediately tie them to solving the customer’s problem or easing a worry.
It’s also powerful to visualize success with the client. Get them picturing the future with their problem solved: “Imagine in a few months, you have twice as many leads coming in through the new website – how would that impact your business?” Let them articulate the positive picture. If they say, “That would let me hire another employee to further grow,” they’re now emotionally invested in the solution. Finally, remember to check in as you present: ask “Does this sound like it would address the challenge you described?” This keeps it a dialogue and ensures you’re on the right track.
Today’s Action: Take the needs from Day 15’s exercise and write down how your product/service specifically addresses each one. For each need/pain, write a short statement like: “Need: ___. Solution: ___,” making sure your solution statement highlights the outcome or relief. If you find any need that your current offer doesn’t really solve, that’s insightful – you may need to adjust your pitch or acknowledge limitations honestly. Practice explaining one of these solution statements out loud as if to the client. Aim for clarity and emphasis on what they gain, rather than on what you do. This will enhance your ability to present compelling solutions naturally in conversation.
Day 17: Embracing Objections
Sooner or later, every attempt to sell or persuade meets with objections – those “Yes, but…” responses or concerns from the other person. Common objections include things like price (“It’s too expensive”), timing (“Not sure if now is the right time”), authority (“I need to convince my partner/boss”), or skepticism (“Will this really work for me?”). Many people dread objections, but today we’ll reframe how you view them. Objections are not personal rejections or dead-ends; they are actually opportunities. An objection is a sign the person is engaged enough to voice a concern, which means they’re considering your offer. It’s your chance to clarify, educate, and build trust further.
First, stay calm and positive when an objection arises. Avoid getting defensive or rushing to argue. Instead, listen fully to the concern – often there’s more beneath the surface. For example, “too expensive” might really mean “I’m not convinced of the value yet.” Thank them for sharing the concern (it encourages honesty) and acknowledge it. Empathize sincerely: “I understand budget is tight; many clients feel that way at first.” This shows you’re not dismissing their worry. Only after acknowledging, proceed to address it constructively.
Use objections as a chance to ask questions and clarify. “It’s too expensive” could be followed by “I hear you. May I ask what you’re comparing it against or what budget you had in mind?” This gets more detail. If someone says “I’m not ready to make a decision,” you might ask “What factors do you need to consider before you’re comfortable moving forward?” Sometimes objections hide the real issue – gentle probing can surface the true barrier. By treating objections as normal and even helpful parts of the conversation, you maintain a collaborative tone rather than an adversarial one. Remember, handling objections with empathy can actually increase trust, because the person sees you truly care about their concerns.
Today’s Action: List the top 3 objections or questions you expect (or have encountered) when you propose your product or idea. For each, script out an empathetic, helpful response. Structure it in three parts: 1) Acknowledge the concern (“I get why you’d worry about X…”), 2) Address or answer with value (“…what we’ve found is Y, and here’s why…”), and 3) Check-in (“…does that help address your concern about X?”). Write these in your journal. Practice saying them naturally. Having thought through objections in advance will make you much more confident when they come up, and you’ll be able to respond in a calm, reassuring manner rather than being caught off guard.
Day 18: Responding to Concerns Constructively
Following on the heels of Day 17, today we continue working on objection-handling skills. Now that you see objections as opportunities, how do you respond in a way that truly resolves the concern and moves the conversation forward? One effective technique is often summarized as LAER: Listen, Acknowledge, Explore, Respond. We touched on the first two: fully listen to the objection and acknowledge it (e.g., “I hear that the timeline is a worry for you”). Next, Explore by asking follow-up questions to understand the objection’s context deeply (e.g., “Is there a specific deadline you’re working against?”). Finally, Respond with a tailored answer or solution that addresses what you learned (e.g., “We can adjust our implementation schedule to meet your deadline, or even start with a smaller phase to ensure we’re on track in time.”). This method ensures you’re not giving a one-size-fits-all answer; you’re directly tackling their unique concern.
Another tip: sometimes reframe the objection. If someone says, “I don’t have time to implement this,” you might reframe it as, “Finding time is hard – which is exactly what this solution helps with, by saving you time in the long run.” Then provide evidence or a story: “For instance, one client initially worried about the setup time, but after using it, they saved two hours daily.” This approach turns the objection into a reminder of the value. However, be careful: always address the objection honestly – if something truly can’t be done, admit it. For example, if your product indeed doesn’t have a feature they want, say so, and highlight what you can do or any workarounds. Honesty maintains credibility.
It’s also okay to admit when you don’t have an immediate answer. If a prospect raises a highly technical question or something you’re unsure about, don’t wing it. Acknowledge it: “That’s a great question. I want to make sure I give you an accurate answer – can I research that and get back to you by this afternoon?” Most people will appreciate your candor. Just be sure to follow through promptly. When you address concerns constructively like this, you not only remove barriers to the sale but often end up reinforcing the buyer’s confidence in you and your offering. They see that you’re solutions-oriented and trustworthy.
Today’s Action: Take the objection scripts from Day 17 and role-play them in a mock dialogue (even if just by yourself). Speak aloud what the other person might say and then your response. Pay attention to your tone – it should be calm, understanding, and confident. If possible, ask a friend or colleague to play the customer’s role and give you a tough objection, so you can practice responding in real-time. Afterwards, note in your journal: How did it feel to handle the objections? and Which responses worked best or need tweaking? This practice will make you more nimble and comfortable with objections in actual situations.
Day 19: The Art of Making an Offer
After understanding needs, presenting solutions, and handling objections, there comes a pivotal moment: you need to make the ask – in other words, invite the other person to take the next step (buy, sign up, agree to your proposal, etc.). This can be intimidating for some, but think of it this way: if you’ve genuinely done everything up to now in the spirit of helping and connecting, then making an offer is a natural continuation of that help. You’re not forcing something on them; you’re offering a solution that you truly believe will benefit them.
To make an effective offer, be clear and direct about what you’re suggesting as the next step. Ambiguity can kill momentum. For example, avoid a vague “So, uh, if you want to move forward, let me know.” Instead, confidently say, “It sounds like this could really solve X for you. I recommend we start with __ (specific package or plan). We can get the paperwork started today and have kickoff by Monday – does that sound good?” Notice this assumes a positive intent and gives a concrete next step. It might feel presumptive, but people often appreciate when you guide them on what to do next – it shows leadership. Of course, phrasing and tone should be polite and not pushy.
Another approach is the summary close: recap what they’ve agreed to or the benefits discussed, then make the offer.