The 16 Worst Sales Email Writing Mistakes

You never get a second chance to make a good first impression. And when that first impression is made via email, it’s even harder to come off the way you want to. Without the benefit of an in-person interaction, you can’t exactly build rapport or pivot your strategy if something you’re saying doesn’t resonate.So it’s imperative that you get that first email right. While you can’t control whether your email garners a response, you can control everything else — and you should.

If the core of your email is an insight or resource, think of your writing as the packaging. Even if you’re an expert, it’ll be hard to build credibility if your online communication is riddled with spelling and formatting errors. Below are the worst errors that’ll cause salespeople to embarrass themselves over email. Beware!

16 Sales Email Mistakes to Avoid at All Costs

1) Misusing “your” and “you’re”

They sound the same, but they certainly don’t mean the same thing. It’s easy to slip up, but asking your prospect, “Do you have any time on you’re calendar to chat tomorrow?” makes you look sloppy and unprofessional.

2) Misusing “there,” “their,” and “they’re”

Another common grammar mistake that makes it harder for you to be taken seriously.

3) Misusing “its” and “it’s”

The last member of the trio of frequently confused homophones.

4) Misspelling your prospect’s name or company

Maybe you were tired when you sent the email. Maybe your eyes were blurry from staring at the screen for too long. Guess what? Your prospect won’t care — they’ll think you haven’t done your research, are sloppy in your work, or flat out don’t care about accuracy. None of the above bode well for your ability to make the sale.

5) Misspelling your own company’s name

This isn’t nearly as insulting to a prospect since you’ve fumbled your own company, not theirs, but it still gives the sense that you just don’t care that much.

6) Mistyping your phone number

This is a mistake I made (and learned from) the hard way. My email signature contained my phone number, but I’d mistyped one digit. I got a frustrated email from a client a few days into his project demanding to know why I never picked up the phone.

If you’re going to provide a way for your prospects to get in touch, make sure it’s correct. If they actually take the initiative to call you, ensure it’s not a waste of their time.

7) Fumbling the date

Scheduling a meeting over email is enough of a pain. Asking your prospect for a meeting on “Thursday, November 16th” when November 16th is actually a Wednesday creates confusion and necessitates an additional two or three emails to correct the mistake. Make sure you’re referencing a calendar when including dates in your emails.

8) Not using paragraphs

If your email’s only two sentences long, this isn’t as much of a problem. But when you’re writing a long follow-up email or a recap of an important call, make sure you’re breaking the text up so it’s easy for your prospect to read.

9) Using inline lists instead of bullet points

To make your prospect’s job even easier, break out lists into easily scannable bulleted lists. Would you rather be asked if a meeting on “Monday at 3:00 p.m., Tuesday at 12:00 p.m., Tuesday at 1:45 p.m., Wednesday at 9:00 a.m., Wednesday at 4 p.m., or Thursday at 12:20 p.m.” works better for you, or receive this email:

Let me know if any of the below times work for you:

  • Monday at 3:00 p.m.

  • Tuesday at 12:00 p.m.

  • Tuesday at 1:45 p.m.

  • Wednesday at 9:00 a.m.

  • Wednesday at 4:00 p.m.

  • Thursday at 12:30 p.m.

You prefer the second option? Yep, me too.

10) Failing to format

In a real conversation, you can use body language, voice tone, and gestures to accentuate important points. But it’s harder to convey tone in emails, so if your email is longer than a paragraph and it contains information your prospect absolutely must read, bold or italicize it to make sure it catches their eye.

One caveat: Don’t go too crazy. An email where every other word is bolded or underlined is jarring to read and looks unprofessional.

11) Including too much information

You can use #10 above to gut check this point. If you’ve written 800 words, but only felt the need to bold one statement, take a moment to check whether you actually need to include everything you’ve written. Save your prospect as much time as possible by cutting right to the point — they’ll appreciate it.

12) Burying your ask

Sometimes, though, you will need to write a longer email. In this case, make sure to pull out your ask into its own line or paragraph so it’s not lost in the rest of the text.

13) Not including an ask

Whether it’s asking for 10 minutes to discuss resources you’ve just sent over or offering a product demonstration, every action you take should be designed to advance a prospect through the sales process if it’s a mutual good fit.

14) Asking too much

Of course, what you ask has to be reasonable. If it’s the first time you’re speaking with a prospect, it’s ridiculous to ask them what contract terms they’d be comfortable with. Tailor what you ask for to your prospect’s stage of the buyer’s journey.

15) Including broken links

Including a link or two in your sales emails is great when it’s applicable. You’re providing more content and an opportunity to click around your site and learn more about your product. Make sure those links are updated and work, especially if you’re using a template — if your prospect is actually interested enough to click through, make sure you’re giving them a good experience. Just as importantly, you’ll appear unprofessional and sloppy if you include links that don’t work.

16) Copying and pasting

Have you ever gotten an email where a single section is much smaller than the others or appears in a different font? If so, you know how distracting it is. This weird issue is caused by copying and pasting without removing the formatting.

To make sure this doesn’t happen with your emails, highlight any sections you’ve pasted and click the “Remove formatting” button in your email browser.

If you’re using Inbox or Gmail, you can also remove formatting by highlighting a section and pressing command + the backward slash key (). Outlook users, press control + space.

Writing good sales emails is an art and a science. Different subject lines and strategies will work better for different prospects and industries. But these are the building blocks of professional correspondence. Get your writing rock-solid so you can focus on selling.

Editor’s note: This post was originally published in November 2015 and has been updated for comprehensiveness and accuracy.

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Source: The 16 Worst Sales Email Writing Mistakes

The 5 Most Common Objections During Prospecting and How to Overcome Them


When we talk about objection handling in sales, it is often focused on the later stages of the buying cycle, usually during negotiations. We focus on pricing and timing issues — the types of objections that prevent a deal from closing. A crucial yet overlooked aspect of objection handling occurs at the very beginning of the buying process, during prospecting. Sales reps who do their own prospecting and sales development reps encounter a myriad of objections in their attempts to connect with and qualify prospects.Get 25+ sales experts' playbooks for free. Reserve your seat at Inbound Sales  Day today.

Prospecting is hard. You are typically barging in on someone, so you’ll hear objections such as, “I’m too busy, call back next quarter,” “Just send me some information,” “We don’t have budget outlined for this,” and so on. The good news is you will begin to identify a set of common objections during prospecting. The key to success is to be prepared to overcome them and move prospects to the next step.

The vast majority of objections heard during prospecting are knee-jerk reactions from busy people who don’t yet see the value in working with you. Nearly all objections at the prospecting phase of the sales process fit into one of two categories:

  1. I don’t understand the value and I’m too busy to think about it.
  2. I’m not ready for a buying conversation. 

Here’s how to avoid and/or overcome these objections.

First, articulate value early and concisely. You can mitigate the value objection by simply respecting the prospect’s time and explaining what you want early in your outreach. Every email, voicemail, and phone interaction should lead with an assurance that you won’t take much time, followed by a short (30 seconds or less, or one to two sentences), buyer-centric, and customized value proposition. For more on the quick value prop, check out this post.

Second, don’t sell the product, sell the next step. It does not matter if the prospect is ready for a buying conversation yet. How could they be? It’s possible they’ve only just learned about you and your product from this call. Don’t get into a discussion of the product yet. If they ask a product question, recommend that you show them in the next meeting.

The Top 5 Prospecting Objections

Here are the five most common objections prospectors face, along with some very simple approaches to responding to them.

1) The Brush-Off

What this sounds like: “Just send me some information.”

This objection varies in intent depending on when it comes up in your call with a prospect. If it comes up before you have had the chance to deliver your value proposition and explain who you are and what you do, it’s very clearly a brush-off. If it comes afterward, but before you’ve had the chance to ask qualification questions, there may be interest, but the prospect isn’t yet willing to talk about it further.

If it comes at the end of your call, after you’ve gone through both your value prop and qualification, the prospect may have decided this isn’t valuable somewhere along the way. No matter where it comes up in the call, it’s the SDR’s duty to uncover what is really going on: Do they not yet understand the value, or are they not ready for a buying conversation? Why not?

Responses: There are a few potential responses to this one, depending on what stage the call is in.

  • Before you’ve delivered the value proposition: “Can we take 30 seconds now for me to explain what we do, and you can then decide if it’s worth a follow-up?”
  • Before qualification: “Can I ask you a couple questions now to better understand how we might help?”
  • After qualification: “Typically, people find it more valuable to see how this works in a demo.”

2) Competition

What this sounds like: “We already work with Competitor X.”

This is where it’s important to know why you are unique, and be able to explain that value clearly. Your prospect just heard, “Hi, we do X” and thought, “Oh, we have a vendor for that, we’re good.” Your prospects are busy — they don’t want to fix things that aren’t broken. It is your duty to change their mindset, and explain why they need the specific value you provide.

Response: “At this point, we aren’t asking you to rip anything out. A lot of our customers used to or still use Competitor X. We’d just like the opportunity to show you how we are different and how we have provided additional value to our customers. We can present some use cases of other companies like yours who work with us and with Competitor X. When is a good time to schedule a follow up call?”

3) Procrastination

What this sounds like: “Call me back in a quarter.”

Prospects are busy. They will push anything off to tomorrow because today is swamped. Don’t let them! You have a solution they needed yesterday. Reassure them that this is not a buying conversation. You just want to show them what you do, and see if there’s value for them.

Response: “Of course. If it really is bad timing, I’m happy to do that. However, I would still like to set up a five-minute call to show you what we are doing and how we might help. That way, if it’s not interesting, we don’t have to worry about me chasing you next quarter, but if it is, we’ll have more to talk about then. When is a good day/time for us to chat?”

4) Budget

What this sounds like: “We don’t have budget for this.”

If budget is an important part of your qualified lead definition (e.g. traditional BANT) this may be a stopping point. Even with BANT however, it is important to dig a bit further to understand what not having budget means. Can they not afford it? Has your buyer burned through her personal budget for the year? Could your buyer find the money elsewhere if you show enough value? In most cases, the prospect doesn’t need to have a budget at this stage of the process, and SDRs should leverage this fact to overcome this objection.

Response: “That’s okay. We don’t expect you to buy anything right now. We’d just like the opportunity to share what we are doing and see if it’s valuable to your company. Can we schedule a follow up call over the next couple days?”

5) Getting in the Weeds

What this sounds like: “Does your product do X, Y, and Z?”

This isn’t so much an objection as an obstacle to closing a call with a prospect and getting them to the next appointment, (e.g., a demo, or a discovery call with the sales rep). However, it is one of the most common obstacles that prevent an SDR from converting the lead to an SQL. Not only does getting in the weeds waste time, you also run the potential of devolving into a features/benefits conversation. The good news is this generally means the prospect is interested. Use this fact to end the conversation and set up the next appointment.

Response: “I am glad you asked that. I think it will be helpful to set up a time where we can answer this question and others with a specialist. When is a good day/time for us to talk?”

When No Means No

Prospects often don’t give you a chance to explain the value you think you can provide. They are too busy, and have too little faith in the hordes of SDRs and sales reps that reach out to them on a daily basis. Unfortunately, they have learned through experience that these knee-jerk objections are the best defense against people wasting their time. This forces salespeople to be more assertive and persistent.

That said, at a certain point no means no. The responses to the common objections above give you a way to pierce through the reactionary objections prospects give without thinking. However, if you have said your piece and the prospect still objects, let it go. Nobody is going to buy against their will. Get as clear as you can on the objection and try to determine what your prospect is really concerned about, but don’t push past the prospect’s point of comfort. Rule of thumb: if the prospect says an objection twice, it’s real. No means no.

Editor’s note: This post was originally published in March 2015 and has been updated for comprehensiveness and accuracy.


Source: The 5 Most Common Objections During Prospecting and How to Overcome Them

How to Win Against the Competition


Salespeople and prospects rarely want to talk about the same things. You want to talk about the buyer’s budget, timeline, and role in the decision making process, while the buyer wants to talk about pricing and the nuts and bolts of the product.

This conflict is especially clear when your prospect brings up the competition. It would be great to keep the focus on your own product — but if you say too little (or nothing at all), you’ll miss an opportunity to differentiate it from their other options. Say too much, and you typically come across as insecure or desperate.

To walk this line and ultimately win the deal, follow these six guidelines.

1) Acknowledge the Elephant in the Room

You and your prospect both know you’re biased. So why would they ask for your opinion on the competition in the first place? Sometimes, it’s a sign of trust: The buyer believes you’ll put their interests first, even though you have a financial incentive not to.

But sometimes, it’s a test. Your prospect is trying to figure out whether you’ll steer them the right way or give them bad information.

Rather than ignoring the elephant in the room, call it out. Say, “Obviously, I have skin in the game. Happy to answer all of your questions, but I can also point you to some third-party resources you might find helpful.”

Your transparency will make you seem 10 times more trustworthy; plus, you’ll set the tone for a candid conversation.

2) Use External Reviews

While you might not be able to convince the buyer yourself, a third-party review will be very persuasive. Look for testimonials comparing you and your competition where you come out ahead — maybe from a customer who switched to your product after using a rival one or one who trialed several different tools before choosing yours.

If your prospect asks, “How do you compare to [competitor]?” or “What do you think about [competitor]?”, you can respond:

“That’s a good question. I’m going to send you a review from a customer who [moved over to us after X amount of time, chose our product after evaluating Y different ones, went with my company for Z reasons]. If you have any questions after reading it, I’m more than happy to answer them.”

If you can’t find any online reviews, look for happy clients or users in similar situations. Then ask them to write testimonials that you can send to future buyers. Or, if you work a relatively small number of high-value deals, see if the customer is willing to act as a reference.

3) Turn the Question Around

To avoid talking about the competition and refocus on your product and the buyer’s situation, try these responses:

  • “Before we go down that road, may I ask why you’re interested in that?”
  • “Quick question first: Is [use case, feature, result] one of your top considerations?”
  • “Would you say X is one of your ‘must-haves’?”

For example, if your prospect just asked, “How does your safety lock compare to Saltzer’s safety lock?”, you’d respond, “We can talk about that. But some context might help me give you a better answer. May I ask why you’re specifically interested in the safety lock?”

The buyer will normally say it’s a priority or key feature. Explain the strengths of your product in that aspect, then end with, “I think Saltzer could give you more details than me about their safety lock, so I’d ask them.”

4) Be Honest

Sometimes, honesty truly is the best policy. Tell the buyer, “I don’t want to comment on [competitor] because I’d hate to give you out-of-date information. They’re nice people over at [company] — I’d recommend asking them.”

This matter-of-fact, straightforward reply will earn you points with your prospect and keep you from smearing the competition.

Alternatively, try a little levity: “I plead the fifth! But seriously, I steer clear of discussing [competitor] — they’re the best people to ask about [competitor’s product]. Getting back to how [prospect’s company] could use [product] … ”

Politely yet firmly refusing to talk about your competition shows the buyer you’re a class act. More importantly, it suggests your offering is attractive enough to stand on its own.

5) Set the Record Straight (When Necessary)

Not everyone plays fair. You might discover one of your competitors is spreading misconceptions (or even complete lies) about your company, products, or clients.

Imagine a buyer lets you know she’s also considering Vendor X — whose reps routinely mislead your prospects. The worst thing you can do is say, “Don’t believe what they tell you about Y or Z. They’re liars.” Not only will you sound like you doubt the buyer’s intelligence, you’ll also make the claim sound more believable by addressing it.

However, if you know what your competitor usually attacks, you can proactively bring up those elements in your sales conversation. Maybe they typically say your customer service is non-responsive. During your presentation, highlight your support team’s lightning-fast response time and high satisfaction ratings. This strategy will put your prospect’s mind at ease without directly calling out the competitor.

What if the buyer says, “Vendor X told me … ”?

According to sales consultant and trainer Jeff Hoffman, the most successful response is simply: “That’s not true.” This statement will satisfy most prospects. If they still don’t believe you, they’ll ask a follow-up question.

6) Lose the Deal

High-performing salespeople understand that winning the war often means losing the battle. In other words, if you realize the competition is a much better fit, be honest with your prospect.

Here’s a sample soundbite:

“Based on what you’ve told me about your [budget, use case, objectives, needs], I think [competitor] might be a better fit. But if you know anyone that fits [2-3 buyer criteria], I’d love an introduction.”

Buyers are blown away by this level of genuine service. They’ll reward you with positive word-of-mouth, referrals — and if and when their situation changes, new business.

Some prospects will even say, “[Competitor] might be a better fit product-wise, but based on how well you’ve treated me before I’ve even become a customer, I’d rather go with you.”

It doesn’t matter who you work for or what you sell — you have competition. And that means buyers want to talk about their other options. Instead of staying silent, or equally damaging, going on a rant, earn your prospect’s trust and influence their opinion by using these six strategies.

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Source: How to Win Against the Competition

9 TED Talks on Effective Communication That Will Help You Close More Deals


Effective communication helps you forge strong connections, collaborate with internal and external stakeholders, close deals, and convince people to share your views. It’s critical to your success, whether you’re a sales leader, manager, or front-line rep. So what makes you an effective communicator? You must be able to explain complex ideas simply and clearly, speak in your own voice, tailor your message to your audience — and that’s just to start.Improve your communication skills by watching these nine TED talks. They touch on every aspect of communication, from what we say, how we say it, whom we say it to, and equally importantly, what we don’t say.

9 TED Talks on Effective Communication

TED Talks for the Workplace

1) “Listen, Learn … Then Lead” by Stanley McChrystal

If you think the United States Army is a rigid organization where decisions and orders come from the top and must be followed without exception, you might be surprised by former U.S. Army General Stanley McChrystal’s TED talk.

In this talk, McChrystal — who joined the Army at age 22 — shares the different leadership styles he encountered as he rose through the ranks, then shares the lessons he’s learned as a general. As the armed forces changed, McChrystal found himself leading groups of people who had vastly different experiences than himself.

“We’re operating a force that must have shared purpose and shared consciousness, and yet [direct reports] have different experiences, in many cases a different vocabulary,” McChrystal says.

To bridge gaps of understanding, it falls to leaders to build credibility through being transparent, willing to listen, and open to being reverse-mentored, McChrystal says.

2) “Remember to Say Thank You,” by Laura Trice

Productive communication doesn’t require agreement — in fact, some of the best meetings I’ve ever had involved disagreement. And that’s to be expected when you work with smart people who have strong opinions. But in order to have productive discussions and keep your team moving forward after conflict, people need to feel heard and appreciated.

In this TED talk, doctor and life coach Laura Trice poses a simple question — why don’t people ask to be thanked for the value they bring to the table, whether in their personal or professional lives? She thinks it’s because by asking for praise, we make ourselves vulnerable.

In this talk, you’ll explore the value of saying “thank you,” asking to be thanked, and the implications of freely giving gratitude.

3) “The Danger of Silence” by Clint Smith

In this powerful spoken word TED Talk, Clint Smith addresses what happens when we simply don’t communicate. Smith, a teacher and poet, gave up speaking for Lent one year — and realized how much he’d already silenced himself.

How many times do you see something happening in the workplace or your personal life that makes you uncomfortable? How many times do you speak up for yourself, a coworker, or a customer? In his TED talk, Smith argues that the price of staying silent is injustice — and that’s too high a price to pay.

4) “The Secret Structure of Great Talks” by Nancy Duarte

Whether you’re in sales or not, you pitch people every day. Want to hire more people on your team? A promotion? A new project? You have to influence the people around you to get your way — and that’s where Nancy Duarte comes in. Duarte, a presentation expert who helped Vice President Al Gore with “An Inconvenient Truth,” believes that all great presentations follow a specific arc.

As a presenter, it’s your job to tell a story that draws in your audience and convinces them of something. In this TED talk, Duarte shares actionable tips to rework how you tell stories — and hopefully help you get closer to what you want.

5) “How to Save the World (or at Least Yourself) From Bad Meetings,” by David Grady

Communication is a good thing. Transparency and openness are both good things. Pulling people from different teams to give input on important projects is a good thing. So you would think that the concept of the work meeting — something designed to deliver information, gather opinions, and make progress, would be good as well.

Unfortunately, there is such thing as too much of a good thing. David Grady, a cybersecurity manager, believes that we’re being deluged by pointless meetings that waste our time. In this TED talk, you’ll learn Grady’s “No MAS” technique for making meetings more productive and valuable — so that when you’re communicating with your coworkers, you’re only talking about what really matters.

TED Talks on Communication Skills

6) “Connected, But Alone?” by Sherry Turkle

We live in a world where it’s easier than ever to reach out to people across generations, cities, and even continents. Yet go to any restaurant, concert, or even funeral and you’ll find people disengaged from their companions because they’re on their phones, MIT social sciences and technology professor Sherry Turkle says.

Besides the fact that it’s bad manners, this increasingly common behavior is preventing us from relating to each other and self-reflecting. In Turkle’s TED talk, you’ll hear about how being overly connected is actually isolating us from our communities, and what we can do to unplug from our phones and plug back into our relationships.

7) “10 Ways to Have a Better Conversation,” by Celeste Headlee

Words are our primary way of relating to other people — whether it’s building strong friendships, getting into arguments, or persuading coworkers to follow your plans. And yet we suck at it — a Pew Research study found that Americans are more polarized than we’ve ever been.

Radio host Celeste Headlee has some experience using words to move people. In her TED talk, Headlee explores the components of a truly great conversation and shares 10 strategies to improve conversational competence.

8) “The Power of Vulnerability,” by Brené Brown

Of course, true connections can’t be formed if we don’t bring our whole selves to our relationships — no matter how conversationally competent we are. In this TED talk, Brené Brown, who researches vulnerability, courage, and shame, suggests that only by confronting what we’re most afraid of can we truly connect with other people.

In her research, Brown found that her subjects who felt the most love and belonging had one thing in common — they were willing to make themselves vulnerable. It’s not easy to get to that point, but Brown argues that if we’re willing to put in the time and effort, we’ll be able to reach a kinder, gentler world.

9) “Comedy is Translation,” by Chris Bliss

When I was younger, I thought Saturday Night Live and The Daily Show were just funny. And they are, but they’re also shows that delivery commentary in a way that makes people laugh and think at the same time.

In this TED talk, standup comedian Chris Bliss explains that comedy isn’t just about entertainment, although humor is obviously central. The elements of comedy — misdirection, its inherent virality, economy of language, and deliberate juxtaposition of seemingly opposite or unrelated concepts — make it a delightful way to entertain people and convey important messages.

Editor’s note: This post was originally published in March 2016 and has been updated for freshness.

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Discover Whether You're a Sales Hunter, Farmer, or Trapper


My coaching client Daniel asked me, “Bill, are you a Hunter or a Farmer? Do you constantly prospect for new business, or do you focus on the clients you currently have?”

I replied, “I’m more of a Trapper. I like to apply the principles of value-centered marketing so people see me as a resource and come to me for further assistance.”

The Hunter Sales Persona

The Hunter is constantly on the lookout for new prospects. They go to many networking events, join other types of organizations, use LinkedIn and other social media platforms to reach out to people, make a lot of calls, and ask for referrals on a regular basis.

An effective Hunter will track down every lead to its logical conclusion. They find it easy to be persistent, but rarely cross the line into pushiness.

The Hunter will thrive in a role where they must generate their own sales and where the problem they can fix isn’t always evident to the prospect. For example, a financial professional may have to ask the right questions and teach the right things to get her prospect to realize there’s a gap in his financial plan.

Likewise, a social media expert or business consultant may have to help their prospects uncover pain that’s currently unknown — but causing problems.

The Farmer Sales Persona

The Farmer is most comfortable fertilizing and watering existing relationships. They may have built a successful business with clients gained when another rep left the firm or with internal referrals from another part of their company. The Farmer rarely loses a client for lack of caring.

An effective Farmer is service-oriented and won’t run away from problems. They build a large number of business friendships.

Unlike The Hunter, The Farmer does not usually have the DNA to beat the bushes for leads and self-generate opportunities. The Farmer loves to nurture existing relationships. They will plant and nurture new seeds when handed to them (like interested prospects raising their hand to say, “I’m interested”), but won’t usually contact strangers to get a relationship going.

Typical Farmers are high-level customer service reps responsible for maintaining and growing relationships while keeping an eye out for new opportunities within the account. They are often found in inside sales and service operations.

The Trapper Sales Persona

The Trapper focuses on client attraction through marketing. They develop value-added tools to send to prospects and share on social media and often work to establish a high-profile reputation in their target market. They’ve also crafted a fine-tuned way to communicate their value in both concise and longer-form methods. For example, a Trapper likely has a client-centric LinkedIn profile that tells a good story and pulls people into their message.

The effective Tapper has probably embraced the power of SEO, YouTube videos, and great content. They’re adapt at generating various forms of social proof, such as testimonials and case studies.

The Trapper is usually a business owner, marketing manager, or business development manager. They don’t mind farming, but hunting does not appeal to them. Trappers are creative people who like to figure out the right bait for the right prey. Trappers become versed in the languages of attraction marketing and direct marketing.

Can You Change Sales Personas?

I’ve been in the world of sales, marketing, and business development (pick a name, any name) for over 30 years. It is rare to find someone who is truly well-developed in more than one of these personas. For example, my predominant persona is the Trapper. I enjoy determining my market, finding prospects, and crafting the right message to pull them in. As I’ve honed these skills, the less hunting I need to do — although when I bring someone into my world, I still need to bring the sale to fruition. I’m a good Trapper, decent Farmer, and okay Hunter.

I no longer attempt to help companies turn Farmers into Hunters or Hunters into Trappers. While there may be some overlap in the DNA, the basic wiring is different for all three.

As you have probably already guessed, every industry, business model, and personal style will ultimately dictate the right blend of these three personas. Great marketing will bring people into your world, but you still have to “close the deal” so to speak. Sometimes they come into your world through marketing, but you have to keep tracking them until the time is right and they truly see your value.

If you’re a front-line salesperson, focus on cultivating the strengths of your sales persona rather than becoming a different one or imitating their approach. If you’re a sales leader or business owner, hire the personas that compliment yours and work together to build a fast-growing, profitable company.

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The 10-Part Checklist for Starting a Successful Referral Partnership


Hopefully, you have already realized that a great Referral Partner can be worth a lot more to your business then any one client.

My question for you is, “Do you have a clearly laid out plan — and are you working that plan — to meet great Referral Partners on a regular basis?”

I believe you shouldn’t let a week go by without some activity to meet new Referral Partners and/or strengthen current Referral Partners. Here is a 10-part checklist to maximize your partnership results.

Referral Partnership Checklist

1) Identify at least five categories of Referral Partners.

Every industry has what BNI founder and the “Father of Modern Marketing” Ivan Misner calls “Contact Spheres.” Identify at least five natural Referral Partner categories. Create a plan for meeting them.

2) Ask clients and other Referral Partners for introductions to more.

You can certainly meet potential Referral Partners at networking events, but your best source will always be your clients and other Referral Partners who can vouch for you and your product.

3) Provide value before trying to get referrals.

Your first goal with a potential Referral Partner is to provide value. Look for ways to contribute to their business with resources, idea, introductions, and thought-provoking questions.

4) Determine the business chemistry.

You’re not going to get along or connect with every potential Referral Partner. Do you generally like this person? Will you enjoy interacting with them? Would you do business with this person? Do you feel comfortable sending people their way?

5) Have a clear, concise way to explain the benefits of your differentiation.

Your Referral Partners will want to know how you, your processes, and your products or services differ or stand out from others who they perceive are in the same business as you. And always, always, always translate how that difference creates one or more concrete benefits for your clients.

6) Make sure you are referable.

One of the most effective ways to become referable in the eyes of a potential Referral Partner is to walk them through your full value proposition. This takes some time, so you both have to be committed to forming a productive referrals partnership. The more they see your process and the many places you deliver value to your clients or customers, the more they will feel comfortable sending people your way.

Hint: Just because you sent your potential Referral Partner one or more referrals, don’t assume that this automatically makes you referable. It doesn’t.

7) Determine your Referral Partner’s ideal customer.

If you believe your Referral Partner is looking for a reciprocal referral relationship, be sure to get crystal clear on who makes a good prospect for them — whom they serve the best. (Note that not every Referral Partner will want or expect reciprocal referrals. Some just want to have a great resource to whom they can recommend others.)

8) Teach your Referral Partner about your ideal customer.

One of the prime reasons why Referral Partners don’t provide great introductions is that they aren’t sure how to recognize someone who is a good prospect for you. Make sure your Referral Partners know how to recognize a great fit.

9) Get clear on how each of you want to be introduced to ideal prospects.

Never assume a Referral Partners knows how you like to be connected with your new prospects. You definitely want more than just word of mouth. You want to be introduced in some way.

10) Agree on how often you will meet.

Productive Referral Partnerships require a certain level of ongoing communication. You both need to remain referable in each other’s eyes. You want to make sure you are meeting each other’s expectations for the relationship. Agree on how often you’d like to meet — monthly? Quarterly? Semi-annually?

HubSpot CRM

Source: The 10-Part Checklist for Starting a Successful Referral Partnership

The Ultimate Guide to Using Live Chat Software in Sales


In the past, buyers relied on salespeople for product information. Now they can discover the same details online in a matter of clicks.

But salespeople shouldn’t be content to hang back and let their prospects do all the work.

Prospects still have questions they can’t always resolve by reading an FAQ or product page: Can that version do X under these circumstances? Will it support Y? What’s the vendor’s policy on Z?

“When a buyer raises her hand, she’s indicating that she wants to speak with you about something specific,” explains David Meerman Scott, author of “The New Rules of Sales and Service: How to Use Agile Selling, Real-Time Customer Engagement, Big Data, Content, and Storytelling to Grow Your Business.” “This is a moment of enormous opportunity.”

However, Meerman Scott says it also poses a huge challenge. Buyers expect salespeople to know more than the content on their website. They also expect extremely quick responses to their questions. After all, they’re accustomed to receiving information as soon as they want it.

Enter live chat software. Sites with real-time messaging allow you to help prospects in real time, engage them at pivotal moments in their buyer’s journey, and generate inbound leads without salespeople lifting a finger.

How to Use Live Chat Software in Sales

What’s Live Chat Software?

Live chat software lives on your website — usually on specific pages, such as your homepage, product, and pricing pages — and enables real-time conversations between your sales team and prospects.

This tool is the latest evolution of buyer-seller communication. In the past, a phone call was the fastest, most direct way for salespeople to connect with prospects. But these calls were often inconveniently timed for the people picking up. Calls also lack context: Prospects think, “Who’s this person, and why should I care?”

Emailing enhanced buyer-seller communication, since a message offers more convenience and context than a call. However, even emails are slower and less efficient than live chat.

When Do People Use Live Chat Software?

Prospects typically use live chat during the consideration and decision stages of the buyer’s journey. Either they’ve defined their challenge or goal and are investigating specific solutions, or they know which offerings they’re most interested in and are determining their final choice.

As a result, most questions will revolve around product benefits, features, proven results, pricing, and various tiers or options.

To make live chat a success, provide a valuable, helpful experience. HubSpot inbound sales consultant Alexis Sells shares her advice on chatting with prospects.

Make Helping Your First Goal and Qualifying Your Second

“Talking to a prospect over live chat is extremely different from sending an email,” Sells says. “They’re talking to you because they have an incredibly specific agenda.”

That’s why your primary purpose is answering the prospect’s question, rather than inciting curiosity, urgency, or giving them a clear call-to-action.

Your secondary purpose is qualifying them for your product or service.

“It’s give and take,” Sells says. “Collect one data point from them, give them a piece of information, collect another data point, and so on.”

She advises setting the expectation you’re happy to help but need context to do so.

“Let’s say a prospect asks me if HubSpot offers mass mail,” Sells says. “I’d reply, ‘Great question. Before I answer, may I ask you a couple questions about your company and goals so we can figure out whether that’s the best solution?’”

In Sells’s experience, prospects are responsive as long as they’re aware why you’re asking for more details.

When those details suggest the prospect is a good fit, say something along the lines of:

“We have a salesperson who can walk you further through [topic]. Do you want to book a time with them?”

When the prospect isn’t a good fit, don’t leave them high and dry. You never know if their circumstances will change or they’ll move to another organization that’s better matched to your offering. Treat them well now, and they could reward you with their business in the future.

Here’s a sample message:

“I’m really happy I could answer your questions. Let me send you an email with a couple additional resources.”

Keep It Short and Simple

Sells recommends capping each message at five sentences or less.

“Prospects start live chat conversations because they want their questions answered quickly and efficiently,” she says. “They’re not looking for an extended discussion. Keep your responses brief, or they’ll get frustrated.”

Along similar lines, reply to the prospect’s first message as soon as you can. According to Sells, prospects typically become impatient if you don’t answer right away.

Once the conversation has begun, you usually have a little flexibility in response time — the prospect knows you’re there, so they’ll wait longer before exiting the page.

Keep track of your average chat length to determine how many separate threads you can handle at one time.

“My live chat conversations generally lasted three to 10 minutes,” Sells says. “I felt comfortable participating in up to three simultaneously.”

The complexity of the conversations also plays a role. If your prospect’s questions demand your full attention, consider limiting yourself to one at a time. However, if you get the same questions again and again, you might be able to chat with five prospects at any given time.

Just make sure the quality of your responses doesn’t suffer. If a potential buyer feels dissatisfied by the interaction, they may drop you from their list of potential suppliers.

Be Human

When Sells first started using Messages, she was constantly fielding questions about being a robot.

“It’s easy to sound robotic over live chat,” she says. “I was sending rapid bullet point answers. People felt like they were communicating with a bot, not a person.”

To humanize your conversations, Sells suggests using phrases like:

  • “Hi, how are you?”
  • “I’m [your name]. How are you doing?”
  • “Nice to meet you, I’m [your name].”
  • “How was your weekend?”
  • “Great question, let me check on that for you.”

“When a prospect cracked a joke, I’d write ‘LOL’ or ‘haha,’” she adds. “Basically, I tried to be myself.”

If you’re struggling to sound natural, draw inspiration from texts you’ve sent your friends and family members. Replicating that style to a tee isn’t wise, as you’ll sound too casual, but this exercise will help you develop a professional voice that still sounds like “you.”

Emojis can humanize your conversation as well. Sells says they add a friendly tone to your message, although she tries not to use more than one or two per conversation.

Finally, don’t forget your demographic. If your typical customer works in a creative industry, like marketing or design, you can be more informal. On the other hand, if they work in finance or medicine, take a more conservative approach.

Never Say “No”

The worst response you can give is “no,” Sells cautions.

“If they ask a question and you shut them down with ‘no,’ or ‘I can’t help you,” they’ll leave and might never come back,” she says.

When your product is missing the feature or capability a prospect asks for, you don’t know an answer, or you’re confused by their request, Sells recommends asking more questions. This way, you can gather more information and hopefully provide a helpful answer.

Put It All Together

Here’s a hypothetical conversation illustrating the key concepts of this post:

Prospect: How do you encrypt patient payment data?

Rep: Hi there, I’m Evan. Happy to help. Mind if I ask some details about your needs so I can give you a more accurate answer?

Prospect: OK.

Rep: Awesome. What’s the name of your organization, and what type of payments are you processing?

Prospect: BlueHealth. The majority are recurring payments, but we also accept HSA/FSA cards and checks.

Rep: Since you’re processing payments on-site, you’ll need point-to-point encryption (P2PE). Our solution encrypts patient data at the point of interaction (POI) so it’s extremely secure. It’s been validated by the PCI Security Council, so it’s fully compliant.

Prospect: Got it, thanks.

Rep: No problem. 🙂 Would you like to set up a time with Irie, one of our reps? She can walk you through P2PE in more detail.

Prospect: That sounds good. I’m free tomorrow after 1 p.m. EST.

Live chat software benefits everyone. Buyers can resolve their questions near instantly, and salespeople can increase their number of qualified leads.

HubSpot CRM


3 Sales Communication Myths Secretly Costing You Deals


Communication between salespeople and their prospects isn’t always straightforward. Each party has their own agenda — and these often conflict. The seller is trying to gauge the buyer’s interest, craft a relevant pitch, and learn how their organization makes purchases and who has power. Meanwhile, the prospect is trying to hide their intent to buy so they can get the most competitive price.

Here are the most common communication errors I see between reps and prospects. Once you’ve eliminated these, critical details will stop getting lost in translation.

1) Assuming the Contact Is a Champion

Reps frequently start referring to their host — or the person who started the relationship, gives them updates, or schedules meetings — as their “champion.” They interpret her helpfulness or early involvement in the deal as indicators that she’ll back them.

But just because someone is friendly doesn’t mean they’re a champion. I have two criteria for customer champions:

First, they want to buy your product or service as much as you want to sell it to them. A champion believes their problem demands fixing. Not in a couple months, not when they get more budget: Now.

Finding someone with this much urgency is pretty rare. However, the second criteria is even harder to meet: True champions are rule-breakers.

That doesn’t mean they act without integrity, but they need to be willing to circumvent internal policies or use their influence to move the deal forward.

For example, a normal contact would say, “It’s going to take three or four months to get Legal’s approval because they have a long queue of contracts.”

A champion, on the other hand, would tell you, “Legal has a long queue right now, so I’m going to ask my friend in that department to expedite this.”

When reps mistakenly believe they have a champion, they take their foot off the gas. They hear, “It’ll take three to four months,” and they don’t push back — because they believe their contact is doing everything they can.

A lot of accounts won’t have champions. Either the rep can create one, or they operate without one.

2) Taking Email Commitments as Truth

Emailing prospects is quick and easy. However, never use email to advance the deal: It’s too easy to misinterpret them.

Suppose you get an email from the prospect with the line, “We’re focusing on you now and not looking at other vendors.”

You might construe that statement as, “They’ve eliminated other vendors.” But it could equally mean the prospect has finished evaluating the competition and now needs to check a final few boxes with you.

Being able to clarify in real-time is crucial.

You can email buyers to:

  • Confirm a meeting agenda
  • Get contact information
  • Red-line the proposal
  • Answer non-critical technical questions
  • Send helpful content

But for deal-advancing dialogue, call, web-conference, or meet in person.

3) Putting Too Much Faith in the Prospect’s Decision Date

Don’t automatically take the first decision date your prospect gives you for granted. Take this fictional conversation, versions of which play out on sales calls all the time:

Rep: “When will you be making a decision by?”

Prospect: “The end of the month.”

Rep: “Why the end of the month?”

Prospect: “That’s when our budget expires.”

Then the salesperson puts the last day of the month as the estimated close date.

The question itself is problematic, since it requires the prospect to predict their future behavior — and that’s nearly impossible for them to do accurately.

In addition, roughly one-third of the time the end of the month falls on a Saturday or Sunday. Customers rarely sign or review proposals on the weekend.

I recommend finding the specific date and verifying it with the prospect. Here’s an example:

Prospect: “We want to make a decision by the end of the month.”

Rep: “Why the end of the month?”

Prospect: “That’s when our budget expires.”

Rep: “I just looked that up on the calendar. It’s a Wednesday. Do you always start new vendor relationships on a Wednesday?”

Prospect: “No. Well, actually we’d probably decide on the Friday before, because that’s when we have our budget meeting.”

Going from a generic “end of month” decision to a real date makes the purchase feel more real for the prospect.

These communication mistakes plague every salesperson. Stop falling prey to them — your pipeline will thank you.

Get more of Jeff’s insights and advice on his blog.  

HubSpot CRM


How to Become an Entrepreneur With No Money or Experience


Being your own boss, calling all the shots, hustling to hit your goals — for many people, entrepreneurship is the ultimate career goal.

But as awesome as running your own business sounds, it’s also incredibly difficult.

How difficult? Nine out of 10 startups fail.

Entrepreneurs are also more anxious than other people and experience more day-to-day stress. After all, when you’re responsible for the bottom line, every setback falls on you personally.

Here’s the good news: Starting a company can be one of the most rewarding, exhilarating, and interesting opportunities you’ll ever get. If you’re aware of the risks and you’re still dead-set on being an entrepreneur, use the strategies and advice in this guide.

It includes:

Let’s get started.

How to Get Startup Ideas

You can’t build a business without an idea. Here are some creative techniques for thinking of a product or service.

1) Ask your friends what annoys them

Founders get inspiration from their frustrations all the time. For instance, Travis Kalanick and Garret Camp started Uber after they had trouble getting a cab.

Andrew Kortina and Iqram Magdon-Ismail founded Venmo (acquired by PayPal) after they had trouble paying each other back by check.

Chris Riccobono launched UNTUCKit — a line of shirts that look good untucked — after getting frustrated with how wrinkly and fill-fitting his regular button-down shirts were when he didn’t tuck them in.

With this in mind, ask your friends to keep track of the day-to-day things that annoy them. Then go through their lists and look for problems you might be able to solve.

2) Prepare for the future

As the world changes, people need different products. As an example, the rise of Uber, Lyft, and other ride-sharing apps created a demand for a third-party app that will tell you the cheapest fares at that exact moment.

You want to get ahead of the curve. Read trend predictions for your industry or market, or check out universal trend forecasting publications like Trend Hunter and Springwise. Then ask yourself, “If these predictions come true, which tools will be necessary?”

3) Look online

Checking out what other people have come up with can be a great way to kick your own thought process into gear. Go to Product Hunt, a constantly updated curation of the newest apps, websites, and games, for digital inspiration. Meanwhile, Kickstarter is great for physical products.

There are also a ton of product review sites like might spark your creativity. Try UncrateWerd, and Wirecutter.

4) Make something better (or cheaper)

You don’t always need to develop something brand-new. If you can offer an existing product at a lower price-point, better quality, or ideally, both, you’ll have plenty of customers. Better yet, there’s clearly an existing demand.

As you go about your day, make a list of everything you use. Then review the list for something you could improve.

5) Focus on a growing category

Licensing expert and intellectual property strategist Stephen Key recommends picking a category that fascinates you but isn’t overly competitive.

“I avoid industries that are notoriously challenging, like the toy industry. There are so many people creating in that space,” he explains. “You will have an easier time your licensing your ideas if you focus on categories of products that are growing as well as receptive to open innovation.”

After you’ve picked a category, Key says you should study all the products in that category. What are each product’s benefits, and how do they vary? What’s their packaging and marketing strategy? What do reviewers say? What are the potential improvements?

Once you’ve picked a product, consider questions like what can be done to improve it? Can I add a new feature? What about a different material? Can I personalize it somehow?

6) Fill an underserved demand

You don’t need to reinvent the wheel if there aren’t enough wheels. Many people start successful businesses after noticing a gap in the market. For example, perhaps you learn there’s a shortage of high-quality sales outforcing. Since you have experience in sales development and account management at early-stage sales companies, you might decide to offer this service to tech startups.

Other suggestions

  • Network with other entrepreneurs: Use Meetup or Eventbrite to find events in the local startup community. Not only will networking with other entrepreneurs help you build valuable relationships, it’ll also give you lots of ideas.
  • Research patent applications: Patent applications are typically made public 18 months after they were filed. Although we don’t recommend outright copying any inventions, browsing through these documents can give you a good sense of where a particular space is headed.
  • Have a brainstorming session: If you need to get your creative juices flowing, invite three to five other entrepreneurial-minded people to a brainstorming session. Ask everyone to come prepared to discuss a certain product category or question, such as, “What’s your favorite type of X and why?” or “Do you use anything to accomplish Y? Why or why not?” The answers may lead to some great ideas.

How to Validate Your Startup Idea

Great, you’ve got an idea. But don’t quit your day job yet. Before you go all in, you need to know other people will actually want your product. (No, your friends and family don’t count.)

Here’s where the idea of a minimum viable product, or MVP, comes into play. An MVP is the simplest, most basic version of your tool or service possible. It’s functional enough to satisfy early customers and get a sense of what you should improve.

Let’s say you want to build an app that will connect college students with virtual tutors. You might create a bare-bones version, manually invite 150 tutors you found online to join, and then post the link to the app on the local university’s Facebook page. If you get a decent number of sign ups, that’s a sign you should move forward. If you get barely any, you should either rethink the idea or start fresh.

Doing interviews with potential customers is another option. Show them a working demo of your product, ask what they like and what they don’t, how much they’d pay for it, how often they’d use it, and so on.

Envato blogger Chris Bank also recommends “listing the problems you assume your product will solve and then asking for opinions and a ranking of each problem.”

If you want to test the market’s interest before building anything, build a landing page that describes your product or service. Ask people to submit their email addresses in exchange for early access; a free subscription, membership, or product; a discount, product updates, or some other compelling offer. Then promote the video on social, paid search, etc., and see how many visitors convert to sign ups.

How to Find a Cofounder

Conventional wisdom says you should look for a cofounder when starting a new business. There are three main advantages to having a cofounder.

It’s easier to get funding. Whether or not multiple founders actually contributes to a company’s success, many venture capitalist investors believe it does. They’re reluctant to back solo founders.

As an example, “single founder” is the first thing on Y Combinator cofounder Paul Graham’s list of causes of failure. He writes, “Have you ever noticed how few successful startups were founded by just one person? It seems unlikely this is a coincidence.”

You have emotional support. Running a company is a stressful, exciting, and unique experience. If you’re riding the emotional roller coaster by yourself, you won’t have anyone to celebrate with during the ups — or survive the downs. A cofounder understands exactly what you’re going through and makes you feel less alone.

They can provide different skills, knowledge, and connections. Maybe you’re great at selling, while your cofounder is more technical. You’ve got lots of connections, and they’ve actually started a business before. Picking a cofounder with a complementary resume is an excellent way to boost your odds of success.

But there are also drawbacks to having a cofounder.

There’s conflict. You and your partner will inevitably disagree. A little healthy disagreement is productive, but if you don’t find a solution relatively quickly, you’ll waste valuable time and energy. Plus, you might hurt your team’s morale. 

You’ll have to split equity. If you’re the sole owner of your company, you start with 100% equity. As time goes on and you hire more people and/or receive funding, you’ll distribute that equity — but you’ll likely be giving 0.005% to 35% to a single entity, depending on who they are. If you have a cofounder, you’re automatically giving up 40-60% of your company in a single swoop. 

Lastly, you have to find a cofounder. It can be really hard to find someone with the same business ethics, work habits, and complementary personality. In addition, they need to believe in your vision, contribute the right skills, and have a desire to be your cofounder in the first place. That’s a tall order. 

It’s worth noting that an analysis of thousands of successful startups showed that more than 50% had only one founder. Make a decision based on your situation, not traditional advice.

Where to Find a Cofounder

If you decide you want a cofounder, the next step is finding one. Look within your own network first. Choosing someone you already know, or whom your connections can vouch for, is much less risky than a stranger.

This concept works in reverse as well: You’ve also got a better shot of convincing them to join you if they’re a first or second-degree connection.

But if you’ve tapped your network without success, there are a few “cofounder matching” services you can turn to.

You can also attend local entrepreneurship events to meet potential partners.

How to Get Funding for Your Startup

You have to spend money to make money. To fund your startup, consider the following TK options:

1) Family and Friends

Many entrepreneurs rely on their friends and family for initial investment, typically called a “seed round.” You can exchange funding for a stake in your startup (i.e., your cousin receives 4% of the company after giving you $12,000), request personal loans (with or without interest), or even donations.

2) Small Business Grants

Federal, state, and local governments have programs to help small businesses, including low-interest loans, venture capital, and grants. To find programs your company qualifies for, check out

Most businesses aren’t eligible, so you might not be able to find anything. But it’s worth looking into, because hey — free money!

3) Crowdfunding

Kickstarter, Indiegogo, GoFundMe,Fundable, and other crowdfunding platforms let you get backing through an online campaign.

This method doesn’t just generate capital, it can also help you get early product feedback, brand awareness, and sometimes, if you have an interesting story or especially cool product, press.

4) Angel investors

Angels look for early-stage companies that can 10X or more their investment. Typically, they put in $25,000 to $100,000. If you do the math, angels are looking for businesses worth $2.5 to $10 million in the future.

They will be extremely diligent in making sure you understand your target customers, the product space, how you’ll make money, and how you’ll scale. Make sure you’re prepared with a solid business plan and early signs of traction (such as “the average user refers two additional users in their first week” or “we doubled our revenue from January to March.”)

Along with an angel’s funding, you’ll get access to their expertise and connections. They’ll receive equity in exchange.

5) Venture Capital

Venture capital firms look for young, private companies. Like angel investors, VC firms are looking for high-risk, high-return investments. The returns they expect depend on just how mature your startup is. If they invest right before your company goes public or gets acquired, a 3X return is good.

But if a VC firm invests very early, they’re probably looking for a 7X to 10X return. 

Venture capitalist Fred Wilson’s blog post about venture returns is a good introduction to these concepts.

6) Credit cards

It’s typically not a good idea to use your credit card to pay for business expenses — unless, of course, you can pay the balance. Sometimes, you have no choice: You need money, and fast. But sacrificing your credit score and racking up credit card debt will hurt your business in the long run (not to mention, your personal financial health). 

7) Loans

You can’t apply for a loan in your company’s first year, as lenders are unwilling to make such a high-risk investment. However, you can take advantage of the Small Business Administration’s microloan program. Small businesses can receive up to $50,000; the average SBA loan is $13,000.

This is a list of SBA partner microloan providers by state

Microlenders and nonprofit lenders are another option. These lenders often seek out minority or disadvantaged entrepreneurs. Their terms are usually very fair.

NerdWallet’s guide to the top nonprofit lenders in the US is a great resource. 

8) Bootstrapping

You don’t need to accept money from anyone else if you don’t want to. Some companies never raise funding at all — their founders pay for initial costs by themselves, and then, when the company becomes profitable, its revenue covers all expenses.

This option allows you (and your cofounder, if you have one) to hold on to a much bigger percentage of your company. But you may grow less quickly without big infusions of cash. If you do decide to bootstrap, keep your budget as lean as possible to extend your company’s lifetime.

How to Incorporate Your Business

At a certain point, you need to decide whether you want to incorporate your business. As a sole proprietor, you and your company are considered to be the same entity.

Once you incorporate, your business becomes separate from you. From a legal standpoint, it can buy and sell property, incur taxes, sue and be sued, set up contracts, and commit crimes.

The advantages of incorporating

First, and most importantly, a corporation protects you from businesses debts and obligations. Creditors can typically only seek repayment from the corporation’s assets, not your personal assets (like your house, car, bank account, and so on).

You’re also not legally liable for the corporation’s actions. In contrast, as a sole proprietor, anyone who sues your business is suing you.

Having a corporation lets you transfer shares. You can sell some of your ownership in a company, transfer it, or give it away. If you want to accept external investments or bring a partner on board, you need the ability to divest.

Corporation status also gives you more credibility, which helps you attract investment capital. 

Lastly, corporations can deduct normal business expenses before they allocate income. 

The disadvantages of incorporating

It creates an additional tax burden: You need to periodically file with the state and pay yearly fees. The process can be relatively time-consuming, and hiring a lawyer can cost anywhere from a few hundred to a few thousand dollars.

You don’t need to incorporate — in fact, 70% of American businesses are owned by sole proprietors. But if you have a cofounder, need external funding, and would like legal protection, it’s a good idea. 

Once you’ve decided to incorporate, you must choose between becoming a limited liability company (LLC) or S corporation. The SBA has a handy guide on choosing the right entity structure

I hope this guide can serve as a helpful blueprint for starting your own business. Let me know in the comments: What do you find to be the most challenging or confusing part about entrepreneurship?

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Source: How to Become an Entrepreneur With No Money or Experience

40 Questions to Create a Sense of Urgency


Your product is a great fit for the prospect. It’s in the right price range for their budget. And you can even get them a discount based on the size of the purchase.

But even though this should be a slam dunk, I can tell you they won’t buy unless there’s urgency.

Urgency gives people a reason to move forward. When it comes down to it, companies always have more needs than resources — so unless they must buy your solution in the short term, the deal will probably stall.

So if there’s no urgency, you should create some. Right?

Wrong. Sales strategist David Weinhaus, who works with HubSpot partner agencies, has a strong view on “creating” urgency.

Instead of manufacturing a cause to act — which isn’t helpful to your prospect and will ultimately backfire — either uncover an existing reason they’re not aware of, or back off.

With the right questions, you can get your prospect to realize they’re unhappy or dissatisfied. And if your questions don’t lead them to those conclusions, accept they’re still in education mode and let your marketing department nurture them until the time is right.

It’s also worth pointing out there are a ton of questions on this list (40, to be exact). I don’t want you to use all of them with every buyer. That would be crazy. The key is picking the most applicable, relevant ones for each prospect.

1) How big is the company today in terms of annual revenue, approximate customer number, and employee headcount?

This question helps you qualify them and start a discussion about how big they’d like to be in the future (and what’s currently standing in the way).

2) Is the business struggling, in a steady state, or in growth mode? Is [company] growing faster than the industry average?

Remind the buyer of their overarching business goals. This is a good tie-in to how your product would play into their strategy.

3) Many of the people in your role I talk to don’t know [surprising fact]. Did you?

I like the Challenger Sale method of teaching your prospect something new — not only will your credibility and authority go up, but you’ll naturally uncover urgency. The buyer will want to act on this information ASAP.

4) What is the problem you’re looking to solve?

The buyer might be focused on a different pain point than you. Use this question to figure out if they’re on the right track. Sometimes, prospects try to address the symptoms rather than the cause by mistake.

5) Is the problem clearly defined?

Learn how much time they’ve spent investigating the issue. Hint: The more clearly they’ve isolated it, the more invested they probably are in fixing it.

6) Have you had this problem before?

Figure out just how persistent your prospect’s pain point is.

7) Is the problem easy or hard to address?

Chances are, the prospect will say it’s the latter. If it was easy to solve, they would have tackled it by now.

8) How does this problem affect the revenue, profitability, culture, or product cycle of the business?

This question highlights the larger implications of what’s going wrong.

9) Does this problem affect a lot of people?

Get your prospect thinking about how widespread the effects are.

10) Are you tasked with solving this problem as part of your regular job, or is this a special assignment?

If your prospect says, “It’s part of my job,” then make sure you tie their overall performance to fixing this issue. If they say, “It’s a special assignment,” then there’s already genuine urgency: They need to identify an answer before a certain date.

11) What happens if you address the problem? What happens if you don’t?

This naturally leads the buyer to compare life with your product and life without. The second is usually much less appealing.

12) When do you need to start seeing the results of implementing the solution?

The prospect would probably love to see results right away. Their answer will help them realize why time is of the essence.

13) What is the one thing that, if we could help solve it quickly, would have the most meaningful impact on the company?

Once you’ve pinpointed a major opportunity to help, urgency will spring up naturally.

14) How would solving this problem affect you personally?

Knowing the buyer’s individual motivators can make or break the deal.

15) How does this affect your boss?

When the prospect’s boss is happy, they’re happy. Connect the dots between your solution and their supervisor.

16) What happens if you keep doing what you are doing?

It’s far easier to stick with the status quo than make a change, even if the long-term ramifications could sink the prospect’s business. With this question, you’ll get them to come to terms with the dangers of ignoring the issue.

17) How can we make you look like a star?

This question turns you into the prospect’s partner, instead of just their rep. It also helps you pinpoint how your product can help them look great at the office.

18) What do you need to do/what objectives must you reach to get a promotion?

Along similar lines as #17, this question reveals why the buyer is personally invested in finding a solution.

19) How does this problem affect you on a day-to-day basis?

Most professionals put up with annoying or deleterious pain points. As soon as you show the prospect there’s a better, easier way, they’ll be more eager to buy.

20) How does this problem affect [department]?

Get them to zoom out and visualize the impact on the wider team.

21) If you weren’t experiencing this pain anymore, which projects/priorities could you focus on?

This question makes the buyer envision a world where they have time, energy, and resources for the tasks or initiatives they’re interested in.

22) What’s the most frustrating aspect of this problem?

Once you learn what’s driving your prospect up the wall, you can position your product accordingly.

23) What [projects, campaigns, initiatives] are you currently working on? How does [challenge] impact your plans?

This is another way of learning how the pain point is interfering with or obstructing their day-to-day work.

24) What problems come up most frequently at executive meetings?

If the CEO cares about an issue, your prospect will too.

25) Which problems keep you at the office late?

Figure out which issues the buyer doesn’t have an easy answer to.

26) Which themes are coming up again and again on [Slack, Hipchat, your knowledge base/wiki]?

While not every company uses internal chat or a wiki, asking those who do about the most common themes can help you pinpoint the most exciting, visible, or challenging things they’re facing.

27) Is your industry getting more competitive?

Most industries are. Capitalize on your prospect’s awareness that they need to act to maintain their edge — or gain one in the first place.

28) Are you worried about [specific competitor]?

Figure out who’s nipping at your prospect’s heels, then show them how your solution will widen the gap in their favor.

29) Do you ever get the sense that [people in prospect’s department] are wasting [time, effort, leads, budget]?

Mitigating (or even eliminating) the inefficiencies in the buyer’s department would be a huge win. Open their eyes to the possibility of a fix.

30) Have you ever lost a major customer unexpectedly?

Whether the answer is yes or no, this question works. If your prospect has, they’ll be eager to take precautions so it doesn’t happen again. If your prospect hasn’t, the wheels will start turning: Wow, it would be really bad if 20% of our business vanished in one stroke.

31) How [did, would] losing that customer affect the business?

Get the buyer to vocalize the negative effects, which will drive their desire to avoid the catastrophe even higher.

32) How do you avoid getting caught in a pricing war?

Chances are, your prospect would love to find a differentiator that would save them from race-to-the-bottom pricing. You just need to explain why your product is that differentiator.

33) Would you be interested in talking to [Customer], who saw a [X%] return on our [solution, service]?

Hearing from someone who got fantastic results will spur your prospect to the finish line.

34) Maybe it would be helpful for you to talk to someone who’s [made this journey recently, faced X similar challenge, resolved the same issue]. What do you think?

If it’s too early in the sales process for references, suggest a knowledge-sharing conversation instead. You’re still connecting the buyer with a satisfied customer — but their shared experiences is the focus, not your product.

The nice thing about this technique? Not only is it helpful for the prospect and your customer, but at some point during the conversation they’re bound to bring up your solution.

35) If we supply all the information you need in the next 24 hours, will you have time to review it and get started by [date in the near future]?

Test your prospect’s commitment to act with this question. If they say they’re not ready, don’t be pushy — instead, ask what else they’d need to make a decision.

36) If I send over the contract when we hang up, can you return it to me in [six days from the current date]?

Sales consultant Jeff Hoffman encourages reps to close this way. Normally, the buyer says they’ll need more time — at which point you say, “Okay, can you do [preliminary step] by that date?” They’ll say yes, and now you’ve gotten a concrete agreement to make progress on the deal within the week. Boom.

(Adjust the date based on your sales cycle. If it usually lasts two weeks, ask if they can sign the proposal that day. If it lasts 10 to 12 months, ask if they can sign the proposal in three weeks.)

37) Define your timeline for solving the problem and getting the right results.

Make sure your prospect’s expectations align with reality. You may need to accelerate the sales process to meet their timeline.

38) When must this problem be solved to avoid negative impact on the business?

Get a firm deadline for the purchase. Explain to the prospect you should shoot for a few weeks or months before this deadline to protect against delays.

39) Is there seasonality in your business? Do you have a busy or slow season? Do you need to address this problem before the busy or slow season hits?

For prospects affected by seasonality (like education, tourism, and entertainment), it can be critical to get a solution in place while business is relatively quieter.

40) If we can work out a solution sooner, how does that help you?

Fixing a problem earlier rather than later is almost always a good thing. The best part about this question is that the buyer puts those benefits in their own words.

How do you create a sense of urgency in your prospects? Let us know in the comments below.

Editor’s note: This post was originally published in February 2016 and has been updated for comprehensiveness and accuracy.

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Source: 40 Questions to Create a Sense of Urgency