45 Sales Prospecting Tips to Help Sellers Identify & Connect with Uber-Busy Buyers

Prospecting is hard for most salespeople. In fact, getting a response from prospects was identified as the hardest part of the sales process in the 2018 State of Inbound Report.

But, it doesn’t have to be. These 45 tips from three remarkably insightful sales experts should make it much easier for you.I’ve shared the virtual stage with 50+ sales experts, including longtime sales heavy hitters like Jeffrey Gitomer (author of the Little Red Book of Selling which has been translated into 14 languages and eight other books), Tom Hopkins (author of How to Master the Art of Selling and 17 other sales books), and Mike Bosworth (author of the seminal sales books Solution Selling and CustomerCentric Selling).

While I only “know of” these three gentlemen, I’ve had the privilege to get to know three other modern sales luminaries on a deeper level during my time at HubSpot: Trish Bertuzzi (author of the newly released book The Sales Development Playbook and president of inside sales consulting firm The Bridge Group), Lori Richardson (owner of Score More Sales and recognized as a top sales influencer by InsideView.com, OpenView Partners, and Forbes) and Jill Konrath (author of must-read books: Selling to Big Companies, SNAP Selling, and Agile Selling).

They are also top-notch experts at prospecting. Jill, Trish, and Lori had amazing sales careers before starting their own businesses. Their prospecting tips are not only based on experience growing their own companies, but also the time they’ve spent helping hundreds of organizations in a variety of industries.

So, without further ado, here are 45 tips on prospecting from three of my favorite sales experts.

Set Yourself Up for Sales Prospecting Success

You can’t wing success in sales, especially when it comes to prospecting. In order to exceed your sales targets (if you’re in a closing role) or your opportunity creation targets (if you’re in a sales development role), you must plan your approach, create your messages, identify and research contacts, and more. Our first 13 tips focus on the many different activities you must master before you even pick up the phone.

1. Plan your prospecting approach

Lori Richardson (LR): Define the who, when, why, what, where, and how. Know “who” your buyer is. Plan “when” you’ll reach out and “how” often.  Know “why” you’re reaching out and “what” your message will be. Know “where” you can you find them and reach them. Know “how” you are reaching out.

2. Invest in data

Trish Bertuzzi (TB): Don’t spend prime selling time figuring out who to call and how to call them. Use data. Consider creating a specialized “data analyst” role to ensure your salespeople have the right contact information for the right contacts.

3. Focus on business value in your messaging

Jill Konrath (JK): Know the primary business reasons why your customers purchase your offerings, and know how you “move” these business drivers. Do you help with lowering cost of goods sold, increasing uptime of machinery, ensuring compliance, maximizing lead-to-customer conversion rates, lowering operating costs, or increasing market share? If so, make this clear in your message.

4. Don’t talk about your product

JK: Don’t talk about your product. Instead, create value proposition statements that demonstrate your knowledge of your prospect’s business drivers.

5. Use numbers wherever possible

JK: Prospects will respond to you at higher rates if they think you can deliver quantifiable business value. For example, “One of our ecommerce clients in your space doubled their conversion rates and increased their average order size by 50%,” or “We help tech companies reduce the usual lag from product launch to break even revenue by up to 38%.” (Need help? Download Jill’s Value Proposition Kit.)

6. Talk to your existing customers

JK: The best way to learn what to say to prospects is to use the words your customers use. Talk to your customers to figure out what problems they were having before investing in your product or service, the cost of those problems, and how you helped them. Know what the status quo was and how you changed it so you can grasp the business case for your offerings.

If you really want to nail your buyer-focused messaging, create a buyer’s matrix by listing out important factors about your buyers, including typical business objectives, external challenges, strategic initiatives, and internal issues.

7. Research every contact

JK: The more time you spend here, the better off you’ll be when you connect with a buyer.

TB: Create a pre-call plan for every contact. Gather six to 12 pieces of data about your prospect that you can use in your outreach messages to start a relevant conversation.

For each contact, go to the places you need to go in order to gather that information such as their website and their LinkedIn profile, and enter it into your CRM. The next time you need to call this prospect or when you connect with them, simply reference your research.

8. Plan to contact a lot of prospects

TB: In a study of 35+ technology companies, for every 1,000 accounts prospected, the average SDR sourced 33 opportunities. You need to call a lot of people to get to your goal.  

9. Use every communication channel

LR: Deploy a multi-faceted approach in order to connect with more prospects. Use every method available to attempt to connect: email, voicemail, phone, social media, events, newsletters, and blog posts, as well as referrals. There is no magic formula. You have to do it all. Prospects are everywhere. So, be where they are.

10. Use your prospect’s preferred communication methods

LR: Don’t spend too much time on social. Stop hiding behind email. Even though it’s faster and more efficient for you, it’s not nearly as effective as a call or a meeting. Different buyers prefer different communication methods. Adapt to each individual buyer’s preference. Do not impose your preference. It’s about their convenience, not yours.

11. Use trigger events

JK: Bring up your prospect’s recent events in order to highlight the need for your offering. Cite events such as earnings reports, new products they’ve launched, personnel changes, jobs posted, acquisitions, layoffs, or macro economic changes like market conditions.

12. Put more effort into getting referrals

LR: Not only are referrals easier to close, the lifetime value of a referred customer is significantly greater than one who finds you through your marketing efforts. Create a list of people in your network who aren’t competitive with you, but who frequently come into contact with your buyers.

Get to know them, send them referrals when it makes sense, and earn a steady stream of referrals in return. For more tips on how to do this, read the ebook “Winning Teammates: How to Build a Hugely Successful Network of Business Relationships, Referred Partners and Respected Peers.” 

13. Stay focused on your prospect’s goals

TB: Sales is about helping people achieve their goals. Don’t let anything distract you from that. 

Do Email Prospecting the Right Way

Whether it’s the most effective method or not, email has become the go-to channel for most modern sales hunters. Leveraging email correctly has become critical to sales success. No surprise that the majority of my favorite experts’ tips on email prospecting is about how not to screw it up.

14. Use email templates

LR: Salespeople can’t write every email from scratch. Not only is it hard to write a crisp, buyer-focused email, it’s time-consuming — a great email can take 30 minutes or more to write. That’s just too much time.

There are so many new services that allow salespeople to store, customize, schedule, and reuse email templates. Redirect that effort into writing great reusable messages and leverage technology to customize and deploy them quickly.

(Pete: Of course, I would be remiss if I didn’t say that HubSpot’s sales software enables this.)

15. Scrap self-serving messages

JK: When you write your nicely bulleted list of unique, state-of-the art approaches to awesomeness, you turn your prospects off. Get rid of the self-promotion altogether. Check your messages for blatant horn-tooting here.

16. Don’t act desperate

JK: Don’t tell them you’d be grateful for “just 15 minutes” of their time. Write like a peer or a colleague would, not like a salesperson begging for a bit of their attention.

17. Optimize your messages for mobile

LR: Prospects are reading email on mobile more and more. If your subject line isn’t effective, they’ll quickly delete it as they scroll through their emails each morning or evening. Keep the message short and make it easy for them to respond to you.

18. If you have a referral, mention it right away

JK: Write “[Referral] suggested we talk” in the very first line of your message. Mentioning the name of a respected colleague early will earn you enough respect to keep them reading.

Don’t Forget Voicemail

While many reps seem to be skipping the important step of leaving voicemails these days, all three sales experts think that’s short-sighted. Even though buyers rarely call you back, most still check their voicemail. Follow these seven guidelines to maximize your chances of being remembered.

19. Make voicemail a key part of your prospecting program

LR: Have realistic expectations about your chances of getting a return call, but leave voicemails anyways. You’re not necessarily trying to get a call back. Instead of a return call, make it your goal to simply pique their interest.

TB: Don’t call and hang up as your caller ID footprint will just make you look like a stalker. Deliver a little piece of your value proposition in each and every touch. Hopefully, this generates awareness even if voicemails rarely get you a call back.

20. Keep your messages short  

JK: You have a maximum of 30 seconds to leave a positive impression. Don’t ramble. Make sure every word matters. Write out a script or at least an outline and practice it before you record.

21. Get right to business

JK: Don’t try and be friendly on a voicemail. Instead, be professional and concise. For example, “Mary. Jill Konrath calling. (123) 456-7890.” There’s no need to mention your position or your company. 

22. Make the message about them, not you

LR: Stop leaving horrible voicemail messages that are all about you. Make it targeted to them and their situation by providing a relevant insight. Adding an insight demonstrates you have ideas that could help them with their job, their team, or their company.

23. Practice 

LR: On voicemail, you must concisely say what you do, which is harder than it sounds. Write a script. Leave yourself a message. Record your voice. Play it back. Have others critique it. Rewrite it. Then, practice it until you can deliver it flawlessly. Join Toastmasters if you need help.

24. Use voicemail to show your follow through

LR: How? When leaving a voicemail, tell the prospect that you’ll send them an email so they can respond there. Or tell them that you’ll try them at a specific time later. Then do it. They’ll respect your follow through.

25. Leave a different message each time you call

LR: Remember to switch up your messaging with each touch. Your first email and voicemail might leverage a trigger event or reference how you’ve helped people like them with the same title or in the same industry. Message #2 could call out a common connection. In message #3, include an insight that’s relevant to the buyer.  

Make Every Connect Call Count

All of those prospecting voicemails and emails are completely wasted effort if you don’t make every connect call count. Of course, not every call will or should turn into an opportunity, but preparing and executing this step well is key to maximizing the number of opportunities in your funnel.

When you finally do connect with prospects on the phone, follow these 12 tips to increase your chances of success.

26. Block off time to make calls, and only to make calls

TB: Just because you have your headset on all day doesn’t mean you’ve maximized your phone time. Block off time on your calendar just to make phone calls.

27. Block out all of the distractions

TB: When calling, turn off internal chat, email, messaging apps with friends, notifications, and anything else that will distract you. Log out of everything and stay focused on making calls.

28. Start your day off with calls

TB: Don’t get sucked into email in the morning. Make 10 calls by 10 AM.

29. Use video chat whenever possible

LR: If the buyer is ready to schedule a phone call, give them the option of doing an online meeting with video instead. This way, you can read their expressions and body language in real time. They can see you too, which will help keep them focused, and enable them to understand and remember you better.

30. Devise and follow a call cadence

LR: Develop a rhythm and sequence for attempting to reach your prospects, in which you alternate email and voicemails.

By having a cadence, you can plan your approach, and track which touches you’ve already made so you know exactly which message is next. In addition, you can easily schedule time blocks for different steps in the sequence for a batch of prospects. 

31. Group similar activities together

TB: Make it easy for yourself by lumping similar activities and types of messages together. Don’t call a prospect for the first time, and then call a different prospect for the fourth time right after. Group all of your first calls together, and do the same with all of your second, third, fourth, and nth calls.

32. Use the 4×4 rule

TB:  If you’re calling into mid-sized and larger firms, target four titles for every account you’re working. Call each four times. Easy to remember: 4 x 4.  

33. Qualify the company — not the contact

TB: Don’t give up when one person at a company says “no.” Call someone else at the company. All it takes is one “yes” to negate all of the other “no’s.”

34. Call high

TB: When you receive a lead that’s lower level, call the likely decision maker and say, “We received a message from someone within your company that indicates [topic] might be a priority. Would it make sense to discuss?”

35. Don’t force a conversation

LR: Be respectful. If it’s a bad time for an in-depth call, try and schedule time for later.

36. Show them you did your homework

JK: Do research and make sure your prospects realize you did by asking targeted questions or giving them specific compliments. For instance, “I noticed the new X module on your website — looks great,” or “What drove the decision to add X module to your website?

37. Mention relevant experience

JK: If you’ve worked with companies like theirs in the past, tell them so. For example, you could say, “I was talking to one of my law firm clients (like you) who was struggling with Y, and we worked together on solving it using tactic X.

38. Share a fresh perspective 

JK: Information is everywhere. But relevant insights are hard to find. Tempt your prospects with ideas, insights, or information that can help them eliminate challenges or realize their goals.  

For example, “I have an idea that can speed up your sales cycle” or “We recently completed some research about how CTOs make purchase decisions.” Fresh perspectives pique curiosity and get you one step closer to booking a longer conversation about their needs.  

(For more help with connect calls in particular, download The Bridge Group’ s Inside Sales Productivity Kit.)

Market Yourself to Prospects

The vast majority of buyers have stopped trusting salespeople. They call us pushy, self-centered, and biased. As a result, it’s difficult to break through that built-in mistrust to get through to them.

In the last few years, inbound and social sellers have figured out ways to not just break down those barriers, but to actually attract buyers to them. Here are seven tips that will get buyers to call you — or at least be more likely to take your call.

39. Optimize your LinkedIn profile for selling, not career building

TB: Don’t use your job title as your headline. Instead, write something that describes your expertise. Use your summary and career experience sections to highlight how you help your buyers, not to brag to recruiters.

40. Build and strengthen your connections on LinkedIn

TB: Block off time on your calendar to grow your network. Connect with customers and other people you know. Join Groups and actively engage. Interact with prospects and request connections after they’ve engaged with you.  

41. Become an influencer in your industry

LR: Twitter is a great tool to establish yourself as an expert in your industry. Start by setting up a profile and listening to the conversation. Engage in conversations with others in your space. Share content — both yours and others.

42. group updates

LR: Create email campaigns that focus on different industries. Include news articles that are pertinent.

43. Blog

LR: Publish blog posts that are helpful and non-promotional. Monitor who pays attention and use that insight to reach out and engage prospects and customers.

44. Don’t get distracted

LR: Social is great, but don’t let it distract you from picking up the phone. There is such a thing as a salesperson who is too focused on social selling. At some point, you need to get off social and actually talk to people.

45. Embrace snail mail

LR: Physical mail volume has gone down significantly in the last decade. With this in mind, if you take the time to send a letter or note via snail mail, you have a greater chance of getting your message open and read. If you have a good conversation with a high value prospect on the phone or an exchange via LinkedIn, but the timing just isn’t right, send them a quick note on stationery with your logo on it.

Include your business card and sign it. This gets your business card on their desk. Many prospects call back when the timing is right.

4 Steps to Sales Prospecting Prowess

In some ways, prospecting has become harder as buyers do more of their research on the internet and wait to talk to salespeople. But, with the right tips from the right experts, prospecting can get a whole lot easier:

  1. Prepare
  2. Create a savvy buyer-focused email and voicemail strategy
  3. Master the initial call
  4. Make a commitment to marketing yourself

Hopefully these tips will be as helpful for you as they’ve been for us here at HubSpot.

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