My name is Deb Calvert, Inbound Sales Influencer, Ask Me Anything!

Hi, my name is Deb Calvert. I'm the author of DISCOVER Questions® Get You Connected (named one of "The Top 20 Most Highly-Rated Sales Books of All Time" by HubSpot) and of the new book, Stop Selling & Start Leading (to be released early 2018). I conduct research with buyers and provide field coaching and training to sales professionals. I teach the Sales Development Principles course at UC-Berkeley, and I'm here to answer your questions about sales behaviors that buyers prefer and respond to. We'll leave the tech and platform questions to the experts at HubSpot, but you can ask me anything about sales, buyers' preferences, and inbound strategies. If I don't know the answer, I'll find it for you! Between the AMA sessions, post questions for me here & I'll get back to you one way or another. 
This AMA will take place over the next three weeks, encompassing my live session at INBOUND. I will be answering your questions live on the following dates:
- Thursday 21st September @ 11:00-noon eastern time
- Thursday 28th September @ 11:00-noon eastern time (right before my live session at INBOUND -- to register for the live session, go to sessionDetail.ww?SESSION_ID= 114933)
- Thursday 5th October @ 11:00-noon eastern time


If you're not sure what to ask, here are some ideas:
  • How can I avoid coming across as a pushy seller?
  • What's the best way to respond when a buyer says they were "only getting educated" by downloading your content? 
  • If a lead asks about price before we even talk about options, should I quote a price or not? 
  • Is cold calling really dead? 
  • How can I get more people to respond to my emails and voice mail messages?
Let's connect here on this AMA! Your questions and input are greatly appreciated!
- Deb
42 Replies 42
HubSpot Product Team

Welcome to the Community @DebCalvert, I'm excited to see conversations spark on inbound sales as we approach INBOUND. 


I'll kick things off with the first question. 

I'm interested to know how much thought sales proffesionals should put into their sales email subject lines in the CONNECT stage? How do you choose to word your subject lines? Are there any factors for success / words to avoid?


I look forward to your answer in the coming weeks!

N.B. posting HubSpot's methodoloy below to reference what I mean by CONNECT stage for anyone else that comes accross this post. I myself am a newbie to sales best practices!



Roisin - GREAT question!


I follow Heather Morgan and others who research sales emails. My answer is based, in part, on their research and also on my own observations as a field coach.


Let me start with what doesn't work. Maybe these tactics were useful in the past, but they're tired and worn out now. Buyers specifically say they do not like it when we:


- Put "Re:" in a subject line when it's the first contact and we're not replying to or referring to something from a previous email exchange. This comes across as sneaky and inauthentic.


- Use someone else's name in the subject line (ex: "John Smith said we should connect"). Buyers think this name dropping is a trick because sellers haven't actually been referred as they claim. And even when there is an actual referral, buyers often think it's an end run. One buyer recently told me "I know she called my boss just so she could make it look like my boss was telling me to take her call."


- Play to guilt or shame. Lately, lots of emails seem to be angling for a "shame on me!" response. They have subject lines like "I haven't heard back from you" or "This is my third attempt to reach you." Most buyers don't fall for the manufactured pressure and don't think very highly of sellers who seem to think they're entitlted to an instant response.


What does work in the subject line is something personal and inviting. Think of the subject line as you would a book or movie title. It should grab your attention and make you interested in finding out more. It doesn't need to be cutesy or clever. It does need to be clear and compelling.


Here are three examples of subject lines on emails I received today. For each, I'm including a revision that makes it stronger. At the CONNECT stage, these are people we don't have strong relationships with yet so the tone must be professional without being clinical. That's why I've edited out phrases like "Hey, Deb" and "regression analysis."


1. "Hey, Deb, don't you want to close more deals today?"


I'm not a fan of fake questions. There's obviously only one answer to this question, but my affirmative answer doesn't make me any more interested in this email. On the contrary, it makes me think that the sender must not understand sales very well if they could even ask a question like this. And then there's the false familiarity that tries to force casualness. It smacks of being inauthentic, and that shuts buyers down. 


One thing this subject line does right is use my name. Putting the name of your prospect in the subject line does get their attention and interest.


A more straight-forward subject line would be: "Here's a way you can close more deals, Deb"


That's a subject line that compels me to read more. And that's the whole point of a subject line!


2. "Using regression analysis in compensation"


Ugh. Maybe this would be more interesting if I were a Compensation Analyst or a Finance Manager. But I'm not. That's why subject lines should take into account who you're sending them to. This one is, for me, a subject line that gets the e-mail fast-tracked to spam. 


Because I am a consultant to sales organizations, I do have an interest in sales compensation. Just not regression analysis or anything too math-y. So, for me (and maybe for a majority of people) getting straight to benefits would be a better approach.


A more compelling, benefits-focused subject line would be "Create a comp plan that keeps your best employees happy"


3. "Re: How to PREDICTABLY generate high-ticket sales"


Here's the fake-out with a "Re:" that isn't real. Did the sender really think I'd fall for it and believe I initated the conversation?


What's good about this subject line is that it emphasizes a key word that is on the minds of many sales managers today. Predictable is good. High-ticket sales is good, too.


Taking the "Re:" out of this subject line would make it stronger and more authentic. I probably would have opened it if it didn't start with a deception.


Recap: Be authentic. Get straight to the point of the email. Include the benefit for reading the email. Use the recipient's name. Don't try to fool anyone. In the CONNECT stage, establishing trust and opening the relationship is your aim.

Recognized Expert | Platinum Partner

Hi @DebCalvert,


Thanks for doing an AMA! Looking forward to your session at Inbound!


My question is in regards to buyer's preferences and unexpected sales calls.


What is the sentiment of buyers regarding unexpected calls (cold or warm) when the sales person actually comes prepared with relevant info, isn't reading from a cookie cutter script, uses context in the call, asks good questions, etc.?  What's the number #1 piece of advice you have for a sales person making these phone calls?


With the growth of popularity of Account-Based-Marketing (ABM), I would expect that more sales people (even if they're practicing inbound) are going to be picking up the phone to make more unexpected calls and would find value in having a better understanding of this. 


Thanks Deb!


Did this post help solve your problem? If so, please mark it as a solution.

Josh Curcio

HubSpot support and inbound marketing for OEMs, contract manufacturers, and industrial suppliers.
HubSpot Platinum Partner & HubSpot Certified Trainer


Thank you, Josh, for a question that a lot of people are reluctant to ask. As a sales coach, working with SDRs especially, I often hear variations of this question or reservations that hint at this question. .

The first misperception I'd like to address is that the calls you make in your job are not the same as the annoying calls you get at home.


Most of us try to relate to what the buyer may be feeling about our call. From our own experience, we liken our unanticipated calls to the ones we receive at home from robo-callers and telemarketers with highly generic offerings. Those are interruptions that provide little or no value because they are irrelevant to what we do and not connected to what we're thinking about or working on when the call comes.


This is not an apples-to-apples comparison. In B2B selling, the people we're calling are engaged in work that's directly related to what we have to offer. They are already thinking about and interested in what we can provide. The problems we can solve for them are problems they need and want to solve. When we come prepared with relevant information, we provide value. When we ask purposeful questions, we create value by making people think and assess their situation. When we keep our focus on our buyer's needs, we become valued partners in helping them solve problems. 


The second misperception we need to talk about is that calling people is rude or pushy. Sure, if you're unprepared or conducting irrelevant fishing expeditions, that's not very considerate. But if you can help someone, it would be rude NOT to call. If you have a solution to a problem they want to solve, calling until you get through and get a chance to demonstrate your solution is the right thing to do. It's not pushy unless it's unwanted. Trust me, real and relevant solutions are wanted. So make it real and relevant!


In our research with buyers, we got an earful about the behaviors buyers want to see more of from sellers and the behaviors they resist. Buyers donn't use words like "pushy" or "rude" when sellers engage in ways that bring value. Instead, they use words like "trust," "partner," and "resource" when sellers call with stimulating questions, a desire to help, and relevant information.


The number one piece of advice I can offer is this: Understand the value of YOU. Value doesn't come from your product or company alone. YOU are the ultimate value. Inbound or outbound, when you connect with buyers, you can create value out of thin air. Doing that requires focusing on the buyer and what they need. Aiming to discover and deliver what's of value to them will make your call one they will appreciate.  

Top Contributor

I'm intrigued cold calling really dead?


No, cold calling is not dead. It's not even dying.


I think there are plenty of people who wish cold calling was dead, buried and forgotten in selling. But the truth is that cold calling serves a purpose for both sellers and buyers. And, done right, cold calling can benefit sales organizations and buyers tremendously.


The problem is that cold calling is done poorly more often than it's done well. In an age of Inbound Sales, we could easily sidestep cold calling and still fill our sales days with plenty of productive activity. Those two factors are what lead to these pronouncements that cold calling is dead.


Perhaps a different way of looking at this -- is cold calling necessary when using an Inbound Sales approach? In my opinion, yes, cold calling still will be necessary at times. Let me explain.


The aim of inbound is to get found online and create a pathway for your buyer's journey from stranger to prospect to lead to buyer. But the aim of every sales organization is to make sales. Inbound strategies will do two things: increase sales by drawing in buyers and turn cold leads into warm ones.


But what happens when you need more? Do you sit around and wait for someone to discover you online and work their way through the buyer's journey? Not if you're needing to make quota this month! That's a long-term strategy, and sometimes you need to supplement it with more immediate action.


Cold calling can fill those gaps if and when they occur.


Inbound and outbound aren't mutually exclusive. I'm an advocate for blending the sales approach in a way that makes sense in your industry, company, territory and role.


Expanding on a previous question/answer about cold calling. In the Inbound methodology, cold calling isn't advised. WIth a mature inbound strategy and ample leadflow in your pipeline, your need for cold calling or cold emailing diminishes. My response is for the gap time -- it does take time to build and execute on an inbound strategy and, during this transition time, you can't abandon all strategies. 


In a perfect inbound world, you will not do as much cold calling. I know, personally, that my own company's outbound work has been gradually replaced by inbound work. But I am not yet able to say that cold calling never works and is dead. For those times when you need it, look to use all your inbound efforts and people-connecting skills to turn cold calls to warm ones!

Participant | Platinum Partner

Ho Ho,


Cold Calling (CoCain) is one of my favourite topic.


By interest, by necessity, and because it's part of my job to explain my customers, what's going to work/or not - within their sales activity.


Is CoCaing dead : YES, when targets + content + objectives are not aligned.


Is CoCaing dead : NO, when you send valuable content to people facing pains you can solve. Just tell them softly. 


  • Add some human interactions,
  • Create business conversations,
  • Show you are the good person to ask for help  >>>




Not applicable

Hi Deb! Can I ask what your thoughts are on field sales / visiting potential customers in person VS meeting remotely on conference calls?

HubSpot Employee

Hi @DebCalvert thank you so much for taking the time to make such an awesome contribution to our community! 


My queston is related to prospecting - what are some of your best practices here for finding qualified prospects, and what are the criteria you recommend considering in this process? 




I wish we all had the Star Trek transporter teleportation technology so we could efficiently beam ourselves to meetings with prospects, leads and customers. There are merits to meeting face-to-face, being able to shake someone's hand and make eye contact.


Since we don't have Scotty to beam us up, we can't easily and efficiently meet with people as often as we'd like. Meeting remotely has merits, too, including:


  • You can meet more people in any given day if you eliminate windshield and sky time
  • You can "cheat" when you meet by phone, referring to notes and screens you can't easily access in person
  • You can make it easier for your buyer if they can take a call instead of taking a full meeting
  • You can track calls and emails and webinars and demos with automation and recordings
  • You can get sales coaching from in-office or recorded calls more often

Learning to use the phone and tools for video-conferencing is essential in modern selling. It may be more difficult to listen and gauge a buyer's reactions when you don't have in-person cues. It may be harder to stay focused and to convey your warmth over the phone. But sellers who master these soft skills will be more efficient and more effective.


See the next question (same as yours). I'll try to answer both at once!

Not applicable

Hi @DebCalvert


I would love your perspective in regards to how much prospecting and networking can be done online as opposed to in person? In a world where we are all tied to our computers and phones, it is convenient to connect through emails and online platforms, but when should we be meeting with people in person? Are human connections still necessary to close a deal or have we moved into a world where emails are just as effective? 


Look forward to your thoughts! 


Be sure to read my response to Nicole's question. It was similar, and yours gives me an opportunity to expand on that answer.


The amount of time spent connecting online vs. meeting in person will depend on the industry you're in, your company's go-to-market strategy, and the products/services you sell.


For example, a local territory Account Executive who sells advertising needs to meet in person with regular advertisers to review schedules, options and ad design. Why? Because the local proximity and complexity of decisions made together is often easier in person. And because that's what most media competitors do. By contrast, a SaaS product that isn't customized for each user might be sold globally by a sales team that exclusively works by phone. It isn't practical for them to meet buyers in person, and it isn't necessary.


For most of us, there are times when meeting in person is possible, practical and essential. I suggest seizing those opportunities when it makes sense to do so. For example, I'll be meeting two potential clients at Inbound next week -- we'll both be there, so it's a chance to visit in person as an extension of the calls we've had so far. Additionally, I'm staying in Boston for a few extra days and will meet a client and a prospect who aren't attending Inbound. When I travel, I look for these opportunities everywhere I go. 


You asked "are human connections still necessary to close a deal or have we moved into a world where emails are just as effective?" In my opinion, emails alone will never be as effective as some human-to-human contact. Voice-to-voice by phone, face-to-face over video conferencing, or live chatting is more personal than email. With Inbound Selling, you can make great strides with content and email. But I recommend against relying exclusively on email. Look for ways to make yourself more real and to connect more personally with your buyers.


Hi @DebCalvert  Thrilled toget your input here. I've been in sales a while. I LOVE inbound sales! Such a refreshing relief from years of cold calling.  Problem is that my boss is old school and thinks inbound is too millenial. What kind of results / data / cse studies  can I show him that inbound works? I've started a blog, set myself as an expert resource instead of sales person. I've seen results but my boss still isn't conviced. Thoughts?



Like you, I LOVE inbound sales. Like your boss, I've been skeptical and reluctant to make a shift.


Fortunately, I've been surrounded by great resources. My digital agency, protocol 80, held my hand during a time of transitioning to more emphasis on inbound strategies. The HubSpot blog and training videos are super helpful, too (I'm hoping to personally thank Kyle Jepson at Inbound next week!). And the book "Inbound Marketing" by Brian Halligan and Dharmesh Shah was a big part of why I decided to give inbound an honest try. That book would be a good resource for your manager.


For Case Studies, I'm going to invite this community to contribute. There are LOTS of them. I'll start by suggesting you take a look at this page from protocol 80 -- it includes several inbound success stories:


I'm also interested in your blog. If you're willing to share it, I'd be happy to help you spotlight specifics that may help you make the case with your boss.



HubSpot Employee

Hi @DebCalvert Welcome to the community! Can you give us a mile-high view of what sales leadership looks like? (Asking for a friend wink winkCat Happy




INBOUND 2017 is just around the corner. Find out more at or check out the post on the main Community page.

Did my post help answer your query? Help the Community by marking it as a solution

So many great questions already! Instead of waiting until Thursday, I'm hopping in early to answer the questions you've already posted and to invite you to keep 'em coming!


Kicking off today's LIVE session with a question that came via LinkedIn -- 


The question, based on a post about my book on questions, was "in your experience what are the toughest questions to ask a prospective customer?"


My answer, modified for an Inbound Sales application, is:


Questions about our own performance and areas where we can improve are the hardest ones to ask.


What makes these questions difficult is that they require a certain kind of humility and patience. They are questions that leave the seller feeling vulnerable. Tough questions, ones I see sellers shy away from asking, include "What caused you to decide to go with our competitor instead of us?" and "What is it that we need to do differently in order to earn your business?"


Asking and learning from questions like these helps in gaining new customers and maintaining existing ones. Setting aside ego and genuinely listening to the prospect's input isn't easy, but it can pay big dividends. In DISCOVER Questions, these are referred to as "Issue Questions." In over 10,000 sales calls, fewer than 5% of sellers asked these questions. So another benefit is that you can differentiate yourself by being the seller who takes a personal risk and asks questions like these.  


When we work with people remotely, it can be even more difficult to say anything that suggests potential weakness. What we forget, though, is that admitting weakness is generally seen as a strength. It humanizes the person on the other end of the phone to know they are trying earnestly and genuinely looking for ways to improve. You can build trust, earn admiration and respect, and learn from your prospects and leads when you ask Issue questions. 

Recognized Expert | Platinum Partner

Hi @DebCalvert,


Stats show that 5+ people are now involved in the buying process (according to HBR). In speaking with people in sales, this can be anyone from an intern to CEO. Do you have any tips for sales people that are more comfortable in speaking with sales managers or executives as to how they might need to shift their conversations and approach when speaking with interns and entry level people involved in the sales process?

Did this post help solve your problem? If so, please mark it as a solution.

Josh Curcio

HubSpot support and inbound marketing for OEMs, contract manufacturers, and industrial suppliers.
HubSpot Platinum Partner & HubSpot Certified Trainer


Hi Deb! 


Thanks for taking the time to answer our questions today.


Just curious how persistent you should be with your emails when a buyer isn't answering. 


Renee - 


When a buyer isn't answering emails, it's time to activate the Sales Time Management formula, E=O. That stands for Effort = Opportunity. The answer to your question is that, with anything in sales, you want to allocate your time/effort proportionally to the opportunity.


Here's an example. I have a lead flow for a management training program we offer in English and Spanish. Occasionally, I get an inquiry or content download from someone who is with a competing company and also offers supervisory skills training. In my experience, these are not likely buyers. If they don't respond to our first email, they probably won't get a second one. For a large company and a person in charge of Learning & Development, there will be lots of persistence (effort and time) on our part because the opportunity is greater. 


It may also help to point out that there are some studies out there that say it takes 19 contacts to get a response. That number, an average, probably includes calls that start cold. But even with inbound selling, my coaching clients usually think it's time to give up much sooner. Three or four emails is not enough. If you have something of value to offer and the opportunity is worth your time, be persistent. Your buyer, busy and pulled in dozens of directions, will appreciate your commitment. 


Hi Deb, thanks for doing this!


Regarding Stop Selling Start Leading, is there anything to consider higher up the funnel to best implement this sales methodology? Is there anything the marketing team should know about lead scoring, passing leads to sales, lead nurturing? 

Top Contributor

Hi Deb, thanks for sharing all of your insight. I'm excited to learn more from your book/Inbound session! I was wondering if you'd be willing to share some of your favorite resources? What other influencers in this space influence you? Do you have any favorite blogs? How do you stay up on what's changing? 




I love this question, mwhiteo51, and I look forward to meeting you at #Inbound17. 


Answering your question could take all day. I feel really fortunate to have had lots of mentors and examples in the sales space. 


I try to keep up with what's changing by conducting research, reading blogs and books, attending webinars, and working with a diverse mix of clients (who use a variety of new tools and approaches). I'm curious, and I use conferences like Inbound to ask questions and meet people. I attend sessions about topics I know nothing about or go to speakers I don't see eye-to-eye with so I can see things from other perspectives and (hopefully!) avoid limiting myself. I also work outside of the sales space to bring new ideas in... Research in the leadership space, for example, turns out to be highly relevant for sellers -- that's the topic I'll be speaking about at Inbound. 


Among the resources I'm closely tuned in to right now --


The HubSpot team and the folks at protocol 80, Inc (a HubSpot partner agency). I've learned a lot, despite my own initial reluctance, over the past year about Inbound methodologies. I'm still learning! HS blogs, videos, infographics, research, case studies, and events are incredibly valuable to me. 


For balance, I also pay attention to the folks who advocate outbound selling. Jeb Blount, Mike Weinberg, Anthony Iannarino (among others) are diehard defenders of cold calling and "the hustle." In my opinion, there aren't two vastly different approaches to selling that are mutually exclusive. The right approach is often a blend of both. The right mix depends on what you sell and who you are. 


Buyers are the best resource of all. I coach sellers to ask buyers about their preferences and to learn from their buyers every day. My books are based on research with buyers, and I'm humbled by how often my hypotheses about buyer responses is different from what buyers actually want. We have to keep asking to keep current!


Specific resources I will recommend in this brief post --


1. The Sales Experts Channel is a group of 63 sales authors, speakers, trainers and coaches from around the world. I founded this channel nearly a year ago with the express purpose of bringing diverse opinions together in one place, and it continues to be a great resource to me, too. The hundreds of webinars here are free and available on-demand.  


2. Consider podcasts that you can find on iTunes and listen to in the gym, on the run, or when you need a shot of sales motivation. Barb Giamanco, Will Barron, Maxwell Bogner, Donald Kelly, and Brian Burns offer a diverse mix of viewpoints to get started. There are lots of other really good ones, too, so search until you find the topics and hosts that are right for you. 


3. The Women Sales Pros site has a fantastic blog with female contributors that bring fresh voices and incredible insights. I strongly recommend this weekly read!


4. If you want fresh content every weekday, be sure to bookmark Top Sales World. Audio, webinar, blog, articles, books and more show up here. It's the "hypermarket" of sales thought leader contributions. You'll find more here for Sales Managers and executives, too, that may be useful.


5. Another content curator is SalesPop from Pipeliner. It's getting stronger every week, and there are contributors here that you won't find elsewhere. Give this one a try, too!


Specific books I recommend frequently: The Leadership Challenge by Jim Kouzes and Barry Posner,  The Perfect Close by James Muir, Selling with Noble Purpose by Lisa Earle McLeod, Selling to the Point by Jeffrey Lipsius, Grit by Angela Duckworth, Mindset by Carol Dweck, Sales Magnet by Kendra Lee, and (of course!) Inbound Marketing by Brian Halligan and Dharmesh Shah...  I read a business book every day, so hit me up if you want a more specific recommendation. 


Hope this is helpful and wasn't more than you bargained for!




Interesting question, ashleywr -- thanks for keeping me on my toes today!


The Stop Selling & Start Leading research with buyers gives us a behavioral blueprint for sellers. From this research, we are able to identify 30 specific behaviors that buyers want sellers to exhibit more frequently. 


In order for sellers to be more effective in exhibiting these behaviors, there are some lead scoring, lead nurturing and lead passing considerations for marketing and others to consider. Let me cover one example of a behavior buyers want + offer some thoughts on the implications for marketing. 


1. "The seller fully answers my questions and provides information that is relevant, timely and useful." This is the top-ranked behavior of all 30 that buyers want to see more often. In the comments we gathered, it became clear that buyers are frustrated when we ask them qualifying questions -- they've already qualified themselves and want to talk about other things. This HubSpot research in the Buyer Perceptions Study is very revealing when it comes to how we're not being relevant, timely and useful. 


What can marketing and others do to enable sellers to exhibit this behavior? Some starter thoughts:


  • Provide buyer insights that will help the seller tailor information provided so it is relevant, timely and useful.


  • Provide a mechanism for identifying buyer interests and questions in advance. Example: use a webinar platform that includes polling or survey features. Ask attendees to vote or identify their primary challenge. Pass this information along to sellers (specifics, by individual attendee). 


  • Invite questions from prospects and leads. Create content that pinpoints where they are in the buyer's journey, what options they're considering, what their buying criteria will be, etc. 

Other desirable behaviors include "The seller demonstrates a personal commitment to fulfilling any promises made or implied by the brand he/she represents" and "The seller speaks with genuine conviction about the higher meaning and purpose of our work and relationship." I'd be really interested to see what others in the community here have to say about what these mean for lead nurturing, passing along leads, lead scoring, etc....

Participant | Platinum Partner


With the booming growth in mediums you can use to reach buyers (email, social media, smartphones, etc.) what are buyers' preferred methods of being communicated with nowadays?




Buyers are not all alike, so that's why it's really important to develop a buyer persona. Some will prefer communication via text while others want email. Some are barely on social media at all while others are very active. We need to meet them wherever they are.


For our established buyers, my best advice is to ask about their preferences. A simple question like "Instead of assuming and always sending you emails, what are your preferences for how we communicate?" will let your buyer know you care. It will make you the seller who stands apart. Being responsive to any communication they initiate is also smart -- I have one vendor who responds to my texts and emails with unscheduled phone calls. Since I'm often in coaching or training sessions, answering my phone and having decent conversations is difficult. I've even asked for written communication, but he responds by telling me that he likes to talk. I get it, but it's not meeting my needs.


The bottom line is that we need to adapt to individual preferences and take the time to understand our customers and our prospects.   


Hey @DebCalvert! Any tips on how to execute a successful cross-selling strategy? How should we motivate other teams (services, support, product marketing) to help source/qualify leads for sales?