Why There Is No Room For “IF” In Selling

I received this email the other day and it started like this;

If you work in sales enablement you should –

Well, I don’t and I suspect most of the other recipients didn’t either. The email then went on to talk about the value proposition of the podcast they were promoting. After a decent list of benefits the email ended like this:

If you are in sales enablement, and need to scale, you will benefit from listening to this podcast.

The email was short, targeted and offered a decent  value proposition. It wasn’t a bad email, except, it started and ended with “If” and that was the problem.

Recently I was on a demo and the rep continued to move through the demo by saying;

If your people post to XYZ then this feature will bring a lot of value. If your company does ABC then . . .

It was driving me crazy. More than 50% of the time, we didn’t do things that way, our people wouldn’t require the feature I was being shown or our company had little value in the feature being shown.

As sales people, when we ask  a client or prospect, “if,” what we’re basically saying is, we don’t know what they do, who they are or how they run their business. That’s not good.

There is nothing worse than advertising to prospects and clients that you are unprepared and not schooled in their business or company. As sales people, it’s our job to know who we’re talking to, what their issues are and how they run their business. If you don’t know something, ask.  But whatever you do, don’t go with “if.”

The good news is, although this is a terrible habit, it can be fixed rather quickly by simply paying attention and being aware of how you engage prospects. Pay attention to how you deliver information. Listen for the times when you’re about to say something that you don’t know the answer to. One of the best ways to avoid this mistake is to know exactly what issues or challenges you’re going to address for your customer before the meeting starts.  Take the time to know your buyer before you engage with them. If you don’t know enough, then don’t pitch. Use the meeting as a discovery meeting to get more information about their business. If it’s an email, know who you’re sending the email to before you send it. Don’t waste their time by sending them an email that isn’t germane to them. I promise you, it was irritating getting an email for a sales enablement person when I’m not.

Rather than sending out bulk emails to your entire list, consider creating lists by title. Have your sales leadership list. Have your sales enablement list, sales operation list, have your sale people list, etc. This doesn’t prevent you from doing bulk emails, but when bulk isn’t appropriate, you can send targeted emails that matter and tells your prospcet you know who you’re talking to.

When you use “if” when referring to your client or their environment you’re telling everyone within earshot you don’t have a fuckin’ clue. Yes, it’s that bad.  Clueless sales people are the worst. The entire value of sales people is steeped in knowledge, don’t tip your hat and let everyone know you don’t have any.

There is no room for “if” when selling. It’s that simple.



Have You Started Using Meerkat?

I got hip to Meerkat about two weeks ago. Like most people, I saw the all the noise coming out of SXSW and so became curious.  This week while at Accelerate conference I decided to take Meerkat for a spin and see what it’s like.  I Meerkatted Hall of Fame QB Steve Young’s talk.   Steve is a pretty funny guy. I tried to upload it here, but it’s too big a file.  It rocked and I’m glad I tried it out. I see so much potential for Meerkat and social streaming that I posted about on Forbes the other day; 5 Unexpected Way Meerkat Will Crush It For Sales And Marketing

Streaming isn’t necessarily something new, but leveraging the Twitter platform and all of your existing followers changes the game.

Today we Meerkatted the filming of  The Word Episode Three Trailer and got feedback from some of the people watching. It was cool.  We’ll be Meerkatting the Actual Episode on Thursday as well. I’m excited.

Here’s the Meerkat from today’s The Word Episode 3 #Social Selling Trailer Shoot. Keep in mind, that in addition to the video stream, Meerkat brings in the Twitter chat as well, so you can engage with those who are watching.

This was streamed live across my entire Twitter stream.

When I started streaming this message was Tweeted:

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Anyone in my Twitter stream who clicked the link would instantly launch  the Meerkat App and be brought into the live stream. Voyeurism to the max.

In addition to being able to watch participants can chat and engage with you and each other  (this part is not captured in the recording, which bums me out). The chatting is captured in a live text stream in the Meerkat as well as on Twitter for others to follow.  It’s all pretty slick.

If you haven’t yet, check out Meerkat. It’s cool and it’s upping the personal brand and social game.

See you on Meerkat!

[Video] How Sales People and Sales Leaders Do A Killer Demo


 “Selling is not just show up and throw up!” 

Mark Roberge


Demos are increasingly becoming the path to making the sale, and if you mess up the demo, it sabotages the sale.  Unfortunately, too many salespeople and therefore sales organizations do crappy demos.  I see this as the fastest growing sales problem today.

So, with that said, I wanted to get someone who knows how to do killer demos to school us all on how to a demo that works and helps the sale, not hurt it. Mark Roberge is that guy and he killed in on this week’s show.

Mark is the CRO of HubSpot and the author of The Sales Acceleration Formula.  He’s grown Hubspot from nothing to 100 million plus in revenue in 7 years.

Mark offers some great insight into how sales people can improve their demo capabilities and how sales leadership can build organizations that deliver killer demos.

If you or your organization rely on demos to make your number, you don’t want to ignore this video. Plus, the beginning is funny.

BONUS: If you’re a CEO, COO, or Sales Leader that is trying to scale your business, his book is a must.  It’s a brilliant combination of art and science.  What would you expect from an MIT grad?

51uqPhk34wL._SY344_BO1,204,203,200_ The book is worth the read.

LinkedIn Is Today’s Suit — Are You Wearing Armani or J.C. Penny



When I first started my career, I was a suit bitch. I wore the most stylish suits I could afford. I wore Boss, Armani, Ralph Lauren, and Canali. I loved them. I knew what stores had the best sales, and how to get these #badass suits for as cheap as possible. As my career progressed and I made more money, I began to have my shirts custom made. They had English spread collars with French cuffs. I wore Ferragamo and Gucci shoes with my suits. I even had a pair of Georg Jensen period cuff links. They were sick. My goal was to be the best dressed; most put together sales person on the planet. I wanted every person who met me to see me as a badass salesperson who knew his shit. I wanted to command the room the second I walked into it. I was going to leave no doubt that I was legit, and they needed to pay attention.

In those days, that being the 90′s, there was no LinkedIn. The Internet, as a tool, was in its infancy. Social media, ha! Whatever! Therefore, like the 100 years before, a suit was your credibility calling card. Suits told the world that you were a professional. It was the first thing people saw and what they drew their first impressions on. Suits established a sort of first impression hierarchy, where those without suits or cheap suits were pegged as lower, less credible than those with nice suits. To prove my point, I knew NOT to wear a short sleeve dress shirt. What’s the first thing you think about when you see a guy wearing a short sleeve dress shirt and a tie? It’s not credibility; I can tell you that.

Because there was so little information available to us at that time, suits and our physical appearance played an enormous role in our branding and first impressions. Today, however, that’s changed.

Today, your LinkedIn profile is your suit.

Today people, for the most part, could care less if you’re wearing a suit. Thanks to LinkedIn people know what you look like, who you are, what you’ve done, and your value to them long before you ever step foot in their office. The need to convey competence via appearance is unnecessary. Suits only matter now at weddings and funerals.

The Internet, Google and in particular LinkedIn has redefined first impressions and how we develop them.

So, here is the question. If LinkedIn is, is the new suit, what are you wearing? Are you wearing a designer Armani or a cheap J.C. Penny suit?

You’re wearing an Armani or Canali suit if:

  • Your LinkedIn profile contains rich media
  • PDF’s, HTML Links, Video (yes video!), PPT. and more showcasing your work
  • You have at least 500+ connections
  • You’ve received at least three recommendations
  • You’ve been endorsed for multiples skills at least 25 times for each skill
  • You’ve given at least three recommendations of others work
  • Your summary focuses on the customer (others, not just you), your value?
  • Clean headshot photo
  • It has your full contact info

A J.C. Penny suit looks like this:

Your LinkedIn profile contains no rich media; you are unable to showcase the work you’ve done or anything you’ve created

  • You have less than 500 connections
  • No one has recommended you
  • You have few to no endorsements of your skills
  • You have a weak summary, listing only your accomplishments or what YOU want not what you give
  • Photo of you fishing, leaning against a tree or swinging a golf club
  • Little to no contact info AND no social media presence

Which suit are you wearing?

When someone shows up on your profile, it’s a first impression. Like a suit, if it’s a bad one you’re in trouble. Your LinkedIn profile is perceived by others as an extension of you. If you don’t have rich media and you can’t showcase your work, it can be perceived that you don’t have any work to showcase. If you have less than 50o connections, it suggests you’re not connected, and you haven’t built a good network over your career. When you have no recommendations, does it mean you haven’t done work worthy of a recommendation? If you haven’t recommended anyone, does it mean others don’t value your recommendation? If your photo looks like something from Facebook, it suggests you don’t understand the value of LinkedIn and the professional nature of the platform. When you’re LinkedIn profile resembles a J.C. Penny suit, you are unable to compete. It undermines your credibility and makes visitors nervous. Recruiters question your qualifications. Future employers questions your capabilities. Customers or future customers dismiss your credibility. When you’re LinkedIn profile sucks, it looks like you suck, and that’s not good.

You would never go to an interview or on a sales call dressed like a clown. When you haven’t cared for your LinkedIn profile, that’s what it’s akin too.

Suits matter less and less when it comes to first impressions. First impressions matter, but first impressions are now digital. We know who you are, what you look like and what we think about your long before we ever see you face to face. Just like in the old days, you need to make the best first impression as possible. The good news now is, unlike days gone bye, everyone can wear an Armani and it won’t cost a fortune.

So, what are you wearing? Is it time to upgrade?

The Greatest Sales Person, Can’t Save The iWatch (Apple Watch)


The iWatch talk is getting hot. Watches as a device are being pumped up as the next big thing, but if you ask me, I’m saying no. (so is my boy Fred Wilson)

Here’s the deal.

I had a badass professor at The University of Chicago, his name was James Schrager.  Some of you might even know of him.  The guy’s a classic. One of the things he taught us was businesses fall into 4 categories (I think it was 4 :) )  One of the categories is the image category.  Image businesses are businesses that rely on image as the core reason for their successes. Clothes, are an image business. Cars, are an image business. Watches, are an image business.  You get it? Products in the “image” business rely on how they make people look, their image as the driver to sales. Watches are the quintessential image product.

Watches are all about image.  Most people wear a watch as “jewelry” first and to tell time second. Time isn’t even the first reason people wear a watch. The main reason watches were created, is now the second reason people wear them. Therefore, adding MORE utility isn’t going to sell more watches.

Do I think the iWatch and all the other wearable devices is gonna bomb? NO!  But, are they the next computing killer product? NOPE!

iWatches and Android wearables are not going to be the hit iPod’s and iPhones and iPads were. They’re just not. They’re getting into the wrong space. Watches are jewelry in spite of their utility and that’s not gonna change because we allow them to text, video, or surf the net.

iWatches will be the tool of the nerd, just like the Casio watch of the 70′s and 80′s. The geeks and nerds who place little value on image will gobble up the iWatch, the rest of us will stick to Fossil, Movado, Rolex, Tag Heuer, Bulova, Omega, and Timex.

As I’ve said before. The days of sales being able to move a shitty product are over. The product comes first. No matter how bad Apple, Samsung and all the other manufacturers want watches to be the next thing, they won’t and dumping money into sales and marketing aint’ gonna help.

Product first, selling second, it’s just the way of the world today.  Deal with it.

The 5 Roles Of Sales People Crushing Quota

I had to share this with you guys. It’s a great Infographic.

I’ve long argued that information is the key to successful sales people and that renaissance people are the best sales people, while teaching organizations are the best sales organizations. This infographic by Salesforce and Kapost on content represents exactly what I’ve been saying. It’s great.

I’m even with them on the transformation argument. Shitty sales people tend to be less informed, less savvy and more self absorbed. In many cases, information or “content” can fix that.

Our job, as sales people, should we truly accept it, is to become a;

  • Teacher
  • Problem Solver
  • Thought Leader
  • Coach
  • and a Partner

When we do, selling becomes as smooth as butter.

I love the TEACH section. It doesn’t get any better when you can provoke or push your prospects to think differently.



Content is absolutely the way to make to become a badass sales person. Get on the content path, it’s a game changer.

Props to Kapost and

The Word! Episode 1: What Sales People Are Missing

We did our first episode of The Word on Thursday. It was sick. We had so much fun. Our guest was Dan Waldschmidt author of Edgy Conversations.  The topic was what sales people are missing. We broke down the key traits we think sales people need more of and why it affects sales. We talked about being great, and why too many people don’t aspire to greatness.  Dan opened up about some of the personal experiences behind his motivation to write the book and more. It was truly one of the best 42 minutes I’ve spent, not on skis, in a while.

Our goal with The Word is to bring you mad sales wisdom in a fun, hip, cool, exciting, challenging, entertaining way.  You know how we do shit around here. We’re a bit irreverent, and so is The Word!

The key things sales people are missing include;

  1. creativity
  2. grit and drive
  3. analysis and assessment skills
  4. business acumen
  5. empathy

Also, you don’t want to miss the discussion on the opening of Dan’s book where he talks about his close call with death by his own hand and how it changed his life.

The Word is tight and I’m excited about the possibilities. Our next episode will be March 12th and we’ll be talking about how to do a badass demo. Our guest will be Mark Roberge, Chief Sales Officer of Hubspot.

So check it out and let me know what you think.

Top 3 Mistakes in Selling to Inbound Leads

Today I’m droppin’ a guest post from my boy and Chief Sales Office over at Hubspot, Mark Roberge. Mark has written a new book and it drops today; The Sales Acceleration Formula. Mark has done some killer stuff over at Hubspot, growing them from 0-100M in revenue. I say that qualifies him on teaching the rest of us how to grow revenue.

But, if 0 – 100M isn’t enough, Anthony Robbins reviewed his book and said this;

A new breed of disciplined, data-driven leaders are re-shaping the field of sales. The Sales Acceleration Formula explains why.

I love this post ’cause we make too many assumptions with inbound leads. Inbound leads are new and as Mark says, too many of us are screwing up in the transitions.

This post does a great job of breakin’ it down.


Top 3 Mistakes in Selling to Inbound Leads

Every day, more and more sales calls are being made to inbound leads rather than cold prospects.  It is a great trend.  These inbound leads are further along in their buying journey.  They close faster and at a higher rate.

Unfortunately, traditionally trained salespeople often struggle with the transition from calling a cold prospect to an inbound lead.  Here are 3 common mistakes salespeople make when calling inbound leads.

Mistake #1: Assuming a non-decision maker is a bad lead

Outbound salespeople are trained to “call high”.  Why deal with someone that does not have the authority to buy?

Unfortunately, the contact on an inbound lead is not always the C-level executive holding the purse strings.  Instead, the contact may be a front-line worker or even an intern.  Traditionally trained salespeople throw up their arms stating, “these leads suck”.

Actually, the leads do not suck.  I admit, the contact on the lead is not a buyer.  The contact has no budget authority.  However, who do you think told the contact to do the research, conduct the Google search, and download the eBook?  It was likely an executive driving the decision… and the budget.

When deciphering the quality of the lead, focus less on the contact’s role and more on the company’s fit with your product.  The fact that someone started the research process indicates a trigger at the company aligned with your product’s value proposition.  A potentially easy deal is on the line.  Don’t let it pass you by.

Mistake #2: Leading with the vanilla elevator pitch

In a cold calling environment, salespeople are throwing darts in the dark.  They have no idea whether the value proposition they are pitching will resonate with the companies they are calling.  With fingers crossed, cold callers deliver a well crafter elevator pitch and hope it resonates with the recipient on the other end of the line before they hang up.

This approach of leading with the vanilla elevator pitch is the kiss of death in an inbound environment.  Your company enticed the prospect with a thought provoking tweet, engaged them with a well written blog article, and convinced them to exchange their contact information for a valuable eBook, written about a problem they have been researching.  Then, you, the salesperson, ignore these breadcrumbs of contextual interest and simply deliver the vanilla elevator pitch?

Inbound leads have much more context associated with them than a cold prospect.  These leads have read blog articles, viewed webpages, downloaded specific eBooks, and even conducted precise Google searches to find your company.  Leverage this context when you first engage an inbound prospect.

“John, I noticed you downloaded our eBook on XYZ.  What specific questions did you have?”

Break the ice with that opener.  Lead with their interests, not the vanilla elevator pitch.

Mistake #3: ABC: Always be closing

Traditional salespeople are trained to “Always Be Closing”.  Connect.  Pitch.  Close hard.

However, today’s buyer is far more empowered than a decade ago.  All the information they need to evaluate a purchase is at their fingertips, whenever they want it.  Modern buyers are not going to put up with these archaic tactics.

Instead of ABC, salespeople need to ABH – “Always Be Helping”.  Once you break the ice with the prospect’s interests, answer their questions.  Do not withhold information. Answer as many questions as the prospect wants to ask. With every question, you are building trust.

Eventually, you can leverage the trust to evaluate whether you can help the prospect’s organization and whether you should both invest more time together.  Ask them questions like:

  • Who asked you to download the eBook?
  • What does your boss expect of you this quarter?
  • What were the CEO’s priorities at the last company meeting?

Now you are in a position to engage the decision maker with deep context that will surely impress.

Inbound leads are gold.  However, traditional sales methods may turn off the buyer… and the sale.  Align your sales tactics with the context of an inbound lead to create a more efficient process for you and the buyer.

2013 Roberge 2


Go check out Mark Roberge’s new book that launched this week, “The Sales Acceleration Formula: Using Data, Technology, and Inbound Selling to Go from $0 to $100M”, about his experience in building the HubSpot sales team. It’ll make you happy and all giggly inside. 

Sales Surge Summit

I did a 30 minute interview on sales people mistakes the other day as part of the Sales Surge Summit.

You can see the entire thing here.

Screen Shot 2015-02-17 at 9.34.02 PM

I tackle the importance of empathy in selling, how to prioritize and a few other fun elements of selling.

While you’re there be sure to check out the other speakers, they put together a good group of sales cats for this summit (Anthony Ianarino, Dan Waldschmidt, Matt Heinz, Ken Thoreson and more.) It will be well worth your time.