Book Review: New Sales. Simplified.

new sales simplified book review

Have you ever finished reading a professional development book and said to yourself: “Where was this book 10 years ago!?”.  This is what happened this morning when I finished up New Sales. Simplified. by Mike Weinberg.  It was sent to me by one of my sales mentors and once I got into it, I simply couldn’t put it down (which is rare for a business book).

Who is this book for?  Honestly, anyone in B2B sales in any industry that is looking for (as the name suggests) a simple strategic and tactical approach to maximizing their sales efforts – with a specific focus around generating new business.

Weinberg uses a refreshing, anecdotal approach to describing his proven sales methodology…which in many ways is close to the approach I have used within my technology businesses, but I still highlighted quite a few sections of this book as solid value-bombs.  It also made me question a few of the approaches I have used in the past, and I am definitely going to try a few new things thanks to Weinberg.

Some of the key takeaways you will have from New Sales. Simplified. include:

The Sales Story

I see so many technology companies today ‘pitching’ features and functions that it makes me cringe.  Any company can benefit from internalizing Weinberg’s chapter on refining their sales story, which places the focus of the sales process around the prospect and what issues you can solve for them.  As Weinberg bluntly puts it: no issues = no sale.

In short, people won’t bang down your door to buy neat things with cool features…they will if you are offering real solutions to their problems.

So many companies have never thought of why their clients buy from them, but this is absolutely key to understand, as this should guide you in how you sell to new customers.

Subtle Tweaks to Cold Calling (Sorry…Proactive Telephone Calling)

I loved Weinberg’s framework for making (as he refers to them) proactive telephone calls.  This is something that so many salespeople struggle with…not only because it’s difficult, but because it is the least-desirable task on the to do list of everyone in sales.

The simple mindset shift that Weinberg proposes makes a huge difference when you are about to pick up the phone to dial for dollars.  Telling yourself that your target customers have problems, and you are offering real business value will make you forget your fear of being hung up on and approach the call with a whole new positive outlook that your prospect will find palpable.

Weinberg also gives some great tactical tips on handling the call that I am definitely throwing in my tool belt.  Many sales reps actually struggle with what to say when the prospect first picks up (the 10% of time you don’t get voicemail!).  Weinberg suggests the line “let me steal a minute” which is only slightly different than “do you have a minute” but doesn’t leave the door open for the prospect to exit stage left.

The other gem was in how the salesperson should introduce themselves.  This is especially important when calling higher ranking executives, and Weinberg suggests using “I head up…” when describing your role with the company.  Even if you are a lowly sales rep, you head up something, right?  Even if all you head up is south-west region business development, it gets their attention and makes them more likely to engage.

It’s funny…some people may think these are tiny points, but for anyone who has done any decent amount of phone prospecting in their careers, they will appreciate how these small techniques can make or break your ability to connect with your prospect.

Premature Presentation Syndrome

I have written before about the problems which stem from skipping the discovery stage with a new prospect during your sales process. Weinberg absolutely hammers this point home in New Sales. Simplified. as he states: “By sales law, a first meeting cannot be a presentation. Ever.”  The book provides a great framework for probing to the heart of your buyer’s motivations which is an absolute must in order to not only get the deal done, but also to be able to utilize your limited time wisely in order to maximize your output.

My personal favourite probing question in the book was: “Along with yourself, who else really cares about this issue?”.  It’s often very awkward trying to figure out if the buyer you are dealing with actually has any authority in making a deal happen, so asking this non-intrusive question would be a great way to find out (while not looking like you want to go around them or over their head).

He also provides a useful reminder for overzealous sales reps that like to monopolize sales calls with prospects – we have two ears and one mouth, so use them in that proportion.  Great advice…and I know more than a few fast-talking sales people who could really benefit from taking this to heart!

What’s so funny about this book is that nothing in it is revolutionary, but in today’s sales world, so many people are doing things so wrong that when someone does it right, it’s so obvious and can be such a differentiator.

If you couldn’t tell, I highly recommend New Sales. Simplified. for anyone in B2b sales.





8 Software Demo Mistakes that Scream ‘Rookie’


Software demo mistakes made by startup and early stage technology salespeopleSo you’ve worked your tail off to get a foot in the door with the perfect prospect, and now it’s time to show them your wares.  It’s demo time, baby.

In my experience, most tech companies are pretty bad at doing demos, and I think that to a large extent this is related to the fact that nobody is ever really taught how to do a proper demo.  Add to that the fact that it often involves presenting to a scary group of people you are trying to impress and things can go off the rails quickly.  I’ve seen my fair share of demo train wrecks, and here is what can make them so ugly.  This is my list of 8 software demo mistakes that scream ‘rookie’.

1. Going in blind

This is one of the most obvious signs of a rookie salesperson – you show up for the demo and know nothing about your prospect.  You don’t know how they do their business…you don’t know their processes…you don’t know how many users they have.  You are unprepared.

The discovery process is an absolutely critical aspect not only of delivering a successful demo, but it plays a huge role in the success of the deal itself.  I learned early on in my sales career that if you need to use the word “if” during your demo, you simply don’t know enough about the prospect.  For example:

  • “IF you have X system and ned to integrate with our product”
  • “IF your team sends invoices by email”
  • “IF you plan to provide access to managers”

You need to know the answers to these “ifs” BEFORE you get on the demo, otherwise you run the risk of wasting your prospects’ time showing them things they won’t use and don’t care about.

No matter how detailed your discovery is, however, there will still be the odd point you will need to clarify during the demo, but I use this as an opportunity to engage with the audience.  Asking something like, “So George, I’m about to get into the [blank] area…can I ask how your team handles [blank] today?”.  Sometimes I will even throw a couple of these engaging questions in if the audience has been a little quiet, already knowing the probably answer.  This can also help you gauge the temperature of the audience (especially over a web demo).

2. Junk data

I cringe when I attend a software demo only to see “test, xxxx, demo” or some other fake data throughout the software.  Not only does this make you look lazy and sloppy, it distracts the prospect from the ability to envision how your technology is used by real people in real businesses like theirs.  Businesses who have actual clients with actual names and actual addresses.

Get creative!  Make up realistic names and show that you know their business by having realistic data in your demo system.  I like to even go the extra mile and tailor some of my demo records to the prospect.  For example, if they are a company that operates only in the state of Texas, show them Texas data.  It’s remarkable how unimaginative some people can be, so if you can reduce the level of friction between showing them your solution and them being able to envision how it would work in their business, it can go a long way.

One more thing – do your prospect and yourself a favor and please don’t try to enter a bunch of data during the demo.  The rule of thumb for me is that if there is data entry that it so involved that you need to stop talking, set it up before the demo.  Plus, for some reason my typing seems to go to hell when people are watching me!

3. Show the damn product!

I recently attended a ‘demo’ that was scheduled for 45 minutes, and 35 minutes in the rep was still going through his slides.  I had to stop him and ask if his demo would actually include looking at the software!

It’s absolutely fine to have a few visuals or slides to introduce your product, and I even like to keep a couple on hand to pop up in order to explain some more complex workflows or other concepts that might warrant it, but if you actually have a good product – show it

4. It’s all about you

I put this one as #4 because it is normally seen in the same natural habitat as ‘never-ending slide guy” from #3 – the salesperson who goes on and on about their company until it makes you want to vomit.  “ABC Company was founded in 1999 in Fargo, North Dakota”…”We are listed on the NASDAQ under symbol ABC”…”Our CEO was named to Fargo Businesses Quarterly top 50 over 50 in 2004”…

They. Don’t. Care.

But, the rookie salesperson might say – we need to show them we are a legitimate company and worthy of their business.  There is a much better way to do this than talking ad nauseam about you and your company and wasting your prospects’ time.  The key here is to establish expertise and legitimacy through the questions you ask and by showing you understand their business in the context of what you are demonstrating to them.  Yes, obviously spend a minute telling them about your company – they will ask questions if they really want to dig in, but don’t fool yourself that they want (or need) the whole history.  It’s about them.

5. But…don’t show too much of the damn product

The most powerful demos I’ve seen are the ones in which the presenter takes you on a wonderful journey of what life could be like with their product.  These people who really know what they’re doing (and probably following our power demo process) don’t go rapid-fire through all of the features of the system to try and show you “all the neat stuff” it can do.  They paint a picture of what life would be like if you should have the chance to someday use their amazing product.

Obviously there are cases where a later-stage ‘deep dive’ is necessary to close a deal, but once you get the prospect excited about their future as a user of your product, this becomes less important.

Don’t make the rookie mistake and ‘show up and throw up’ – powerful storytelling will win the day every time over this approach.

6. Avoid the avoidable

Inevitably you will have demos where something just goes wrong – your phone cuts out, the server is slow or you hit a nasty system bug that triggers some kind of unstoppable perspiration in areas you didn’t know could even sweat.  It happens.

The way you can minimize the chances of something disastrous happening is to stay on a planned path and do not deviate.  Whether it be running a report with parameters you have never tried before, taking an unexplored workflow path or upgrading your demo software at the last minute and hoping it works…unpredictability will eventually bite you.

You should know exactly what will happen in your demo system with every click of the mouse.  Also be sure to guard it with your life.  I was notorious for staying on older versions for way longer than my release management team wanted me to because I preferred to err on the side of caution.  Worst case scenario, if a prospect asks about a feature I didn’t have yet in my version, I simply pop into another system to show them the upgraded feature.

<<Check out our Demo Success Checklist!>>

7. Your screen is making me dizzy

I once worked with a sales engineer who, possibly through some kind of nervous tick, would shimmy and vibrate and oscillate his mouse around on the table so aggressively during a demo that is made me want to jump across the boardroom table and smack it out of his hands. Watching a cursor zipping around on the screen aimlessly can be very distracting to the audience.  Similarly, I have seen people scroll so fast down a page that is gives the audience whiplash.

There are three simple things you need to think about when navigating your software demo which will make a huge difference in helping your audience follow along:

  1. Never click on anything unless you explain what you about to do.
  2. Don’t touch your mouse while talking (this is a quick fix for the cursor shakes).
  3. When scrolling, assume the audience wants to read everything you are scrolling through on the page.

Remember, you know your product better than probably anyone in the world – you work with it every day.  It is SO easy for people to get disoriented and lose interest if you are moving too quickly.

8. Wrap it up

Don’t make the rookie mistake of trying to cram as much content into your time slot as you can.  The most important part of your presentation is actually the last ten or fifteen minutes when you aren’t showing anything at all.  This is the magic moment where you have the opportunity to solicit feedback and field questions and is the true gauge of how your demo was received by the audience.

Sometimes you will run into a situation where you get no love at all from the audience at this point.  This doesn’t necessarily mean they hate what you just showed them – sometimes the group dynamics or the fact that everyone is dialing in remotely can play a part in this.  One tactic I tend to use in this situation is purposely creating an awkward silence.  I simply say, “so, what do you think?”…and then shut up.  Simple as that.  This is a tactic that Jeffrey Gitomer talks about in The Sales Bible, which is very powerful, but often very difficult for many salespeople.

Someone is going to break the silence…and as long as it isn’t you, you win.  Yes, I’ve had some pretty awkward pauses in the ballpark of 30-60 seconds (or more!), but I have found it super-effective in getting the audience to give you the straight goods.

Lastly, you need to close off the demo with agreeing on what the next steps are going to be with the prospect.  It might be a presentation to the higher-ups or perhaps a proposal, but setting the stage for the next step in your process is key.  And remember, the information you are gathering during your demo is just as important as the information you are presenting…so ask a lot of questions.

Happy demoing!

Successfully Navigating Technical Buyers

Navigating technical buyers in enterprise and B2B sales

I used to have bad sales habit of not being honest with myself about certain things.  One of the most frequent lies I told myself was, “We might be able to get this deal done with the business and not involve IT at all.”  What I found out by trying this time after time was that successfully navigating technical buyers is crucial to closing any enterprise or B2B sale.

Throughout my entire career, it hasn’t happened once.  Not a single time.  Now, if your product is geared to smaller businesses or is inconsequential to their core operations (e.g. travel expense software or something like that) you might be able to pull it off, but on a real enterprise deal, you’re more likely to see sasquatch wander by the boardroom than circumvent the IT technical buyer.

Be careful however, because often your business buyer will fuel this false belief…not because they actually believe it, simply because they just don’t know any better.  If you haven’t read Strategic Selling by Miller Heiman (first off – read it!), one of the key takeaways which hit me early in my selling career was that the technical buyer is unique, because they can’t say yes, they can only say no.  They are professional gatekeepers.  This gives them a very different type of power over the deal…one that requires specific attention.

This is why in my sales process, I would insist to the business buyer (or the user buyer to use the actual Strategic Selling terminology) that following a successful user demo, the next step is a detailed technical presentation to IT.  You will get push back on this approach.  As I mentioned, sometimes the business people actually believe they don’t need IT involvement, and sometimes frankly they just hate dealing with them so they try to avoid it!

This is where you have a heart to heart with your business buyer and explain that the later you get IT involved in the process (and they will get involved!) the more resistance they will put forth.  And this isn’t good for anyone.  What cemented this approach for me was getting lambasted by a pissed off CIO in a demo in front of 20 people…we won him over and saved that deal, but let my experience be a caution to you.

This IT-focused presentation should attempt to proactively answer all of the questions and issues which might be raised by the IT team.  You know these questions are – just think about the last 5 deals you went through and what questions and objections were raised by IT.

Inserting this into your process actually has four other interesting side-effects:

  1. It gives you the opportunity to personally address the IT objections. Trust me, you don’t want the business buyer taking a proposal to IT and then being forced to answer questions about integration, service level agreements and security.
  1. This also give you another set of contacts to call on should the deal stall and the business team stops returning your calls. I have found a deal coach more than once within the IT team that helped me navigate the business side.
  1. By asking specific questions that your business user wouldn’t be able to answer, you can gain further insight into deal timing, budgeting and other key aspects of the deal. For example, simply asking “what other major IT projects do you have going on right now?” can give you a good indication as to whether the timeline the business team is shooting for is even close to realistic.
  1. The odd time, the technical team might identify a show-stopping technical issue that is best to catch as early as possible in the process. Maybe your product is an on-premises solution and uses a certain database they don’t support…I would rather not waste six months working the deal only to find this out at the eleventh hour!

I know you what you might be thinking at this point – man, these IT people can be a real pain.  Just remember that they have goals and objectives in the organization too (beyond just making your life a living hell).  Part of your job is to find out what these objectives are and how your solution can help them achieve their goals.  Easy, right?  Nobody said tech sales was going to be easy.


Start-up Founders: Lose the Big Shot Title


Startup founders sales titles

As a two-time co-founder of B2B technology companies selling to large enterprise customers, I learned the hard way when it comes to selecting sales titles for startup founders.  From my experience having been on the sales front lines with a big shot title, this does you absolutely no good.

In the first company, I was “Vice President of Business Development” (pretty impressive, huh?) and although I had one or two people helping on sales support, like most early-stage tech companies, I was the one actually doing the sales – calls, demos, negotiations, etc.

In my second business, which focused on the same target market, but was a SaaS product with a lower ticket price, both myself and my co-founder (both of us with a sales focus) chose the title “Account Executive”.  At first this title was somewhat of a joke, paying homage to Bud Fox – Charlie Sheen’s character from the movie Wall Street: “Dad, I’m not a salesman, I’m an Account Executive!”.  What we learned very quickly is by putting our egos aside and printing a rather modest title on our business cards, it paid huge dividends to our business.

Here is what I learned from this experience:

What is this guy doing here?

If you’re selling to mid-level management (which is quite often the case in enterprise deals), they tend to find it odd that a Vice President is taking meetings with them to pitch a product (never mind the times our “CEO” would also be in a demo with me).  This screams to them that you’re a tiny company, and if you are selling larger enterprise products, this often makes the buyer quite wary of doing business with you.

I can’t count the number of time in my first business I was asked: “How many people do you have?”  Let me tell you, when you are an 8-person shop selling to a financial institution with 8,000 people, giving an acceptable answer to this question takes some dancing.  After taking on my lower-level title, I rarely received this question from a prospect – probably twice in 200+ deals.  Not only did the prospects now feel like they were dealing with someone at their own level in our sales process, since my partner and I often worked together they also thought to themselves – well, so far I have seen this company has at least two Account Executives…so they must be a decent sized business!

The sales hot seat…

If you’ve ever seen the movie Fargo, you will recall the hilarious scene where the used car salesman tells the buyer he needs to get approval from his boss to give them a better deal, so he proceeds to go sit in the back and have a coffee while the couple waits.  Giving yourself a less impressive title gives you a huge advantage not only during your sales and negotiation processes, but in every aspect of your business when it comes to dealing with customers.

Back in my first company, you can picture the situation – myself (the big shot VP) and the CEO are sitting in a room with the prospective client and they say: “We need a better deal…can you do [fill in the blank]?”.  We were stuck.  We had no option of telling them we needed to “talk to the boss” or “get management approval”…the buck stopped with us!

Needless to say, we got pretty good at doing on the spot calculations in our head, but this is not the way you want to run your business.  Especially with more complex deals, you need time to plan your negotiations and be strategic.  Looking back, we made some real mistakes in a few pressure-packed situations.

In the second company, when I was asked by a prospect for a deal…guess what?  I am only an Account Executive pal – “I will see what I can do!”

Not only that, because I was working at their level, I would be able to fight for them to my management.  This is a very powerful tool to have in your toolbelt – the ability to be able to limit your authority.  In a situation where the negotiations get heated, you can even use the man behind the curtain as a bit of a scapegoat.

“Joe, I’m telling you…12% off the standard license is all I can do.  I asked management for more and I basically got laughed out of the sales meeting”.

This isn’t a sleazy sales tactic, and I wasn’t lying when I said I needed to discuss this with my management team – I absolutely did.  The advantage here is that I allowed myself the ability to be deliberate with my process and carry on a more strategic negotiation.

Going up the Ladder

On larger, more strategic deals with more high-level approval involved, it’s sometimes necessary to pull rank on your prospect – essentially engage with their superiors to get the deal done.  If you are parading around as the CEO or VP dealing with their middle managers…good luck.  You have played all of your cards at this point and it can be kind of awkward when you ask to get their boss involved in the process (Read: can I speak with someone here who actually has authority?)

As Account Executives, we regularly pulled the like-rank selling card and insisted that because the deal was so important to us, our chief wanted the opportunity to speak with their chief.  In practice, we typically had one of our senior advisors make this call (I wouldn’t recommend just masking your voice and coming up with a fake name!)  This phone call usually took the format of, “Hi chief, this is the chief of the company selling you something…we are really excited at the opportunity to work with your company, so I wanted to make myself available in case you had any questions from your level that I can assist with”.  This is a great tactic discussed in another great sales book I highly recommend: New Sales. Simplified. by Mike Weinberg.

That’s it.  If the person on your end dealing with the lower-level team makes this kind of call, you look like a weasel…going over their headsusurping their authority…how dare you!?  If your senior executive is the one to reach out, that’s just standard protocol.

I know at first it might be hard to digest taking on a less elegant title in your business, but trust me, it pays off.  I did field a few questions from friends who saw that on my LinkedIn I went from VP to a lowly Account Executive…but in the end, closing a ton of deals and rapidly scaling our business up made it all worthwhile.