The Bug-out Bag of a Sales Professional

I believe in being prepared. Not ‘bunker in the backyard with 25,000 rounds of ammunition’ prepared, but…Boy Scout level prepared. The kind of prepared that anticipates both likely and potential scenarios and has a plan for each. The kind of prepared that involves knowing how to do stuff and having the right tool for the job.

A fundamental component of preparedness theory is the concept of a “bug-out bag.”

A bug-out bag is a portable kit at the ready that can be grabbed if one has to bug-out, or leave quickly. Potential scenarios include earthquakes, forest fires, or even social unrest triggered by the impending end of Game of Thrones. But not zombies. There are no zombies coming. I’m reasonably certain about that.

A bug-out bag contains enough food, gear and clothing to support you and your family for a few days in the event that you need to leave your home with little warning. Recommended items include a first-aid kit, flashlights, necessary medicines, water, packaged food, copies of important papers, warm clothing, toiletries, etc.

This is not a fringe concept supported only by camouflage draped survivalists with a strange penchant for machetes.

This is basic good planning. The American Red Cross recommends and sells them. I have one packed and ready in my garage.

Which brings me to my work bag. I treat the bag that I bring to presentations and meetings as my professional bug-out bag, containing all of the gear that I may or may not require to conduct or support a successful meeting with my team or to deliver a talk to an audience.

Everything I may need is always in this bag.

I take nothing out of it unless I’m using it. I have 100% confidence that when I grab this bag to head to the airport or drive to a meeting, what I need will be in there.

I also have a backup of a lot of these items in my office, car or other bags so that I never have to pull something out of my core work bag.

Here is a list of the items in my bag, which is a Briggs & Riley Relay Convertible Brief. I like this bag because it is clean and professional but can serve as a backpack when needed with straps that stow in the back padding. It also travels nicely when set on top of my rolling luggage and moves easily through an airplane aisle.

  1. Video dongles. Both HDMI and SVGA. Not having a dongle is unacceptable. Period. Apple makes a Mini Display Port to VGA adapter, but for some reason they don’t make one to HDMI so you need to get an aftermarket adapter for HDMI like this one from Belkin. I don’t know what people with Windows machines do, presumably something involving string.
  2. Slide advancer. These make for a much smoother and professional presentation than hunching over a laptop to advance a slide. I like the Logitech R400.
  3. Dry-erase markers. My good friend and colleague Jon Ott turned me on to this idea and it’s genius. Whiteboarding is a critical skill, and meeting room dry-erase markers are notoriously unreliable – dry and faded. Bring your own.
  4. Portable Bluetooth speaker. Video is a great tool in presentations, ensure you’re able to provide your own amplification. The JBL Flip 2 is a good size and less than $100.
  5. Laptop. I have two laptops, a souped-up MacBook Pro in my office and a MacBook Air that I use for travel. The MacBook Air is lighter and slimmer. I keep everything synchronized between the two with programs like DropboxBox and iCloud so it’s easy to move back and forth from one system to the other and not lose work.
  6. Chargers. Phone, tablet, laptop – especially laptop. Plug in your laptop when presenting so the display doesn’t power down, unless you’ve changed your energy settings properly. And you probably haven’t, even if you think you did.
  7. Phone/audio headphones. It’s difficult to move through an airport and hold a phone to your ear at the same time. I have multiple sets of the standard Apple EarPods (some pilfered from my children) and keep them (and all my cords) bound with Nite-Ize cord ties so they don’t get tangled. I also have a pair of Klipsch in-ear headphones that are noise canceling and can be used for phone calls.
  8. Notebook. Don’t take notes typing on a laptop. It’s distracting and potentially disrespectful. Use a regular notebook. Moleskine notebooks are timeless.
  9. Pens. Good ones. Have extra in case someone in your meeting needs a spare. Sharing is nice.
  10. Business cards. You’re a professional. Always have business cards.
  11. Toothpicks. Minor in the grand scheme of things but very important when you need them. Nobody wants to watch a presenter with food in his or her teeth. Whole Foods carries these great Tea Tree Therapy mint toothpicks.
  12. Tissues. No explanation required.
  13. Meal replacement bars. Sometimes we don’t have time to eat – have a backup plan. I personally like Clif bars – they’re resilient, avoid getting horribly smushed in a crowded bag and are substantial enough to cover a skipped breakfast. I keep two in my bag and am happy about it at least once a week.
  14. Personal stationary. Handwritten thank you notes are a professional courtesy that is worthy of the time and effort. Have personal stationary in your bag so you can send a quick follow-up letter to the people with whom you’ve met. Have some stamps, too.
  15. Non-work book. Not everything in life is about work. Take advantage of airplane time or unexpected downtime by reading something that has nothing to do with work. Here’s an amusing piece from The Awl on how to read more.

What do you keep in your bag that I may have missed? Please share your thoughts in the comments section below. If you enjoyed the post, please share it with your network and click the ‘Like’ icon to let me know.

Ethan Zoubek is Regional Vice President of Sales at Krux Digital, an advisor and speaker, and author of the Self-Aware Sales blog.

When and How to Present a Proposal – Six Rules

Just because you’re asked for it doesn’t mean you should provide it – yet. And when you do, it should inspire.

(Part 2 of 3)

Irony abounds. Sales professionals tend to hedge and delay when asked the “how much does it cost” question as we reviewed in Part 1 of this series, but we’re quick to scramble to put together a proposal almost as soon as a prospective customer asks.

We should do the opposite.

As with jumping to the “how much does it cost” question, it makes sense that prospective customers are quick to ask for a proposal. It’s a clear, easy, concrete request to make and most buyers haven’t been trained in how to evaluate and purchase something. Asking for a proposal after an initial discussion is a simple and seemingly logical thing to do.

When to Deliver a Proposal

A formal proposal is one of the LAST things we should provide to a prospective customer. It must be complete and clear, and there’s no way that we can deliver such a proposal early in the sales cycle.

A formal proposal is one of the LAST things we should provide to a prospective customer.

Sales professionals should be constantly summarizing and feeding back to their buyer their understanding of the situation – requirements, objectives, timing, pricing parameters, etc. This can be done in emails after calls or meetings, in formal summary of understanding documents, or in ‘what we’ve heard’ sessions at the beginnings of presentations.

The important thing is to make no assumptions and continually validate – and challenge when necessary – the understanding of your buyer to ensure you and s/he are talking about the same thing and working collaboratively toward the same goals. No guessing, no speculating.

It is only at the end of comprehensive discovery and differentiation activities when you’ve received indication that you’re a viable vendor or even a finalist that a formal proposal should be delivered – though you’ve been doing the work to prepare it all along.

Then you do so with incredible thoughtfulness and care.

How to Think About a Proposal

Proposals are ambassadors. An ambassador is the highest ranking official representative a government can place in a foreign country. They are charged with representing policy, negotiating agreements and protecting their citizens within a host country. It is a position of tremendous gravity, honor and prestige.

Our proposal must serve as our ambassador within the buying organization, speaking for us when we’re not there

Our proposal must serve as our ambassador within the buying organization, speaking for us when we’re not there and communicating to decision makers with whom we’ll never meet, like the CFO approving the spend or the purchasing committee reviewing a requisition request.

For this reason, a proposal is perhaps the most important document that you can prepare throughout the sales cycle.

More often than not, the proposals that are delivered to customers are repurposed pieces of crap that are unreadable

But what happens? More often than not, the proposals that are delivered to customers are repurposed pieces of crap that are unreadable. Sales reps do a find/replace on company name, update a pricing table, and deliver the same voluminous nonsense that they deliver to every other prospect. Nonsense that they in all likelihood have never read.

It’s amateurish and disrespectful, and it should not be allowed to continue in any sales organization.

Six Rules of Good Proposals

Proposal Rule #1 – No Surprises

A proposal should be a formal summation of an understanding that you and your buyer have already established. There should be no surprises at all. Pricing should have already been reviewed in another format, important commercial terms discussed ahead of time, and delivery schedules considered as part of an engagement planning process.

The only thing your buyer should be surprised by is how clean, accurate, thoughtful and gorgeous your proposal is

The only thing your buyer should be surprised by is how clean, accurate, thoughtful and gorgeous it is, because they have been trained by lesser sales professionals to expect uninspiring proposals as the norm. They should be surprised by how inspired they feel reviewing yours.

Proposal Rule #2 – Decision Makers Don’t Read

You barely read the material that your own company produces – why should you expect a senior executive at your prospective customer to do something you yourself can’t be troubled to do?

Make your proposals clean and readable. Lots of white space, lots of crisp bullet points. Stick to the facts and make the document easily able to be skimmed. Strike large blocks of text and complicated graphics that you pilfered from some product team’s PowerPoint. If it doesn’t add clarity, it takes away. Get rid of it. If you must, place expansive detail in the back of the proposal in an appendix section.

Assume that the CFO at your prospective customer has the attention span of a 15 year-old boy sitting in class on a Friday afternoon

Assume that the CFO at your prospective customer has the attention span of a 15 year-old boy sitting in class on a Friday afternoon and you’ll be just about right. Structure your proposals for them.

Proposal Rule #3 – Show the Math

You’re asking your buyer to spend their money on this project instead of another, and with you instead of somebody else. Do them the courtesy of showing the math to support why that’s a good idea. It’s hard to argue with math. It’s math. Outline a clear and concise business case – what you expect your solution to deliver, over what period of time, in real dollars – either savings, revenue growth or both. Try for both.

Always, always, always include some sort of business case that shows the outcome of what you’ll deliver in real dollars

Always, always, always include some sort of business case that shows the outcome of what you’ll deliver in real dollars. This is table stakes. This is not optional.

Then make sure that your pricing explanation doesn’t require an accounting degree to decipher. See rule #2.

Proposal Rule #4 – It Must End

Please, I beg of you, include an expiration date. Anytime you deliver a summary of pricing, put an expiration date. Every quote you send, every time. And especially in your proposal.

I beg of you, include an expiration date

You know from your Engagement Plan by when your buyer needs to make a decision and complete all paperwork and signatures to meet their desired outcome – so put it in there. That’s the expiration date. It helps you, it helps them, it helps everybody.

Proposal Rule #5 – Make it Beautiful

While there is absolutely no empirical data to support this, we will assume for the sake of this discussion that all ambassadors are so strikingly handsome and gorgeous so as to make one’s heart skip a beat. So too should your proposal be. These are not to be white papers, they are to be compelling messages of premium value and extraordinary experience.

Convince your marketing organization to lend you a designer

Convince your marketing organization to lend you a designer and then spend time with them on layout, fonts, imagery and readability. You’ve trimmed most of the junk already by making the content readable and clear, your designer should be able to turn back to you a proposal layout that’s more engaging than anything your sales organization has produced…ever.

Proposal Rule #6 – Make it Repeatable

You can’t keep that designer forever, and sales professionals need to be self-sufficient, so ensure that all of this work is done with an eye towards repeatability and scalability. There are a number of ways to do this.

I like using PowerPoint as opposed to MS Word. Word demands that users possess an advanced degree in ‘How to Format Stuff Without Losing Your Patience and Smashing Your Laptop to Bits.” It also invites verbosity. PowerPoint is much easier for layout changes and the nature of it forces lots of great whitespace. An easy Page Setup change and – voila – you’ve got yourself a portrait oriented document that’s facing the “right” direction for a proposal.

Upload into Google Slides, fix some formatting, and now you’re cooking with a document on which your team can collaborate, copy and share. You’ve got an artifact in which best practices, positioning and content can be shared throughout your sales organization.

Extra credit to those who print, bind and hand deliver their gorgeous proposals to the buyer in creative ways

Reminder: always print to PDF – don’t deliver a proposal in its native format. Extra credit to those who print, bind and hand deliver their gorgeous proposals to the buyer. With some chocolates. Or tchotchkes relevant to their business. Something. Anything. Set yourself apart and show that you cared enough to take the time to do something special and different. Pressing ‘send’ on an email with an attachment isn’t doing something special and different.

A great alternative is to subscribe to a SaaS service that automates this process for you. One of the best companies for this is TinderBox and it provides sales automation tools for everything from presenting through proposals contracts in a platform that integrates directly with your instance.

If Nothing Changes, Nothing Changes

Regardless of the tool or service you use, commit to treating your proposals with the respect they deserve. You and your teams work too hard during the sales cycle and spend too much energy crafting a compelling value proposition to diminish that effort so badly with a sub-standard proposal. A little care and attention with this critical deliverable can make a world of difference.

How to Handle the “How Much Does It Cost” Question – Part 1

It’s a fair question. “It depends” is not a fair answer.

Interested is seeing a sales professional stumble and squirm for a bit? Ask them how much what they’re selling costs.

Anyone outside of the selling profession can be forgiven for thinking that talking about price would be one of the first things we learn as sales professionals. After all, the concept of pricing and cost is one of the most central and fundamental components of a business transaction. Trading money for something is the quintessential representation of a value exchange.

Those of us who make our living selling know that it’s not that easy.


We’re taught how to  dodge the question by well-meaning sales leaders.

No one really teaches sales professionals how to handle the question. What we’re taught is how to dodge the question by well-meaning sales leaders who tell us that we should defer the question until later in the sales cycle. That we should be selling on value. That we’re to understand the budget of the buyer first. That we’re not supposed to show our cards too early.

Those positions aren’t inherently wrong. They just don’t answer the question. And it’s a fair question. Prospective customers have a right to ask their salesperson what a solution costs, and we have a responsibility to give them a clear and direct answer.

We have a responsibility to give prospective customers a clear and direct answer.

For anything that’s not a fixed good with a readily quoted unit cost (professional services, enterprise software, consulting, etc.) the pricing tends to be variable and that’s part of what makes it difficult to provide an answer early in the sales cycle.

Most customers haven’t been trained in how to evaluate and purchase something.

Most customers haven’t been trained in how to evaluate and purchase something, and they may only do it a few times in their careers. As professional sellers, who do this all day, every day, it’s our job to help them frame their thinking around “price” or “cost” in a manner that will allow them to make the most informed decision.

What something costs is one factor among many in a purchase consideration. For less sophisticated buyers, however, price is the most concrete factor and the most logical to which they can go, which is why they ask about pricing so quickly. Even more sophisticated buyers can press the price question early. It’s easier.

“It depends…” are the two words that most commonly tumble out of a salesperson’s mouth when asked about price.

We know that early in the cycle we don’t have enough information to provide an accurate price – the prospect isn’t clear on their requirements, there’s more for everyone to learn, etc. This is why “it depends…” are the two words that most commonly tumble out of a salesperson’s mouth when they’re asked about price. We then proceed to explain, using far too many words, why we can’t actually give them a price. But that doesn’t answer the question and it frustrates the buyer.

Provide a framework with your response.

Here’s how to answer the question.

Provide a framework first – this gives your prospective customer a sense of what goes into your pricing and why you structure it the way that you do. Don’t just give a number. Explain to them the components of your pricing. What they’re asking for (the price) isn’t what they actually want to hear (which is how you’ll help them determine value to their organization.) The framework gives structure to the how you’ll help them determine that value.

For example, if you sell enterprise SaaS software, this is sample framework:

There are three components to our pricing model – annual subscription, utilization, and professional services.

  1. The annual software subscription is the cost for accessing the core platform that we’ve had in market for years and continue to enhance and improve.
  2. The utilization is a variable component based upon how much you plan on using, and this is different for every customer. (Note: ideally this utilization is based on whatever the value metric is – users, storage, messaging volume, API calls, etc.)
  3. Professional services costs are based upon real human beings doing work to help implement the software and train you on its use and are scoped with you as part of the project planning.

So that’s it – we price on those three things: annual subscription, utilization, and professional services.

Our average selling price when you combine all three of those components is about $300,000. Lots of things impact that, which is why we always setup a discovery and strategy session with your team to help map out a path and plan. We’d like to do that once we both have a sense that there’s a good fit between what you need and what we do. That session will allow us to provide you with a thoughtful and accurate proposal, which will be based upon the value you’ll receive as a business across those three components.

Then stop talking. Please. Stop. Talking. Let them process what you’ve just told them.

This framework gives the prospect’s brain what it wants.

What have we accomplished? We’ve given a structure to our pricing model that the customer can consider. We’ve given them buckets into which they can place their assumptions and ideas to organize their thinking. The human brain likes to organize into groups (for example, grouping everything our eyes see into semantic neighborhoods.) This framework gives the prospect’s brain what it wants.

We’ve structured what we deliver into three discrete functions instead of one monolithic block, which allows us the opportunity to articulate not just a general value statement, but specific instances of value in each of those areas.

We’ve also established some qualification criteria – for both us and the prospect. If they hem and haw all over the $300,000 number, then we know something is off – either there’s total misalignment, we’re talking to the wrong level of buyer, something. But we now know that we have work to do, and we know that early in the cycle.

It also helps the buyer understand where this kind of purchase fits into their budgeting cycle, levels of approvals that will be required, etc. It establishes a baseline so we and the prospect can work together to craft an engagement plan to guide the evaluation. 

It doesn’t really matter what you’re selling or what the pricing structure is – always provide a clear and consistent framework.

There are infinite variations and ‘what if’s’ that come up with the question of positioning price, but I contend that it doesn’t really matter what you’re selling or what the pricing structure is – the method of providing a clear and consistent framework allows you to help educate the buyer with how to think about your solution and it puts your initial, general price figure in some context. Use a framework, pick the right three things to be in the framework, and then answer the question by introducing the framework.

Without context a number is just a number. Maybe too high, occasionally too low, never just right – so spend your energy on articulating the framework, not equivocating on a number.

A structured response should roll off the tongue of every sales professional in your organization.

Practice this with your team and colleagues. A structured response should roll off the tongue of every sales professional in your organization. You and your teams should feel empowered to answer this perfectly appropriate question early in the cycle – because it will be asked early in the cycle – and to answer with clarity and conviction. Doing so is a signal of professional competence that your prospects will appreciate it and it will be a point of differentiation from your competitors.

This post is the first in a series of three on the subject of discussing price and cost in selling situations. The next two topics are “When to Present a Proposal” and “How to Frame Your Price Negotiations.

Treat Sales Presentations Like Performances

You will see a dramatic improvement in the delivery of your sales presentations with the application of techniques from public speaking and dramatic acting. Sales professionals that want to deliver killer presentations would be wise to consider pressing their comfort zones a bit and exploring new ways to structure and prepare for these engagements.

The shift is to approach presentations like performances and I’ve been fortunate to learn from two of the most recognized leaders in the discipline of effective public speaking.

The first is master coach Bill Hoogterp, founder of Own The Room in Montclair, NJ. I spent two months working with Bill and his senior team and had a chance to observe and participate in a number of day-long coaching sessions with their corporate clients. Own The Room boasts an incredible roster of repeat customers including the likes of Facebook, LinkedIn, Siemens and Twitter and the impact that their coaches have in the span of eight hours on individual speaking skills and executive presence is nothing short of remarkable.

The second experience was with the legendary Michael Port, renowned actor, speaker, trainer and author of the recently published Steal the Show. At the suggestion of my friend Jay Baer – a world class speaker in his own right – I attended Michael’s three-day Heroic Public Speaking workshop in Ft. Lauderdale with more than 300 other individuals and professional speakers determined to sharpen the saw and improve how they communicate their message to the world.

The idea of approaching speaking engagements (and by extension, sales presentations) as performances is one of the core concepts put forth by Michael Port. It’s a little uncomfortable. It’s a little weird. But the fact of the matter is that the most effective and compelling sales presentations are disciplined and thoughtfully planned performances.

The most effective and compelling sales presentations are disciplined and thoughtfully planned performances.

Sales presentations are often the culmination of long, diligent sales processes in which great care is taken to uncover customer needs, align solutions, and craft a narrative that will tell a compelling story of delivering business value.

When it comes to show time, however, too often sales professionals just dust-off their most recent PowerPoint, change some logos and copy, and deliver their routine. The difference between “ehh, it was OK” and “wow – that was really something” is the degree of rigor, care and precision that is taken with the preparation, the content, and the delivery. In short – how much it is treated like a performance.

As you approach your next big sales presentation, here are some key tips and performance concepts to consider:


The camera is the best coach. – Bill Hoogterp

Do the work. You’re not as good at winging it as you think you are, so practice and rehearse. With other people. Collaboration is incredibly important and constructive feedback is a gift – so ask for it. There is always something to improve, press your colleagues to tell you what it is.

You play like you practice. When preparing, try to replicate the conditions of your delivery. Role play like it’s live and don’t break character. If you blank on your delivery, stay with the audience and keep pressing forward, even when practicing.

Prepare thoroughly. People expect you to be incredibly prepared. When you’re letting it go and letting it come to you at the same time – people can tell. The space for that to occur can only be created with practice and preparation.

Rehearse. Presenters tend to push back on rehearsal. They think that it will make them stiff and the delivery feel staged. They’re right – when one tries only a little bit of rehearsal, that’s what happens. When you rehearse enough, though, you can step on the stage or into the meeting space and let it all go and be there in the moment. It will not feel staged; it will feel inspired.

Do it on camera. The best way to identify areas to improve is to take out your iPhone and film yourself delivering the material, little bits at a time. The camera is the best coach – there’s no place to hide.


Performance isn’t fake. Performance is authentic behavior in a manufactured environment. – Michael Port

Be clear in your objective and go there. Know what you’re going after and push through, that’s what moves a performance forward – the authentic pursuit. The audience wants to take the journey with you whether they’re conscious of it or not, even in a pitch meeting. They want to see the objective reached because they know that there’s something in it for them too.

Utilize the three act structure. Exposition, conflict, resolution. It’s been around for thousands of years for a reason. Let it be your guide.

Frame it out. First work out the following, then start creating your content:

  1. The big idea
  2. The promise of what they can expect
  3. How to convey that you understand the way the world looks to the people in the room
  4. How to articulate the consequences of not taking action
  5. How to demonstrate the rewards of achieving the promise 

People don’t buy ideas, they buy protocols. They want a very specific process that has a beginning, middle and end; if your audience can see where it goes then they can see the delivery on your promise.


Most people coast on talent. They never really go out and learn advanced techniques. – Bill Hoogterp

Be aware of filters. Your job is to get through to the audience. Everyone has filters that block the information coming at them; your job as a presenter is to get the filters down so your message can get through to them and help them see a new way of doing things.

Start differently. Almost everyone starts their presentation with “Hi my name is X from Y, it’s great to be here at Z and I really appreciate you taking the time today…” Don’t ever do that again. It sends the filters flying up. Open with a (short) story, an insightful question – something, anything other than what everyone else does.

Engage the audience. Use people’s names to keep them engaged or draw them back in if you see that their filters are up. Eye contact helps you connect with people, but lock eyes for a few seconds so you actually make that connection, otherwise you’re just skimming faces.

Give yourself some space in which to operate. Use the space you’re given – it’s your stage. Lean in to your message, and propel key points forward with forward motion. Stay off your heels – you’ll end up leaning back which weakens your position and makes you look unsure and amateurish. Stagger your feet a little, which will keep you from rocking side to side.

Punctuate with your voice and movement. There is no punctuation when speaking – you need to use the inflection of your voice and the movement of your hands and body to provide structure and contrast. Harmonize the movement of your hands and your body with your content.

If you care more about being in service than being impressive than you can do this. – Michael Port

There are scores of other tips and tricks that you can employ to up-level the quality of your presentation. I encourage you to seek them out and try them. Experiment.

The important thing is to accept that you can always improve and that a new perspective, a new approach, is often the way that improvement is shepherded in. The job of selling is, above all else, a job of communicating, of identifying obstacles to understanding and removing them, of seeing paths to clarity and illuminating them. Your performance is the story of that journey, and it deserves to be done well.

Break a leg.

Please share your thoughts in the comments section below. If you enjoyed the post, please click the ‘Like’ icon below to let me know and share with your friends and colleagues.

The Most Important Sales KPI Isn’t A Sales Figure

(As originally posted on OpenView Labs)

Sales is primarily viewed as a numbers game, so it’s common for sales professionals to take a step back and ask “of all of these numbers that I’ve got in front of me – and holy mackerel there are a ton of numbers in front of me – which ones are the most important?”

The answers that most frequently come back are informed and appropriate considerations of metrics like lead flow, pipeline size/ratio, deal velocity, weighted pipeline average, conversion rate, etc. Those are all important, and while some are leading and others lagging, they are all good indicators of the health of the business.

In my opinion, however, the most important KPI relates to the proportion of time dedicated to enablement and training.

There are 21.75 workdays per month on average. At minimum, each person in the sales organization should dedicate one day per month to enablement. One full and focused day. Minimum. That’s less than 5% of their time.

Why is this so important? In sales, many times it’s a game of inches. The product sets of competing solutions are generally on par or they wouldn’t be in an evaluation. Pricing tends to settle into the same general area absent incredible skill at value creation that truly supports premium pricing. Delivery approaches and promises of timing to delivery don’t tend to vary widely.

How can a professional selling organization differentiate then, when all other things are created equal – and beyond our control anyway? I was given the answer by a mentor and sales leader of mine many years ago.

Sales execution. 

We differentiate with our sales execution. And the only way to continually impact sales execution is to foster a culture where training is valued and enablement opportunities seized wherever possible. Otherwise, reps fall back on habit, muscle memory and path-of-least-resistance.

Assume that an enterprise sales rep has a fully-loaded cost of $175,000. A 5% time investment can be equated to a cost of $8,750 per year. If that 5% of time investment in training nets a 10% increase in booked business – either by way of higher close rates or increased deal size, the impact is substantial.

On a $2M annual target that’s an additional $200k in bookings a year.

That’s material, and that’s a compelling return of $200,000 on $8,750 invested – more that a 20x return on money. I’ll do that all day long. All. Day. Long.

How do we accomplish this? We simply choose to make the time. We play the long game rather than lament taking our reps out of the field for a couple of days per month.

We support a culture where learning is valued, preparation is expected, and moving out of comfort-zones encouraged and applauded.

How else can we expect to get better? Great sales professionals weren’t born that way. They were taught by the mentors and leaders that came before them. They observed, they experimented, they worked at it. They were trained. They were enabled to become the skilled professionals that they are.

Without enablement, all we have a right to expect is more of the same.

My most important responsibility is to ensure that every person with whom I interact is better for the time they spent with me, even if the impact is indiscernible to me. Especially when the impact is indiscernible to me.

With my colleagues and reports – direct and indirect – I can do this by ensuring that they know that taking the time to learn and grow is encouraged and supported, that it’s viewed as an important component of how they spend their professional time. My job isn’t to drive yield – it’s to help my team become better versions of themselves. The rest seems to just take care of itself.

Sales Strategy – There’s No Way That Deal Should Be At 75%

The Importance of Objective Sales Stages

We’ve all been there. We look at a deal in the sales forecast with which we’ve been involved, see that the probability is set to a percentage that corresponds to one of the sales stages setup in our CRM system, and say to ourselves “WHAT?! I know that deal! There’s no way that deal should be at 75%! What is he thinking?” We then pick up the phone or pound out an email to the sales rep and/or his manager and ask for an explanation.

The response that we get is… sort of not terrible. When we listen to the explanation we understand how the rep could make a case for the later stage. We can see how they might feel that it’s further along than we believe it to be. We listen to the rationalization and it passes a loose sniff test. The logic may be a little flimsy, but we can see where they’re coming from. But here’s the problem:

 Sales Stages Are Not About How We Feel

There are two ways to structure sales or opportunity stages in our sales process: 1) based upon what our reps think the close probability is, or 2) where the deal is in the sales cycle based upon objective measures – upon what’s actually happened.

The first way is the wrong way. End of discussion.

Sales reps are, almost as if it were a law of the universe, prone to hearing what they want to hear and destined – absent any structure and discipline imposed by sales leadership – to think a deal is further along than it actually is. There’s a name for it – Happy Ears

Without a degree of objectivity, forecasting falls into a world where reps and their managers end up thinking “well, this could go either way. We’ve got a 50/50 shot right now. I feel pretty good about it. Lots to do, but it really does feel 50/50. So let’s forecast this at 50%.”

What happens is that we get a TON of deals forecast at 50%. And that throws off our forecast. It reflects the wrong numbers to the rest of the business.

I know this because I did it myself over the years, probably hundreds of times. Even when I knew better. I got too close to a deal and missed my blind spots. I was thinking positively because I wanted to hit my numbers. I became friendly with the project sponsor and trusted that it would get done even though I really had no idea of what their legal review process was or how long it would take.

Whatever the reason – left to our own interpretive devices, we become optimistic and over-confident and we start to feel that a deal is closer than it is. Then the end of the quarter comes, deals start to slip, and everyone is wondering what’s going on.

The Path to Accurate Forecasting – Objective Questions

I operate with a tight set of sales stages that correspond to a percentage probability (with amounts of 0%, 10%, 25%, 50%, 75% and 100%) and I have found, working with other sales leaders and colleagues, that the easiest way to move toward accurate forecasting is to overlay a set of objective qualifiers on top these sales stages. These are binary, black or white questions that must be asked and answered before the sales rep can move the deal to the next stage. Think of each stage as a column, with a clear question at the top. Ask that question to see if it should be moved to the next stage.


For example, an objective qualifier for moving a deal from 25% to 50% would be “has the prospect narrowed the competitive field down to three or fewer vendors and are we one of them?”

If the answer is ‘yes’, it can move. If it’s ‘no’, it stays.

It’s that straightforward. If there aren’t three or fewer vendors remaining, and we’re not one of them, the deal doesn’t advance to the next sales stage. It’s clear, it’s objective, it’s binary, and it is immune to subjective interpretation.

Here’s another example. To move from 50% to 75%, we must be formally advised that we are the selected vendor and we must receive a first round of redlines back from the account. These qualifiers have yes or no answers. Formally selected in writing? Yes – we have the email right here. First round of redlines back? Sure thing – we’ve sent them to our counsel. The deal can be moved forward.

Now, there’s a HUGE amount that happens between moving from 50% (field narrowed to three) and 75% (first turn of redlines.) A huge amount. And that’s the point. Which brings me to…

Why Sales Stages Are So Important – Reason #1

Deals are lost or slip because of things that we have missed. There are always a ton of moving parts. Managing to disciplined sales stages provides a predictable, repeatable system to apply to all deals so that things don’t get missed.

Some reps are great at discovery but start to fall apart during late-stage selling. Others are incredible at understanding the legal cycle and negotiations, but aren’t great at articulating business value early in the cycle. No one is great at everything. It’s natural for people to migrate to their strengths and avoid their weaknesses. No problem, as long as the gaps are covered – and a clear and objective set of sales stages with criteria for each stage helps ensure that a rep and their sales leader can formulate a plan to cover all bases and ask for help where needed.

Why Sales Stages Are So Important – Reason #2

Beyond giving a sales rep and her leadership a means by which to understand deal progression and priorities, the point of sales stages is to enable the business to have visibility into pending transactions so that the business can plan – plan for necessary resources (both human and technical) plan for spending, etc. It allows the professional services organization to forecast headcount requirements and staffing needs. It enables finance to get visibility into things that are critical to run the business, like how much cash can be expected to come in at any given point in time.

It would not be an overstatement to say that the entire functional operation of the business is dependent upon accurate forecasting.

When sales reps understand this – when it’s clearly outlined to them that sales stages aren’t simply a mechanism by which to have their chops busted by their managers, we get more accurate forecasting. Reps start to understand that the forecasting goes beyond them and that doing so accurately helps the business – and most reps genuinely want to help the business.

When you start to apply these objective questions, the organization can look at any deal by stage and know what has or hasn’t happened simply by a function of the stage in which the deal is found. Sales leadership can start to identify falloff points in the process, indicating areas that may be in need of more enablement. What it provides is consistency and predictability, which is the greatest gift a sales leader can bring to their finance and executive team.

What Big Nick Taught Me in High School

When I was a sophomore in high school in the late 80’s, I was in an elective course that had students from all of the upper classes. One of the students in the class was a senior named Nick. Big Nick.

Nick looked like he was 25, weighed about 250 pounds, and had a pretty serious mustache for high school. Nick was broad shouldered and built like a bouncer. He always wore a light brown leather jacket. I knew of him mostly by reputation and by the undeniable physical presence that he brought to the hallways, where people instinctively parted to make room for him. You did not mess with Nick. Nick was a little scary.

During class, only a week or two into the start of the semester, another student was sharing an observation on whatever it was we were discussing and they used a big word. A juicy, twenty-five cent SAT word like ‘effulgent’ or ‘parsimonious.’

I could not, for the life of me, believe what happened next. Nick – the huge, hairy, scary, badass – proceeded to politely interrupt this student and said “Excuse me, I’m not familiar with that word. Could you tell me what it means?”

I almost fell out of my chair. Never in a million years would I have had the stones to do that.

At sixteen I wasn’t even remotely close to having enough confidence and self-respect to admit that I didn’t know what a word meant. In a class. Out loud. With other people. I can barely do it now, at 42.

But Nick did. Nick just straight-up asked. To him, this was no act of courage. It was natural. He didn’t know what something meant, so he asked.

In an instant my impression of Nick changed so dramatically as to have stuck with me for the next twenty-five years. It was the first time I could remember seeing someone so comfortable with who they were that they didn’t have to pretend for anybody.

This does not happen frequently in high school. It doesn’t happen frequently anywhere.

In that moment Nick shifted from being a big scary dude with whom I could never possibly interact to someone who was genuine, someone who told the truth, someone I could trust.

Simply because he was authentic and real.

We Can’t All Be The Smartest Person in the Room

We all fake it sometimes. We all find ourselves in situations where we can either choose to be authentic and say “wait, hold on a second – I’m not entirely sure I’m following you” or we can choose to just nod along and pretend that we know exactly what someone is saying – even if we have no idea what they’re talking about.

Why do we do it? Because we’re afraid of looking stupid. Because we’re afraid of what other people will think of us if we admit that we don’t know something. This fear of being found out, this imposter syndrome, isn’t natural. It’s something we were taught.

Nobody Really Cares

The reality is that the amount of time we spend worrying about what others think of us is directly proportional to precisely how much nobody else cares.

Everyone has got something on their mind, everyone has issues of their own. We walk around thinking that people are watching us, always judging. It’s just not true. We’re too busy thinking about ourselves to spend more than a few seconds thinking about anyone else.

Somewhere along the way we learned that we are to be perfect and infallible from the very start, from the moment we show up. And we’re supposed to know everything when we get there. How could we not be afraid of being found out? So we pretend that we know things we don’t, all to avoid being exposed. It’s exhausting.

There is a cost to this habit of just nodding along. When we pretend that we know what’s going on when we really don’t, two things happen:

  1. We rob ourselves of the opportunity to learn, and
  2. We rob others of the chance to know who we truly are.

A small authentic act of being genuine, unpretentious and real is a tremendous thing because it is only in that authenticity that we are able to feel a sense of connection with others.

Choose Authenticity

Pretending to know something you don’t, pretending to be something you’re not – it serves no purpose. Authenticity breeds connection, respect, and admiration. People are naturally drawn to it, and they want to be around authentic, genuine people.

The most fearlessly authentic people that you have known are the ones that attract the most to them in the form of friends, esteem, success and admiration. They are the happiest of people.

My profession is sales. I know for a fact that the most consistently successful salespeople are very genuine and authentic while not being afraid to show up with a point of view and to challenge a customer’s conventional thinking with new ideas and new approaches. They don’t pretend to know things they don’t, they are open to learning, and they maintain a genuine desire to help where they can.

In the executive ranks, the most admired and respected leaders have an authenticity and humility to them – they are the leaders that have legions of employees ready and willing to do whatever they ask, just because they ask. Wielding fear and shame as a tool for motivation can have short-term impact, but it is fleeting and ultimately toxic. It is not leadership, it is tyranny.

In everyday interactions with friends and colleagues, the people who are truly authentic are the ones who everyone seems to like, for no other reason than they feel like true, real people – and we yearn to be close to that because it brings that out in us.

Nick taught me that when you’re honest, genuine and real you can have a deep and meaningful impression on someone, even if you have no idea that you’re doing so.

To practice, start with something simple. The next time you’re in a small-talk situation at a cocktail party and someone makes reference to a topic with which you’re unacquainted, simply acknowledge that you’re not familiar with the subject and ask them to explain. It could be a movie, a current news event, an industry article – doesn’t matter. Just practice. Ask some questions. Then pay attention to how you feel, and how the other person responds to you.

I promise that you will be better for it. You will find it to be freeing, invigorating, and refreshing.

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When and How to Present an Engagement Plan

In last week’s post (Stop Calling it a “Close Plan”) I wrote about the criticality of incorporating into the sales process a mutual plan with the customer. I continued by calling attention to the folly of sales leaders using terms internally (read: Close Plan) and not expecting that some of their troops in the field would, consciously or unconsciously, use those same terms directly with customers. Words matter, and leaders have a responsibility to choose them carefully and deliberately – for their teams repeat what they say.

I recommended as an alternative to Close Plan the term Engagement Plan (Evaluation Plan is another good substitute) and promised that I’d review what I’ve found to be the best approach for presenting and structuring such a plan. I’ve also included a link to download a sample plan layout at the bottom of this post.

When to Present The Plan

When we consider the sales stages with which sales organizations manage a qualified deal cycle, we’ll find a discovery stage at the beginning. This observation is akin to stating that the sun will come up in the morning. Every sales engagement must have as its foundation deep discovery.

Immediately following that is a stage in which we look to establish clear answers to the “why change? why now?” questions. When we know that an evaluation exists, that the customer has agreed that they are going actually do something and they are considering doing it with us – that’s when we present the Engagement Plan.

An Engagement Plan is not a tool to be used at the end of the deal to make sure you get it in for the end of the quarter. It belongs at the beginning, when it can most help.

The intent of this plan is not to help us close the business. It will help us do that, and it will dramatically improve the chances of that happening – and at the highest possible value – but that is not the intent. The intent is to help the customer conduct their evaluation thoroughly and responsibility and to move through their engagement with us in a clear and deliberate manner.

Our Customers Need Help Buying

Our prospective customers don’t know how to buy what we sell. We spend all day, every day thinking about our particular corner of the market and the solution we have been trained on, believe in, and – in some cases – truly love. Our customers do not. They have demanding jobs with requirements that go far beyond just procuring our particular type of product, something they likely do no more frequently than once every few years.

As stewards of our company, our industry and our profession, it is our responsibility to help our customers through this process – independent of whether or not the end result is a sale or order that benefits us. That’s what professional salespeople do.

What to Say

When I have my teams present an Engagement Plan to their prospect, the objective is to help share all of the steps that we know a company must go through to conduct a complete and thorough evaluation to find the right solution to meet their business needs. The words they use are quite literally something like:

“Look – I know that you don’t buy (marketing software / spaceships / combat robot waffle irons) every day. But we do this all the time, and our customers have always found it to be helpful to have us put together an Engagement Plan with them. We’ll include all of the things that typically have to happen for a complete evaluation so you don’t miss anything, and then we’ll go through it with you. That way you’ll have a full checklist with dates, all working back from the day you told me you wanted to have this live and ready. Would you find that to be helpful?”

Many sales executives resist doing this, however, and as a result this incredibly useful tool – a tool that sets clear steps and dates for everyone – goes unutilized. Why? Putting aside those who are simply lazy or undisciplined, some sales executives feel uncomfortable – they fear that the customer will resist this as a tactic designed to get them to buy something. And the customer should resist it – if it’s a tactic designed to get them to buy something. But if the real and true intent behind the presentation of this plan is to help the customer, independent of outcome, then they will welcome it.

Be Conscious of Your Intent

Motive and intent. Motive and intent are the differentiators here. They are the differentiators everywhere. When we approach a situation with an intent that is clean and a motive of helping others, people respond. It is human nature. We are then in a position to help and to be of service. If we are providing the absolute right solution to solve their problem, if we are clear about the value we deliver and the business case that supports it, then an orderly and smooth business transaction is a natural extension of this alignment. When we detach from outcomes, all finds itself in order.

Components of the Plan

Some items to consider when you’re crafting and presenting an Engagement Plan:

  • Include anything that you know most buyers don’t think about, even if it’s not always necessary. An example is a security review by IT. They may not need to do it, but you want to find that out sooner rather than later. This is not a monster under the bed – it won’t go away just because you’re not looking at it. Surface these things as early as you can. Nothing kills the timeline of a deal and gets in the way of the customer getting what they need like an IT security review. See you in six months.
  • Do not make the last item in the plan the signing of the contract – that is self-interested and self-serving. The signing of the contract is the beginning of the next phase for the customer, which can include things like project kickoff, key milestones for the customer, etc.
  • Ensure that, if possible, you review this plan in person. Go through each item, confirm the necessity of its inclusion, validate that the target dates you’ve included are attainable, and note any changes or comments. Then revise the document and send to them.
  • Use the review as an opportunity to ascertain decision making authority, purchasing protocol, approval chains, etc. Remember – this is about helping your customer attain what they need to solve their business problem. A clear understanding of the process helps the customer get what they need in the time they need it, and sales professionals are better than anyone at figuring out that process. If it feels too early in the cycle to dig into those items, don’t – but list them and tell your customer that you’ll come back to them in a future review.
  • Revisit this plan with your customer routinely. Just like an entrepreneur’s business plan, an Engagement Plan is never right the first time. Or the second time. Or the third time.

For a sample layout of an Evaluation Plan, click here to download. This plan is an oversimplification, but provides a general framework for how to structure a plan that will work for you or your team. Tailor the particular line items to reflect the important milestones in your deal process and the important steps for your customer to consider. Remember – the intent is to help your customer conduct the most thorough evaluation they can.

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Stop Calling it a “Close Plan”

The importance of a plan to address the ‘last-mile’ of a sales cycle cannot be overstated. It is critical, especially for large and complex deals, that the sales executive draft and review with their sales leader a detailed plan to earn the business in question. Doing so is how we ensure that things don’t get missed, that the account team is in alignment, that senior executives are clear as to what is required of them to support the deal and that everyone is focused on the most important tasks to reach the desired outcome: closed business that will bring clean revenue to the company and a valuable solution or product to the customer.

Close Plans Are Necessary

Most evolved sales organizations have a process for this. At certain stages in the sales cycle, for deals of certain dollar amounts or strategic importance, sales leadership will require that the sales executive convene a review in which the sales executive presents the plan. Sales leadership will help strategize on tactics and iterate the plan until a final list of action items is determined. Most of the time, this plan is referred to colloquially as a Close Plan.

Invariably, there will be components of this plan that require collaboration with the buyer to do things like:

  • Align incentives “…and to confirm, we’ve agreed to this pricing structure with the understanding that you’ve agreed to take reference calls and sign the contract by the 25th of this month…”
  • Validate steps “…and you’re sure that the procurement director approves and then sends to the CFO for signature…”
  • Confirm dates (“…and we are certain that the CFO isn’t taking a trip to Bora Bora the week that we are planned to have him sign…”

A plan created in a vacuum isn’t a plan – it’s a hope and a dream until we confer with our buyer.

Don’t Call Them Close Plans

So, being fortunate enough to have one of those top deals in the pipeline and recognizing that it’s necessary to consult with our buyer on the items in the plan, we call our buyer and we propose that we sit down together to review our plan.

When this happens, please – for the love of all that is holy, DO NOT REFER TO IT AS A CLOSE PLAN.

To some this may be a statement of the obvious, but I can’t tell you how many times I’ve heard sales professionals and their managers actually state to their prospective customer that they would like to review their Close Plan with them.

But why wouldn’t they? For months or years everyone in their sales organization has talked simply about the Close Plan. After a period of time, muscle memory and habit kick in. If we consistently refer to something as a Close Plan when we’re inside the four walls of our organization, it’s a safe bet that we’ll refer to it as a Close Plan outside those four walls.

Words Matter

The words we choose matter. They convey the motive behind our actions and the intent that we bring to an engagement. When we talk about a Close Plan, we de-humanize our buyer and we diminish the importance of their needs and values in the process. We turn them into an object that is to be conquered, a deal to be won. We turn them into a thing.

Buyers sense this – consciously or unconsciously. They must. The result of choosing our words inelegantly is that we turn what may have been a very collaborative and mutually respectful process up to this point into a tug-of-war that trades on angles and leverage, a zero-sum game with a winner and a loser.

What the buyer hears us say when we use the words Close Plan is “this has been nice up until now, but I’ve got to get to work and close this deal. And that means I’ve got to close you.” It signals to the buyer that the situation has changed and that they must now be on guard against tactics designed to extract as much money from them as efficiently and smoothly as is possible. And we are the person with whom they must be on guard.

This is unfortunate. Most sales professionals genuinely enjoy their work and the opportunity to be of assistance and utility to the customers they serve. Most attempt to be as genuine and authentic as they can. Most work for organizations that legitimately believe in the importance of customer satisfaction and shared success. It is an error of sales culture and a result of bad habit that a couple of irresponsibly chosen words can undermine what are otherwise thoughtful and deliberate efforts to provide genuine value.

Sales Leaders: Lead

Sales leadership bears the bulk of the responsibility for shifting the tone of the sales organization and the words that our teams use, both in the field and in the office. Our people look to us to get direction – both spoken and implied – as to how they are to engage with the market, the competition, our prospects, our customers and our co-workers.

This is encouraging, because it means that in many ways all we have to do to start to engender a more value-driven culture is to choose our words more carefully. This is a discipline that is easily begun and, with practice, develops reliably. It does demand awareness, however. Many of us run-around barely conscious of the words that spew out of our mouths, oblivious to the emotional wake that we leave and the downstream impact of the words we choose. So we must consciously decide to begin.

There are any number of ways to convey the intent of a close plan – mutually agreed upon steps to reach a mutually beneficial outcome – without calling it a Close Plan. If you’re a sales professional, I’d encourage you to share this post with your leadership to initiate a conversation on the subject. If you’re a sales leader, discuss this with some of your managers and sales executives to collaborate on some new terminology that more accurately reflects the type of organization that you want to be.

For the past number of years I’ve favored the term “Engagement Plan” and have required my teams to use it in lieu of “Close Plan.” It maintains the word “plan,” and it’s important to call things what they are as simply as is possible. The term “engagement” conveys a sense of collaboration and forward momentum.

Next week I’ll spend some time reviewing what I’ve found to be the best approach for structuring an Engagement Plan and when to present it to your buyer. Hint: it is NOT at the end of the sales cycle. To make sure you know when it’s published, click here to sign-up to be notified.

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