There Are No Stupid Questions in Selling. Actually, There Are Plenty.

By Sharon Gillenwater

From the time we’re quite young, we’re assured by the adults in our lives that there are no stupid questions.

That may be true when we’re kids – when we need to develop the confidence to ask about what we don’t know; however, the same does not apply to adults working in enterprise sales. Live by that philosophy and you are going to be like the old Maytag repairman – very lonely.

We’re not saying you shouldn’t ask ANY questions. We’re saying you should be aware of the ones that will reveal a lack of preparation. Ask “stupid” questions and you could lose credibility, trust, and, as a result, opportunities.

According to Tom Searcy’s book, How to Close a Deal Like Warren Buffett, America’s greatest dealmaker goes into meetings with “an encyclopedic” level of knowledge about the other party. He doesn’t ask about industry, market, competitors, or advantages because he already knows all about them. He does his pre-meeting homework religiously so he can cut right to a meaty business discussion.

Now consider how you and your team approach a meeting with a new prospect. There are just some questions that shouldn’t be asked – because they show you haven’t done the most basic legwork.

Forbidden questions include:

  • “What does your company do?”
  • “Who are your customers?“
  • “Who is your competition?”
  • “What is your company’s business strategy?”

All of these will be cringe-worthy to a C-Level executive. Why? Because their time is their most precious asset – and they don’t want to waste it talking about things you could have learned from reading a few articles and earnings call transcripts. You should already know all these things before you walk in the door.

Sales-i has designated, “What does your company do?” as among the laziest of questions. As they write, “Anyone can Google a company, look up a contact on LinkedIn and get a general gist of what a company does. It takes 5 minutes, if that. Not only does it allow you to qualify out some companies without even having to lift the receiver, but understanding a little bit about the company you’re about to call will only put you in good stead to divulge exactly where your offering can help.”

But that’s just baseline. Sales pros at the top of their game are not content with doing the bare minimum. Their goal is to demonstrate some knowledge about the company, its competition, its strategic focus and challenges, its current market environment, and how it plans to grow.

Another cringe-worthy question to ask executives is whether they are the decision maker. You should know that already, too. What you should ask instead is, “Who else is involved in the decision making process?” since C-level leaders typically ask for input from subject matter experts and other stakeholders.

Also verboten: Don’t ask if they are in the market for your product or service. What if they have a need they don’t even recognize yet? Your goal is to have a business discussion that helps them understand what’s possible and position yourself to be an expert partner, advisor, and – if all goes well – vendor.

Be careful of mixing budget talk with business talk. While this conversation has to happen eventually, pushing too hard to deliver a proposal could be a turnoff. You want an executive to see you as being a helpful problem solver; let them take the lead on driving toward proposal stage. By the time you reach that point, it should be clear to your customer that what you’re proposing is worth the cost. This approach also keeps your offer from being commoditized in the eyes of the customer – because you have already delivered so much value in the pre-sale phase.

Jeremy King of Element Three has a list of 15 dumb sales questions to avoid that include some of the ones above and some others you should consider:

  • “Is this a good time to chat?”
  • “What level of service are you willing to pay for?”
  • “What will it take to earn your business?”
  • “Who was the best salesperson who ever called on you?”
  • “What do you dislike about your current vendor?”

These questions, he says, invite dismissal. No one wants to talk to a salesperson who is so blatantly self-serving. Buh-bye.

Now let’s talk about smart questions – the ones that show a genuine interest in your customers and a desire to help them achieve their goals. Look back at that paragraph about Warren Buffett and strive to know everything he would insist on knowing. Search for articles about the company and its executives and read the most recent earnings call transcripts. Make a cheat sheet by jotting down the highlights and share it with anyone else from your company who will be in the meeting.

It can make for a deep dive, but the information you collect will help you connect the dots between your customer and how you might be able to help them. You can then use your meeting to explore your hypothesis by asking smart questions.

So, instead of asking who the competition is, you can instead ask about how a recent acquisition announcement by competitor A is impacting their priorities and strategy.

And, instead of asking what their technology investment priorities are, ask if they are concerned that their back office or supply chain technology may be inhibiting growth in specific areas that you know they’re focused on.

The more you know about a potential customer the better you can demonstrate how you can serve those needs. If you have “stupid” questions, get them out of your system by answering them through research before you go anywhere near the customer. Then you can refine your questions and turn them into jumping-off points to more meaningful conversations that lead to strong, long-term relationships and bigger deals.

Sharon Gillenwater is the founder and editor-in-chief of Boardroom Insiders, which maintains an extensive database of the most in-depth executive profiles on the market – from Fortune 500 companies to independent non-profits – to help sales and marketing professionals build deeper relationships and close more deals with clients. Gillenwater is a long-time marketing consultant with expertise in marketing strategy, account-based marketing, and CXO engagement programs.

Compassion Fatigue: It’s Here, It’s Real, and It’s Hurting Your Sales Game

By Karyn Mullins

You’re constantly outsourcing your energy. Every customer and salesperson who needs compassion, you’re always there for them. But filling up their tanks is draining and that can quickly attack your team’s sales numbers.

Believe it or not, this feeling has a name. “Compassion fatigue” is defined as fatigue, emotional distress, or apathy resulting from the constant demands of caring for others or from constant appeals from charities.

Especially in sales management, the strain from being a mentor and sounding board leads to a reduced sense of personal accomplishment, increased stress, and mental exhaustion. And this stress is an epidemic in today’s workplace.

According to a 2017 Udemy report, “Workplace Confidential: The Real Story Behind Stress, Skills, and Success in America,” millennials, Gen Xers, and baby boomers all admitted to having increased stress levels over the past year.

Compassion fatigue is real and it could be putting your sales career in danger. Take a look at how to determine if it’s a problem for you – and learn steps for dealing with it at work.

Why Compassion Fatigue Is a Problem in Sales

As sales managers, it’s your job to lend an empathetic ear to your customers and salespeople. All successful sales managers understand sales isn’t about selling, but rather about relationships. Building those relationships depends on your ability to care about every life aspect a customer is willing to share.

However, caring too much can hurt.

Becoming overly empathetic means you’re feeling customers’ or salespeople’s emotions, experiencing their fears, and relating to their dreams. Becoming overwhelmed with everyone else’s issues and concerns leaves little time to address your own. This distracts from other customers, your team, and, ultimately, your sales goals.

More importantly, it’s easy to lose your sense of self when compassion fatigue hits. You lose that spark, motivation, and goal-oriented attitude that made you a success from the start.

How to Recognize an Issue

Like I said before, sales management jobs require a certain degree of empathy. Without it, you’ll be unable to connect with customers and your team. However, being aware of the signs of compassion fatigue will help you recognize when that compassion has begun affecting you in a negative way.

A few signs are:

  • Decreased focus
  • Lowered cognitive abilities
  • Unusual drop in productivity
  • Emotional intensity especially surrounding work issues
  • Lack of energy
  • Decreased overall well-being
  • Lack of interest

Remember, compassion fatigue isn’t something you wake up with one day. It happens over an extended period of time after offering too much empathy and energy to your customers and team. Simply being aware of the symptoms and taking note of how you’re feeling at the end of each day is a good way to keep yourself in check.

Overcoming without Offending

Sales jobs require you to focus on your own well-being from time to time. If you’re not up to par, it’ll be impossible to strategically plan your sales management goals, give customers the information they need, and, overall, be your sales-powered self.

However, stopping compassion fatigue from hurting your sales career means you’ll need to remove yourself a bit from the empathy role. Not approaching this carefully leads to hurt feelings and dented egos.

Overcoming compassion fatigue starts with self-care and self-management. Take time outside of work or even a few days off to do activities you enjoy. Go for a walk, eat at your favorite restaurant, or meet up with an old friend. No matter what you choose to do, try to disconnect from all work-related activities.

When you come back, practice self-management. Be proactive rather than reactive when it comes to empathizing with customers and team members. Strategically schedule your days so you’re not spending back-to-back calls with the emotionally needy.  

Regain your focus and put time and energy back into selling by creating a step-by-step action plan for helping your team hit your sales goals.

Karyn Mullins is the president at, a job board that gives members access to the most sought-after medical sales jobs and pharmaceutical sales jobs on the Web. Connect with Karyn on Facebook, Twitter, and LinkedIn.

How to Set Prospect Expectations During the Sales Process

By Sam Holzman

Picture this: A sales rep and a prospect begin the last of several meetings in the hopes of making a deal. Everything has gone smoothly so far, and both the sales rep and prospect expect to leave the meeting satisfied. However, when the sales rep gives the final details of the purchase, the prospect has objections. Eventually, they both leave the meeting frustrated and, ultimately, the sale falls through.

So, what went wrong? This scenario is all too common in the sales world – and it boils down to one thing: The sales rep failed to manage the prospect’s expectations throughout the sale process.

Today, we teach you how to avoid this situation with four easy tactics to manage your prospects’ expectations. Keep reading.

Four Tactics to Manage Prospect Expectations

Tactic #1: Establish goals.

Clear goals are the foundation of any sale. They ensure that both the sales rep and the prospect are working toward the same thing. If you fail to establish goals early on, you risk losing the prospect in the later stages of the sales cycle.

Here’s where many sales reps go wrong: They set goals during the first meeting, but fail to check in on them throughout the process. To start, discuss small goals to provide structure to your meetings. How long do you want the process to take? What do you hope to accomplish in each meeting? What are the next steps?

Then move on to bigger goals, like what the prospect hopes to accomplish with your product and what their ideal price point is.

Tactic #2: Be clear about anticipated outcomes.

Case studies and customer testimonials can be effective sales tools. They give prospects specific examples of what your product has done for past buyers. However, these materials showcase the best possible outcome and can often lead to unrealistic expectations during the sales qualification process – leaving your prospect disappointed and confused.

When you walk the prospect through the anticipated outcome, be hopeful but realistic. Don’t promise the best-case scenario just to sign a deal. If you promise results and then fail to deliver, you will lose any potential business with the prospect in the future.

Tactic #3: Work to extract specific answers.

A vague answer like “maybe” might seem harmless during an early conversation. But, down the line, these non-committal responses from prospects may result in deal-breaking problems. Therefore, it’s important that you push for specific answers from your prospects during your discovery calls. This might seem uncomfortable, but it will prevent either side from making incorrect assumptions about the other’s priorities.

For example, let’s say you want to establish a timeline with your prospect. You ask if they will be ready to make a decision on the deal by the end of the month, to which they say “maybe.” You don’t press for more details – and then, at the end of the month, the prospect reveals they still aren’t sure if they’re interested, and the deal drags out indefinitely. Avoid these last-minute roadblocks by getting concrete answers from the prospect early on.

Tactic #4: Get everything on the table.

Sales reps often hesitate to be upfront about important issues for fear of losing important deals. But building trust in sales is important. So be upfront and address potential roadblocks or issues as soon as you recognize them.

Yes, this means you might have to deliver bad news at times. But deal-breaking issues don’t just disappear if you ignore them. When you wait to address them until later in the process, you may have wasted the prospect’s time and your own.

Worst-case scenario: You disclose that your product may not be the best fit – or that it’s more expensive than the prospect’s allocated budget. You lose the deal and shift your attention to more qualified prospects. Best-case scenario? The prospect appreciates your honesty and works with you to overcome any barriers. Either way, you come out on top.

Final Thought: Not Every Prospect Is a Good Fit for You

Sales reps and buyers are rarely on the same page. Here’s a quick example: According to research from Hubspot, 83 percent of sales reps don’t think they’re pushy, yet more than 50 percent of buyers disagree. Using these four tactics, however, sales reps can better manage prospect expectations – leading to a better experience for all parties involved.

And remember: Not every prospect will be a good fit for your products or services. Setting prospect expectations early on can weed out the bad from the good and make your sales conversations more productive. With more productive and honest sales conversations, you’ll generate more deals and more lifelong customers.

Sam Holzman is the content marketing specialist at ZoomInfo, where he writes for their B2B sales and marketing blog. ZoomInfo is a leading B2B contact database that helps organizations accelerate growth and profitability. Visit for more information. 

How to Solve One of the Biggest Problems in Sales

By Chris Beall

Following up with prospects and customers is a staple of sales. Everyone knows they “should” do it. In fact, you could argue that CRM systems exist primarily to support following up, broadly speaking.

Think about it this way. Contemporary CRMs define a “lead” as someone worth a follow-up attempt, to be converted into a “contact” (a person) at an “account” (a company) when that follow-up bears fruitsometimes when a discovery conversation is scheduled or maybe when that conversation discovers there is an “opportunity.” Opportunities are worked through defined stages until they close as wins or losses.

It all sounds very neat and orderly. Interest, followed by contact, followed by discovery, followed by opportunity, followed by closing. A nice, linear process.

The Real Flow of Your Sales Funnel

We call it a “funnel” to recognize inevitable attrition along the way. Then we do “funnel math” to figure out how many leads need to go in the top of the sales funnel to produce the desired flow of closed deals out of the bottom.

The sales funnel metaphor tells us lots of important things. But, unfortunately, it paints a picture that leaves out the most common – and, therefore, the most important – outcome of any sales interaction. The flow of the funnel makes us pay attention to the positive flow: the conversations that end in yes! The shape of the funnel tells us that no is also heard along the way.

The Proper Approach to Your Sales Funnel Math

But what about those other two sales conversation outcomes: “not me” and “not now”? Are they important to our funnel math?

It turns out that a conversation that ends in “not me” can, if handled deftly, yield a referral: a semi-magical lead that has a good chance of being reached and being the right person to talk with. Referrals transform so-so leads into “right parties.”

In terms of funnel math, however, a “not me”  doesn’t really do anything. One “Ray Wrong” becomes one “Rae Right” – nice, but it creates no real change to how many leads must go in the top to make your sales goals.

If the obviously positive “not me” doesn’t affect funnel math much, then it would seem “not now” would do even less. After all, if someone isn’t ready to do business with us now, shouldn’t we boot them out of our funnel and send them back to the marketing department to be nurtured until ready to engage in our sales process?

You see, “not me” is treated like dark matter – that stuff that makes up 60 percent of all the mass in the universe. Dark matter bends space-time so galaxies spin way faster than they should, yet it is invisible to us and our instruments.

In other words, dark matter dominates the shape and velocity of our “funnels” (the Milky Way and all those other galaxies) but doesn’t yield new stars or even a little light to brighten up our dark skies.

Two Problems with Prospects and Timing

Why does the “not now” factor dominate and cause so many salespeople to have conversations with prospects who say they’re not ready to make a purchase right now? There are two factors:

  1. Product replacement cycles tend to be long. When we buy a product (or a service to solve a problem) we usually aren’t looking to replace it for about three years. That means an intrinsically qualified buyer (our dream client) is only in the market for our category of product for one out of every 12 calendar quarters. That means a perfectly executed sales conversation with a perfectly qualified buyer will yield “not now” almost 92 percent of the time. That’s dominance!

  2. There is only one reliable way to find out if the timing is right for the prospective buyer to consider your product category: have a live conversation. Sure, there are vendors who claim they have dark matter detectors that can tell you when buyers are ripe and ready to make a purchase. But none of their techniques based on publicly available – and, therefore, competitively irrelevant – data can compete with a skillfully managed conversation.

So, we have a 92 percent dominant sales factor – timing – that can only be reliably determined by a rather expensive measurement: a conversation. Our standard funnel treats this dominant set of potential opportunities as “disqualified” and sends them back to marketing for nurturing. In other words, they’re thrown away in the vain hope they will come back on their own when they are ready.

But what if we could capture that 92 percent instead of throwing them aside? The effect on our funnel should be massive! This is especially true if we are capturing them, and our fiercest competitor is using the standard “send them to marketing for lead nurturing” program.

It turns out that, by using one simple mechanism, we can do that: by systematically following up “not now” conversations with (wait for it…) conversations! These can certainly be interspersed with the usual email “drip campaign,” (by the way, who named this anyway? Is being dripped on really that great?), but the key is the follow-up conversation itself. An email, no matter how full of compelling content, won’t give you the answer to the question of whether “now” has arrived.

The Benefits of Following Up with Phone Conversations

The good news is that the numbers work strongly in your favor, three ways:

  1. It’s usually easier to get prospects on the phone when making a follow-up call. The “2017 Follow-Up Conversation Study,” which analyzed almost 20 million dials in 2017, found that follow-up dial attempts reach the right party 1.35 times as often as cold dial attempts. This is not because these people are psychic and know it’s their favorite salesperson calling. It’s because follow-up lists consist entirely of people who have answered the phone before. In other words, the first conversation (or cold call) yielded one additional piece of information: this person is more likely than average to answer phone calls.
  2. The same study found it is 1.68 times easier to set a meeting from a follow-up conversation than from a first conversation. The reasons for this are more subtle. First, if the timing is ever going to be better, it will be in the future – and, on a follow-up call,  the future is now! Second, the conversation is easier to get started with rapport, because you can begin where you left off – especially if you wrote your future self a mini-script based on the previous conversation. Third, it is possible that humans are more likely to listen to someone whose voice they have heard before.
  3. The combined effect of harvesting all this “not now” dark matter is that follow-up conversations are 2.26 times more efficient than cold conversations end to end – from the dial attempt through setting the appointment. This is like having your team of 10 sales professionals magically turn into a happy band of 26 without spending a penny.

To summarize, “not now” timing is the dominant problem to be solved in B2B sales. Like dark matter, it makes up the bulk of our sales conversation universe. But, unlike dark matter, it turns out there is a simple way to tame the bad timing problem: systematically follow “not now” conversations with appropriately timed future conversations.

What’s even better: Follow-up conversations are cheaper and easier to get, more pleasant to have, and have much higher yield than first conversations!

In a way, there’s nothing to solving the biggest problem in sales. Here’s the formula:

  1. Use cold conversations to manufacture follow-up opportunities – and some meetings.
  2. Have follow-up conversations to set more meetings or at least to manufacture more follow-up opportunities.

Problem solved. Must be time to go back to figuring out that dark matter thing.

Hear Chris Beall speak at the Sales 3.0 Conference March 12-13 in San Francisco, where he will present “What Every Sales Leader Must Know about the Artificial Intelligence-enabled Salesperson” with Bruce Lewolt, CEO and Co-founder, BrainX and

Chris Beall is CEO of ConnectAndSell. He has been participating in software start-ups as a founder or at a very early stage for most of the past 30 years. His focus has consistently been on creating and taking to market simple products that can be used successfully the first time they are touched, without taking a course or reading a manual. His belief is that the most powerful part of any software system is the human being we inappropriately call a “user,” and that the value key in software is to let the computer do what it does well (go fast without getting bored) in order to free up human potential.

How to Sell to Their Natural Values

By Jim Cathcart

Whether you are leading a sales team or presenting a product, the same fundamental forces are at work. People are persuaded by what they care about…period.

You might argue that holding a gun to someone’s head would work to motivate every person, but that’s not true if they don’t want to stay alive more than they want to cooperate with your demands. It’s the motive, not the motivation, that causes the action. A desire to live equals a  willingness to cooperate to avoid being shot.

The same applies to incentives and rewards. If you offer a vacation in Tahiti to someone who fears air travel, then it might miss the mark. In fact, you could potentially achieve more motivational impact by offering something that has only 10 percent of the financial value of that vacation – if it aligned with their natural values.

A “value” in this sense is: the relative importance of…whatever it is, when compared to other things. The value of a meal versus a magazine subscription, for example. Values come in two types:

  1. Values that are learned and
  2. Values that are natural to you.

A learned value is what you acquire from your parents, schools, churches, and social culture. You learn to be patriotic, a good neighbor, respectful, clean and well groomed, etc. A natural value is something that is innately important to you. Beyond air, food, and water (the survival needs) we tend to be motivated by our natural values. Maslow popularized the needs hierarchy and that’s a useful model, but here we are talking about motivators (values) that transcend Maslow’s model.

There are seven natural values – and all of us care about all seven of them, but not in the same order. My number one might be your number seven and vice versa. Therein lies the secret to motivating you and me. The value is your motive; the motivation is a stimulus to activate it. There is no universal hierarchy of these values because they differ from person to person. Here are the seven:

  • The relative importance of your physical experience: sensuality value
  • The relative importance of feeling connected with others: empathy value
  • The relative importance of tangible wealth: wealth value
  • The relative importance of being in charge, gaining recognition and prestige: power value
  • The relative importance of beauty, balance, symmetry, and organization: aesthetic value
  • The relative importance of doing what is right and having a mission or cause: commitment value
  • The relative importance of learning, discovery, and knowing: knowledge value

For ease of memory, you can use the first letter of each value to form the acronym: SEW PACK. Think of the little sewing kits that are made for travel, and imagine there are seven different colors of thread: Sensuality, Empathy, Wealth, Power, Aesthetics, Commitment and Knowledge.

Motivating with values means learning to observe the values as each person expresses them through their choices, tastes, actions, and priorities – then connecting your incentives, rewards, and appeals to the individual’s priority values. You can see the patterns in people when you know to watch for these values.

If a person places high priority on the feel of clothing over the look or quality of it, they are showing the sensuality value. The person who is more excited about a backstage VIP meet-and-greet than the performance on stage is expressing the power value. One with a high empathy value will be more drawn to spending time with their friends than by a trophy in their honor. The commitment value shows when a person is moved by the cause or “the why” behind an action (for example, when they can see a higher purpose to their work). Profit is a motivator to the wealth value but so is high quality (e.g., an item with great resale or investment value). People who love to learn are expressing the knowledge value. A visually appealing and well-organized presentation will go a long way to impress one with high aesthetic value.

If you sell automobiles, for example, the prestige of the brand and performance will appeal most to the power value. Resale and residual to the wealth value. Comfort and drivability to the sensuality value. Economy and responsible energy use to the commitment value. Looks and system design to the aesthetic value. Understandable and impressive technology to the knowledge value. And the effect or appeal of the vehicle to passengers will be a priority to the empathy value.

This can even guide you in selecting gifts for special occasions or designing incentives for people:

  • Sensuality: a physical experience or something pleasant to the touch or taste.
  • Empathy: an interpersonal experience or something that has meaning to others they care about.
  • Wealth: a valuable item such as a gold coin, insider tips for growing wealth, or a luxury item that will endure.
  • Power: a special experience or privilege. Something others wouldn’t have or be able to do. A position or special recognition.
  • Aesthetics: an item of beauty or an experience that appeals to their visual and auditory sense.
  • Commitment: the ability to make a difference, or a way to show their contribution to something they care about.
  • Knowledge: a learning experience or private coaching, gaining access to a mentor or master.

Values are moving targets. It’s not like behavioral styles, where you can readily observe one pattern over another. This one takes more observation. Tune in to the ways people make decisions and invest their time and money. Notice what they react to strongly and what they are indifferent about. You’ll start seeing value choices everywhere. Once these patterns become clear to you then you will know more about how to motivate others – and even yourself.  

Jim Cathcart, CSP, CPAE is the original author of Relationship Selling and one of the world’s leading professional speakers. Jim is a regular contributor to Selling Power and a certified Mindset Trainer. Contact Jim at You can read more about the principles outlined in this blog post in his book, The Acorn Principle: Know Yourself, Grow Yourself.

Planning Your Sales Conversations with CIOs for 2018

By Sharon Gillenwater

Earlier this month, Gartner unveiled its 2018 CIO Survey, which summarizes what is top of mind with CIOs moving into 2018. The respondents were 3,160 CIOs from 98 countries and all major industries, representing approximately $13 trillion in revenue/public sector budgets and $277 billion in IT spending.

So what did they have to say?

The first thing that sticks out is that CIOs are routinely driving business outcomes in partnership with business leaders. In years past, CIOs have spoken about their struggles to gain a seat at the table with business owners and their challenges in trying to align with the business. Today, at least 84 percent of the CIOs surveyed say they now have responsibility for areas outside traditional IT and many reported they are close to an “ideal balance” with more focus on business outcomes rather than IT delivery. Their roles are transitioning from controlling costs and engineering processes to driving revenue and exploiting data.

For 2018, 26 percent of CIOs surveyed say their No. 1 priority is growth – to use digitized products and services to drive new forms of revenue, business value, and customer engagement.

Yes, CIOs have come a long way from the data center. And their jobs have become more challenging than ever. They have to manage more change and complexity than ever before, evaluate a steady stream of new technologies and vendors, and navigate an ever-shifting landscape of skills and talent. Plus, they have to make sure all the basic infrastructure is up and running – and that everything is safe and secure.

What does this all mean for those of us who are in the business of helping CIOs?

Well, for one thing, it means the percentage of CIOs exclusively focused on “keeping the lights on” is falling. The pivot to growth as a main focus of top CIOs opens the door to more sophisticated business conversations and solutions – ones that some CIOs may not have been ready for just a few years ago.

That’s not to say everyone is there yet. Gartner noted that some are “trailing” when it comes to digitalization, so there are CIOs out there who are still mainly “keeping the lights on.” It could be challenging to engage this type of CIO around a broader business transformation vision when they are still operating in survival mode.

So how do you know who’s a leader and who’s “trailing” – or at the very beginning of their digitalization journey? You can usually tell by doing some homework on the company and the CIO you are targeting. Look at what the company’s executives are saying on earnings calls. Does the CEO call out technology, innovation, and digital as investment priorities? Or is the focus mainly on cost cutting? These things can give you a clue as to how you should focus your conversation for maximum relevance.

Finally, if you are targeting CIOs, prepare to live in a state of near-constant change. Why? Because that is their reality; 95 percent of CIOs surveyed by Gartner expect their jobs to change, thanks to digitalization. For those of us who want to help them, it means we need to keep up – and keep on coming up with ideas and solutions for helping them meet their business goals.

Sharon Gillenwater is the founder and editor-in-chief of Boardroom Insiders, which maintains an extensive database of the most in-depth executive profiles on the market – from Fortune 500 companies to independent nonprofits – to help sales and marketing professionals build deeper relationships and close more deals with clients. Gillenwater is a long-time marketing consultant with expertise in marketing strategy, account-based marketing, and CXO engagement programs.

Let Us Say R.I.P to the RFP Process

By Dr. Roy Whitten and Scott Roy, Whitten & Roy Partnership

The process variously called RFP, RFQ, RFI, etc., was developed in the late 18th century to create a cost-effective methodology for businesses to acquire manufacturing components. Today, when applied to purchases of complex goods and services, it drives a process of buying and selling that is fundamentally flawed.

Anyone involved knows that the playing field is not really level (both businesses and suppliers “game” the system) and the process consumes valuable resources and generates significant frustration. The greatest issue, however, is that it prevents the analysis of the problems to be solved that is required for effective selling and wise buying.

If you want to start pushing back on this crazy system, here are some steps we and our clients have found helpful.

Step 1: Count what it costs you to participate in RFPs.

Perform an honest cost/benefit analysis of participating in RFPs. One of our clients found that, on average, each salesperson responded to two RFP processes per month – through which they landed four contracts per year.

  • The annual value to the business: $250K per sale x 4 contracts x 9 percent net margin = $90,000
  • The annual cost (staff salaries and benefits for everyone who worked on the RFPs) was $12,500 x 24 RFPs = $300,000, plus opportunity costs!

Yes, there’s pressure to participate: from your own business (we have no choice) and from your customers (if you don’t play, you can’t get to the next round). However, if the cost to participate is great enough, you can convince your business to let you explore options.

Step 2: Repurpose your selling process.

The best selling process is one that leads your customer to make the best possible decisions for their businesses. This requires getting them to do four things, in this order:

  1. Identify the full extent of the problems they are trying to solve
  2. Estimate the financial cost of leaving these problems unsolved
  3. Understand your solution to these problems
  4. Calculate the value of your solution for their business

Step 3: If you can, offer an analysis instead of an RFP. .

If you can refuse to participate (even as an experiment with a few lesser accounts), take these steps with a prospective customer:

  • Share the grave limitation of the RFP process: its prevention of discovering the full extent of the problems to be solved
  • Have them estimate the cost of proceeding with an incomplete problem analysis
  • Ask with whom you can engage to help them with that analysis
  • If they won’t do these things, walk away

Step 4: If you must participate, stand out from the crowd.

Go into an RFP process fully aware of its limitations and the cost to your business.

  • Raise questions about the problems to be solved – questions that illustrate the incompleteness of their analysis and the insight you bring
  • Suggest they calculate the cost of proceeding with the RFP without a full analysis of the issues to be addressed
  • Offer a range of solutions and prices that will be dependent on your eventual problem analysis
  • Do only the minimum to get to the next level – don’t run up your costs

Step 5: Either way, get ahead of the game.

Use your contacts within your company and theirs to start exploring the next set of problems to be solved before they develop an RFP. Let your analysis be the foundation of how the next RFP is written, and smile when you see your own words contained in the language of the RFP! Yes, “game” the system.

Step 6: Introduce an alternative process: the RFPI.  

With our own clients, we strongly suggest an alternative that might be called an RFPI: a request for problem identification. After taking the steps outlined above, we usually see prospective clients pull the RFP in order to more fully understand the issues they must address before shopping for suppliers. And, nearly always, we win these deals because of the trust our honesty and insight engenders.

We wish you the best. May your boldness and creativity finally help the RFP process rest in peace.

Whitten & Roy Partnership is an international sales consultancy that helps leading businesses and organizations transform their sales results. Founded in 2009 by sales experts Dr. Roy Whitten and Scott Roy, Whitten & Roy Partnership today comprises a network of consultants operating in 34 countries around the world. For more information visit:

How to Amplify Your Connections with Customers

By Jim Cathcart

Garth Brooks is the number two best-selling music artist of all time. By number of albums sold, he’s outsold Elvis, Michael Jackson, and even Neil Diamond! What does this have to do with sales leadership? He has incredible selling power. He’s sold hundreds of millions of albums and performed at more than 350 concerts, which have grossed hundreds of millions more.

But, you say, “I’m not a singer or celebrity! I can’t do what Garth Brooks does.” Okay, granted – there’s a big gap between building a winning sales organization and being a celebrity. But let’s learn from Garth. He’s one of the most accessible successful singers in the world. So, how does he do it?  

  1. Garth is on social media regularly communicating on a personal basis with his customers (aka: fans).

  2. He is willing to be human, to listen to those who have no power, to show respect to others, and to openly express gratitude for the blessings of being able to do a job he loves. As a result, people can’t wait to pay to come see him. His fans aren’t just reflections of his musical talent (and the ability to do the job he is paid for) but, rather, he is followed because people really like and trust him.

  3. He looks out for fans and does nice, unexpected things for them too. At a recent Garth concert, a woman held up a sign with “Chemo [cancer treatment] this morning, Garth tonight!” written on it. In the middle of his signature song, “The Dance” (“I could have missed the pain but I’d have had to miss the dance”), he walked to the edge of the stage, sat down in front of her, held her face in his hands and gently kissed her. Then he took off his guitar and gave it to her! That is the strength of connecting with your customers! Everyone in the audience, and me watching on video, burst into tears at the power of that tender moment.

Do you care as much for your customers as he does for his? They don’t “know” each other; they simply share the experience of his product. How could you get to know the feelings and cares of your customers like he seems to understand his? Once you truly get it as to why people buy from you, you acquire a connecting power that could be immense. Here are some questions to consider:

  • What life or business problem do you help people solve?
  • What feelings – and maybe hopes or fears – are connected to that?
  • If you sell cars, how can you make the delivery of the new vehicle a powerful emotional triumph for the buyer?
  • If you’re a banker, could you find creative ways to thank people for investing their trust in your bank?
  • If you provide a software service, could you make people part of a “club” of insiders whom you protect and empower through your service?

Tommy Emmanuel is arguably the best popular guitarist alive today. Not the best known, flashiest, nor even the top selling, but clearly one of the best skilled you’ll ever see. (Christopher Parkening holds the best classical guitarist title.) Chet Atkins dubbed Tommy a “Certified Guitar Player,” a title he wears proudly. Watch Tommy’s YouTube performance of “Classical Gas.” You’ll be speechless.

Last week I met Tommy before his show in Santa Barbara and I presented a silver acorn to him to thank him for his art and to encourage him to keep on giving. His performance was one of the most joyful I’ve ever seen. He was having a great time – and so were we! Tommy loves playing guitar and people love to see him do it. How can you cultivate your love of what you do? How can you make it joyful to work with others and to provide the value you bring?  

Finally, let’s look at the SBAIC, the Santa Barbara Acoustic Instrument Celebration, organized by Kevin Gillies. This amazing gathering of instrumental artists takes place annually in California and brings the finest guitar makers (luthiers) from around the world. They hold three days of clinics – all day, each day. Customers and fans are encouraged to touch or play the instruments, talk with the artisans who made them, and learn techniques for inlays, wood choices, playing, and more. Hundreds of thousands of dollars worth of instruments are sold and the art and craft of luthiers is advanced. I conduct a seminar there for the guitar makers titled “The Art of Marketing and The Marketing of Art.”

How could you create an event or a special experience around your product or service so customers can learn the inner workings, get a hands-on experience, and get to know the people who provide the value you offer?

You may not be another Garth Brooks in your own field (or you might) but, even if all you do is learn from his example, you can still add tremendous value to your career and customers. You might not love what you do as much as Tommy Emmanuel does, but you could learn to enjoy and savor it more if you tried. Your “experience” event might not have the same qualities as SBAIC, but I’ll bet there are dozens of ways you can make your work more fun for your team and more enjoyable to your customers.

Jim Cathcart, CSP, CPAE is the original author of Relationship Selling and one of the world’s leading professional speakers. Jim is a regular contributor to Selling Power and a certified Mindset Trainer. Contact Jim at

Is Your Sales Presentation Suffering from Information Overload?

By Terri L. Sjodin

In today’s competitive marketplace, a sales professional’s success often depends upon his or her ability to deliver a polished and persuasive presentation. Although salespeople spend a significant amount of their time verbally communicating, many suffer from common shortcomings in their sales presentations that adversely affect their results.

One of the most common mistakes is delivering overly informative presentations. Of course, every solid presentation requires a certain amount of “data,” but many professionals spend too much time informing rather than persuading.

It’s very easy to deliver an informative rather than persuasive presentation. The reason? A prospect typically won’t say “no” when you’re only disseminating information. The problem is they don’t say “yes” either!

A young woman I recently worked with reluctantly confessed that she suffered from the data-dump syndrome. Like many of us, she felt more comfortable in the information zone. Her strategy was simply to provide more information than her competitor. She was hoping that her prospect would like her more, or at least feel obligated to buy from her because she had been so thorough. She came to realize that she had been spending a great deal of time sharing and consulting with her sales prospects without completing any transactions. (Ouch!)

After stepping back and evaluating her presentations, she realized she needed to move beyond merely relaying information; she needed to build her case. By focusing more on brevity and tailoring her strongest points to her prospects’ needs, this young professional eventually became a consistent producer in her organization.

What Makes a Persuasive Case with Prospects?

Prepare like a debater or an attorney. Debaters and attorneys win cases based on persuasive arguments and supporting evidence. Focus on your most compelling arguments with each client or prospect.

Do you deliver a presentation that creates a true need for your product or service that your prospect may not even be aware of? (Ask yourself: why you, why your company, why now?) Don’t just deliver a standard list of features and benefits. (Remember, a feature is what something is. A benefit is what that something does. These two concepts alone are inherently informative.) Think proactive versus reactive. Design a presentation that anticipates common objections and overcomes them within the body of the presentation before they become reasons not to buy.

If you have been meeting with a substantial number of prospects, but haven’t been completing a significant number of transactions, maybe the big question you need to ask yourself is… “Is my presentation overly informative or is it persuasive?”

After recognizing the danger of data dumping, you are poised to tackle any topic that comes along. Your goal is to be both informative and persuasive, pairing rock-solid information with compelling arguments. Your presentation should be a blend or a combination of the two. I have seen it play out time and again. If you are too informative, nothing happens. If you are too aggressive, nothing happens. Find a balance, and you’ll see results.

Terri L. Sjodin is the author of the national best-selling book, Small Message, Big Impact. Her new book, Scrappy: A Little Book About Choosing to Play Big, was just released by Penguin Random House. She is the principal and founder of Sjodin Communications, a public speaking, sales training, and consulting firm. For more than 20 years Terri has served as a speaker and consultant for Fortune 500 companies, industry associations, academic conferences, CEOs, and members of Congress. She lives in Newport Beach, CA. For more information visit:

Five Mistakes You’re Making with Your Sales Proposals

By Adrian Davis

If you’re like most sales leaders, you have a nagging feeling there is something wrong with the sales proposals your team sends to prospects and customers. You just don’t know where to start when it comes to reworking them.

Here are five things they should stop doing immediately:

  1. Not understanding the target audience. In most cases, the individual receiving the proposal is not the person actually making the decision. Ensure your salespeople have a clear understanding of the approval process and who the final decision maker is. From now on, never allow a proposal to begin with these words: “We are really pleased to have the opportunity to submit this sales proposal.” When people read this line, they immediately disengage from the proposal.

    You need to come out swinging and ensure every line counts. The most powerful word at the start of a proposal is the word, “You.” Ensure your salespeople articulate very clearly the strategic goals of the decision maker and how the current situation is jeopardizing the achievement of these goals. This opening will emotionally engage the decision maker. The needs and objectives of other stakeholders should be articulated within the context of the strategic goal and challenges of the key decision maker.

  2. Not understanding what a proposal is. Most salespeople believe a proposal is a 100-page document. Lacking a clear understanding of what a proposal is creates confusion for the buyer.

    Simply put, a proposal is a request for a proposed course of action. “Will you marry me?” is a proposal. So is, “Will you buy my product/services?” The 100-page documents your salespeople are generating should be thought of as technical appendices. Lower level people will comb through these documents to ensure they understand the specific details. Executives will not read these documents. They will, however, read the Executive Summary or the Transmittal Letter. If those documents are well crafted, your chances of winning will significantly improve.

    Most salespeople fail to realize that the more senior the executives are, the more they want to be told what to do. They tire of people bringing problems to them without any solutions. Your proposals must clearly articulate the problem the organization is facing and then provide a clear course of action.

  3. Not providing a transition vision. When people are confused, they do nothing. Many opportunities stall because the buyer is unclear how the change will take place. Buyers want change – the movement from a current state through a transition state to a future state. The transition state is messy and risky, which is why, without a clear vision of that transition, buyers are reluctant to take the risk. Therefore, a section of your proposal should clearly articulate how the change will be made – reassuring the buyer that you have an approach that will work and that they will feel comfortable with.

  4. Not focusing on outcomes. So many proposals focus on the price and the process. This is not what buyers want. What they really want is outcomes. The prices and the process are necessary evils. Ensure your proposals paint a picture of their new reality. Fire up their imagination about the transformation they are about to undergo. The unconscious mind loves contrast. This section should provide a strong contrast to the needs and challenges identified in section 1.

  5. Not providing a clear next step. You need to keep the ball moving forward. Right now, inertia is working against you. You need inertia to work for you. For that to happen, you need to request the smallest action that will demonstrate real commitment to moving toward your solution. In some cases, this may be scheduling a project kick-off meeting; in other cases, you may need a signature for an agreement.

If you can get your people to stop making these common mistakes, you will improve the number of wins when your opportunities get to the sales proposal stage.

Adrian Davis is president of Whetstone, Inc, where he has worked with organizations such as Johnson & Johnson, KPMG, Motorola, PwC, Phonak, Aviva, and DuPont. His highly talented team has developed a reputation for leading organizations to innovative and practical solutions that enhance customer value and dramatically increase sales. Adrian is the author of Human to Human Selling: How to Sell Real and Lasting Value in an Increasingly Digital and Fast-Paced World, a Certified Speaking Professional (CSP), a certified professional in Business Process Management (P.BPM), and a certified Competitive Intelligence Professional (CIP).