Chapter 9
Insight Selling Mistakes

Too many sellers have a canned pitch and just go through their mental checklist like selling robots. “Here’s why we’re great, here’s how we’re going to help you, here are other people that we do this for that are in your industry.” They’re just hoping that something they throw at the wall sticks. Then they just don’t listen. They’re not having a conversation with the intended customer or client.

The other thing I see are sellers trying to educate the prospect from the moment they walk in, but it’s like they throw an entire textbook at the prospect when they may only be interested in one chapter. If you throw 50 points at them, they will tune you out. Instead, do some research on what you know is likely to be important to them; then start a conversation about why they agreed to meet and what some of the pain points are, then pick two or three salient points and talk about why these, specifically, apply to them and will help them run their business.

—Jeff Somers, principal, Rothstein Kass

In our What Sales Winners Do Differently research, “helped me avoid potential pitfalls” of implementation was the sixth greatest factor separating winners from second-place finishers. In this chapter, our goal is to do the same for you.

It’s not our intent, however, to present a laundry list of all selling mistakes. The focus is specifically on the concepts and application of insight selling. Some points are tactical, and some are strategic. Some we cover elsewhere in the book, and others we note only in this chapter. We wanted to include them all in one place for you to use as a checklist of pitfalls to avoid.

Perhaps the greatest challenge writing this chapter was focusing on the mistakes that are most common and most important. If we hadn’t focused, we’d have the long sequel to Insight Selling, not merely a chapter. Meanwhile, we’ve taken our research, buyer discussions, and observations from training and consulting for what not to do, and we present it here.

General Mistakes

1. Treating Insight Selling as a Tactic Rather Than a Pursuit

When we interviewed buyers about their recent interactions with sellers, a number of them reported an increase of sellers who seemed like they were trying very hard to be provocative, even suggesting it felt like sellers had received some training that told them, “The secret is pushing back on what buyers say!” Other buyers reported they have seen a marked increase of sellers who blindly send white papers, news clippings, and Web links to “things I thought you’d be interested in” that had no real relevance to them.

The buyers are right. Some sellers think insight selling will work if they simply share content and antagonize. They’re applying it like it’s a tactic, when the fact is insight selling is a pursuit, a way of thinking.

Yes, sellers should push back—and not hold back—when it will help buyers. Yes, sellers should introduce new ideas and new possibilities that help buyers make better decisions. Doing this right takes dedication, training, practice, coaching, and time.

It takes intense focus and effort to be perceived as a knowledgeable insider, to learn and be able to communicate the impact of offerings, to lead discussions masterfully that take buyers out of their comfort zones, and to build trust all the while.

Some people try to take the easy way out of everything. No news here, but when sellers and companies do this with insight selling, you can hear the loud thud as it crashes.

2. Not Embracing the Mind-Set of Seller as Change Agent

At the heart of insight selling is bringing forward ideas that make a difference. Difference means change. If sellers are just a part of the status quo and are not pushing buyers out of their comfort zones, they’re probably not selling anywhere near their potential.

3. Being Arrogant or Meek

In Chapter 8 we covered the attributes of the insight seller and what problems and mistakes can crop up when attributes are missing. At the end of that chapter, you’ll find a summary of those.

Two problems—arrogance and meekness—deserve special attention.

In their quest to push buyers out of their comfort zones, establish a point of view, and change a buyer’s thinking, many buyers report sellers are pushing too far, too hard, and too fast. Even sellers who have the chops to add value are being dismissed by buyers simply because they don’t want these sellers around.

On the other hand, a quiet, hidden killer of insight selling is a quiet, hidden seller—sellers who don’t make their opinions known, aren’t willing to challenge the thinking of buyers, and generally blend into the background don’t bring insight to the table. These sellers get dismissed as not ready for a seat at the table. Pushing buyers out of comfort zones and inspiring them to do things differently is risky. Some sellers aren’t willing to take the risk. No risk = no reward.

A point worth making here is that not every buyer’s assessment of arrogance and meekness is the same. A Decisive Danielle and a Consensus Claire (see next chapter) tend to have different tolerances for direct push back. Sellers have to be able to read their buyers and adjust their provocativeness throttle as situations and buyer preferences dictate.

What Winners Do and Don’t Do

It might seem obvious, but to succeed with insight selling, sellers should do what winners do. In Chapter 1 we outlined the major findings of our What Sales Winners Do Differently research, including detail about the 3 levels: connect, convince, and collaborate.

Leaving any of these factors out can hinder sellers’ abilities to apply insight selling and jeopardize their success. In the following section we don’t cover each individual point we made in the various chapters on these topics. We do, however, cover what we observe to be the common mistakes and misconceptions.

Connect

Equating Insight Selling with Pitching

We noted in Chapter 1 that some people believe accepting insight selling concepts means rejecting solution selling concepts. When sellers make this major mistake, they forgo questioning, listening, and understanding in favor of taking up the mantle of an idea and pitching it forcefully.

Insight selling includes concepts, such as introducing buyers to new opportunities proactively, pushing back on buyer thinking, and advocating for a point of view. These are, however, only tools in a toolbox, to be used at the right time for the right purpose. Other essential selling components include understanding needs, crafting solutions, and listening. When buyers don’t get these, it matters. (See Figure 9.1.)

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Figure 9.1 Top 10 Mistakes with Greatest Impact on Purchase Decision

The part of insight selling that includes idea advocacy is not as a replacement for the behaviors that tend to be classified under the words solution, consultative, and relationship but rather as a complement to them.

Lacking Customization and Customer Focus

Even decision makers at large businesses that get sales overtures all the time report that sellers don’t take the time to craft messages, conversations, and presentations so that they’ll resonate with them personally. This is true across the sales cycle.

  • Prospecting: Sellers focus only on their message, not on the particular buyers—their needs, their company, their industry, their context—when reaching out to engage conversations.
  • Needs discovery: Sellers don’t craft questions and prepare messages that will resonate and create deep connections with specific buyers.
  • Convincing story: Sellers don’t craft the story itself around a particular buyer. They leave it general and generic. With a little effort, sellers could create much deeper engagement with buyers by demonstrating understanding and tailoring an interaction uniquely for them.
  • Solutions: Sellers don’t connect the needs of the buyer to particular products and services that are just the right fit and don’t customize the solution as a whole. They get all the way down the path, and lose because of lack of, or poorly designed, customization.

Convince

Not Doing It

The cardinal sin in the convince category is the sin of omission: not doing it at all. We’ve made the point throughout this book that sellers must be able to take a point of view, defend it convincingly, and persuade others to believe. Sellers who aren’t willing or able to do this are not insight sellers.

Conducting Ill-Timed Needs Discovery versus Presenting

When buyers request a meeting with a seller because they have a felt need, they have an agenda they want to cover. The buyer owns the meeting. If a seller walks into this meeting, engages in pleasantries, and then starts pitching, buyers are turned off. They think, “This is my meeting. Why is this guy pitching? He hasn’t even asked what I want to get out of this meeting. He should ask me questions and let me talk first.”

On the flip side, let’s say a seller requests a meeting and a buyer accepts. Often these meetings are set under the premise of introducing the buyers to something they should be considering. The seller owns the meeting.

In these cases, most buyers want sellers to get to it without wasting time. Certainly buyers tend to be open to pleasantries and expect a few questions at the beginning of meetings, but when they’re expecting a presentation, they tire quickly of the third degree.

Sellers need to know when it’s time to share a point of view and when it’s time to understand before being understood. Unfortunately, they get the timing wrong all too often.

Making Presentation Gaffes

Much to the chagrin of sales pundits who are vehemently opposed to pitching, presentations are both a necessary and a helpful selling tool. Sellers constantly make cringe-worthy presentation mistakes, but that doesn’t mean presentations—delivered right and at the right time—aren’t essential to sales success.

The list of common presentation gaffes is long: bad story, bad slides, too many slides, improper use of slides, use of slides at all in some cases, improper use of humor, lack of humor, inability to establish a peer dynamic, and so on. These are all important, but even when sellers do the nuts and bolts well, we often see them make the following three mistakes:

  1. Not making presentations interactive: Before and after delivering a story, the seller should be interacting with buyers, not just talking at them. Even during presentations, pausing to ask questions and create conversation can be the difference between success and failure.
  2. Not making the buyer the hero: Too many presentations leave the buyers thinking, “I don’t care.” When the audience is the hero of the story, this doesn’t happen. From the moment sellers begin to present until the moment they are done, everything should be meaningful to the audience. Following the convincing story framework will help here, along with the right preparation and customizing of the story for each buyer.
  3. Not mastering the presentation: It may seem mundane, but too many sellers don’t master their material, don’t know what questions they’re likely to get and have good answers at the ready, and don’t know exactly how to deliver so that the presentation runs smoothly. The results are not confidence inspiring.

Dismissing Trust

What’s convince all about? Getting someone to take your advice. To do this, trust is essential.

When buyers don’t trust sellers (see Figure 9.1), the buyer’s perception of risk is just too high. The more sellers build trust in themselves, their offerings, their companies, and the results buyers will receive after they buy, the more sellers will be able to influence buyers’ action. (See Chapter 7.)

Collaborate

Equating Collaboration with Consensus

Just as buyers can be Consensus Claires (see Chapter 10), so can sellers. Consensus Claires are neither bad people nor bad decision makers. They just have a predisposition to get people on the same page before taking action.

When sellers have this predisposition, they hear collaborate and think that means getting more people involved at the buyer organization than is necessary. Sellers should involve buyers they need to move the decision forward and involve buyers who, if they are not included, might block the sale. Involving anyone else increases the likelihood for failure.

Collaborating means interacting with buyers deeply in the process: engaging them in needs discovery, solution crafting, and moving the process forward. Collaborating means working toward achieving mutual goals. It doesn’t mean getting absolutely everyone on the same page, and it doesn’t mean including people who are tangential to the decision-making process.

Being Unwilling to Involve the Buyer

Some sellers are afraid to collaborate with buyers. They are afraid they’ll lose control of the sale. Others worry that collaboration will take too much time and effort. (It certainly will take some.) Although they rarely admit it, sellers can be intimidated by working closely with buyers they feel might be more senior and more knowledgeable than they are.

It can be a lack of skill that prevents collaboration, but even when sellers have the skill, they often lack the will. They don’t believe collaboration will help them. Based on our research and experience, they’re probably wrong.

Creating Psychological Ownership, Then Stealing It Away

Collaboration builds psychological ownership. However, sellers commonly don’t allow the buyer to take the credit for ideas and thus don’t create the ownership. For example, a buyer might say, “The best thing to do is this . . .” This might be exactly what the seller wants! Sellers then often say, but shouldn’t say, “Yes, I’ve been thinking that for much of the meeting” because it steals psychological ownership away. “I agree” will usually suffice.

Not Taking Control and Guiding the Collaboration

Collaborating does not mean relinquishing control. Sellers sometimes don’t have the gravitas or skill to prevent a buyer strong-arming them after they open the door to collaboration. If it’s a skill issue, then sellers need to build their skills. If it’s a gravitas issue, they first need to recognize it and then need to work on it long term. Remember, insight selling is a pursuit, not a tactic.

Not Being Proactive

Buyers rarely call sellers and say, “Let’s have a brainstorming session for how you can help us next year,” or “Have you done any research that can give me new ideas for where the future of this area is going and what I should be doing about it?” Sure, it happens—especially when sellers have already established themselves as a source of insight—but for the most part, sellers must drive collaboration by setting meetings themselves (see next point). During meetings, sellers must also invite collaboration proactively. When they don’t, buyers can be disengaged. When sellers aren’t proactive, they leave opportunities untapped and collaboration to chance.

Generate Insight Meetings

Not Trying to Generate Insight Meetings

We covered in Chapter 6 that expanding business with existing relationships is perhaps the greatest untapped revenue growth opportunity available to sellers.

Yet year after year account leaders do not set up meetings to share ideas and inspire buyers to consider new ways they could work together. Before sellers can succeed with inspiring buyers and influencing their agendas, they need to get on their calendars.

When prospecting for new accounts, sellers pitch meetings by offering to demonstrate a product or present service capabilities. This might be an effort to generate a meeting, but it’s not an insight meeting. It’s more effective for sellers to introduce themselves to new buyers by offering some kind of valuable information and valuable interaction in the meeting itself. Product and capability pitches are not particularly exciting for buyers. Not only do insight-focused meetings get accepted more often than product pitches, but they also go better. (See the RAIN Selling Online e-learning lesson Ideas for Insights: www.raingroup.com/insightbooktools.)

Sending Information and Believing That’s Insight Selling

Sellers will e-mail (or mail) a buyer a white paper, article, or some other piece of content, thinking this will generate meetings for them and establish themselves as sources of insight.

The problem is buyers see this for what it is—a noncustomized prospecting strategy that communicates the seller is not making an effort. Sellers should think very carefully before they send anything. If it’s not relevant, the buyer will dismiss the seller as not paying attention and not really getting it or getting them.

When sellers send relevant content that they customize for each buyer (e.g., they highlight specifically why that buyer might find it worthwhile), buyers notice. Buyers won’t respond to everything, but it will make a positive impression on them. This kind of message customization takes effort, but this is what the sellers who establish themselves as sources of insight do.

Not Leveraging Relationships to Get Meetings

Most sellers who have been around for any amount of time have relationships they can leverage to get meetings, but they don’t try. They don’t think to ask their existing relationships for introductions.

If they do try, they don’t think about it broadly or creatively enough. One seller told us, “I have to get to the vice president of information technology for Asia Pacific, but I don’t know them and my contacts don’t know them.” When we asked the seller what his plan was to get an audience with him, he was at a loss.

True, none of his contacts knew him, but several of them were just one step removed. So he asked for introductions to people who would be in a position to introduce him. It took several steps, but he got the introduction in about eight weeks.

Not Going Direct If You Don’t Have Relationships

On the other hand, some sellers rely only on their networks and won’t reach out to new buyers if they can’t get an introduction. Six out of 10 buyers say they don’t accept cold calls,1 but that means that four out of 10 do. Some will say, “Those odds are terrible.” Actually, they’re fine. So you won’t get to everyone. This isn’t a game of succeeding with every call or e-mail outreach, but succeeding enough to create new opportunities at a good rate.

If no warm call option, so to speak, is open to generate a new meeting, sellers should build a strategy, reach out, and work to set meetings directly.

Create the Insight Organization

Expecting Everyone Can Be an Insight Seller and Not Hiring for Insight

Not everyone is destined be an insight seller. There’s a specific set of knowledge, skills, and attributes necessary for insight selling to work. (See Chapter 8.)

Do sellers need everything in place to practice insight selling? No, but there needs to be enough critical mass. If organizations want to transform their sales forces into insight forces, they (1) don’t want the development process to take forever (this is as much a training and development challenge as it is a hiring challenge) and (2) don’t want to invest in people who have too many cards stacked against them.

Training aside, assessing and hiring candidates who are likely to succeed with insight selling is critical for organizations that want it to become a part of the sales culture.

Lacking the Tools and Resources to Execute Insight

One organization we worked with wanted its sellers to bring ideas to the table that would expand buyer thinking and expand the sellers’ business. A small subset of its 300 salespeople had been doing this successfully already, but efforts to train the rest weren’t gaining traction.

We asked the organization what the sellers who were executing insight selling successfully were doing. It turns out they were doing similar things as a group and bringing forward similar ideas. Nowhere, however, had they captured this finite list of core ideas and shared them with the rest of the sales force. Essentially, they were expecting that all 300 people would come up with all the ideas on their own.

We worked with them to capture the ideas, codify them, and literally place them in the hands of the rest of the sellers. It turns out many of the sellers had the skills and the inclination to practice insight selling but not the knowledge. With this tool and the accompanying training, the sales force’s ability to broaden and deepen the discussions improved across the board.

Not Coaching for Insight

Unfortunately, sales coaching (when it’s even offered) too often focuses on process: what a seller needs to do to close a sale, when sellers expect it to close, which buyers need to be involved, the revenue side of the opportunity, and so on.

Rarely do sales coaches give encouragement, offer ideas, and provide tools and resources to make the seller more effective with insight selling. For those on the path to becoming insight sellers, coaching is a critical component of the process.

Providing Training That Fails

Here we come full circle. It’s not just the sellers who must view insight selling as a pursuit and not as a tactic. Companies must, as well. If insight selling is simply this quarter’s training program, don’t expect traction. For training programs to work to build effective insight sellers, leaders should think of training less as an event and more as an ongoing priority and initiative. This is the subject of the last chapter in Insight Selling.

Chapter Summary

Overview

Common mistakes and misconceptions hinder the ability of many sellers to succeed with insight selling. To be successful, follow the lead of the winners—connect, convince, and collaborate—and avoid the common pitfalls.

Key Takeaways

  • To succeed with insight selling, you must cover all 3 levels: connect, convince, and collaborate.
  • You need to understand buyer personas to apply insight selling well. For example, buyers who are Consensus Claires versus Decisive Danielles will have different tolerances for seller assertiveness. (See Chapter 10.)
  • To win with insight selling, do the top 10 things that buyers say the winners do better than the second-place finishers:
    • Educated me with new ideas or perspectives
    • Collaborated with me
    • Persuaded me we would achieve results
    • Listened to me
    • Understood my needs
    • Helped me avoid potential pitfalls
    • Crafted a compelling solution
    • Depicted purchase process accurately
    • Connected with me personally
    • Overall value from the company was superior to other options
  • Avoid these common pitfalls when applying insight selling:
    • Overall:
      • Attempting to apply insight selling as a tactic rather than a pursuit
      • Not embracing the mind-set of seller as change agent
      • Being arrogant or meek
    • Connect:
      • Equating insight selling with pitching
      • Lacking customization and customer focus
    • Convince:
      • Not doing it
      • Conducting ill-timed needs discovery versus presenting
      • Making presentation gaffes
      • Dismissing trust
    • Collaborate:
      • Equating collaboration with consensus
      • Being unwilling to involve the buyer
      • Creating psychological ownership, then stealing it away
      • Not taking control and guiding the collaboration
      • Not being proactive
    • Generate insight meetings:
      • Not trying to generate insight meetings
      • Sending information that’s not customized and relevant
      • Not leveraging relationships to get meetings
      • Not going direct if you don’t have relationships
    • Create the Insight Organization
      • Expecting everyone can be an insight seller and not hiring for insight
      • Lacking the tools and resources to execute insight
      • Not coaching for insight
      • Providing training that fails (see Chapter 11)

Note

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