What is Insight Selling? A Beginner's Guide

What is Insight Selling? A Beginner's Guide

The term "insight selling" has been floating around in the business community for quite some time, but when pressed to define it or explain how it works, the average salesperson struggles to move beyond industry jargon. In fact, only about 10 percent of salespeople have actively embraced this methodology though it has long been heralded as the next step in the evolution of sales. 

In response, Business.com has put together a quick guide to help newbies who want to give insight selling a try, but aren't quite sure where to start. 

Insight Selling Defined

So, what is insight selling? According to most dictionaries, insight is the ability to form an accurate and intuitive understanding of a person or thing. When you apply insight to sales, you use data, trends analysis, market research and experience to help customers sift through all relevant information, diagnose problems, determine their needs and ultimately, make informed buying decisions.

The RAIN Group's Mike Schultz and John Doerr, who have written extensively on the topic and published a book by the same name define insight selling as "the process of creating and winning sales opportunities, and driving change, with ideas that matter." In other words, the salesperson, especially in B2B environments, must become a strategy consultant or business coach that helps a customer navigate the purchasing decision. 

As Eric Quanstrom, chief marketing officer of CIENCE, explained, "Most buyers are looking for ways to address the problem behind the problem. They tend to favor sellers who can teach them useful things about their own business."  

A Brief History of Insight Selling

To understand what insight selling is, it's helpful to get a grasp on what it is not. Brian Signorelli offers a detailed overview on HubSpot's blog: Not so long ago, sellers didn't have to work very hard to pitch their product to potential buyers. They simply explained its benefits and features, and buyers often didn't have the means to compare their product to competitors' offerings to determine if, in fact, it was the best option for them. 

In the 1980s, sellers began asking customers big open-ended questions, such as "What are your top three priorities this quarter?" or "What keeps you up at night?" and using the answers to shape potential solutions for the customer.  

Though obviously more effective and personalized, this approach lost some of its luster with the advent of the internet and the oversaturation of information. Customers began to conduct research on their own, but were overwhelmed by the barrage of information they encountered. They had a hard time sorting through all the choices and determining what mattered most. 

"Increased access to information has made traditional solution sales a thing of the past," said Steve Wunker, managing director of New Markets Advisors and co-author of "Costovation: Innovation that Gives Your Customers Exactly What They Want — and Nothing More" (HarperCollins Publishing, 2018). "Buyers no longer need to listen to a sales presentations to understand your product; they simply browse online." 

Wunked added that buyers are looking for advice to help them make sense of all the noise. They want to learn from what others are doing in situations similar to theirs, and ultimately feel confident in their decisions, he said. 

Today, this information overload continues to leave buyers confused, overwhelmed and searching for sellers that can cut through the clutter and partner with them to make sense of it all. This is where insight selling comes in. 

According to studies cited in Forbes, 79 percent of business buyers say it's absolutely critical or very important that they interact with a salesperson who is a trusted advisor. Additionally, 94 percent of B2B decision makers report looking for sales teams that demonstrate specific insight into their organization's struggles. 

"With insight selling, you come to the table bubbling with new ideas, perspectives, and potentially, data points," said Wunker. "Insight selling is about becoming a true partner to your customer, not just a salesperson. You need to offer value beyond the research that buyers can conduct on their own."  

Two Categories of Insight Selling

There are two types of insight selling: opportunity insight and interaction insight. 

Sellers who make use of opportunity insight aren't sitting around waiting for prospects to raise their hands and ask for help. In fact, they recognize that the customer may not even realize that a problem exists. Instead, the salesperson proactively brings up a specific idea, engages the customer, and guides the buyer through the process of realizing that that idea addresses one of their needs. 

Opportunity insight often works hand-in-hand with interaction insight. It focuses on building connections with customers by encouraging creative thinking, inspiring "lightbulb" moments and challenging assumptions. 

Sellers who use interaction insight ask questions and push customers to reach outside their comfort zone. As a result, customers may come to their own realizations about what solutions work best for them, and the salesperson will be there to help craft a product offering in response. 

3 Keys Actions to Insight Selling 1. Research

How do you pull off insight selling? The key is to do better sales research, according to Wunker. 

"Don't just learn the basic metrics about your customers – instead, push to develop a deep and holistic understanding of the jobs your buyer is trying to get done," he explained. "Some jobs might be functional, like building a business case for a new venture. Other jobs might be more emotional, like being the hero to a tough, unsolved problem." 

Salespeople need to dig deep to understand the issues and challenges faced by their customers and offer them new and innovative ways of addressing their concerns. You can use data analytics tools to help identify trends, pore through statistics, follow buying patterns and tap into a range of other methods to source information that will get your clients to their ideal solution. 

"Once you understand what your buyer is trying to do, you can pinpoint obstacles that are getting in the way of that, and you can help them overcome those pain points," added Wunker.  

2. Synthesize

Salespeople often service one particular industry or profession. Thus, they are in the unique position of being able to spot reoccurring or distinctive issues in their focus market long before they are even a blip on their customers' radar. 

 "Sellers have a useful seat at the table in that they typically sell to a similar cohort and can listen, synthesize information, and see patterns across businesses dealing with the same problems," said Quanstrom. 

Communicating the insight amassed from varying interactions within an industry is preferable to old-school sales tactics, according to Quanstrom. 

3. Listen

Getting insights requires the ability to ask really good questions and actively listen to the responses. Insight selling works most successfully when salespeople start their interaction with the buyer by listening. They use their knowledge to help customers identify what they need instead of simply telling them what to buy. 

Though it seems simple enough, listening does not come easy, especially to a salesperson who may be conditioned to always be ready with the next pitch. 

"The risks are that this is hugely demanding of salespeople," said Quanstrom. "They cannot be transactional, tone-deaf, nor shallow in their approach." 

But salespeople who get it right are well on their way to establishing themselves as trusted advisors. 

Wunker added, "Your customer will relish feeling heard." 

4 Morning Rituals to Improve Your Day

Most of us follow early-morning rituals that help us start our day. Typically, we follow our schedules because we tend to like a sense of organization and sameness in our lives.

As it turns out, there are scientific benefits to establishing a productive morning ritual. Forbes relayed how a University of Nottingham research team dug into productivity and how that ties to your energy levels and impulse control. The research revealed that your daily energy and self-control are similar to a muscle. The more you use them throughout the day, the more “exhausted” you can become.

Why is this important?

According to this research, we are the most alert as soon as we wake up. Even if you’re not exactly a morning person, early in the day is the best time to start establishing healthy rituals to make you a happier, more productive, person.

Let's look at some morning rituals you can do every day to improve your quality of life.

Exercise your body for a healthy mind

There’s no doubt you should work out a few times a week either at home or at work to develop a healthy body, and making your workout routine part of your morning ritual can have some seriously positive effects on your mind.

You don’t have to worry about a full-hour routine if you have a jam-packed schedule. A brisk 15-minute walk can do wonders.

The way that exercising helps is quite interesting. Harvard University  reported a correlation between people who exercise in the morning and those who are high energy. After just 10 minutes of exercising, your body releases a neurotransmitter called gamma-aminobutyric acid, otherwise known as GABA. GABA binds with your brain and can promote calmness and self-control.

Open your fridge before your email

Since we were kids, we’ve always heard that breakfast is the most important meal of the day. No one is questioning that it’s good to eat breakfast, but far too many people don’t eat anything in the morning.


Because they get caught up checking their email, watching the news, browsing social media and getting prepped for work. Basically, all of the stuff we tend to use our technology for every single day.

Before you even think about opening your laptop, make yourself something to eat. This simple ritual will not only fill you up but also give your mind the fuel it needs to get you through your busy day.

Make a detailed to-do list

The average to-do list may hurt you more than it helps you. Typically, we jot down the things we need to do, look at it throughout the day and get done what we can.

Your to-do list can become harmful if you start to stress out and worry about the things you didn’t get done yet, or things you thought you would get done but haven’t even started yet.

When you wake up in the morning, make a habit of not just writing down the things you have to do today, but also get detailed with your information. Include a time frame and any additional information that may help you get the task done more efficiently. Adding a time frame to your to-do list has multiple benefits. Besides giving you a tangible period of time to get your daily activities done and preventing procrastination, you will also begin to understand how long a task is going to take during a given day.

Having this information allows you to hone your planning skills and can lead to you being generally more productive since you have less clutter in your mind. 

Handle tasks one at a time

We have a bad habit of trying to multitask, especially first thing in the morning. When we are wide awake and have a laundry list of things that need to be done now, we have the habit of trying to take it all on at once.

It turns out that we were wrong. The American Psychological Association did a number of studies to see how the brain handles multitasking. As it turns out, multitasking actually makes us less productive over the course of the day. When we try to do multiple things at once we expend extra brain power that could be used to perform other tasks. We end up spending less time and brain power doing single tasks one after another instead of grouping multiple tasks together.

These four morning rituals will help you live a more productive life. After you are done eating breakfast and exercising, the last two tips play off one another. Once you’re done making your to-do list, you can start accomplishing your tasks one at a time.

Before you know it, these rituals will become healthy habits that you hold with you for life!

Scaling Your Business? Office Depot Exec Shares How to Get It Done

If you thought getting your business up and running was a difficult task, wait till you see what it takes to get it to the next level. Launching a business from scratch is a huge undertaking that takes countless hours of meticulous planning and hard work. However, what comes next – scaling your business – can be even more laborious.

Deciding when it is time to expand, figuring out how fast to grow and doing so in a way that doesn't alienate your customer base is a strenuous affair. As the executive vice president and chief retail officer for Office Depot, Kevin Moffitt has unique insight into the thought process of taking your business to the next level. In his current role, Moffitt is responsible for the company's retail business unit, which includes more than 1,400 locations throughout the U.S.

Moffitt has also served as Office Depot's chief digital officer, senior vice president of e-commerce and direct business unit leader, and vice president of e-commerce product management and customer experience. Prior to joining Office Depot in 2012, he served as director of e-commerce for Dillard's, vice president of strategy and customer experience for CrossView, and director of e-commerce operations and development for Circuit City.

We recently had the chance to speak with Moffitt about scaling your business and the steps you should take to ensure you don't damage your customer relationships in doing so. In addition, we were able to ask him some rapid-fire questions about technology, his career and advice he has received over the years.

Q: How do you know when it is time to start scaling your business?

A: When you have so many clients that you find yourself spending most of your time on operational overhead [rather] than your primary value proposition to those clients, it is time to seek assistance. That help usually takes the form of professional partners in the beginning, but eventually requires part-time or full-time employees to maintain focus on client experience and efficiency.

Many small business owners struggle to make this transition, and that's why we started our Workonomy business services – to give these entrepreneurs the ability to focus on their product while we provide the day-to-day infrastructure they need to grow their business.

Q: What should you do if you notice that your growth is hurting your customer relationships?

A: Once you start developing your own team of employees, you need to clearly assess your personal strengths as the company's leader, as well as areas you either aren't especially skilled in or simply don't enjoy (often the same areas).

Finding new team members who will complement your strengths is critical, especially in the early stages of growth. So, if you really enjoy and are skilled at building client relationships, hire someone who is a talented administrator or operational expert who will allow you to remain focused on maintaining your customer experience.

In my experience, many small business owners don't want to spend their time in areas like IT support, human resources or bookkeeping. Fortunately, these skill sets are easily outsourced to business services partners like Office Depot.

Q: When scaling your business, how should you train your new employees to ensure they have the same passion for customer relationships that you do?

A: I believe everyone needs to be passionate about serving a company's customers, but not everyone needs to be equally skilled in actively managing their relationships. It takes many types of people to create a successful team. Ensuring you have the right mix of personalities and skill sets to support both business operations and maintaining healthy client relationships is the key.

Q: How should you communicate with current customers that your company may be going through some changes as you scale up?

A: No customer wants to feel like they are a low priority. Ensuring consistency in the client experience, both for existing customers and new acquisitions, should be the No. 1 goal of any growth plan.

The main changes should be that perhaps they will be served by a different person, but reducing service levels as a whole is rarely beneficial for long-term growth.

Q: When scaling your business, is it more important to keep your positive relationships with past customers or build relationships with new ones? Should you be prioritizing efforts one way or another? 

A: It may prove more difficult to keep the first cohort of clients happy, but that doesn't mean it isn't important. In fact, these 'early adopters' of your company's service can be a valuable source of feedback as you scale up and grow.

Treat them like the founding members of your business community, like VIPs, and include them in key decisions. This approach can create very deep loyalty and a strong group of clients who not only were part of your key decisions but will be much more understanding when inevitable challenges arise during the process.

Rapid fire

Q: What piece of technology could you not live without?

A: Clearly, it's my mobile phone. I now get notifications every week telling me how many times I access it, and it's a bit scary. Our lives are in a state of constant communication, and the challenge isn't staying connected – it's being able to prioritize, as well as being able to shut off at times to focus and work through more strategic challenges that are often much more important.

Q: What is the best piece of career advice you have ever been given?

A: When I started my career, I met with my team's leader one-on-one for the first time. I was very fortunate that she was one of the strongest professionals I've ever seen in action, and her advice to me in that meeting was to always stay focused on the long-term potential of each customer – not just what the customer bought or didn't buy today, but what that person might or might not be buying from you 10 or 20 years from now. This was a very simple but incredibly powerful insight, and I have tried to stay true to it every day since.

In fact, this has been one of the fundamental characteristics of our Workonomy business services platform. We want to create long-term relationships with our small business customers and help them scale and grow.

Retail is a very transactional business. With Workonomy, we're much more focused on customer retention and loyalty. Businesses are often neglectful of customer needs in general, but even more frequently lack a focus on long-term client relationship management, and I believe it can be a powerful competitive advantage.

Q: What's the best book or blog you've read this year?

A: I was a history major in college, and I still believe the past holds many important lessons for us. My favorite read this year was William Manchester's biography of Winston Churchill, titled The Last Lion. As someone who faced one of the most serious leadership challenges in modern history, Churchill is someone we can all learn a lot from. I also loved Gary Oldman's portrayal of Churchill in the recent film Darkest Hour.

Q: What quality do you most seek in an employee?

A: A passion for success. I look for a positive attitude, a desire to work on a multitalented team, a sense of curiosity, and a desire to innovate and improve. I also seek to surround myself with people from different backgrounds and with very different skill sets. Teams that encourage diverse thinking have a big advantage.

One of the biggest benefits of coworking spaces, like our Los Gatos Workonomy Hub, is that the small business owner – a team of one – no longer has to toil in isolation in a home office. They're surrounded by other entrepreneurs and remote workers in totally different industries but who may be dealing with the same problems. This environment creates lots of collision opportunities where people from diverse backgrounds can collaborate with each other.

Q: As a leader, what's the biggest challenge you face?

A: The biggest and most important challenge is to create a positive culture with shared objectives and outstanding execution on those objectives. People do their best work and achieve strongest results when they are empowered, respected, challenged, and feel they are having a real impact.

That's the culture I strive to support, but it's never easy. Staying focused on the human side of business, both the internal team and the customers, is what makes the difference between a manager/operator and a true leader.

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