Customer Insights to Transform Sales Conversations


We hear a lot about equipping salespeople with customer insights to help them move from simple questioning to exploring challenges and discussing solutions with customers. But what are these insights that will transform the conversations salespeople have?

Sales customer insights

Let’s drill down into the market and customer insights that can really add value for salespeople, under the following sections:

  1. Qualifying characteristics: Things to look for in an organization that make it a good target
  2. Persona insights: Intelligence on the typical decision-makers, influencers and users of your proposition
  3. Market insights: Topical themes and drivers that can open conversations
  4. Use cases: Business activities and workflows addressed by your proposition
  5. Customer business challenges/opportunities: Issues that customers face or opportunities to improve the way they do things that can motivate prospects to engage

1. Organizations’ qualifying characteristics

What are the characteristics of organizations that are likely to make them a good fit for the products and solutions your company sells? This isn’t simply about describing the different target segments, it’s about sharing those snippets of intel that help salespeople focus on the right prospects early on.

This is important for anyone who prospects or handles inbound calls – could be both inside sales and field sales.

Guidance shouldn’t just be around high-level attributes for the prospect like revenues or number of offices but should get into factors that are specific for your proposition. For example, a minimum number of maintenance technicians would be critical if you sell a field service app.

You also need to equip salespeople to qualify prospects who already have a solution from a competitor – are there some tell-tale indications of dissatisfaction? If not then you may be wasting your time but we will come back to disrupting the status quo later.

Knowledge and flexibility to engage prospects

Most organizations develop a set of qualification questions for salespeople to use. However, what they often don’t do is equip salespeople with the broader knowledge needed to have flexible initial discussions – to engage the contact and ‘set the hook’ for a more in-depth follow-up meeting. Persona and market insights come in here – even though we’re at an early point in the sales process.

2. Persona insights and intelligence

There’s not always great alignment between the ‘persona profiles’ that get produced by product or marketing teams and what salespeople actually find useful when they are preparing to talk to a customer.

This is because the information product managers find useful in designing new products and the insights marketing teams need to take products to market, are not the same as the persona intelligence salespeople are really after.

Salespeople are interested in:

  • Guidance on the business roles to target for the products they sell and the segments they sell into
  • Education
  • Example job titles
  • Roles and responsibilities
  • What keeps them awake at night
  • Critical business activities and workflows they are involved in
  • Specialist knowledge
  • Where they go to get information
  • Other personas they work with

It’s also crucial to give salespeople a heads up on the types of challenges faced by different personas.

3. Market insights and topics

To get initial traction with a prospect and then build credibility, it’s important for salespeople to be up to date with the latest developments in the industry in which the customer operates. These themes and topics will be driving change in that industry and, potentially, opportunities and challenges for the customer.

A small team in marketing or sales enablement needs to keep an eye on market shifts, new regulations, moves by big players in an industry, etc., and capture them.

How you then get these topical insights in the hands and heads of salespeople in a timely fashion is another problem – one that most organizations find hard to solve. Sending out a monthly market insights note used to work, but email overload means messages like this now get ignored.

If you have a sales enablement platform, one option is to add a latest insights panel on the home page, so salespeople’s attention is drawn to the most up-to-date ideas whenever they log on. Ideally, the user should be able to set up filtering, so they only see insights that relate to the markets they sell into.

4. Use cases you address

When you onboard new salespeople or bring new products to market, you need to equip people with a solid understanding of the customer business activities and workflows served by your company’s solutions.

If salespeople don’t properly understand the relevant business processes they can’t have credible conversations around the opportunities and challenges the customer may face. Their business proposals will end up being generic, regardless of how well they write them.

Pulling together this sort of information isn’t usually an issue, and is typically done by the Learning team working closely with relevant product managers. Making this knowledge accessible in a way that’s easy to dip into and use before calls and meetings can be more problematic. Delivering insights to salespeople is discussed in Part 3.

5. Customer business challenges and opportunities

Perhaps the most important thing you can do for salespeople, is to equip them with a heads up on the challenges and opportunities that could be top of mind for the different decision-makers and influencers they call and meet. Maybe 10 years ago, a salesperson could rely on good questioning technique and easy going prospects who were happy to sit there and answer question after question. This is no longer the case.

Buyers expect salespeople to understand their business and want to be engaged in thoughtful conversations to explore how they might improve processes or workflows to take advantage of new opportunities or address new threats. To do this, a salesperson needs to prepare him or herself with an understanding of what a particular persona type may have on their mind.

Disruptive insights

There’s been a lot of talk about disruptive insights and a number of selling methodologies put them at the heart of the early sales process. The idea is to bring new insights and ideas to prospects that might get them thinking about new ways to do things – to disrupt the status quo.

Market themes can be a good place to start when you’re looking for insights to get conversations going right at the start of the sales process. But to be disruptive in a situation where the prospect isn’t yet thinking about changing the way they do things, you have to instill fear – the fear of missing out (FOMO) or fear that they are taking unacceptable risks.

To do this, you have to know about:

  • The risks they may be taking based on what you know about the type of operation they run and your knowledge of the risks faced by other similar companies
  • How similar companies have changed what they do and gained benefits

Taking a disruptive approach and trying to get the contact out of their comfort zone doesn’t work well if the customer is already in the market for a solution. In this case, they already understand the challenges they face, so aggressive-disruptive tactics may be a turn off.

Issues vs. impacts

As any good consultative salesperson will tell you, it’s not enough to uncover the issue or problem the customer is facing. You also have to drill down to discover what the impact of addressing that issue might be in terms of improved efficiency, lower costs, higher revenues, mitigated risks, etc.

When you work with stakeholders to capture the likely top of mind challenges for different personas, you need to capture guidance for salespeople not only on the issue the customer may face but also how they are likely to see the impact, based on the persona role in question.

Different personas will see value in different ways.

Imperative for salespeople to be better prepared

More than ever, in this time-challenged world, preparation has become the key to successful conversations with customers. Business executives expect salespeople to add value to their day by bringing them new insights and ideas. Sit there and just ask questions and you’ll be out of the door after 10 minutes.

You can’t rely on salespeople to figure out these insights into potential customer challenges and opportunities all on their own. Product marketing and sales enablement teams need to work with knowledgeable people across the business to capture this information.

Who to get input from and how to prepare

Let’s start with the people you need to engage with to capture customer insights.


You’ll need to get input from your best salespeople. They are close to the customer and will understand the kind of issues and opportunities they face and how these are impacting or could impact the business. Also, if other salespeople see that the project has team members they respect contributing to the process, they are more likely to buy into the outputs.

Marketing or product marketing

People from Marketing who have knowledge of customers and the markets they operate in, will be able to make an important contribution. Product marketers will also be immersed in the type of language customers understand.

Product management

Product managers should have an intimate knowledge of the customer business activities and workflows addressed by a given product or solution. They will have regular conversations with customers, as part of the process of deciding future product direction and prioritizing development work.

Professional services/customer success

In firms with professional services teams who work with customers to devise and implement solutions, these people often have excellent insights into customer workflows and the challenges your products are solving. Customer success teams can also provide valuable insights.

Customers and prospects

You may also need to recruit and get input from decision-makers and influencers at target accounts, to validate the thinking of the internal team. For existing products and services you may feel this is unnecessary, but for new propositions, it will be essential.

Preparation steps

Now, let’s go through the steps you need to prepare.

1. Put the stakeholder team together

Now you have to get commitment from people to participate in the overall process; get commitment from a core group to attend workshop sessions; and get commitment to participate on separate calls or online.

2. Specify the market and customer insights to be captured

From the range of possible insights you might want to capture to power better sales conversations, you need to decide which are most relevant and useful for salespeople at your company.

For most B2B propositions, the critical items will include:

  • Market themes that are driving challenges and opportunities for your target customers
  • Top of mind challenges and opportunities in the different business areas your products serve and for the personas you must sell to
  • Disruptive insights that could motivate prospects to engage with you and explore alternative approaches

3. Determine segments, workflows, and personas to be addressed

In advance of the first session you should work with one or two core stakeholders to develop a view over:

  • Target segments with insights into the characteristics of a company that would make it a potentially good fit for your products
  • Business activities and workflows that are addressed by your solution with a brief description of each
  • Personas who are likely to be decision-makers or influencers in any decisions to engage with your firm and buy from you

Don’t leave the discussion on segments, workflows, and personas to the first workshop. If you do this, you will find the first one to two hours of your workshop are taken up into huge detail on exactly what the target market is and who you sell to. Ideally, you should arrive at the workshop with a view from one or two senior stakeholders that can be quickly and efficiently tested with the broader stakeholder team.

4. Identify and recruit customer contacts

If validation with actual customers and prospects is going to be part of your project, then you will also need to:

  • Determine the sets of customer and prospect contacts that will be required to get Insights across the defined segments, workflows, and personas
  • Research contacts at customer organizations who may have the necessary knowledge to provide insights across segments, workflows, and personas
  • Determine the most appropriate inducement (e.g. payment, donation to a charity)
  • Determine the optimum interaction method (e.g. round table, phone interview, online survey)
  • Make contact with customers to get their agreement in principle to take part in the research project

5. Mine existing materials for relevant insights

Unless you are working on a brand new product or proposition, there will always be existing materials to mine for insights, in advance of the workshop. Doing this will ensure you arrive at the session armed with the output from previous work done by the company on customer insights. Stakeholders are always very keen to see past work they’ve done being leveraged and taken forward.

6. Conduct desk-based research

Using the web and other research tools you have access to, conduct research into current themes in customer markets that could be driving opportunities and challenges your company can solve.

7. Produce workshop pre-read

To show stakeholders that you’ve undertaken a significant amount of preparation work in advance of the workshops and have leveraged any past work, you should pull together a short workshop pre-read document. Asking attendees to scan through the pre-read document in advance of the session will also ensure they are ready to hit the ground running when they arrive at the workshop.

Running customer insights workshops

Now let’s discuss how to run a customer insights workshop and how to structure one.


The typical agenda for a customer insights workshop might look like this:


Timings for a half-day workshop might be as illustrated below.

Project kickoff

Don’t be tempted to omit the project kickoff section. A number of the attendees may not have been involved in earlier discussions about the project and won’t really know why they have been invited – busy people want to understand what the project is about, why it’s valuable, and what’s going to come out of the work.

Ideally, you will set up a half-hour project kickoff call before the main workshop to make sure everyone buys into the project and you address any concerns in advance. This will mean you can get straight to the intake discussions with attendees in the actual workshop.


Whoever is leading the session will need to make sure they keep the pace going while allowing people to ‘get on the table’ what they want to say. Getting the balance right between pushing the discussion along and frustrating someone who has an important point to make isn’t easy. One technique is to have a flip chart ready to capture and park any contentious or peripheral points for discussion by the team at a later date.

In the themes and drivers section, explain how these need to relate to the areas of business your company serves and should drive challenges and opportunities for customers that your products and solutions can address. Try to steer the conversation away from general market themes that don’t meet this criterion.

For the opportunities and challenges session, you can focus either on one business area / use case for the customer at a time or do this by persona. My recommendation is to work through thinking about challenges and opportunities by business area and then assign the relevant personas at the end.

Remember, for each challenge don’t just capture the business issue but make sure you get a view from the team on how the customer is likely to see the associated pain or opportunity.

Value of in-person sessions

Getting some of your most knowledgeable and experienced people together to figure out what’s going on in your customer’s marketplace, the top of mind challenges they face, and opportunities to improve processes and performance is hugely valuable.

The team dynamic is always more powerful and generally more positive when people are physically in a room together! It’s also far easier to facilitate sessions to make sure everyone gets the opportunity to contribute and everyone is engaged and focused on the task at hand. So under normal circumstances, the travel costs are more than offset by the benefits gained from getting people into a room.

Remote sessions demand greater facilitation skills

However, COVID-19 has made a huge difference to the way people work, which is likely to persist beyond the pandemic. The appetite for travel is lower and people are getting used to working together via video call.

Customer insights sessions can be undertaken with stakeholders attending remotely and I’ve run successful sessions using video conferencing or web collaboration tools for many years. But facilitation takes a lot more skill. Knowing that people are paying attention and aren’t doing their emails can be difficult. Advising people in advance that they should turn cameras on for the session helps a lot.

Finally, with remote attendance, you have to run shorter sessions to ensure you keep people’s attention. This may mean you have to run a series of two-hour workshops on different days to get all the input you need.

Managing conversations

Making sure one or two people don’t dominate the conversation, without being rude and cutting them off can be tricky. But it’s vital to do this if you want to get a balanced view and tap the knowledge of all those attending.

This is where the facilitation skills of the person leading the session really come in. They need to have the presence and strength of character to guide and control the conversation and make space for everyone to have their say.

Having a clearly articulated agenda and a set of supporting slides that indicate a structured process is going to be followed is vital. This will help stop a powerful character taking the session down a rabbit hole and help steer things back on course.

Team alignment

Attendees often comment that they have really enjoyed one of these customer insights sessions. In addition to the primary purpose of capturing and developing the company’s understanding of its customers, these workshops often deliver huge value to attendees, as they share knowledge and get aligned around a common point of view.

Capturing output

To be efficient and get maximum value out of workshop sessions, you will need to find some way to capture output from attendees as the workshop proceeds. Flip charts and sticky notes used to be the standard way of doing this. You soon find out this is a pretty inefficient way of capturing insights, as everything has to be unscrambled and written up after the session, and people forget exactly what they meant at the time.

The other problem is you have to physically have all attendees in the room so they can take part and share what they are thinking. In a post-COVID world, where travel is likely to become far less usual and people expect to join sessions via video call, flip charts and sticky notes simply won’t work.

Delivering insights to salespeople

So far we’ve focused on what insights to capture and how to capture them. But how do you deliver this knowledge to salespeople in a form that ensures all your hard work actually gets used?

Just-in-time learning

The key today is to give salespeople access to relevant learning on-demand when it’s needed. A well-constructed sales playbook can do exactly this. Sales playbooks should be designed to equip salespeople with the critical chunks of knowledge they need to successfully interact with customers at different points along the sales process. You want to make it easy for them to access this just-in-time learning for the call, meeting or communication they are focused on now.

How to structure a sales playbook

The different types of things you need to know to sell effectively depend, of course, on the sales situation and where you are in the sales process. So it makes a lot of sense to structure the presentation of information around the sales process – to facilitate just-in-time access.

A typical playbook structure might look like this:

Sales Stage 1: Prospecting

  • Insights into the markets served by the customer
  • Possible top of mind issues for target personas
  • How to position your company as relevant and of potential interest
  • Conversation openers and questions

Sales Stage 2: Exploration

  • Likely goals, issues and pain for different personas
  • How your company has solved problems for similar customers
  • How to articulate ‘what life could be like’ with a solution

Sales Stage 3: Needs Analysis

  • Needs discovery questions
  • How your products address particular customer challenges
  • Challenges solved for other customers and value delivered

Sales Stage 4: Solution Evaluation

  • Top points of differentiation for your company and products
  • Corporate credentials
  • Positioning vs. competitors

The idea is a salesperson can quickly jump to the right page in the playbook for the current step in the sales process and grab relevant ideas, insights and guidance – to go alongside the account-specific research they do for the prospect.

If your company sells one product into one industry segment to one main buyer, then you could fit this type of information into a PDF. On the other hand, if your reps sell into more than one segment, to multiple personas and have several products and services to offer, then they are going to need access to a whole load of knowledge to sell effectively.

Putting all this into a 50 page PDF – even one that’s designed around the sales process and has information separated out by persona – will ensure it gathers dust in the bottom drawer of the salesperson’s desk.

Digital delivery options

Traditionally, sales playbooks have been delivered as PDF documents, but the arrival of HTML5 has spawned a new generation of digital sales playbooks that deliver a far more engaging experience including interactivity, video, quizzes, and just-in-time’ access to information before meetings and calls.

Learning playbooks

A good option for building learning style sales playbooks that include videos, knowledge checks and navigable content, is to use an industry-standard software package like Articulate Rise, Lectora or Adobe Captivate. Using an authoring tool like this dramatically shortens the time it takes to produce HTML5 content that can be deployed as a SCORM package on an enterprise learning management system (LMS), and rolled out to salespeople for access via phone, iPad or laptop.

Guided selling tools

Having something on-screen that’s more interactive and flexible than a traditional presentation deck – to catalyze and guide the conversation with the customer – can be extremely useful. When you’re not face-to-face, you can no longer rely on traditional relationship sales skills to get the prospect to start the buying journey with you.

This is where interactive, guided sales tools can really help. With the problem of maintainability fixed, expect to see the use of interactive tools that help salespeople guide early conversations with customers, provide thoughtful insights and deliver the right messages, to increase exponentially.

Also published on Medium.

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