7 Discovery Call Mistakes Successful Sales Reps Avoid — and What They Do Instead, According to Experts

Discovery calls seem straightforward: learn about your prospect and present your solution. But in reality, they derail more often than they succeed. I’ve been there — watching a prospect’s energy fade as I talked too much, only to receive a polite “we’ll think about it” before they disappeared forever.

The truth? Most sales professionals unknowingly sabotage these calls and make predictable mistakes that kill rapport and crush their chances before the deal even begins.

After turning my own approach around and consulting with dozens of sales experts, I’ve identified the critical errors that cost deals and the simple adjustments that improve conversion rates.

Free Download: Sales Plan Template

Table of Contents

Why Discovery Calls Matter

So why do you even need discovery calls? Discovery calls happen when prospects already understand your tool or service’s basics and evaluate how well it fits their needs.

Since 96% of consumers research tools before ever speaking to a sales rep, they don’t need a feature rundown during discovery. What they need is hyper-relevant insights tailored to their business, industry, and unique challenges. They want to see exactly how the tool benefits them through customized use cases, industry-specific examples, and expert-level consultation on ROI.

This means your discovery calls must get deeper and show more value than ever. The data points to one clear conclusion: Connecting person-to-person and expert-to-expert has become the differentiator.

That’s because trust cultivates long-term relationships — 72% of company revenue comes from existing customers, proving that loyalty and retention matter more than one-time wins.

Mistakes to Avoid During Discovery Calls

discovery call mistakes

Discovery calls often fail due to common but avoidable errors that sales professionals make when interacting with prospects. Understanding these critical missteps — from talking too much to rushing into solutions — improves your conversion rates and builds stronger relationships from the start.

1. Talking too much, listening too little.

Ever been on a call where the sales rep talked at you for 20 minutes straight? You nod along, waiting for an opening, but it never comes. It’s not a conversation. It’s a monologue.

It’s easy to feel pressure to prove your expertise by over-explaining what you or your product does. But, the entire purpose of a discovery call is to find out what the prospect needs.

“Dominating the conversation — talking excessively about products or services without allowing the prospect to express their needs — can make the interaction feel one-sided,” warns Andy Springer, chief client officer at sales training company RAIN Group.

Try this: Ask three open-ended questions before you say a word about your product. See how much more you learn.

  • “What’s been your biggest challenge with [area your product solves]?”
  • “What would success look like for you in [specific timeframe]?”
  • “How are you currently approaching [problem], and what’s working (or not working)?”

“I think many sales teams forget to focus on listening and staying curious — what is the prospect’s tone, why do they go into certain areas, what do they care about?” says Stephen Findley, enterprise account management at Qwilr, an interactive proposal creation platform.

Next time you’re on a call, close your eyes for a few seconds while they speak. You’ll tune into their words, tone, and hesitations — and catch their real pain points, objections, and urgency.

I used to jump into calls with a head of marketing at a B2B SaaS company, ready to showcase my experience and list all the ways I could improve their content. But, I learned quickly that rattling off my skills wasn’t the way to win trust.

So, I stopped talking and started asking:

  • “What’s been frustrating you most about content?”
  • “Where do you see the biggest gap in your current strategy?”
  • “If you could fix just one thing about your content today, what would have the biggest impact?”

When they answer, I follow a three-step process: take notes, ask follow-ups, and only then introduce solutions once I fully understand their challenges.

The result? A natural conversation where, by the end, they’ve convinced themselves you’re the right fit.

2. Rushing to solutions before understanding the problem.

Would you trust a doctor who prescribes medication without asking a single question? Then, why should a prospect trust a sales rep who pitches a solution before understanding their real problem?

“The biggest mistake I see is rushing to present solutions before truly understanding the problem,” says Ali Newton-Temperley, agency revops consultant at The Agency Growth Pad.

According to Newton-Temperley, sales reps often listen for keywords that match their offering rather than deeply understanding the prospect‘s situation. This can signal to the prospect that you’ll recommend your solution no matter what and that you don’t have time to listen to them.

Instead, discovery calls are about finding out whether your solution makes sense at all.

“I think reps often approach these calls with their own agenda and prioritize this over meeting the client where they are in their journey. Making space and focusing on listening will help to build trust and, when done well, can often uncover all the insights you need to help agree with the prospect if it’s worth continuing a conversation,” says Findley of Qwilr.

Slow down. Ask thoughtful questions. Create space for the prospect to share. When you focus on the conversation — not the close — you’ll understand their real priorities, pain points, and what’s driving their decision.

3. Failing to go beyond surface-level information.

I sat in on five sales calls last month. In every single one, the rep jumped straight into pitching after the first problem surfaced.

For example, a prospect might say, “We need better lead generation.” Instead of asking what “better” means or why their current approach isn’t working, the rep immediately pitches their tool as the fix.

“Another critical error is failing to explore the ‘why behind the why,’” says Newton-Temperley. “When prospects share a need, many reps take it at face value instead of exploring the deeper motivations. There’s always a personal and emotional component to business decisions that gets overlooked.”

Christina Brady, CEO and co-founder of predictive enablement platform Luster, suggests going further instead of stopping at the first answer.

“Focus on questions that get to the personal impact of the problem. How does this problem affect the company, their department, and them individually?” Brady notes.

According to Brady, once reps understand the problem and the impact, they should drill down even further to uncover if there’s an urgent need to act. Brady suggests asking the following:

  • How long has this been a problem for?
  • Why is it still a problem?
  • What have you tried in the past to solve it?
  • Why haven’t those solutions worked?”

For example, if a head of marketing at a B2B SaaS company tells me they struggle with low content engagement, I don’t jump into tactics. I ask, “How are you currently measuring engagement?” or “What kind of reactions do you want your content to generate?”

These underlying questions tell me whether the issue is traffic quality, brand positioning, or misaligned messaging.

4. Not securing clear next steps.

A great discovery call is worthless if it ends with a vague “I’ll follow up soon.” Without a clear next step, deals stall.

In fact, 36% of sales managers believe that follow-ups sent to high-quality leads are the most important tracking metric.

“Many discovery calls fail because reps don’t establish clear next steps,” says Newton-Temperley. “The conversation might go well (in fact, it might have been incredibly positive), but without concrete follow-up plans, momentum gets lost, and ghosting becomes more likely.”

It’s not enough to assume the prospect will get back to you.

“Own the process and never leave a call or meeting without having mutually agreed on your next steps,” advises Marty Bauer, director of sales and partnerships at Omnisend, an email marketing platform. Setting a clear follow-up removes ambiguity and keeps things moving.

Before ending the call, lock in a concrete next step:

  • Schedule the next call: “Would next Tuesday work for a follow-up?
  • Confirm deliverables: “I’ll send over a content audit with recommendations by Friday.
  • Clarify decision-making: “Who else on your team should be involved in the next discussion?

In my own calls with B2B SaaS heads of marketing, I continuously wrap up with a firm next step — whether it’s sending a detailed proposal or booking a strategy session.

5. Not establishing clear expectations.

A discovery call without clear expectations wastes time. The prospect leaves uncertain, and you leave without a clear next step. Without direction, both sides walk away unsure: Was that a real opportunity or just a nice chat?

Heidi Fortes, GTM strategist at SalesCaptain, an outbound agency, suggests:

“Have a clear agenda for the call, state that agenda at the beginning of the call, and get confirmation from the customer if that sounds like a plan.”

Setting the tone upfront keeps things on track.

“An upfront contract is great for setting expectations and managing the time you have, but I think there’s a balance to making this feel natural and unobtrusive,” says Findley. “Summarising what you hear and then asking for permission throughout a call are all useful for me to gain further interest, and I try to focus on making a recommendation when I can.”

Instead of making the call feel rigid, think of it as guiding the conversation so both parties know what to expect. Here’s how to put Findley’s advice into practice.

Start with a simple agenda:

  • “I’d love to learn about your current challenges and share how I typically help teams like yours. If it makes sense, we can discuss potential next steps.”

Throughout the call, summarize what you hear and check-in:

  • “It sounds like your main challenge is scaling content without losing quality. Did I get that right?”

A structured yet natural conversation makes prospects feel heard, builds trust, and ensures every call leads to a clear next step.

6. Coming unprepared for the conversation.

Discovery calls should reveal a prospect’s real challenges, budget, and decision-making process. But if you haven’t done your homework, you’ll ask basic questions like, “What does your company do?” — wasting time and losing trust.

It’s no coincidence that 82% of top performers say they perform research ‘all of the time’ before reaching out to prospects. This preparation is what separates successful sales professionals from the rest. They’re able to ask questions about a prospect’s pain points, goals, and decision-making process to ask informed questions that show credibility from the start.

“Insufficient preparation — jumping into calls without researching the prospect’s business, industry, and challenges — can lead to generic discussions that fail to resonate,” says Springer.

But don’t just do surface-level research and read a company’s About page.

Research the prospect, spot potential challenges, and ask sharp questions like, “How are you currently handling [specific problem]?” or “What’s stopping you from hitting [specific goal]?

Before I hop on a call with a B2B SaaS head of marketing, I check their company’s latest blog posts, press releases, and LinkedIn activity.

If they recently launched a new product, I ask how they’re incorporating it into their content strategy. Or if their competitors are ranking for key industry terms, I bring that up.

When prospects see you’ve done your research — knowing their industry, challenges, and goals — the call stops being a pitch and becomes a business discussion.

7. Asking the wrong types of questions.

One of the biggest mistakes I made was relying on closed-ended questions that can be answered with a simple yes or no.

“Asking closed-ended questions limits the depth of understanding and can stifle meaningful dialogue,” says Springer. When you ask, “Are you happy with your current solution?” you might get a one-word answer, but you won’t learn why they feel that way or what they actually need.

Instead, ask questions that invite real conversation.

“I always ask direct questions, like what led them to speak with me today — they‘re busy, so there’s a reason they’re on this call,” says Bauer. “Then, follow up with questions about what they like and don’t like about their current solution. This is pretty uncommon but gets to the root reasons for their search.”

When I speak with a head of marketing at a B2B SaaS company, I ask questions like:

  • “What kind of feedback do you get from sales, customer success, or leadership on your content efforts?”
  • “Have you had any content initiatives in the past that didn’t work as expected? What happened?”
  • “How do you currently measure the success of your content, and what results are you hoping to improve?”

How to Get Discovery Calls Right

discovery call mistakes, how to get discovery calls right

You’re not there to take orders or recite a pitch. You’re there to guide the conversation, uncover real needs, and set the stage for a decision.

Here’s what the experts recommend to make your calls more productive, insightful, and actually worth your prospect’s time.

1. Structure the call for engagement and flow.

Follow a clear, natural flow that keeps the prospect engaged while giving you the insights you need.

Instead of running through a checklist, treat the conversation as an opportunity to learn.

Newton-Temperley recommends structuring discovery calls like a good conversation rather than an interrogation. Here’s a format she recommends:

  • Start with context-setting to establish trust and expectations. Explain the purpose of the call and outline what you hope to accomplish together.
  • Begin with broader questions about their current situation before narrowing it down to specifics. This helps your prospect open up, and you get a wealth of context and areas to follow up on.
  • Dig into their problem and their beliefs about how they might solve it. Avoid pushing your solution at this point — if you come across as unbiased, your help will mean more to them. Try asking questions and framing information with “typically we see clients with this experience…” This allows you to add value and make your responses engaging and less of an interrogation.
  • Lastly, discuss your solution and the ways it may be a fit. Understand their budget and the other stakeholders involved. Explore what those people will need to see in the proposal, too, and what you can do to make this look good for your prospect.

2. Use storytelling to build rapport and credibility.

During a discovery call, a well-placed story builds trust, makes your insights memorable, and helps prospects see themselves in the solution.

When buyers experience interactions that validate their challenges and affirm the value they’re seeking, they are 30% more likely to complete a high-quality deal. Storytelling is one of the most effective ways to create these moments where prospects feel truly understood and can see how your solution addresses their specific pain points.

“Using ‘typically’ stories can be a powerful way to dig deeper without triggering your prospect’s defensiveness or making them feel interrogated,” says Newton-Temperley. Instead of bombarding prospects with questions, share real-world examples that validate their challenges.

Here are some storytelling tips:

  • Frame their challenge with a relatable example. — “I recently worked with a Head of Marketing at a B2B SaaS company struggling with organic traffic. They were investing in content but not seeing conversions. Their real issue? They weren’t targeting decision-makers, just end-users.”
  • Use “typically” phrasing to ease tension — “Typically, when I speak with SaaS teams, I hear they struggle with content ROI. Is that what you’re experiencing, or is it something else?”
  • Make your story relevant — If they mention lead generation, share an example about pipeline acceleration. If they mention churn, highlight a retention-focused case study.

A compelling story makes prospects feel understood and turns a transactional conversation into a trusted partnership.

3. Balance guidance with flexibility in the conversation.

Understand how to guide the discussion while giving the prospect enough space to express their real challenges.

“At the end of each call, ask the prospect how they would rate your product from 1 to 10,” suggests Bauer. “Then, follow up with, ‘What would make it a 10?’ to refine their needs.” This shifts the focus from pushing a solution to collaborating on one.

Here’s how to strike the right balance:

  • Lead with curiosity, not assumption. Instead of assuming you know their problem, ask, “What’s driving your search for a solution now?”
  • Give space for their insights. Use silence strategically. After asking a key question, pause and let them think instead of rushing to fill the gap.
  • Adapt based on their responses. If they shift the conversation toward budget concerns, don’t force product talk — address their financial hesitations first.

Guiding without controlling keeps the conversation natural, deepens trust, and ensures the prospect feels heard rather than pushed.

4. Adapt your approach to different personality types.

No two prospects think the same way. Some want data and numbers. Others need a personal connection before they can trust you. Adjust your approach based on how your prospect processes information.

“Many reps don’t adapt their approach to different personality types,” says Newton-Temperley. “Analytical buyers need data, while relationship-focused buyers need trust-building conversations.”

Trying a one-size-fits-all approach? That’s a fast track to losing deals.

Here’s how to read and adjust to different buyer types:

  • The Analytical Buyer — Prefers logic and proof. Focus on numbers, benchmarks, and ROI. “Most companies see a 30% lift in conversions after implementing this.”
  • The Relationship-Oriented Buyer — Needs trust and personal rapport. Share stories and make the conversation more human. “I’ve worked with teams like yours, and what helped them most was…”
  • The Action-Oriented Buyer — Moves fast and hates fluff. Keep it direct. “Here’s the quickest way to solve X. Does that sound like what you’re looking for?”

The key? Listen to how they speak, not just what they say. When you match their style, the conversation flows naturally.

5. Take initiative.

Say you enter discovery calls without a clear structure. Reactive rather than proactive.

When you fail to take the initiative, prospects control the narrative, often leading the call down tangential paths that don’t reveal their core problems or establish your expertise. This results in insufficient qualification data and weak follow-up opportunities.

Fortes mentions, “They forget who is leading the call. Allowing the customer to lead and steer the call will always end in failure. It’s up to the AE to guide the customer through the buying journey while still allowing a degree of flexibility for questions and opportunities to advise.”

Prepare a flexible conversation framework with specific questions designed to uncover pain points. Balance listening with gentle redirection when conversations drift.

For example:

  • If they jump to pricing too early: “Before we discuss cost, let’s make sure this solution fits your needs.”
  • If they start venting about past vendors: “That’s helpful context. What’s most important to you in a new solution?”
  • If they hesitate on the next steps: “Would it help if I walked you through how others in your position approached this?”

How Small Adjustments Improved My Discovery Calls

I used to treat discovery calls casually — showing up, winging it, and assuming deals would close themselves. They didn’t. Instead, calls went nowhere, prospects lost interest, and I was left wondering what went wrong.

I’ve learned the hard way that every successful call requires structure, curiosity, and control. Sales pros who guide the conversation, ask the right questions, and build trust don’t just have better calls; they book second meetings, shorten sales cycles, and close more deals.

Apply these strategies, and your discovery calls won’t just improve. They’ll close more deals.

Inside Holding Companies — The Entities That Own Popular Businesses [+ Expert Tips]

Most people are unaware that they’re doing business with a holding company when they bank, buy a jacket, or sign up for a health club membership. I know firsthand because that was me.

Until I launched into the world of business reporting, I never considered the underpinnings of a company offering the service or goods I wanted. Back then, I was looking for a good price and a good value — and sometimes, perhaps shamelessly, for bragging rights about my latest purchase.

Since then, I’ve learned about holding companies, or businesses that own smaller operations. In this post, I’ll share everything I know about holding companies, including important definitions and how these business entities make money. Let’s dive in.

→ Download Now: Free Business Plan Template

Table of Contents

What is a holding company?

“A holding company is a parent company, usually a corporation or LLC, whose purpose is to buy and control the ownership interests of other companies,” according to the National Association of Secretaries of State (NASS).

The holding company doesn’t conduct any active business itself. Instead, it owns controlling interests in other companies, called subsidiaries, which may sell and manufacture goods and services. Holding companies are also referred to as “holdcos” or “umbrella companies.”

In many ways, the name “holding company” is self-explanatory in that it is “a company that exists to hold other business interests,” said Crystal Stranger, senior tax director and CEO of the tax consultancy OpticTax.com. By owning a majority of a subsidiary’s voting stock, the holding company can control that business’ policies and operations.

Business leaders can start a holding company by launching a new subsidiary and retaining a portion or all of its shares. Leaders can also create a holdco by buying the voting stock or shares in an existing company, according to the accounting firm Lauterbach & Borschow.

The holding company may choose to own different percentages of a subsidiary to maintain control, wrote NASS. These companies, whose management oversees how the subsidiaries are run, may have a smaller share if there are several owners. Their leaders can elect corporate directors and make major policy decisions, like deciding to merge or dissolve an operating company.

Alphabet, Inc. is one holding company you’ve probably interacted with. This holding company has a controlling share of Google and YouTube. Every time I search for and then watch a Bruno Mars video online, I’m interacting with a holding company.

Holding Companies vs. LLCs

A holding company can either be a corporation or an LLC, which stands for a limited liability corporation.

A corporate holding company pays taxes at the corporate level (21% of taxable income, which includes revenue minus expenses). These operations take advantage of losses from some of their ventures to balance out gains from newer companies, depending on the overall structure, said Stranger.

An LLC is a “pass-through entity,” so the ownership of an LLC holding company is, for tax purposes, the same as owning these companies individually, said Stranger.

Purpose of a Holding Company

Holding companies allows you to unify several businesses under one umbrella. This unity can help business leaders advance a common mission. For example, owning both the company that creates a product and the one that brings the offering to stores can improve a business’ operations.

Beyond that, a holding company can make major decisions through its single controlling entity that can apply to all the businesses or subsidiaries. That means policies across the board will be standardized and consistent under the same umbrella.

There are also risk mitigation benefits. Each subsidiary’s liabilities are generally contained within that entity, which protects other parts of the holding company. This benefit makes holding companies an effective way for business owners and managers to guard their assets and act as a “liability shield,” according to NASS.

Holding companies may also enjoy financial benefits from taxes and other areas. This umbrella structure helps businesses raise capital and manage investments across subsidiaries, too.

Types of Holding Companies

types of holding companies

Not every holding company has the same structure. There are four common types, which I describe below.

Pure Holding Companies

“A pure holding company is one that only has passive investments in other entities,” Stranger told me. Britannica Money explained it as “a corporation that owns enough voting stock in one or more other companies to exercise control over them.”

You probably haven’t heard of the Dutch-Belgian holding company Ahold Delhaize, but, more than likely, you know at least a few of its subsidiaries. The holding company owns grocery store chains Stop & Shop, Food Lion, Hannaford, and Peapod Online Shopping Company.

Mixed Holding Companies

A pure holding company only owns shares in subsidiaries. Meanwhile, a mixed holding company engages in its own business operations while simultaneously maintaining controlling interests in its subsidiaries.

These types of holding companies generate revenue both from their own business activities and from their subsidiaries’ earnings.

Nestle is one example of a mixed-holding company. A Swiss multinational food and drink processing conglomerate, Nestle owns subsidiaries like Gerber, KitKat, and Toll House. Nestle also owns and runs its manufacturing operations.

Financial Holding Company

Financial holding companies (FHCs) exclusively own financial assets, such as banks, insurance companies, and other financial services providers. In the U.S., FHCs must meet specific capital and management requirements that are usually more strict than other types of holding companies.

JPMorgan Chase & Co. is one prominent financial holding company. JPMorgan Chase Bank provides commercial banking services. That’s where I might open a bank account. J.P. Morgan Securities specializes in investment banking. Meanwhile, Chase Insurance Agency provides insurance coverage, as the name suggests.

Personal Holding Company

A personal holding company (PHC) is made up of a small or related ownership group, which are investors who own the holding company, that must meet special tax regulations to avoid a 20% penalty tax. In these companies, “more than 50% of the value of its outstanding stock is owned (directly or indirectly) by five or fewer individuals and which receives at least 60% of its adjusted ordinary gross income from passive sources,” according to Henssler Financial.

One example is Walton Enterprises LLC, the personal holding company for the Walton family who founded Walmart. This PHC owns a significant stake in Walmart and other family investments.

How do holding companies make money?

“Holding companies make money through their investments and the profit centers of underlying businesses,” said Stranger. These profit centers can involve selling goods and services, selling or renting real estate, providing financial services, and leasing or selling intellectual property rights.

NASS wrote that a pure holding company can generate funds to make investments by selling equity interests in itself or its subsidiaries. These companies can also borrow from payments they receive from subsidiaries. A mixed holding company can also earn revenue from its own business operations.

Pros and Cons of Holding Companies

“The choice to form a holding company can be life-changing for a founder who wants to scale several different ventures,” said Neal K. Shah, founder of the holding company CY MultiHealth, which owns CareYaya Health Technologies and Counterforce Health, both AI technology companies in the healthcare arena.

However, Shah notes that holding companies require “a sustained period of thoughtful decision-making.”

Below, I’ll cover the pros and cons.

The Benefits of Holdcos

A holding company’s appeal lies in its structure. Leaders can unify operations while offering liability protection. Each business is independent legally, meaning that each subsidiary has its own debts and obligations, according to Lauterbach & Borschow. This helps minimize risk.

Further, losses from one venture can balance out gains from other subsidiaries under the same holding company. When one venture is faltering, the holding company may still be able to come out ahead overall when other entities are thriving. That scenario can be especially common when the holding company owns businesses serving different industries.

Holdcos Challenges

Even with their benefits, running a holding company comes with challenges. If the holding company owns subsidiaries in diverse fields and different locales, parent companies need expertise in multiple areas to deal with distinct environments, according to the accounting firm Condley and Company LLP. The holdco’s management team must carefully balance the parent company’s strategic objectives with the rights and expectations of minority shareholders.

Diverse business types and regulations reinforce the importance of a holding company’s structure. For example, a holding company will need tax and legal professionals who can sort through the requirements of different localities and states. You may even need to navigate international law if you are operating outside of more than one country.

As a result, “the formation and compliance costs [of holding companies] can be significant, especially if the holding company controls multiple subsidiaries,” according to Condley and Company LLP.

Holding Companies in the Real World

While researching this blog, I learned that my own bank is part of a huge financial holding company. Some of my favorite vendors and even a former employer are also subsidiaries of a large holdcos. These companies are a large part of the business world today. So next time you make a purchase, you might want to look up who really owns the company you’re buying from.