The Art of Objection Handling

Estimated reading time: 10 minutes

This article is part of my Founder Led Sales Series, where I’ll tackle how to handle objections from prospects. For the complete overview of the series, see The Startup Founder’s Guide to Early-Stage Revenue Success.

When most Founders encounter objections during sales calls, their natural instinct is to get defensive, start hard-selling, or avoid the objection entirely. But what if I told you that objections are actually one of the strongest signals of genuine prospect engagement?

After a decade of leading sales teams and helping startups scale from early revenue to eight figures, I’ve learned that mastering objection handling isn’t about memorizing clever responses. It’s about fundamentally changing how you think about resistance in the sales process.

Mindset Over Everything

Most people have this Hollywood version of sales in their head, like Don Draper delivering the perfect pitch. Or the smooth-talking closer who has the right line to close every deal. The underlying assumption is that salespeople are ‘naturals.’ That you either have it or you don’t. This is problematic because it sets an impossibly high standard for Founders. And it’s also simply not true. I fundamentally believe that anyone can be successful in sales.

In reality, sales performance rests on three pillars, in order of importance:

1. Mindset (most important)
2. Behavior
3. Skill (less important)

Most Founders focus on what to say instead of how to think. Objections are make-or-break moments in your sales process and your mindset when a prospect pushes back will determine whether you close deals or watch them slip away. Even if you know the perfect sales techniques, they will fall flat upon execution if you have the wrong mindset. 

Here’s the thing: this approach is actually easier for Founders too. It’s impossible to memorize the right thing to say for every situation. There are countless potential objections and concerns. Too many to create canned responses for. It’s much easier to learn how to think about objections. The Founders I work with are smart people and this mindset framework allows them to unlock the right way to handle any objection that comes their way.

The Three Mindset Shifts That Change Everything

Before covering the sales tactics and frameworks, let’s review the mindset to succeed in objection handling.

1. Embrace Curiosity

When a prospect raises an objection, your default mode should be genuine curiosity. However, that’s not the case for most Founders. When you’re the Founder, every objection feels personal. They’re not just questioning the product, they’re questioning you. Your vision. Your judgment. Your life’s work. Most Founders feel defensive and a laundry list of other disruptive emotions. 

Not only are you dealing with personal emotions, you’re also fighting uphill against ingrained prospect skepticism. As salespeople, you start with a trust deficit. Prospects are naturally skeptical of salespeople and often have their guard up when they first interact with sellers. They’re constantly wondering if they’re being sold, manipulated or about to be pressured. This is very different from how Founders are used to being perceived in other contexts as visionaries, experts, or leaders in their field.

But it’s nearly impossible to be defensive when you’re genuinely curious about what your prospect is sharing, what their needs and wants are, and what’s driving their concerns. Curiosity also helps to bridge the trust deficit by changing the dynamic entirely.

Prospects can sense your curiosity and they respond well to it. Instead of feeling like they’re being “sold to” or questioned they feel heard and understood. If you’re defensive, prospects close down. When you’re curious, they open up and share more valuable information. Once they feel heard and see you differently from other salespeople, they’ll be in a receptive state to listen to you and consider your product. If you aren’t curious about them, why would they be curious about you?

2. Detach from the Outcome

This is especially challenging for Founders doing early sales where every deal feels like it matters. The stakes feel high when you have a short runway, you’re desperate for validation of product-market fit, and you need proof that your GTM strategy works. But when you’re attached to closing every deal, your natural inclination becomes pushing harder when you encounter resistance which typically pushes prospects away.

Here’s what happens when you get overly attached to outcomes: you become the stereotypical “pushy” salesperson you probably hate dealing with yourself. You prioritize closing the deal over solving the prospect’s actual problem. Your responses become less sincere and more calculated.

For example, when a prospect asks if you have a certain feature, attachment to the outcome creates pressure that leads to hand-waving or bending the truth instead of giving an honest “no.” You might say “we’re working on that” when it’s not even on your roadmap, or “our customers have a workaround for that” when you simply don’t have the capability. This dishonesty reinforces and exacerbates the trust deficit I highlighted earlier.

Detaching from the outcome allows you to stay curious, ask better questions, and counterintuitively, close more deals. When you’re not desperate for the sale, you can focus on whether there’s genuine fit. You can give honest answers that build trust. You can walk away from bad-fit prospects instead of trying to force square pegs into round holes.

This doesn’t mean you stop caring about results. It means you focus on the process, having genuine conversations, understanding real problems, and determining mutual fit rather than attempting to force a prospect towards a predetermined outcome.

3. See Objections as Engagement Signals

Here’s a counterintuitive truth: every prospect has objections and it’s important that they voice them. 

It’s counterintuitive because most Founders think objections are a bad sign and view the lack of objections as a positive one. In reality, it’s the reverse. Prospects who raise tough objections don’t concern me. But prospects who say, “This looks great” without any questions do. They’re the ones who ghost you. Just because someone doesn’t state objections doesn’t mean they don’t have them.

Their silence typically means that either they’re not engaged enough to care or not comfortable enough with you to share their real concerns.

When someone takes the time to voice objections and ask hard questions, they’re signaling genuine interest and engagement. They’re spending time and energy processing your solution and thinking through potential roadblocks. Ask yourself: why would someone spend more time engaging with you if they weren’t interested?

This reframe is crucial for founders because it transforms your emotional response to pushback. Instead of feeling attacked when prospects raise concerns, you start recognizing engagement signals. You shift from defensive to curious.

Prospects who care enough to raise objections are prospects who are actively considering buying. 

These three mindset shifts work together to transform how you experience objections. Approaching prospects with genuine curiosity, detaching from the outcome, and recognizing objections as positive signals changes how prospects perceive and respond to you. This mindset creates the foundation that makes the objection handling skills we’re about to cover easier to implement and significantly more powerful.

How to Respond to Objections 

Now that we’ve established the right mindset, let’s talk sales skills. The following frameworks will help you navigate objections effectively.

The Power of Reversals: Questions Are the Answer

The most powerful objection handling technique isn’t having the perfect answer, it’s about asking the right question. A reversal is simply responding to a question with a question. 

I know this might sound like playing games but stay with me. It addresses the core challenges Founders face when prospects push back and there are compelling reasons why this approach works.

Reversals work well because prospects often reveal only surface level information initially. We must dig deeper to uncover their true problems and emotions. This approach also helps you avoid the mutual mystification that kills deals. This is when prospects say one thing, you interpret it differently, and both parties leave with completely different understandings.

Reversals provide four key advantages for Founders handling objections:

• Uncover the Prospect’s Pain
  • Reversing helps reveal the underlying issues or concerns that the prospect may have. By asking clarifying questions, Founders can better understand the prospect’s pain points.
• Resolve Objections
  • Questions help the prospect resolve objections. Some people need to speak out loud to make sense of a situation.
• Avoid Getting Boxed In
  • Reversing keeps the conversation fluid and prevents Founders from being cornered into providing premature answers. It maintains control over the direction of the dialogue.
• Gain Credibility
  • By asking insightful questions, Founders demonstrate their understanding and expertise. This builds credibility and trust with the prospect.

The simple rule: Whenever a prospect says something that leaves a question mark in your mind, ask them a question.

Example

• Prospect: “This seems expensive.”
• Instead of defending your pricing, ask: “What were you expecting to invest in a solution like this?”

Most importantly, reversals demonstrate genuine curiosity, which aligns perfectly with the first mindset shift we covered.

For the complete framework with detailed examples read: Questions Are the Answer: Asking & Reversing.

The ARQ Method

A – Affirm/Acknowledge

Acknowledge or validate what the prospect is saying. This shows you’re listening and understand their perspective.

Affirm → Positive validation 

• Example: “That’s really helpful context.”

Acknowledge → Neutral recognition of a statement

• Example: “Okay. That makes sense.”

R – Repeat

Restate their point in your own words to ensure clarity and confirm understanding.

• Example: “It sounds like cost is very important to you.”

Q – Question

Conclude with a question that digs deeper or to transition the conversation to a new topic.

• Example: “What is your budget?”

Putting It Together

Founder: “That’s really helpful context. It sounds like cost is very important to you. What is your budget?”

Prospect: “We don’t have a set budget but I know we’d be much more likely to get this approved by leadership if it stays under $50k.”

Notice how this approach gets you crucial information before making pricing concessions. You are getting information, rather than giving it. When you do this, you might discover they can afford your full price or learn they need a smaller discount than you planned to offer.

For more on The ARQ Method, including tips, read: The ARQ Method.

Getting Started

The three mindset shifts create the foundation for effective objection handling. Curiosity prevents defensiveness, outcome detachment keeps you focused on fit rather than forcing deals, and seeing objections as engagement helps you welcome tough conversations. Use reversals to dig deeper and the ARQ method to structure your responses.

Start applying these techniques in your next sales conversation. Remember that you’re not trying to overcome objections, you’re trying to understand them. When prospects feel heard, they become more receptive to your solution.

📥 Download The Art of Objection Handling Deck