Make Selling Fun Again with Hubspot Style Techniques

Modern sellers can transform pressure-filled outreach into enjoyable, human conversations by borrowing Hubspot style techniques that focus on fun, authenticity, and value instead of hard closing tactics.

The original story behind these ideas comes from a classic sales article about rediscovering joy in selling. This guide turns those lessons into a practical, step-by-step how‑to you can apply in your own process.

Why Fun Matters in Hubspot Inspired Selling

When selling feels forced, prospects sense it immediately. The classic article this guide is based on explains how one discouraged salesperson turned things around by treating every call as a chance to connect, not to pressure.

Fun in selling matters because it:

• Reduces anxiety for both you and the prospect
• Makes you more creative and curious
• Leads to more honest discovery conversations
• Builds long-term trust instead of short-term wins

These outcomes align closely with a Hubspot style, inbound-first approach: help first, sell second, enjoy the process throughout.

Step 1: Shift Your Mindset with a Hubspot Style Approach

The original story starts with a salesperson who hated cold calls. Every dial felt like a test of worth and a battle with rejection. The turning point came when he reframed the entire job.

Adopt a Help-First Mindset

Instead of trying to get something from prospects, decide that your role is to:

• Learn about their world and challenges
• Offer ideas, resources, and introductions
• Leave them better off whether or not they buy

This shift mirrors inbound, Hubspot style thinking: you are a consultant, not a closer.

Detach From the Outcome

The salesperson in the story realized that pressure came from obsessing over quotas and yes/no answers.

To detach from the outcome:

1. Set behavior goals (calls, conversations, follow-ups), not just revenue goals.
2. Measure learning per call: what did you discover?
3. Celebrate effort and improvement, not just deals.

When you are less attached to the outcome, you relax. Prospects relax. Conversations become more natural and, paradoxically, more productive.

Step 2: Turn Every Call Into a Game

The heart of the source article is a simple idea: making a game out of selling. Instead of dreading each call, the seller decided to have fun regardless of the response.

Design Your Personal Sales Game

Create rules that make selling enjoyable for you. For example:

• Point system: 5 points for a live conversation, 10 for a new discovery, 20 for a booked meeting.
• Daily challenge: Ask at least one brave question on every qualifying call.
• Curiosity quota: Capture three insights per day about your market or buyers.

By turning calls into a game, you focus on actions you control. This is completely aligned with Hubspot styled, data-aware selling where consistency beats occasional heroic efforts.

Use Lightness to Lower Resistance

In the story, humor and genuine curiosity changed the tone of otherwise tense calls. You can apply that by:

• Opening with a relaxed, human greeting instead of a rigid script
• Admitting when a question is bold: “This might be a big question for a first call, but…”
• Letting prospects say no quickly so you both save time

Prospects are used to aggressive pitches. When you show you can laugh, listen, and accept no for an answer, you stand out immediately.

Step 3: Build a Simple, Repeatable Hubspot Style Process

Fun without structure quickly fades. The salesperson in the original article found success by repeating a light, consultative routine day after day, similar to how a Hubspot user might follow a consistent pipeline playbook.

1. Prepare a Short, Flexible Call Framework

Instead of a rigid script, use a loose framework:

1. Warm opening: Who you are, who you help, and why you are calling.
2. Permission: “Is now a bad time?” or “Do you have 2 minutes for a quick question?”
3. Discovery: 2–4 open questions about their current approach and challenges.
4. Value: A quick idea, story, or suggestion tailored to what you just learned.
5. Next step: Only if it clearly makes sense for both sides.

Keep it short. The goal is a natural conversation, not a monologue.

2. Track What Makes Selling More Fun

Use a simple spreadsheet or CRM to note:

• Which questions spark the best conversations
• Which types of prospects enjoy your style most
• What topics make you most energized when you talk

Over time, you will see patterns. Lean into the types of outreach, industries, and problems that you genuinely enjoy discussing. This is where your best results will come from.

Step 4: Communicate Like a Human, Not a Script

A central lesson from the source article is that people respond to honest, relaxed communication. The original seller stopped pretending to be overly polished and started speaking plainly.

Use Clear, Simple Language

To keep sales conversations light and effective:

• Avoid buzzwords and heavy jargon
• Explain what you do like you would to a friend
• Ask questions one at a time, then listen fully

This human style is a hallmark of a Hubspot style, inbound experience, where clarity and empathy matter more than cleverness.

Invite the Prospect to Co-Create the Next Step

Rather than pushing for a rigid outcome, ask:

• “What would be most useful for you after this call?”
• “Would a quick walkthrough help, or should I send you a short summary first?”
• “Is there anyone else on your team who should weigh in?”

When prospects help design the process, they feel ownership. That makes your funnel both more collaborative and more enjoyable.

Step 5: Keep Learning from Every Interaction

In the original narrative, the salesperson did not suddenly become fearless. He improved by reflecting after each conversation and tweaking his game plan.

Run a Simple Daily Review

At the end of the day, ask yourself:

• Which call felt the most fun and why?
• Where did I notice tension in myself?
• What did I learn about my market or product today?

Document these insights. Over weeks and months, they become a playbook just as valuable as any formal Hubspot learning resource.

Experiment with Small Adjustments

Choose one thing to test at a time:

• A new opening line
• A different discovery question
• A revised way of explaining pricing or value

By keeping experiments small, you reduce pressure and keep the spirit of play alive in your selling routine.

Additional Resources and Next Steps

If you want to see the original inspiration for this approach to fun selling, read the classic article that sparked this guide on the Hubspot blog: If It Isn’t Fun, It Isn’t Selling.

To build systems and automations that support a light, consistent selling style, you can also explore specialized consulting resources such as Consultevo, which focuses on scalable digital growth frameworks.

When you mix structure, curiosity, and a spirit of play, selling stops being a grind and becomes a series of engaging conversations. Borrowing these Hubspot influenced ideas about mindset and process, you can rediscover why you started selling in the first place: to talk to people, solve meaningful problems, and enjoy the work you do every day.