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Selling Isn’t Easy, So Why Do We Keep Hitting The Easy Button? (And What To Do Instead)

Michael by Michael
23/11/2025
in AE's, Demo & Closing Strategies
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Selling Isn’t Easy, So Why Do We Keep Hitting The Easy Button? (And What To Do Instead)

Every salesperson knows, deep down, that selling is hard. Not hard in a vague motivational-poster way, but hard in the gritty, everyday sense: missed quarters, ghosted deals, sudden market shifts, and buyers who are drowning in information and still can’t decide.

Yet despite that reality, the sales world is obsessed with shortcuts. New tools, new hacks, new frameworks promise that this time, it will finally become easy. But if selling really isn’t easy, why do we keep hitting the “easy” button—and how is that hurting us?

Let’s break down what’s really going on and how top performers are winning by embracing the hard work instead of running from it.

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The Myth Of The “Easy Button” In Modern Sales

Walk through any sales tech expo or scroll LinkedIn for five minutes and you’ll see the same promise over and over again: faster pipelines, effortless prospecting, one-click personalization, AI that “writes your emails for you,” and playbooks that practically close the deal on your behalf.

None of these tools are bad on their own. The problem is the mindset they quietly encourage: the belief that if you just find the right shortcut, you can skip the hard parts of selling—learning, thinking, preparing, and engaging deeply with customers.

In reality, the environment around selling has become more demanding, not less:

  • Buyers are overwhelmed by information, vendors, and internal politics.
  • Change and disruption are constant—what worked last year can be irrelevant this year.
  • Unpredictability is the norm—budgets freeze, priorities flip, champions resign.

In this world, chasing “easy” isn’t just naïve. It’s expensive. It leads to bloated tech stacks, shallow skills, and teams that confuse activity with progress.

What Selling Actually Demands: The Hard, Unsexy Work

High-performing sellers quietly accept something many others resist: selling is a craft, not a trick. It doesn’t become easy, but through discipline it can become far more predictable and rewarding.

1. Focus: Doing Less, Much Better

The hardest thing in sales today is not finding more to do; it’s choosing what not to do. The average seller is bombarded with notifications, dashboards, enablement content, and internal requests. Without ruthless focus, your attention gets shredded.

Practical ways to build focus:

  • Define your critical activities: conversations with real stakeholders, discovery that deepens insight, follow-up that moves the deal one step forward, and targeted prospecting.
  • Time-block your calendar for these essentials—and defend those blocks like they’re client meetings.
  • Turn down background noise: limit how often you check email, Slack, or CRM dashboards. Depth beats constant motion.

Focus is the opposite of the “easy button.” It forces you to admit that not everything is equally important and that real selling happens in a few key moments that deserve your full attention.

2. Discipline: Showing Up The Right Way, Every Day

Discipline in sales isn’t just about making more calls. It’s about consistently doing the right things even when you don’t feel like it—and doing them to a standard, not just to a quota.

Examples of disciplined selling behavior:

  • Preparing thoughtfully for every meeting instead of “winging it” because a deck is available.
  • Documenting next steps clearly with customers and following through on time, every time.
  • Updating the CRM accurately so you and your team can make real decisions instead of guessing from half-truths.

None of this is glamorous. But this is the work that actually compounds over time. Discipline turns good intentions into reliable execution.

3. Mastery: Treating Sales As A Profession, Not A Phase

Because selling is hard, the temptation is to look for scripts, templates, or playbooks you can blindly follow. They can be helpful—but only if you understand why they work and when they don’t.

Mastery looks like:

  • Deep discovery skills: you don’t just ask questions, you listen for patterns, contradictions, and unspoken risks.
  • Business acumen: you understand how your customer’s world works—how they make money, lose money, and measure success.
  • Conversation agility: you can move from problem to impact to value to decision, without sounding scripted.

Mastery is slow to build and never truly finished. But it’s also the one advantage competitors can’t copy overnight.

4. Relentless Execution: Turning Strategy Into Signed Deals

Most organizations don’t suffer from a lack of strategy. They suffer from poor execution. There’s a plan on paper, but what happens in the real world is inconsistent from seller to seller, deal to deal.

Relentless execution in sales means:

  • Running every opportunity through a clear methodology rather than treating each one as a unique art project.
  • Using your sales process as a coaching tool, not just a reporting checklist.
  • Reviewing deals honestly: where are you guessing, where are you relying on hope, and where do you have real evidence?

When execution is rigorous and repeatable, results become more predictable—even if the environment remains uncertain.

Why We Still Reach For The Easy Button

If we know all this, why do teams still fall for shortcuts? A few reasons keep showing up across sales organizations:

  • Pressure for quick wins: Leadership wants faster results, so they invest in tools that promise speed instead of skills that build durability.
  • Confusing automation with improvement: Sending more messages doesn’t mean having more meaningful conversations.
  • Fear of discomfort: It’s easier to buy new tech than to confront broken habits, weak coaching, or a flawed sales culture.

The irony is that most “easy” solutions actually create more complexity: more tools to manage, more data to interpret, more dashboards to explain. What was meant to simplify selling often ends up burying it.

What To Do Instead: Build A System That Honors The Hard Work

If selling isn’t easy, the goal isn’t to pretend it is. The goal is to build a system that supports the hard work of focus, discipline, mastery, and execution—so your team can spend more time selling and less time fighting chaos.

That means:

  • Designing your sales process intentionally, based on how your best deals have actually been won.
  • Using technology as an enabler: to surface the right actions, highlight risks, and guide decisions, not to replace thinking.
  • Embedding coaching into the workflow, so managers don’t just inspect numbers but develop skills in every opportunity review.
  • Tracking leading indicators (quality of discovery, stakeholder engagement, deal progress) instead of obsessing only over lagging results.

When your system is built around reality—around the fact that selling is demanding, complex, and human—you stop searching for magic tricks and start compounding real advantages.

Conclusion: Stop Chasing Easy, Start Choosing Effective

Selling isn’t easy, and it’s not going to become easy next quarter, or after the next tool rollout, or when the market finally “stabilizes.” But it can become far less chaotic and far more controllable when you commit to the fundamentals: focus, discipline, mastery, and relentless execution.

The question to ask yourself and your team is simple: are we investing in making selling easier on the surface, or are we investing in becoming truly better at selling?

If you’re ready to move beyond the easy button and build a sales system that actually reflects how hard selling is—and how rewarding it can be when done right—start by examining your own process, your coaching, and your tech stack. Trim what’s noise. Double down on what drives real customer outcomes.

And if this resonates, share it with your team and start a conversation: where are we still chasing shortcuts, and what would it look like to truly commit to the craft of selling?

Michael

Michael

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