Why Your Sales Strategy Isn’t Working

Let’s be real, sales is not for the faint of heart. The game is fast. The targets move. The pressure never sleeps. And if you’re leading the function, you already know: the old playbooks don’t cut it anymore.

You’ve got a team. A target. A ton of effort going in. But the results? Not what you hoped for.

Here’s the truth:

  • The fix isn’t just “try harder.”

  • It’s not about more calls or louder pitches.

  • It’s about better systems, sharper structure, and understanding what’s actually broken.

Let’s break it down, starting with why your strategy might be off track in the first place.


The 7 Pillars of Sales That Can Break (or Make) Everything

If your numbers are falling short, it’s usually a sign one (or more) of these seven areas isn’t working as it should:

1. Product

Sometimes… it’s just the product. Even the best sales team can’t sell something the market doesn’t want, or trust.

That said, plenty of average products sell well. Why? Because of the other six pillars. So unless you’re hearing the same brutal feedback from every lead, don’t assume this is the core issue.

2. Positioning

This one gets overlooked constantly.

You might have a great product, but if you’re showing it to the wrong people, or pitching it in the wrong way, it won’t land.

  • Product is what you sell.

  • Positioning is how you frame it.

Right product, wrong audience = silence.

Right audience, wrong message = missed opportunity.

Fix this, and your leads get better, fast.

3. The Sales Team

Now we’re in your zone.

Even with great product and positioning, performance falls flat if the team isn’t equipped, structured, or supported right. Three big things to check:

Process

Sales thrives on rhythm and repetition. If you don’t have a clear customer journey, strong tracking, and a live sales dashboard you trust, you’re flying blind.

Discipline

You’ve got the process. But are they following it? Discipline is a culture issue. It’s fixed with accountability systems, personal ownership, and motivation, not micromanagement.

Skills

Enthusiasm isn’t a substitute for capability. You might have a team that wants to win but doesn’t know how to prospect, pitch, or close.

This is where real coaching matters. Group-level training for patterns. One-on-one for skill gaps. And a clean map of strengths so you can match the right rep to the right kind of sale.

4. Tools

A solid sales tech stack is not optional anymore.

CRMs, prospecting tools, call trackers, AI analyzers, these aren’t toys. They’re time-savers, performance trackers, and pressure-relievers.

  • Save your team from pitch-deck purgatory.

  • Capture patterns (like common objections).

  • Spot who’s converting and who’s coasting.

Bonus move? Use AI to analyze call transcripts for patterns, objections, and styles, then build coaching sessions around those real insights.

5. Analytics & Insights

Gut feeling has its place. But sales without data? That’s a gamble.

You need to:

  • Track performance by product, rep, region, and month.

  • Run gap analyses to see what top performers do that others don’t.

  • Build dashboards that go beyond vanity metrics.

This is where having a dedicated sales analyst on your team becomes game-changing. Don’t just manage people, manage the patterns.

6. Pipeline & Forecasting

If your pipeline isn’t clean, current, and qualified, it’s not a pipeline, it’s a distraction.

You need to know:

  • What’s in the pipe?

  • Where it’s stuck?

  • How long it takes to close?

  • What % is likely to land this month?

For B2B or government clients: Plan backward from average deal cycles.

For digital/retail: Focus on funnel conversion math and campaign cadence.

Clean up the fluff. Follow-up ruthlessly. And review velocity, not just volume.

7. Reward & Motivation

Sales is driven by emotion and energy. Your comp model needs to reflect that.

It should:

  • Reward performance fairly

  • Avoid burnout or shortcuts

  • Be lean, motivating, and tied to your actual business goals

Pressure alone won’t build a team. Smart reward systems will.

And Then There’s the Cross-Functional Piece…

Let’s talk stakeholders.

Sales leaders often end up in tension with marketing, product, finance, or ops. But here’s the truth: great sales strategy cannot survive in a silo.

  • Build a strong bridge with marketing, share insights, compare personas, and work on targeting together.

  • Spend time with product, understand their roadmap, pain points, and decision-making cycles. Learn their language so you can sell your requests better.

  • Translate your sales data into stories that help everyone win. Make it easy for other teams to align, not compete.


Practical Fixes: How to Pull This Together

Here’s what to do when things are off, and you don’t have time for fluff:

Start with a Full Sales Strategy Audit

Break it down:

  • Product

  • Positioning

  • Team (process, discipline, skill)

  • Tools

  • Insights

  • Pipeline

  • Rewards

Rate each. Identify your weakest two. Focus there first.

Use the Effort vs. Impact Matrix

You can’t fix everything overnight. Use this matrix to prioritize:

  • Low Effort - High Impact >> Do It Now

  • High Effort - High Impact >> Block time/Schedule it

  • Low Effort - Low Impact >> Delegate or drop

  • High Effort - Low Impact >> Avoid completely

Block Time to Think Like a Leader

Book calendar space to:

  • Review performance trends

  • Watch call recordings

  • Look at pipeline health

  • Coach 1:1s with data, purpose & care

You can’t lead clearly if you’re stuck reacting all day.

Bring in the Team

Create rituals that scale learning:

  • Objection-handling roundtables

  • Win/loss deal reviews

  • Cross-rep coaching

  • Peer-led sessions (your stars teaching others)

Get creative. Get collaborative.

Sales isn’t a volume game anymore. It’s a clarity game. You can’t keep fixing performance with pressure. You need rhythm. Insight. And a team that’s not just working hard, but working smart.

And remember, the problem isn’t always the pitch. Or the person. Or the market. Sometimes it’s the way it’s all tied together.

So, Stop guessing. Start diagnosing.


Final Thought: Fixing Sales Isn’t a Hustle. It’s a System.

“The best sales leaders don’t just chase targets. They build systems that hit them.” - Every founder who got tired of doing it all manually

Start there. Lead from there

“Fixing sales isn’t a hustle. It’s a system.”

Stick that on your dashboard. Then go build something that works.


🤔 What’s one part of your sales process you’ve been tolerating, but you know it needs fixing?

📌 Know someone drowning in sales chaos? Send this their way. They might not need a new team, just a new system.

♻️ If this gave you clarity or a checklist to work from, share it. Someone else might be stuck in the same revenue loop.


Want to audit your sales strategy, performance and 10x your revenue? Reach out

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