Apr 7 • Tomas Chatila

7 B2B Sales Mistakes That Are Stalling Your Pipeline

If your pipeline looks full, but you’re not closing deals, this post is for you.

Most B2B sales reps today are not struggling because of a bad product, a bad market, or a bad team.

They’re struggling because of silent stallers in their sales process. And if you don’t catch them early enough, they’ll drain your time, energy, and market expansion fast.

Here are the 7 most common B2B sales mistakes that are quietly crushing conversion rates, and how to fix each one with a smarter and a sharper strategy in 2025.

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📊 What Numbers Say About B2B Sales Performance in 2025

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Why Mastering Objections Matters:

🧱 Where's the problem?

It's important to understand these key elements below especially when it comes to selling in our modern landscape today. 

  1. Buyers don’t want general calls, emails, messages... They want clarity.
  2. It’s not about volume anymore like it was in 2018 and before. Today the focus has leaned more on velocity + intent. 
  3. The truth is that a sales team today should be trained to navigate multi-threaded accounts, compressing cycles, and selling through disruptive markets.


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Why Mastering Objections Matters:

⚠️ Mistake 1: Spraying Outreach in an Intent-Driven Market

📉 The Problem

Look, reality is that buyers today don’t want to be treated like the old times.

Why? 

  • Your target decision-maker sees 30+ sales messages per day.
  • Most outreach sounds the same, feels the same, and gets ignored the same.

The problem is irrelevant, untimed, untargeted messaging that never gets past the first glance. That's why volume isn't cutting through as it used to back in the days. 

🔍 The thought process goes like:

  • "More volume equals more chances."
  • "If I reach out to 100 people, someone’s bound to reply."
  • "I'll keep it quick, personalization takes too long."

✅ Your Recalibrated Approach:

I am pretty sure you're operating in a B2B space. In this case buying cycles are going to be more complex, stakeholders are layered with multiple departments sharing their thoughts, and timing is everything.

  1. Tier Accounts

    Separate Tier 1 from Tier 2. Tier 1 accounts should get personalized messaging based on recent intent signals, LinkedIn behavior, press releases, or even funding events. If your product is an ideal fit for their segment and use case, prove it in the open.

    How? If you're using Sales Navigator, then you can track buyer job changes, role movements, and new initiatives they’ve launched.

  2. Trigger-Based Sequences Only

    Your targeted focus should go into build outreach sequences based on real moments. Don’t send a “checking in” message unless the prospect:

    - just launched something,
    - hired someone,
    - or posted a relevant thought.

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Why Mastering Objections Matters:
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⚠️ Mistake 2: Losing Control in the First 30 Seconds

📉 The Problem

Buyers aka 'decision-makers' today are busier, sharper, and quicker to cut conversations. The first 30 seconds of your call, or the intent of your text message or email will determine whether the conversation even continues.

So doing openers like it’s 2018, and being hesitant, overly polite, or soft-spoken will have decision makers opt out from what you are talking about.

The key here is to become a value driver, by speaking like a trusted advisor.

🔍 The thought process goes like:

  • "If I ease in the conversation gently, they’ll stay on longer."
  • "I don’t want to sound aggressive."

✅ Your Recalibrated Approach:

How you say the things you say make a COMPLETE difference in how a decision maker perceives your message. Your message needs to travel through your tone, the pace, cautious pauses, and the pitch you make. 

  1. Start with a controlled presence

    Separate Tier 1 from Tier 2. Tier 1 accounts should get personalized messaging based on recent intent signals, LinkedIn behavior, press releases, or even funding events. If your product is an ideal fit for their segment and use case, prove it in the opening.

    How? If you're using Sales Navigator, then you can track buyer job changes, role movements, and new initiatives they’ve launched.

  2. Trigger-Based Sequences Only

    Your targeted focus should go into build outreach sequences based on real moments. Don’t send a “checking in” message unless the prospect:

    - just launched something
    - hired someone
    - posted a relevant thought

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Why Mastering Objections Matters:

⚠️ Mistake 3: No Deal Navigation Strategy (Especially Mid-Funnel)

📉 The Problem

The top of your funnel might be moving, but your mid-funnel is where deals can stall. In most cases during 1-1 calls with sales reps, I've identified that reps lose steam after the discovery call. I realized reps aren't multi-threading their objective.

Or in other cases they don’t map out the influence with the person they are speaking with, which is highly important inorder for that person to promote and sell the idea internally in the company.

Why is this important? Because in B2B sales processes take time. And the larger the organization, the more involvement is required. So you really need to be creating links with the people you are speaking with. 

🔍 The thought process goes like:

  • "The decision maker will take it from here."
  • "If they’re interested, they’ll follow up."

✅ Your Recalibrated Approach:

You need to think multiple steps ahead over here. A better approach is to consider how you could support the person you're interacting with to help them sell behind closed doors. 

  1. Find your Internal Champions

    One contact isn’t enough. Ask: “Who else needs to see this before we move forward?” Then include that person in the next step. If you can’t, equip your prospect with material they can forward confidently.

  2. Send Internal-Sell Kits After Every Discovery Call

    - A 1-pager recap
    - ROI calculator or use case summary
    - 2–3 bullet benefits that matter to Finance/Leadership/IT etc..
    - A Loom, Tela, or vidyard video walking through it in under 2 minutes

  3. Plan the Next Step

    Never end the discovery call without: 

    - A calendar hold for the follow-up
    - Defined internal next step for them
    - Timeline check: “Is there a reason we wouldn’t circle back on this same time next week?” (this is a great one to check the pulse and any uncertainty).

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Why Mastering Objections Matters:

⚠️ Mistake 4: Not Initiating Objections Early Enough

📉 The Problem

The objection came in too late in the sales cycle because the sales rep didn't lean into initiating it earlier in the process. This is a mistake that occurs on a continuous basis from the myth of "always pushing for a yes" which is taught in our negotiation course.

Here's whats happens when objections are late:

  • Price comes up too late 
  • The buyer gets unclear on outcomes
  • Procurement slows down the decision
  • Reps default to either defending, discounting, or dissapearing.

🔍 The thought process goes like:

  • "I’ll handle objections when they come."
  • "It's better to push for a 'yes' rather than leaning into the no"

✅ Your Recalibrated Approach:

To recalibrate your approach here, consider reframing objection handling from something you just respond to, into something you prepare out of the conversation ahead of time.

  1. Identify Your Top 5 Resistance Points Across the Funnel

    Every sales org has recurring objections. The origin point is usaually in:

    - Price resistance: unfolds during unclear value in discovery
    - Competition: unfolds when differentiation isn’t sharp
    - “Not now” = unfolds when urgency isn’t tied to revenue or risk

    By identifying the origin of these resistance points, you'll know exactly when to initiate the objection and how to manuever through it.

  2. Brainstorm pre-handling language specific to your buyers 

    A) For pricing:

    - "Now before we even talk pricing, I want to show you where the ROI comes from so that you can make a financial decision that actually fits your goals, not just your budget."

    This respons reframes the price from 'a number' to a strategy (short & long-term).

    B) For timelines:

    - "Most teams we work with originally thought this would be a Q3 initiative, until they saw how many breaches were happening in Q2."

    This method allows you to neutralize the timeline objection without adding pressure, tension, or resistance to the conversation.

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Why Mastering Objections Matters:

⚠️ Mistake 5: The Follow-Up Still Looks Dated

📉 The Problem

Follow-up is one of the highest-leverage activities in B2B. Yet, it is still under-leveraged.

“Just checking in...”
“Circling back on this…”
“Did you have a chance to review?”

Let me be clear, that’s NOT what an effective follow-up is, let alone in todays marketplace. 

In a market where attention = currency, sending a follow-up that adds no value, insight, or motion can lead to a dead end before you know it. This in-turn actively reduces your positioning and trust. 

🔍 The thought process goes like:

  • "I just need to stay top of mind."
  • "As long as I follow up, I’m showing persistence."
  • "I don't want to push too hard."

✅ Your Recalibrated Approach:

  1. Build a Follow-Up Stack

    Have 6–8 follow-up assets you can rotate through:

    - Loom/Tela/Vidyard video recap of key value points
    - ROI model or deal-specific mini calculator
    - Case study with a company in the same vertical
    - Quote from another champion in their org
    - Recent LinkedIn post they shared → mirrored back with insight
    - Personalized article or internal slide they can forward
    - Audio note with 3 key points + 1 new idea

  2. Keep building the momentum, not lag

    Instead of: “Just following up to see if you had time...”. 

    Change your approach and say:

    - "Wanted to send over this 90-second demo breakdown. If you share this internally, it’ll give your Ops lead a clear view of the 3 key outcomes we discussed.”

    Always think from the buyers perspective, it’s not about you. It’s about helping them move forward internally which will support the entire outcome.

  3. Use Follow-Up to Multi-Thread

    To build internal motion and think from your buyers end, try an approach similar to this:

    - “Would it be helpful if I put this into a version that’s forwardable to your CFO or RevOps lead?”

    See? Asking them doesn't hurt. They know how things move internally. By simply asking and hinting that you could support with certain material, they won't have to think on how they could position it themselves solely relying on what they understand. But rather, on what they have from you as supportive material. 
      
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Why Mastering Objections Matters:

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⚠️ Mistake 6: No Defined Exit Criteria Per Deal Stage

📉 The Problem

When a pipeline feels bloated, unpredictable, and full of “maybes,” without clear certainty on the direction its heading at, no defined exit criteria is likely the reason. 

🔍 The thought process goes like:

  • "We had a good call, this should definetly move forward."
  • "They seemed interested, so I pushed to proposal." 
  • "They asked for pricing, that’s a buying signal, right?"


Such responses are usually driven by gut feelings we heaave on the specific situation with the client. The next step is to have a defined exit criteria to move deals through stages based on clear alignment of the situation.

✅ Your Recalibrated Approach:

An example of a recalibrated approach is demonstrated with the table below: 

1. Every Pipeline Stage Should Have Clear Exit Conditions

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2. Run Sales Stage Audits Weekly

     Every Friday, sales managers and reps should ask:

  •   Why is this deal in this stage?
  •   What’s stopping it from moving forward?
  •   What’s the next internal action the buyer is taking?

3. Create (Stage-Based) Enablement Tools

     Each stage of the sales cycle should trigger new sales assets:

  •   After discovery: Send an overview deck.
  •   After proposal: Send a stakeholder-specific FAQ.
  •   After contract: Send a post-sale onboarding preview.

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Why Mastering Objections Matters:

⚠️ Mistake 7: Not Training Daily

📉 The Problem

Yes motivation is important. But you need to have the right systems in place to operate through the speed in which everything is moving at today.  

The common issues I hear from learning & development managers as well as sales directors is:

- "Our reps have the talent, but there is no rhythm."
- "Reps are making calls, sending emails and LinkedIn messages, but there is no feedback or review of their approach and tone."
- "Reps are learning but then forget what they learned in the next weeks and there is no consistency in the approach."

My bottom line response is that a system needs to be in place. Consistent and active training with review and feedback is neccessary to develop an enduring position as a sales professional.

Endurance is what top organizations and successful individuals have. It's not easy to develop, but it's what allows them to create great solutions and innovations in this marketplace.

🔍 The thought process goes like:

  • "I’ve been in sales for years. I know what I’m doing."
  • "We did onboarding... I’ve got the playbook."
  • "I’ll improve when the pipeline is hot again."

✅ Your Recalibrated Approach:

  1. Track Performance the Way You Track Pipeline

    From contacts made (real conversations & outcomes, not just call quantity), meetings booked, presentations held, proposals sent. All these are table stakes.

    Start logging the following:

    - Objection types per week
    - Wins lost by stage
    - Best time blocks, seasons, events
    - Outreach variations and reply rate changes

  2. Practise Running Daily Sales Drills

    - 3 objection reframes per day
    - 1 new cold open practiced live
    - 1 deal review with manager feedback
    - Record yourself for 60 seconds & play it back

  3. Use the Desatmos ARC-1 Journal (Totally free & utilized by enterprises)

    Arc-1 was made to structure & track daily pipelines, prioritize high-value actions, and measure execution velocity. The highest performers in sales, business, and entrepreneurship don’t wait, they are focused on endurance by the best velocity measures. 

    Check out ARC-1 below and download your copy. We also made a full-guide on how to utilize it!

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Why Mastering Objections Matters:

🎯 ARC-1

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