Mastering Meeting Obstacles: A Powerful Guide to Unstoppable Sales Success

In an ideal world, sales meetings would be all about building relationships, aligning expectations, closing gaps in the sales process, and moving deals forward. In the real world, they often end up doing the exact opposite. 

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Technical difficulties arise, conversations go off-topic, key decision-makers fail to show up, and objections get too hard to handle – there’s a lot that can go wrong. 

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While you can’t control everything, navigating common meeting challenges is a big part of building a winning sales team.

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In this article, we discuss the top meeting challenges that creep into sales conversations and how they can impact your team’s progress. Plus, we’ll share tried-and-trusted strategies so you can ensure every meeting stays focused, strategic, and worth its time.

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What are Meeting Challenges?

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Some of the most common meeting challenges include missing or misaligned objectives, distracted or disengaged participants (92% of workers admit to multitasking during meetings!), ineffective time management, poor communication, distractions, and technical challenges.

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These challenges are a big reason for meetings getting the bad rep they do – over 70% of senior executives view meetings as unproductive and inefficient.  Identifying and tackling meeting challenges should be a priority for any leader – especially in sales – where reputation and revenues are both at stake.

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While how the challenges play out varies based on the purpose, setting, and context of the meeting, there are a few common meeting challenges that any business would do well to avoid.

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Most Common Universal Meeting Challenges

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While issues can affect any meeting, they take on a new level of importance when revenues, relationships, and resources are on the line. 

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Before we get into the specific challenges that sales teams face in meetings, here’s a broader look at common hurdles that crop up across all meeting formats— in-person, remote, or hybrid:

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• No Clear Agenda or Purpose: When a meeting lacks an objective, you can see how easy it is for it to end in either disengagement or disappointment. Conversations tend to meander or fizzle out, leaving participants – say, your clients – unsure of the next steps, the meeting’s overall purpose – and as a result– your ability to handle something much bigger, like their goals.

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• Ineffective Communication: Muddled messaging, talking over each other, and making assumptions are some of the most common contributors to this issue. When this happens, you can’t fault meeting participants for tuning out, multitasking, or simply going silent—leaving the conversation flat and the meeting ineffective.

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• Low Engagement: Keeping everyone engaged can be a challenge, especially in meetings with more than eight people. There’s also the aspect of non-verbal communication to consider. A good meeting is as much about words as it is about what’s not explicitly said. You can miss cues like body language and facial expressions in online meetings. And not surprisingly, this creates a disconnect between participants, making it harder to build rapport or gauge reactions.

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• Technical Issues: Nothing ruins momentum faster than repeatedly having to say "Can you hear me?" As common as they are in today’s remote and hybrid work environments, technical problems like spotty Wi-Fi, poor audio/video quality, etc. are like those annoying speed bumps or rumble strips that do nothing but slow you down.

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• Missing Meeting Minutes and Follow-Up: A meeting isn’t over when it ends – technically, it’s over when it accomplishes what it was supposed to. This could be clarity on responsibilities, next steps, key concerns, or improved understanding of details. Without note-taking and follow-ups, important details are bound to slip through the cracks, the next steps are unclear, and delays, disappointments, and missed opportunities are par for the course. 

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While these issues plague meetings across contexts, sales meetings face additional, high-stakes challenges that make things even more complex.

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3 Most Challenging Types of Sales Meetings

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Sales meetings are, by design, often stressful. There’s a lot to do – handle apprehensions, capture meeting minutes, enter data into the CRM, and more importantly, ensure that the meeting is worth everyone’s time. 

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It takes skill, attention, and a ton of experience and reflection on your performance – especially when it comes to these challenging sales meeting scenarios: 

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1. Meetings with Senior Executives or Large Teams

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We’ve all been there. Pitching to senior executives or large teams often feels like stepping right under the scanner.  

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To engage a room full of decision-makers – especially those at the executive level – you need confidence, preparation, and the ability to command attention. These meetings are often make-or-break – even a small misstep can cost you the deal or your team’s reputation. 

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To add to the pressure is the challenge of tailoring your message to a diverse but highly discerning audience—you could have some participants focused on ROI, others on long-term strategy, and others on operational issues.

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And yes, all of them expect you to know your stuff inside out.

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2. Objection Handling and Negotiations

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When you’re fielding stinging objections or tough negotiations, the stakes are high, and so are expectations. It is not exactly a walk in the park to present detailed product or service information while handling objections on the fly.

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What makes this harder is walking the fine line between providing enough information to assuage doubts and coming across as desperate and pushy. 

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And when the conversation shifts from objection handling to negotiations, you’re walking a tightrope of assertiveness and diplomacy. 

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It’s easy to see why sales managers continue to prioritize sales coaching on objection handling or sales negotiation for their sales teams.

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3. Firefighting in Problem-Solving Meetings

Sometimes, sales meetings aren’t about winning new deals—they’re about fixing problems. When a deal is in jeopardy or a client is dissatisfied, you need to use your communication skills and empathy to reassure the client that you’re on their side – and often get your hands dirty to fix the problem at hand.

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It’s times like this when your sales team needs to balance empathy with a bias for action.  One misstep, one more delay, a slight disappointment, and the situation could escalate, costing your team both trust and business.

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How to Solve Sales Meeting Challenges at Every Stage

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As a sales manager, you’re no stranger to the minefield that sales meetings often turn into. 

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From prep work to meeting execution to follow-up, every stage is crucial, and mishandling any part is sure to set you back. 

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To understand sales meeting challenges, it’s helpful to look at them in key stages – i.e. pre-meeting, during meetings, and post-meeting.

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Pre-Meeting Challenges or Meeting Preparation Challenges

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1. Failure to Understand Customer Needs

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Despite being such an obvious first step, poor preparation continues to plague most sales meetings. Often it’s not the volume of preparation that’s the problem – it’s the nature of the prep work. 

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What sales reps tend to forget is that it's not just about knowing your product—it’s about understanding the customer’s context, identifying trends from across customers, and even going back to things customers may have shared in the past.

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How you can prep to better understand customer needs:

The key is to anticipate potential objections, gather relevant data, and customize your approach to address the client’s specific needs and industry trends. Here are some recommended best practices for this step: 

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• Share a detailed agenda with clear objectives two days before the meeting. Even better, seek the client’s input on the agenda. This does two things – it shows respect for their time and also ensures everyone is aligned on the purpose of the meeting.

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• Equip your team with client insights from similar meetings. As a sales manager, encourage them to review previous call notes and recordings before each meeting, especially those in similar contexts or with similar clients.

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• Develop sales best practice or exemplar playlists that are scenario-specific or domain-specific. Make this mandatory listening as they prepare for important calls. This focus on targeted preparation will set the tone for the expectations from your sales team – and over time, bring a level of consistency and quality to your meetings over time.

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2. Technical Challenges

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Everyone knows the pain of tech hiccups, but there’s nothing quite like the palpable drop in energy when you see a professional struggling with a malfunctioning screen. 

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Technical challenges are often overlooked because of how commonplace they are. But, thankfully,  you can reduce their frequency of occurrence – with ingrained discipline in your sales team.

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As a sales leader, here’s what you can do. Consistently, use your check-ins to ensure your team knows their tools inside out and always has a plan B. Make sure your rehearsals or role plays closely resemble actual customer meetings – with the same tech setup and tools. It’s the only way you can reduce these entirely preventable tech issues in customer-facing scenarios.

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Lastly, ensure that sales reps have a Plan B email handy for all customer meetings – with a backup conferencing link ready in case of tech issues.

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Challenges During the Meeting

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1. Communication Breakdown

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Miscommunication – or even the lack of soft skills in your sales reps – is more common than we realize. 

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 It's not just about what your sales reps say, but also about ensuring that the client’s understanding aligns with their intent. Misunderstandings can also arise from unclear messaging, too much jargon, or assumptions about how much the client knows about your product.

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How to improve communication effectiveness in your sales team: 

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Encourage your team to pause for understanding checks throughout the meeting. Simple questions like, "Does that align with what you’re thinking?" are an easy way to clarify any potential misunderstandings. Active listening skills like paraphrasing and summarizing are key – make sure that your sales coaching covers communication skill training, active listening, best practices in product positioning, objection handling, etc.

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2. Difficulty Building Trust

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You can’t leave building rapport to chance. Too often, salespeople rush into the hard sell without spending any time to establish a connection with the client. It’s this lack of personal engagement that makes most sales conversations seem like transactions or near-hostile negotiations – not a mutually beneficial partnership.

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How to improve rapport building in your meetings:

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• Start with a personal connection: Make sure your team begins meetings with a personal touch to build rapport. A good start is discussing industry news, talking about the client’s personal interests, or drawing on a shared experience.

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• Show transparency: Your sales team needs to be upfront about any limitations or potential challenges with your product or service. It’s this honesty that will build credibility and show you're focused on finding the best solution for them, not just making a sale. Lead with a sincere interest in understanding the client’s problems rather than just pushing your product. Building trust takes time, but it’s crucial for a successful sales relationship.

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3. Too Much Sales Talk i.e. Sales Monologuing

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We’ve all been in conversations with people who seem to love the sound of their own voice. It’s a lot worse in a sales meeting – when the conversation is about something that’s going to cost you money. One-sided meetings are a shortcut to disengagement. The best sales reps on your team are the ones with a trained ability to read the room – and know when to stop. 

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If clients feel like they’re being talked at rather than understood, you can’t fault them for tuning out. This can also drown out actual client feedback and insights that can help your sales reps in future conversations.

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Here are a few ways to build your sales team become better listeners: 

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• Encourage your team to center their focus on the customer — to ask open-ended questions, truly engage with client responses, and adapt the conversation based on their input. 

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• Train your team to involve the client at every stage. Questions like, "How does this sound so far?" or, "What’s your take on this?" are easy ways to draw customers into the conversation and switch to listening mode. 

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• Ensure that your sales team receives granular insights on how they conduct their meetings – show them data on aspects like listening time/ratios, patience, listening pauses, time for customer stories, etc. 

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4. Too Many Choices Causing Decision Fatigue 

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Decision fatigue is when your sales reps overwhelm your customers or prospects with too many choices. It is a subtle but significant issue. 

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This is especially important given how customers today expect your sales reps to put some thought and effort into finding the right solution for them. While your sales reps need to offer flexibility, too many options end up being a drain on your customers’ mental energy. 

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The solution is simple and seemingly obvious. Make sure your sales reps limit options to a few highly relevant solutions. Ensure they focus on the most impactful next step, not the entire roadmap. 

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Of course, you can’t expect your sales reps to do this on the fly. Besides preparation, they need practice and the right supporting resources. For instance, a playlist of calls that focus on narrowing down choices for different types of prospects and clients is a simple but effective strategy.

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5. Distracted Note-Taking 

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The benefits of note-taking are often underestimated. It does a lot for maintaining the momentum of a deal. If meeting minutes are incomplete or unclear, valuable details, decisions, and action items are sure to slip through the cracks.

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While documenting the meeting’s proceedings is important, it shouldn’t be at the risk of losing engagement. Giving customers their full attention while taking accurate and detailed notes is a high ask of your sales reps.

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To avoid the risk of note-taking slowing down or distracting from the conversation, consider recording all your meetings and reviewing/summarizing them later.  

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Alternatively, use a conversational intelligence tool that transcribes the meeting for you and automatically identifies key portions for review or sharing with the team. Also, establish clear protocols for documenting and reviewing meeting notes to maintain follow-up effectiveness and ensure that important details are always accessible.

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Post-Meeting Challenges

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1. No Actionable Items and Accountability

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So the meeting went great, but what next? As impressive as your sales reps’ meeting performance might have been, without clear next steps, it can all come to naught.  Promises may be forgotten, timelines can slip, and just like that, promising deals might fall apart. 

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Here’s how you can avoid common meeting challenges by bringing more accountability into your sales meetings:  

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• Implement processes and use tools that track action items while driving ownership as well as ensuring visibility into it. This way, follow-ups are timely, sales reps are held accountable,  and your team and the client know exactly what the next steps are.

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• Outsource the tasks of summarizing meetings, outlining key takeaways, and assigning tasks immediately after the call. Tools like MeetRecord can integrate with your CRM to better manage sales pipelines and ensure your sales reps stay on top of follow-ups.

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2. Missing a Chance to Capture the Voice of the Customer (VoC)

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Your sales reps are your company’s ears on the ground. How they capture VoC from sales meetings will influence marketing, support, and products within your company. You need to equip them to capture the exact vocabulary that customers use to articulate their needs and feedback.

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This is another area where meeting intelligence tools help – they capture and analyze client feedback accurately. In addition, maintain a shared repository for notes and ensure that customer-speak and feedback are captured and shared with the rest of the organization.

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3. Missed Future Sales Opportunities

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In post-meeting follow-ups, your sales reps could end up often focusing solely on immediate action items. This means they’re potentially leaving future revenues on the table – opportunities for cross-selling, upselling, or even referrals.

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Here’s what we recommend: 

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• Encourage your sales team to review the entire conversation for clues about broader needs or growth opportunities.  After important meetings, review calls with your team and identify potential success stories, case studies, or referral opportunities. 

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Immediately share meeting snippets or testimonials with the marketing team so you can approach the customer at the right time – after a good meeting that left them impressed.

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• Set up regular internal debriefs or pipeline reviews to discuss potential upsell opportunities. Deal intelligence tools can help sales managers like you with insights into calls from all the sales reps in their team – so all upsell opportunities are caught at the right time. 

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Sales Tools to Help You Overcome Common Meeting Challenges

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To address the challenges that arise throughout the meeting process, the key is to have the right processes and the right tools to support them. 

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Here is a helpful framework to find the right tools with capabilities to help you handle common meeting challenges:

Pre-Meeting Tools: This category of tools ensures that your sales teams are well-prepared for the meeting and that everyone – including the customer – is on the same page.

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CRM systems like Salesforce, Zoho, etc.,  can help your sales team prep for the right call. If you have a meeting intelligence tool like MeetRecord with a two-way CRM integration, you have up-to-date data from every meeting fed back into the CRM.

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A purpose-built agenda management tool like SessionLab can help you design and create a custom agenda in minutes.  

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Meeting or Meeting Management Tools: In addition to video conferencing platforms and collaborative document editors that anchor your meeting, meeting intelligence tools – often integrated with your calendars – come with capabilities like note-taking, summarizing, capturing actionable items, and creating shareable meeting snippets. In addition, they offer additional sales-specific capabilities like sentiment analysis, meeting performance tracking for each sales rep, recommendations, and clear next steps. 

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Look for tools that can capture real-time insights and offer deal intelligence from each sales call – and across calls. By identifying key patterns—both positive and negative—tracking deal health, and analyzing sales performance through key metrics, they keep sales meetings focused and on-brand. 

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Post-Meeting Tools: This category is for managing action items and follow-ups. Make sure these handle tracking progress, analyzing meeting outcomes, as well as documenting and automating next steps and actions. A good meeting intelligence tool typically meets most post-meeting requirements – such as CRM logging, creating actionable summaries, assigning action items, and even post-meeting recommendations for sales reps.

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Run Better Sales Meetings with MeetRecord 

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We hope this article helps you tackle your meeting challenges head-on with the right tips and techniques.

We’ve built MeetRecord to help sales managers like you address the full spectrum of meeting challenges—from preparation to engagement and follow-up—by going beyond just note-taking to advanced features like deal intelligence and sales coaching. Here’s what this looks like in action:

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• Seamless CRM Integration: For instance, MeetRecord’s two-way integration with all leading CRMs ensures that your team enters each meeting fully informed – and leaves it with all insights captured and fed back into your CRM. 

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• Call Analysis with AI: With MeetRecord, you can listen to every call, leave targeted comments, and use AI to score each conversation, offering in-depth analysis and actionable insights on the deal as well as your sales reps’ performance.

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• Deal Health Monitoring: As a manager, you can track deal health, recognize positive and negative patterns, and support your sales reps with contextual feedback on their communication skills, active listening, objection handling, and more – with every call. You get detailed stats and automated follow-ups for every cal – so no opportunity slips through the cracks. 

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• Automated Sales Coaching: Listen to every call, leave targeted comments, and use AI to score every call your sales reps are on. MeetRecord’s sales coaching capabilities deliver insights summaries to support you in your one-on-one check-ins. It also comes with automated capabilities to help you create and manage custom libraries and playlists for your team. This ensures that your sales meetings are productive and collectively contribute to the continuous improvement of your sales motion.

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There’s a lot more MeetRecord can do to help your sales team conduct better meetings and avoid common meeting challenges.

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