Month: August 2025

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Uncategorized

How AI is changing sales forever

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How AI is changing sales forever

In today’s issue, I’ll share how AI has changed sales forever. Since ChatGPT became mainstream, salespeople are using AI daily (and if they are not, they are trying to). This means a lot of untrained people are using a tool they don’t understand, which creates negative results for everyone.

So today, I’m going to share a few aspect of sales AI has changed forever, some other that haven’t changed, and common mistakes to avoid. These points are the results of our conversation with Dominic Klingberg during my summer Sales Creator Content Party in Berlin.

Let’s dive in:

What has changed with AI

AI has had a massive impact on buyers. Back in the days, they could only access information through salespeople. With internet, they got more and more disconnected from salespeople, finding relevant information by themselves.

AI has accelerated that trend. You now have AI summaries on Google searches, making it even easier to access all the information you need to make a buying decision. This makes sellers who only pitch features completely irrelevant. They are slower, less informed, and more annoying than any AI could be.

Another key aspect that has changed with AI is the quality of cold outbound messages. It’s now impossible to spend a single day without being flooded by AI-written emails, DMs, and comments on LinkedIn. This reduces the attention of buyers even further, making it important to use multiple channels (cold call, email, LinkedIn, etc.) to get some attention.

What hasn’t changed with AI

Luckily, a few things didn’t change with AI. Specifically, being able to build authentic relationships with prospects, either in virtual sales calls or in person is more important than ever.

In a world where prospects are constantly asking themselves if they are speaking with a human or getting tricked by an AI, standing out and showing your human traits makes all the difference. That’s why LinkedIn DMs are so important when prospecting. I use them to start conversations with messages like “what’s up?” because it stands out in a sea of corporate jargon.

Another aspect that remained the same is the ability to connect specific problems with specific solutions for buyers. Some AI tools help you surface information that is relevant to your prospect, but they don’t replace reflection and critical thinking. It’s still very easy to see if an email has been written by an AI or a human.

Mistakes to avoid

Finally, I see 3 common mistakes that are easy to avoid when using AI. The first one is to believe that AI tools can be configured to run everything on autopilot on your behalf. For example, most AI agents are completely failing at making any significant impact on meetings booked.

Second mistake is to let an AI write emails and DMs for you. The act of writing your own copy is what makes you different in my opinion. It helps build your voice, and it makes you more knowledgable about what your prospects really need.

Finally, some people are completely opposed to using AI. This is a mistakes because it makes them too slow. For example, taking notes during a call when an AI notetaker can do it for you is a mistake I see all the time.

And this is how AI is changing sales forever. Most aspects of sales are impacted, but the basics remain the same. If you can show how human and unique you are, while using AI to free up some time, you’ll win big time.

Hope this helps.

Cheers,

Thibaut

And whenever you are ready, there 3 ways I can help you:

→ Enroll in The Prospecting Engine

→ Want to work with me? Let’s talk about it

→ Sponsor my content and get in front of 46.000+ salespeople

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Categories
Tactical Selling

My ultimate guide to booking meetings with LinkedIn

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My ultimate guide to booking meetings with LinkedIn

In today’s issue, I’ll share the exact process I follow to book meetings with LinkedIn. This is a tactic I detail in my Prospecting Engine, and if you can replicate this system, you’ll increase your chances of getting replies and booking meetings.

The main goal of this tactic is to use the digital footprint that can be found everywhere on LinkedIn, and use it to prospect as scale.

Here’s how, step-by-step:

Step 1: Find a relevant LinkedIn post

If your customers are active on LinkedIn (logging in at least once a week), then it’s highly likely that some people have built large audiences speaking about your prospects’ problems, and how to solve them.

I’ll take sales as an example. The domain is filled with thought-leaders who have built massive audiences on LinkedIn. Same goes for marketing, HR, and operations.

Your first step should be to build a list of 5 – 10 thought-leaders who post regularly (daily is best) on LinkedIn. Go check step 3 of this article if you want to know how.

I’ll take the example of Florin Tatulea who posts daily about outbound prospecting tactics (a lot of them are available in my Prospecting Template Swipe File).

Image #1

He has over 71.000 followers, and a lot of them may fit with my ICP.

I can go through a list of his posts to identify something my prospects would find valuable.

Remember, prospects are always faced with various problems, and posts related to these problems (and solutions) attract their likes and comments. Content that educates, challenges, entertains, or empathizes with prospects’ problems generates engagement.

In my example, I scrolled through Florin’s activity (filtered by post) and found this post. It’s a guide to using LinkedIn & Sales Navigator to its full potential.

This post got over 300 reactions, 36 comments, and 4 reshares. I’m pretty sure I can find some interesting people in there.

Step 2: Extract prospects who fit with your ICP

When you click on the lists of people who engaged with the post, you can see their reaction, and their connection degree with you.

Image #2

Now you just need to scroll and look for people who fit with your Ideal Customer Profile. In my example, I found 19 prospects who were a fit.

An additional benefit of this tactic is that you can use the same exact message for all the people who fit with your ICP

(Note: you can also use Amplemarket’s “Export Leads” feature to find prospects faster, and directly add them to your sequence).

Step 3: Tease their interest with a resource related to the post

As these prospects engaged with the post, it’s likely that they may have similar experiences with their SDRs. Which means they may have problems I can help with.

Let’s go back to the initial post. It’s a list of 5 tactics to use LinkedIn & Sales Navigator to its full potential. I could share the article you’re currently reading as a resource to help the prospects who liked this post book meetings with LinkedIn.

Now that I have my triggers, I can use a simple framework to write a message, or a connection request.

Trigger + Teaser: Paul, saw you also liked Florin’s post about 5 ways to use LinkedIn & Sales Navigator to its full potential. If you’re interested, I wrote a complete guide to booking meetings with LinkedIn.

Worth a peek?

As you can see, these texts are less than 300 characters, so they fit as connection requests, or direct messages:

Image #3

Step 4: Navigate conversations and book meetings with interested prospects

If the prospects I contacted are trying to use LinkedIn to book meetings (everyone is these days), then some of them will be curious to know about the resource I shared. When prospects reply, follow these steps:

  • Share the resource
  • Give them 2 days before following up
  • Ask them for feedback about the resource
  • When you get the feedback, ask if hoping on a quick 15 min call would be a bad idea

In my experience, if you follow this workflow, most people who are serious about solving the problem your resource is solving will book a call with you. The call will also be easier to start, because you already know about their problem, and you come with ideas to solve it.

And these are the 4 steps I follow to book meetings on LinkedIn.

TL;DR:

  • Step 1: Find a relevant LinkedIn post
  • Step 2: Extract prospects who fit with your ICP
  • Step 3: Tease their interest with a resource related to the post
  • Step 4: Navigate conversations and book meetings with interested prospects

Cheers,

Thibaut

And whenever you are ready, there 3 ways I can help you:

→ Enroll in The Prospecting Engine

→ Want to work with me? Let’s talk about it

→ Sponsor my content and get in front of 46.000+ salespeople

Subscribe to the Newsletter

Get my free, 4 min weekly newsletter. Used by 5.900+ salespeople to book more meetings and work when, where, and how they want.

Subscribe to the Newsletter

Get my free, 4 min weekly newsletter. Used by 5.900+ salespeople to book more meetings and work when, where, and how they want.

Categories
Tactical Selling

5 humans sales mistakes we keep making during sales calls (and what to do about them)

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5 humans sales mistakes we keep making during sales calls (and what to do about them)

In today’s issue, I’ll share 5 of the most common human mistakes salespeople make during sales calls. I’ve been in thousands of sales calls since I started my sales career, and I’ve coached thousands of salespeople, and we keep repeating the same mistakes, again and again.

Luckily, this has been changing with AI, making it easier than ever to be coached in real time, so we can focus on the conversation, instead of stressing about avoiding making mistakes.

Here are these mistakes, and what you can do about them:

Mistake 1: Not coming prepared (or having the time to prepare) to a meeting

A lot of salespeople (me included) don’t come prepared to sales calls. They are either too busy or too lazy and they end up asking questions that could have been answered through preparation. This creates a poor buying experience for prospects who often feel like they are wasting time speaking to a rep.

To avoid repeating that mistake, I recommend using WINN AI’s AI Meeting Prep. It provides smart prep summaries so you can catch up in minutes, including: deal status overview, key info about the account and who’s attending and suggested focus points based on unanswered questions, playbook gaps, and more.

Mistake 2: Not sticking to a methodology

We’ve all hear of methodologies like BANT or MEDDIC. These methodologies often include questions to ask in a specific order, making sales calls sound like interrogations for prospects.

As a result, salespeople prefer winging it, and go in the complete opposite direction. They focus on having a sincere conversation, but end up forgetting to ask questions to qualify their deals.

This is where the Playbook Tracker from WINN AI makes a ton of sense. It integrates directly into your call, guides you through the playbook your sales team is using, so you can focus on the conversation instead of trying to stick to your script.

Image #1

Mistake 3: Not qualifying enough

I see this mistake all the time with inexperienced sellers, or when salespeople start a new job. We work super hard to book meetings with prospects, and we tend to have “happy hears”. This means we interpret sentences like “send me an offer” as a good thing (it’s never a good thing).

A good way to reduce this kind of mistake is to use WINN AI’s real time guidance. When you run your call, the AI is reminding you of things you may have forgotten, suggests ways to dive deeper into qualification, rather than having to organize follow-up calls and emails because you need more information.

Mistake 4: Trying too hard to stick to the script

This mistake is also really common when people start a new sales job. We’re trained on a specific way to sell (in bigger organizations) and we end try too hard to stick to a script. This turns a conversation between two humans into an interrogatory.

WINN AI’s real-time guidance is again a great solution. With the AI tracking your call, you can focus on having a conversation without taking notes or worrying about forgetting to ask a question. You get reminded to ask specific questions if you miss them, and suggested ways to go deeper when identifying a challenge.

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Mistake 5: Not debriefing and staying on top of your deals

Finally, not debriefing or taking too much time to write follow-up emails is another classic. I keep making this mistake again and again, letting too much time pass between a call and a debrief email, forgetting half of the conversation in the meantime.

With WINN AI’s Magic Follow Up emails, you can send a personalized debrief of the conversation right after the call, so you stop pushing it to ‘later’ and keep your deals moving fast.

And these are 5 common human mistakes I see salespeople making again and again when running sales calls.

Hope this helps.

Cheers,

Thibaut

And whenever you are ready, there 3 ways I can help you:

→ Enroll in The Prospecting Engine

→ Want to work with me? Let’s talk about it

→ Sponsor my content and get in front of 46.000+ salespeople

Subscribe to the Newsletter

Get my free, 4 min weekly newsletter. Used by 5.900+ salespeople to book more meetings and work when, where, and how they want.

Subscribe to the Newsletter

Get my free, 4 min weekly newsletter. Used by 5.900+ salespeople to book more meetings and work when, where, and how they want.

Categories
Tactical Selling

How to find your prospect’s problems: A step-by-step guide

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How to find your prospect’s problems: A step-by-step guide

In today’s issue, I’ll share the exact process I follow to find prospects’ problems. If you can replicate these steps, you’ll be able to catch the attention of your prospects, because you’ll show them you understand what problems they are trying to solve, in details.

Understanding prospects’ problems is a big mindset shift for many salespeople because they are trained to sell a product, and pitch features and benefits, instead of trying to put themselves in the shoes of their customers.

That’s what I’m going to show you, step-by-step:

Step 1: Understand their goals and metrics

Every prospect you are trying to reach has one or more metrics they are evaluated on. A VP of Sales will be evaluated on revenues, a CFO on bottom-line, a CPO on shipping speed and so on. Your prospects get promoted or fired based on their performance against these metrics.

Your goal when finding prospects’ problems is to get a clear understanding of these metrics, and the goals associated with these metrics.

Here are a few places where you can get an idea of these metrics and goals:

  • Podcasts/webinars where your Ideal Customer Profiles are interviewed
  • Job descriptions
  • Current and past customers

When you have an idea of the metrics your prospects are evaluated on, your next step is to understand their goals. You can ask yourself the following questions:

  • Are they trying to maximize or minimize this metric?
  • What happens if they miss it? What are the concrete consequences on their jobs/lives?
  • Do they have stretch goals?

Below are some examples for different types of prospects:

Image #1

Step 2: List their key initiatives

When you have a clear metric and goal, you need to find out the initiatives related to these goals. Ask yourself the following questions:

  • What are they working on right now to achieve their goals?
  • What are the tools/services they are evaluating to avoid missing their goals?

Again, look for any information that can help you understand these initiatives in podcasts, webinars, 10-K reports, and so on.

Here’s an example of what an initiative could look like:

Image #2

Step 3: Find their problems

Now that you know more about their initiatives, you can start listing problems they would typically face when pursuing these initiatives.

Ask yourself the following questions:

  • Are they having a hard time finding/implementing the right tools?
  • Did they try other solutions, without success?
  • Are they going to miss their goals because they can’t find a service provider to do a job they are incapable of doing?

Here’s an example of problems related to initiatives:

Image #3

Step 4: Find symptoms

Finally, list the exact symptoms of these problems, so you can highlight them in your prospecting messages.

Problems are often not enough to get a reply. They tend to be vague and full of jargon. For example, “Not having an upsell playbook” is a problem a lot of my prospects have.

Symptoms of this problem are:

  • AEs are missing on easy expansion revenues
  • Customer Success Reps are only order takers, they have no sales skills
  • Expansion metrics are missed, quarter after quarter

I like to compare this with a doctor consultation. When you say “I have a cold”, you’re mentioning a sickness (a problem), but when your doctor asks you about your symptoms, you’ll say you:

  • have a runny nose
  • have regular headaches
  • feel exhausted
  • have fever

Think about what is more vivid in your mind? Problems or symptoms? It’s the same with prospects.

Here’s an example of typical symptoms:

And these are the 4 steps you can follow if you want to find your prospects’ problems.

Hope this helps.

Cheers,

Thibaut

P.S. This is a small preview of my flagship course, The Prospecting Engine. 14 chapters and 114 lessons of instructional video that will teach you how to start conversations, book meetings, and generate a healthy pipeline in 2025 and beyond. (even if you’re just getting started).

And whenever you are ready, there 3 ways I can help you:

→ Enroll in The Prospecting Engine

→ Want to work with me? Let’s talk about it

→ Sponsor my content and get in front of 46.000+ salespeople

Subscribe to the Newsletter

Get my free, 4 min weekly newsletter. Used by 5.900+ salespeople to book more meetings and work when, where, and how they want.

Subscribe to the Newsletter

Get my free, 4 min weekly newsletter. Used by 5.900+ salespeople to book more meetings and work when, where, and how they want.