You’re struggling to book meetings with qualified prospects and it's having a big impact on your pipeline. 1000’s of emails sent from the sequencer… 100’s of DM’s a week but no response.

You know this needs to change or you’ll be in trouble.

Here’s a simple framework to have better conversations (& get those meetings!)

  • Step 1: Send a DM
  • Step 2: Ask strong questions
  • Step 3: Make it or break it question
  • Step 4: Interested in resources?
  • Step 5: Send 3rd party resource
  • Step 6: The ask

Now that you’ve got the TL;DR, let’s dive into the details that make it work.

Step 1: Send a DM

This is all about making a great observation so you can make a bold statement or ask a question. You’ll probably laugh reading this but… I always think about the TikTok trend:

“Tell me, without telling me”

This is all about demonstrating a shared understanding by the way you open the conversation.

Themes I constantly use for DM's:

  • The ultimate compliment → What do you admire about them?
  • Lean into your curiosity → What instantly caught your eye that you can’t ignore?
  • Professional quick win → How can you make their life easier (or get promoted)?
  • Trendy topics of interest → What trends are relevant to their world?
  • Passion play → What can you both nerd out on?

For example:

“I don't come across many fellow audiophiles. I have to ask, what's your go to music source? Spotify just doesn't cut it without hifi, but are our ONLY options Apple & TIDAL?!!! - Nick"

Step 2: Ask strong questions

Do you EVER get tired of superficial conversations?

You know those ones where they ask about the weather or ask how you are — but don’t wait for you to answer — Seriously?!

This is why most DM’s go nowhere… it’s not REALLY a good conversation. It’s usually just a generic pitch, irrelevant product information or something else not interesting to the other person.

The MOMENT you dive deeper into the conversation by asking strong questions, it stands out.

This is why — actually how — you get to the root of things. Ask questions that go beyond the surface level to 3 levels deeper to create a conversation that they can’t ignore.

PRO TIP: Map this out for the different themes. I compare it to the WIRED’s 5 Levels series explaining big topics to a different audience: child, teen, college student, grad student & expert.

Step 3: Make it or break it question

This is where you go ALL IN to see if they’re part of your pack → worth investing in

I personally wouldn’t recommend that you start talking about politics, religion or other edgy topics, but… you do want to force them to pick a side.


  • Woodworking: Hand vs power tools?
  • Sales: Does automation actually have a place in sales?
  • Computers: Is apple worth the premium?

You get the idea!

Maybe don’t follow my lead on this one… but I usually start with this tactic by using the Passion Connection Strategy to find people with “nerdy” keywords in their profiles.

Step 4: Interested in resources?

This is where we gently end the conversation and RUN like the Ikea commercial… Just kidding haha. This step was a hard won battle that I learned from my in-person networking days and it never lets me down.

People do NOT want your content right away in a DM: it feels salesy.

I started discussing great books, articles, podcasts, LinkedIn posts — insert other 3rd party content here – and use the content as a way to validate they want to nerd out on categories of interest.

The TRUE art is getting categories of content that dare to get closer to problems you solve so that you can see how they think about their role, company or the profession.

Where I messed up… I would randomly send the article without asking if they were interested AND without a summary. OUCH

Asking if they were interested — aka getting permission to send ANYTHING — before hitting send increased engagement rates from the content by more than 5X.

So, now it’s become it’s own step

PRO TIP - This had the same impact on meetings:

"I can grab some time on the calendar for us. Is it easier if I use your meeting link or should I send mine?"

Wait for a response:

If they say no, this is where that conversation ends.
If they say yes, move to step 5!

Step 5: Send 3rd party resource

Now we can send that 3rd party resource you love. Where the power comes from is the summary of the resource & why you picked it for them. I always try to reference a past conversation or a passion that I know they love to nerd out on.

I found that pointing to a very specific part of the article to get their opinion or ask if they’re interested in discussing it goes a LONG way.

Step 6: The ask

This is where we answer the question: What’s next?

Hands down the most effective way I’ve found to answer that is in the form of an ask. So, what do you want from them?

This usually falls apart because it’s self serving… only YOU get something. Without making this a win-win… it won’t work. This is where I encourage you to take your time before firing off this DM. This is where your ENTIRE investment comes together… no pressure!

As long as you can answer,”What’s in it for them?”

You won’t have any issues.

Common asks:

  • Ask questions to validate your value hypothesis
  • Ask if they want to have a beer or coffee
  • Ask for a meeting

Don't be afraid to skip step 6

I can’t tell you how many times those relationships have turned into opportunities a few weeks or months later. The more you put in --> the more you get in return

Rules of Engagement:

  • Vampire sales (don’t pitch unless invited)
  • The Flip (go from vendor/seller to expert practitioner by offering learning & development material or real insight into their company)
  • 15 minute rule (98% of meetings book in 12-15 minutes, the rest circle back because of insightful content in feed)

WARNING: This will completely fall apart if you don’t follow Vampire Sales. That means no mention of your company, product, solutions OR anything else until you’re invited.

This most common invitation is: “So what do you do?” OR “Tell me about yourself?”

Practice how to answer those questions & this workflow will turn into a goldmine.