Diagnose prospecting issues

Kyle Asay outlines a three-step process to diagnose why an AE might struggle to set meetings.

His advice focuses on targeting the right accounts, engaging the right contacts, and crafting effective messaging.

1. Call the right accounts

• Are they investing in areas tied to your solution? Look for signs like hiring trends.

• Do they have multiple use cases for your product? More use cases = more chances to win.

• Do you understand their business? If you can’t speak their language or discuss their priorities, they aren’t great targets.

2. Engage the right contacts

• Would this person personally benefit from your solution?

• Are they responsible for solving the business pain your solution addresses?

No benefit or relevance = no reason to respond.

3. Use the right messaging

• Make it emotionally relevant: Address the problem they most want to avoid.

• Be specific: Avoid generic messaging that could work for any prospect—or worse, could come from your competitor.

Creative ways to book more sales meetings

Elric Legloire lists 37 creative and unique ways sales professionals are successfully booking meetings.

Here’s the full list (check out his post for examples!):

1. Use prospect tools: Create outreach using the prospect’s own tools, like building a Notion page for a Notion prospect.

2. Taco costume: Wear a taco costume and follow up on Tuesdays with a playful email.

3. Enterprise reports: Research prospects deeply, buy their products, and send detailed reports to execs.

4. Whiteboard photo: Send a LinkedIn voice note, followed by a photo of a handwritten whiteboard with their name.

5. Celebrity cameo: Hire a celebrity from Cameo to record a personalized video for your prospect.

6. Music in emails: Reference songs or artists the prospect mentions on LinkedIn in your email.

7. Same last name: Email prospects with the same last name as yours to build a personal connection.

8. Office swag drop: Drop off swag or goodies at the prospect’s office, even if they’re not there.

9. Spotify playlist: Make a custom Spotify playlist for the prospect and share it with them.

10. Blind calendar invite: Send a calendar invite to referrals, then follow up with a LinkedIn voice note.

11. Ketchup bottle costume: Dress in a ketchup bottle costume with a whiteboard that says, “Just ketch-ing up with you.”

12. Hourglass gift: Send an hourglass with a note about timing and invite them for a quick call.

13. Conference invite: Book flights and hotels for key prospects to attend a relevant conference.

14. Invisible ink gift: Send invisible markers with a personalized note tied to your pitch.

15. Rebel letter: Mail a crumpled letter with witty, self-aware messaging to stand out.

16. Video + dance: Send a personalized video featuring a dance tied to the prospect’s interests.

17. Whiteboard Tuesday: Send a LinkedIn voice note with a photo of a whiteboard personalized for them.

18. Puppy + whiteboard: Include a picture of your puppy holding a sign with a clever sales message.

19. Personalized email photo: Snap a picture of yourself in front of a screen displaying the prospect’s logo and send it with an email.

20. Donut office drop: Deliver donuts to the office of a prospect who opens emails but doesn’t reply.

21. Whiteboard outside office: Stand outside their office with a whiteboard and send them the video.

22. AI mascot: Use AI to create images of your company mascot in scenarios relevant to the prospect.

23. Store shelf photo: Snap a photo of the prospect’s product on a store shelf and pitch how you can help boost sales.

24. Custom songs: Use AI tools to create and send a personalized song for your prospect.

25. Gaming console gift: Send a Nintendo 64 with a game the prospect mentioned online.

26. Transformer toy: Send a Transformer toy with a note tying it to your pitch.

27. Diving analogy: Use ChatGPT to craft analogies based on the prospect’s hobbies or background.

28. Poems: Send a personalized poem to prospects who are poetry fans.

29. Hot sauce gift: Send hot sauce to Below-the-Line contacts and personalized gifts to Above-the-Line contacts.

30. Toy drones: Gift branded toy drones with a playful message about their use case.

31. Champagne campaign: Send champagne with a note congratulating the prospect on recent funding.

32. AI + thought leadership: Use tools like ChatGPT to find and personalize outreach using the prospect’s content.

33. Lottery tickets: Send fake scratch-off tickets with a prize that ties into your offering.

34. Custom demo video: Send a video demoing how your solution solves their specific challenge.

35. FedEx delivery trick: Show up at their office pretending to deliver a package to get past security.

36. Custom AI art: Use AI to generate visuals tied to the prospect’s industry or interests.

37. Crumpled letter campaign: Mail pre-crumpled letters with a witty, self-aware sales pitch.

How to focus on high-fit accounts

Jason Bay shares tips for working your territory effectively and focusing on high-quality accounts instead of wasting time on bad-fit prospects.

Analyze past deals

Look at the last 6 months of deals to find patterns:

• Which two industries did you win in most often?

• Who were the first meeting personas for closed/won deals?

• Why were closed/lost deals a bad fit?

• What size were the companies?

• Were there patterns in department size or growth?

• What common triggers (e.g., hiring, funding) did successful accounts share?

Revisit closed/lost deals

Some lost deals may now be worth revisiting:

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