The Conference Season Special Edition: How to Lose a CxO in 10 Easy Steps

The Conference Season Special Edition: How to Lose a CxO in 10 Easy Steps

A tongue-in-cheek guide for those who excel at burning bridges before building them

Dear Enthusiastic Sales Professional,

Ah, it's healthcare conference season! That magical time of year when VIVE, HIMSS, and countless other acronym-laden events fill the calendars of healthcare executives everywhere. As a Healthcare CIO who often encounters the traditional badge-scanning gauntlet (where my badge is scanned faster than a patient's insurance card), I feel compelled to share this comprehensive guide on how to absolutely, positively ensure that no executive ever takes you seriously.

1. Perfect the Art of Copy-Paste

"It was great meeting you at [INSERT CONFERENCE NAME]!" Send this to everyone whose badge you scanned, including those who merely walked past your booth while avoiding eye contact. Nothing says "meaningful connection" quite like not remembering if you actually met them. Bonus points if you reference the wrong conference entirely!

2. Demonstrate Your Complete Lack of Research

"After our deep conversation at HIMSS..." (The exec wasn't even there) "Following up on our chat about your pediatric needs..." (They run a senior care facility) Because why let facts get in the way of a good sales pitch?

3. Master the "Conference Follow-Up Blitz"

  • Day 1 post-conference: LinkedIn connection request
  • Day 1 (2 hours later): Sales pitch
  • Day 2: "Did you get my message?"
  • Day 3: "I know you're probably still catching up after the conference..."
  • Day 4: "Perhaps my previous messages got lost in your post-conference inbox..." Because nothing says "I respect your post-conference recovery time" like daily reminders of your existence.

4. Embrace the "Spray and Pray" Philosophy

Why tailor your message when you can send the same pitch to all 3,427 badges you scanned? Sure, some of those might have been other vendors, bathroom breaks, or accidental double-scans, but why discriminate?

5. Perfect Your Guilt-Trip Game

"I stood for three days at my booth hoping to catch you..." Make sure to sound personally offended that they didn't visit your booth, which was conveniently located in the furthest corner of the exhibit hall's basement level.

6. Leverage Your Complete Ignorance of Healthcare

Show off your industry knowledge with gems like "I know you were too busy to stop by our booth at HIMSS, but our revolutionary AI-powered coffee maker will transform your patient outcomes!" Because nothing says healthcare innovation quite like a smarter coffee machine.

7. Name-Drop Competitors Incorrectly

"Just like I mentioned at the conference, we're working with ALL your competitors..." (Lists three organizations from different states, serving entirely different populations)

8. Master the Art of False Urgency

"Our special post-conference pricing ends before you've even unpacked your suitcase!" Because clearly, enterprise healthcare decisions should be made while still suffering from conference jet lag.

9. Show Off Your LinkedIn Stalking Skills

"I noticed you liked three posts about the conference keynote..." Nothing builds relationships quite like mentioning every single social media interaction they've had in the past week.

10. The Grand Finale: The Breakup Message

After a week of no responses, send the classic: "I guess all that talk about innovation at the conference was just talk. Good luck with your digital transformation journey!"

Special Post-Conference Bonus Tips:

  • Reference conversations that never happened: "As we discussed over coffee..." (They never left the keynote hall)
  • Send meeting invites for 8 AM the Monday after the conference
  • Mention how you saw them "really enjoying" the Wednesday night vendor party they didn't attend
  • Follow up about that "definite pilot project" they supposedly committed to during their 3-second walk past your booth

In All Seriousness...

To the genuine sales professionals out there who actually do their homework, personalize their approaches, and respect the sacred post-conference recovery period - we see you, and we appreciate you. To the rest: perhaps consider that the "scan and spam" approach isn't just ineffective - it's becoming a running joke in executive circles.

Remember: The best sales relationships start with genuine understanding, respect, and the radical notion that maybe, just maybe, your prospect needs time to work through their 2,347 unread emails before responding to your "urgent" meeting request.

P.S. If you've read this far and recognized your own post-conference follow-up tactics, there's still hope. Step away from the LinkedIn messenger, take a deep breath, and try something revolutionary: actually remembering who you really met and what you actually discussed.

#healthcareonlinkedin #HealthcareIT #Sales #LinkedIn #ProfessionalHumor #HIMSS #CHIME #HealthcareTech #VIVE2025 #VIVE


Wisdom@Work


Jonathan Wilkie

Business Development Senior Manager | Audit, Tax & Risk Management Advisory

1 周

Is it worth going after the volumes of bad salespeople versus simply sharing the positive ways as you did in the end. I can’t speak for everyone. As a tenured sales rep, I understand all of what you’re saying. Just seems interesting that people take so much time to go over bad sales tactics when highlighting and sharing the right ways and focusing the traunch of your post there may be more helpful. Sorry there are people out there who don’t humanize and don’t yet understand (some never will) how to create true connection and build a proper relationship. Side note - there are hundreds if not thousands of sales companies praying on their teams desk eom, eoq, eoy that tell their team idc what u do sell this today. So some of this stems from sales leaders/orgs caring more about org profits than again - true business relationships.

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Dawn Whitney

Founder & CEO, Board Member, Executive Search Recruiter, Transformational Mindset Coach, Keynote Speaker, Mental Health Podcaster. CORE Values: Service, Gratitude, Growth, Wellness, Authenticity and Integrity.

2 周

Friend, you write a lot of amazing content, but this by far might be my favorite! But you missed a very crucial one at the end… The infamous “inexperienced sales person“ that corners you at one of the after parties, but has had a few too many cocktails and can barely stand. I might’ve ran into that one last night ????

Reid Anderson

Healthcare IT Staffing Expert | Connecting Top Talent with Leading Healthcare Systems

2 周

Excellent to meet you in person and shake your hand, Khalid.

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JD Yoni Levine

Enterprise AI Solutions || Former Olympic & NCAA Ski Coach

2 周

Love this! ?? Do you think conferences are still even an effective way of meeting with vendors? Maybe it’s time to fix this broken model ??

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