September 6, 2025 | Read online
When September hits, the SaaS/Tech conference season kicks into high gear, anchored by Hubspot’s INBOUND and Salesforce’s Dreamforce.
This week I was at INBOUND out in San Francisco and I came to a painful realization that I’m pretty sure I’ve passed my prime when it comes to events.
For context, ever since I got into Sales, I realized I couldn’t just rely on my cold outbound efforts to keep my pipeline full and needed to find other channels of lead generation if I wanted to excel.
I was introduced to business social networking events in Boston and started going to every single one of them I could find.
I went to at least 2-3 evening events every week and joined 2-3 networking groups like BNI that meet in the mornings.
Networking became my main lead source and also was a great way to “market” my first start up when we had almost no money.
I did this for 7 years straight which helped us become one of the fastest growing companies in Massachusetts and eventually sold to Staples.
Fast forward to when I started working for the training company Basho and got Salesforce as my main account. Their yearly Dreamforce conference ended up becoming my SuperBowl. I went to every single one of them for over 10 years and went full speed from the minute I landed in San Francisco until the minute I got back on the flight to Boston.
I would wake up every morning early to check emails and set my goals for the day, have breakfast with a partner or client, hit the conference room floor, network and meet with people all morning, meet with partners or clients for lunch, go back to the conference floor all afternoon, come back to the hotel to change around dinner time, go to multiple evening events each night and get up the next day to do it all over again.
COVID was the only thing that stopped me from that insanity. Since COVID I’ve been a lot more selective with the events I’ve gone to and I tend to avoid the huge ones any more, instead opting for the more curated experiences.
But, this week I had some sponsors at INBOUND and I wanted to get out of my house so I made the trip out Tuesday night.
I was in the studio recording content all day on Wednesday and then planned to hit the conference all day on Thursday.
Thursday morning I got ready and headed down to the conference room floor.
I wandered around, met a few people, showed up at a few of the presentations that some of my friends were speaking at and kept myself busy.
By the afternoon I found myself aimlessly wandering around the conference room floor like a lost puppy with absolutely no purpose.
As I went back to the hotel to freshen up and get ready for the evening events, I came to the harsh realization that I think I’m just too old for this shit at this point in my career.
The idea of going to a packed bar, waiting in line to get a mediocre drink and then having to yell at someone so they can hear you over the music just isn’t appealing to me any more.
I ended up going to the event and made the best of it but then did the Irish exit which I’ve come to perfect over the years.
It did bring back some memories and made me think of some of the tips and tools I’ve used over the years when I was in my prime.
So, I thought I’d share some with you in this week’s newsletter in case you’re not an old man like me and still have the energy for these types of events.
TACTICAL TIPS:
Getting Out of Awkward Conversations
When I'm in full networking mode (which I was definitely not this week), I set goals for how many people I want to meet and how many follow up conversations I want to schedule. I then set a time limit for each interaction/conversation.
For instance, if I only have an hour at an event and want to meet 10 people and get 2 follow up meetings then I have about 6 minutes for each conversation.
5 minutes is usually a good enough amount of time for me to figure out if this is a good conversation worth following up on or a bad one I need to move on from.
If it's a good conversation that has potential, I try not to "oversell" so I can leave enough for the follow up discussion.
I usually end the conversation by saying something like "It sounds like there's more for us to talk about, why don't we find some time next week for a more detailed conversation. Do you have your phone on you?"
And then I schedule the meeting right there and move on.
If it's not a good conversation then I say something like this:
"I'm sure you're here for the same reason I am, which is to meet as many people as you can and find some potential clients or partners. With that, what are the types of people or companies that you want to meet?"
After they tell you the details of their ICP, say this...
"Ok, great! I'm going to go around and introduce myself to some new people. If I come across anyone who fits your profile I'll send them your way ok? Thanks for your time and good luck!"
This way you can end the conversation on a positive note and move on to another without it being awkward. Also, it's genuine since if I do end up talking to someone who fits that profile, I will send them over or make the intro if it makes sense.
Give it a try and let me know what you think.
SALES TECH/RESOURCES:
How to Win Friends and Influence People
Networking events aren’t just about swapping business cards, they’re live practice for Sales. You learn how to break into conversations without being awkward, how to keep someone engaged, and just as importantly, how to notice when they’re checked out.
When you give your pitch and see someone’s body language shift, you get immediate feedback on how well (or poorly) you’re connecting. That’s EQ training you can’t get sitting behind a screen. And honestly, I think we’ve lost a lot of that since moving into a more virtual-first world.
That’s why I think it’s worth going back to the fundamentals. Dale Carnegie’s How to Win Friends and Influence People might be nearly 90 years old, but it’s still one of the best playbooks for grounding yourself in human connection.
Here are some of the timeless lessons:
- Remember names (my biggest weakness). It’s the sweetest sound in any language.
- Smile. Sounds trivial, but it disarms tension instantly.
- Be genuinely curious. Ask questions to learn, not just to wait for your turn to talk.
- Listen more than you speak. People will tell you exactly how to connect with them - if you let them.
- Talk in terms of their interests. Center the conversation on what matters to them.
- Make people feel important - and mean it. Authentic recognition builds trust faster than any pitch.
If you want to sharpen your EQ, networking events are one of the best classrooms. And Carnegie’s book is still one of the best guides.
SALES FROM THE STREET:
Conferences Are For Closers
One of the things I always do at conferences is walk the expo floor, albeit this time was a little more aimless than most.
Part of it is curiosity and to learn what new tech is out there and what solutions are coming to market. But the bigger reason is to study how the Sales reps at the booths actually sell. It’s my own way of doing some market research.
It still blows me away how many reps treat conferences like Marketing events instead of Sales events. If you’re going to spend a full day at a booth, why wouldn’t you be laser-focused on qualifying and booking meetings?
At INBOUND, I probably stopped at 20 booths where I was genuinely curious about the solution. Out of those 20, almost none of them asked me what I did before launching straight into their pitch/demo. Most scanned my badge, gave their pitch, and let me walk, which I think is a massive missed opportunity.
Since Otter.ai is one of my sponsors, I stopped by their booth for a couple hours to see what I could do to help drive some traffic.
Even though I said earlier that I think I’m past my prime for events like this I can still run a booth better than most so I knocked off the dust and went to work.
I walked out into the traffic in front of the booth and started making conversation with people who even glanced our way.
If they didn’t ask what Otter was immediately, I asked the simple question - do you have meetings at your company?
Of course they would say yes and then I would ask if they’ve ever heard of Otter.
When they would ask me what it was, before I jumped into a pitch, I would qualify them and say something like:
“Otter does a lot of different things. So I can put it in context for you, could you tell me what kind of company you work for and what your role is in that company?”
After engaging in the conversation and asking a few more qualifying questions I would then tailor my description and only talk about the components of Otter that I felt were most relevant to them (Sell to the 20%).
After they showed interest, I would hand them off to the Otter rep to book a meeting.
It was like riding a bike.
Maybe I’m not riding as fast these days and probably should be wearing a helmet but I still got it ;)
| How did I do with this edition? |
|
|
|
|
