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The JB Sales Learning Lab Newsletter

Feeling Anxious and Stuck


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June 14, 2025 | Read online

Helping elevate the people and profession of Sales by sharing authentic conversations, practical tips, expert advice, relevant tech and real-world lessons from my experience selling every day. Delivered to your inbox every Saturday.


Before Covid I flew 2M miles in less than 10 years. I was training across the globe and went to almost every event you can think of.

These days it’s a lot harder to get me out of the house.

I don’t go to events any more just to go to events. IF I go, they need to be unique, intimate and with people I know and respect.

Last week I wrote about going to NYC for the GTM Fund Event. This week I was back in NYC for the RevFest conference on Tuesday and back home to Boston on Wednesday for Allego’s Sales Summit.

RevFest was a different kind of conference. It was at an extremely unique venue called the House of Yes in Brooklyn. They had a tattoo station, comedians, people walking around on stilts, dancers, airbrush artists and more.

I took advantage of the airbrush/make-up artist since I know how much they love to “paint” on a bald head 🙂.

The venue, people and structure of the event were different and got me thinking about how we need to change the way we think of events and how we engage with each other.

There was also an overwhelming feeling of anxiety and being ‘stuck’ that I sensed in many of the conversations I was having which is why I’m going to be sharing my keynote this month for free during Free Training Friday.

Let’s get into it.

(p.s. Members - I’m opening up office hours for 1:1 coaching. Sign up below in the Members Only section)


TACTICAL TIPS: Create Experiences, Not Presentations

TECH/SALES RESOURCES: Vidyard

SALES FROM THE STREETS: Feeling Anxious and Stuck


TACTICAL TIPS:

Create Experiences, Not Presentations

I remember the first time I went to Salesforce.com’s Dreamforce conference and was blown away by the size and scope of it.

I overprepared and went through the entire schedule with all the different topics to find the sessions I wanted to attend and learn something from.

I went to the Keynote early to make sure I got a seat, eager to listen to what these ‘important’ people had to say.

I was ready to learn!

I quickly started to realize that although some of the sessions were interesting and provided small nuggets of value, I wasn’t really learning anything.

So I stopped going to the sessions and started focusing on meeting the attendees and going to the social events which is where I found the real value of the events - human connection.

Over the years, I can’t think of a single presentation (at a conference) that fundamentally changed my perspective or where I walked away with something that I could apply to my life that made a measurable difference.

Since time is our most valuable asset, why should we waste it listening to presentations that we can’t engage with and ultimately don’t make a difference?

That’s why I think we need to completely rethink conferences and stop with the "presentations."

One of my favorite parts of RevFest was the roundtable discussions. Everyone was put into groups of 10 with a moderator and a topic to discuss.

The conversations were rich, people shared experiences and advice and most everyone walked away with some actionable items they could use.

This is where my tactical tip comes in.

I think anything that has to do with one-way, non-collaborative communication like presentations on certain topics should be handled by video and we should only get together to work on things that force collaboration and focus on solving problems.

Here are a few examples:

  • Product updates
    • Do we all really need to all get on a call for an hour in the middle of the day to listen to someone in Marketing drone through a bunch of slides on the new product and “leave questions for the end” when no one has any?
    • Instead, why not record the product update, send it out to everyone to review on their own time and then schedule a Q&A session or workshops to create messaging and/or role play different scenarios.
  • General Demos
    • If a client asks for a canned demo and won’t give you any context on their specific needs so you can tailor the presentation, why waste both your time trying to schedule a live call?
    • You can pre-record your own general demo and send it to them to see if it hits the mark and ask for a follow up meeting to talk through the details.
  • Forecast reviews
    • Forecast reviews should be collaborative, they should NOT be an interrogation.
    • Record yourself reviewing each deal, highlight the areas you have concerns about and need help and then meet with your manager to dive into the different strategies.
  • Conferences
    • I think we should stop presenting at conferences all together other than one or two main keynotes.
    • Instead, let’s treat conferences as Hack-a-thons where everyone fills out a form before they attend with the topics they’re experts in and topics they want to learn more about. Then we pick the topics, assign tables with diverse groups who match profiles and work on specific issues with the goal of walking away with actionable solutions.
  • BONUS TIP: Company Sales Hack-a-thon
    • Once a month, get together on Friday afternoon as an entire GTM team (Sales - SDR/BDR/AE, Marketing, Ops, Sales Engineers, etc). Break up into groups of 5-8 and make sure they’re a mix of different roles and levels of experience. Pick a topic related to the sales process that needs improving (preparing for meetings, researching accounts, certain internal processes, forecast reviews, etc.). Give the teams 30-60 minutes to find a better solution using AI or whatever other tools they can find. Have each team present their solution at the end and have the group vote on which one they like best. Spend the following week applying that solution to see if it makes a positive impact on results. Rinse, repeat. This approach improves collaboration, team moral, business acumen and usually finds solutions that can help streamline your processes and reduce your tech stack.

If we use video more for the one-way communications topics, we can leverage our time together to work on things that matter and get a lot more value out of being together.


TECH/SALES RESOURCES:

Vidyard

That was a long “Tactical Tip” so I’ll keep this one short.

I use the free version of Vidyard (not a sponsor or affiliate) to do all the video stuff I was talking about above.

Here are a few of my other favorite usages of video:

  • Objection Handling
  • When you get that email from the prospect saying “we’ve gone in a different direction” or “we need to puck this to Q4” - instead of trying to handle the objection over email or call them and leave a voicemail, open up Vidyard and record yourself saying something like this:
  • I got your email and am a little confused since you said that your priorities were X and timeline was Y when we talked and now it seems like something has changed. Would you mind jumping on a quick call to help me understand what changed?
  • Proposal Delivery
    • Obviously the main goal of delivering a proposal is to deliver it to the decision makers but in many cases we get blocked and forced to send it to our below-the-power-line contact. Instead of sending an email with the proposal that they will just forward to the executives who will then usually scroll to the pricing page, send a video instead.
    • Open up Vidyard, record the screen and video (which shows your computer screen and a little circle at the bottom with your face) and then walk them through the main parts of the presentation. Present it as if you’re presenting to the executive team. Then send it to your point of contact. You can see if they watch it, how long they watch it and if they forward it to anyone else. If they do, you’re now presenting in front of the executive team. It’s not as good as a live presentation but it’s better than an email.

SALES FROM THE STREETS:

Feeling Anxious and Stuck

Something else that struck me when I was at these conferences and talking to everyone was how stressed everyone is and how a lot of people are feeling stuck right now.

I’ve spoken about this before as it relates to business and the “indecision” issue highlighted by the book Jolt Effect.

The general take-away is that businesses are scared to make decisions right now because things are moving too fast and there are too many options to consider.

I’m picking up a similar sentiment for individuals. Many people are stuck and don’t know what to do right now. They’re freaked out about the future (specifically related to AI) and horrified by the present (specifically what’s happening here in America), leading to a sense of uncertainty, indecision and struggling to find hope.

I know the feeling.

That’s why I decided to deliver my Keynote - Continue Growth Mindset - for this month’s Free Training Friday.

It’s about what I learned after my Dad passed away after Covid and I was stuck in neutral not knowing what to do about it.

This is a very personal Keynote that I’ve only delivered in front of a live crowd only twice. The feedback was overwhelmingly positive with many people crying and thanking me for helping them gain some perspective and give some ideas on how to keep moving forward.

It’s about Alignment, Execution and Gratitude.

During this session, I’ll walk through my journey and share some of the things I learned along the way, including how to align my values, priorities and energy.

If you, or someone you know, is feeling overwhelmed, stuck or just needs some hope and encouragement to keep going, join me on the 27th at 11:00am EST and let’s see if we can get through this together.

#Makeithappen


MEMBERS ONLY

I didn’t get a ton of votes on topics you guys want me to do workshops on so I’m not going to do them any more until I see some interest.

Feel free to vote here if you haven’t already.

In the meantime, I'm going to host office hours on the 27th to give 1:1 support to members. I’m opening up (8) 15 minute slots which are first come first serve.

Also, if you’re not a member yet and still reading this, check out this unsolicited post by someone I trained. If you want to level up your sales game, join the membership today using COUPON CODE: NEWSLETTER for 20% off.

 

ADDITIONAL WAYS YOU CAN LEVEL UP YOUR SALES GAME

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