February 14, 2026 | Read online
I think we’ve collectively lost the ability to “figure it out” and it’s starting to really concern me.
I constantly get questions that are effectively asking for the ‘silver bullet.’
- “What’s the best question to ask to create urgency?”
- “Do you have a good email template I can use to improve my response rates?”
- “What’s the best subject line to use?”
- “Do you have a prompt/tool that can write personalized emails at scale?”
Or even worse, I get feedback from reps who say their company hasn’t invested in the right tools or training for them to be successful.
I did a training a while back where I was showing the custom GPTs I created and one of the reps legitimately raised their hand and asked – “Our company doesn’t invest in the upgraded version of ChatGPT which means we can’t use those so what would you suggest we do instead?”
Are you kidding me? Take out your credit card, stop going to Starbucks for one day and spend the f-ing $20/month!!!
This isn’t just my experience or opinion. I’ve talked to countless leaders and managers who are frustrated with the lack of their team’s ability to “figure it out” without being told exactly what to do.
Speaking as old man GenXer here, it’s really hard to wrap my head around this mentality based on how we grew up.
We were forced to figure it out our entire lives with little to no guidance or structure. Our parents barely paid attention to us. There were even commercials on TV to remind them we even existed.
These days, almost every minute of every kid’s life is structured, if not scripted. Kids go to school, then have soccer practice for 2 hours, then get to play on their iPad/iPhone for 30 minutes, then do their homework for 2 hours and their weekends are jam packed with Club practices and travel team tournaments. Any free time they have is usually spent on their iPhones.
To make things even worse, schools have removed recess, gym, art, and mainly focus on teaching to the test (MCaST) instead of doing anything to help develop critical thinking skills.
Their entire lives have been structured so when they get out into the real world and someone in leadership tells them to “figure it out” they look at you like you have 3 heads and effective ask to be told what to do.
When faced with that response, most leaders react the wrong way and end up telling them exactly what to do.
They script out the exact messaging and put it into the cadence tool without allowing the reps to customize any of it.
They certify reps on the demo deck and penalize them when they miss one point on a slide.
They develop a cold call script and force them to memorize it.
Scripting things out is one of the worst things we can do because it turns the reps into robots and unfortunately now, they’re starting to get replaced by robots.
The answer isn’t scripts or templates. The answer is structure.
I personally hate it when people try to put structure on me, but I love creating structure, and that’s the key in my opinion.
The older generation needs to create structure for the younger generation to execute within because they’ll execute withing that structure better than I/we ever could, but they fall apart without it.
This is why I’m such a fan of A/B split testing everything and using the team to do it at scale. It’s also why I’ve personally moved my training away from specific techniques and more towards an agile structure we can use to test different approaches.
For instance, for cold calling, I use the AIDA (Attention, Interest, Desire, Action) structure so we can break down each section and test different components of it to see what works.
For “Attention,” how you introduce yourself in the first 5 seconds dictates where the rest of the call goes. So, we go into ChatGPT, ask it to give us 10 different ways to introduce yourself on a cold call and pick the two we like most. Then we break up into two groups for a call blitz and one group uses one intro and the other uses the other one and we track to see which works best.
I also work with clients to turn their Sales/GTM orgs into a Sales/GTM Lab where we get together once a week and do a SalesHackathon. We identify one aspect of the GTM motion that isn’t working or could be improved, break up into diverse teams of 5-6 (SDR, AE, SE, CS, Marketing) provide some structure and guidance on how to approach the problem and then let everyone work for an hour to figure out a solution using AI, existing internal tools or whatever. At the end of the hour everyone presents their solution to the problem, we vote on which one we like best and then we implement it next week to see if it improves results.
These are just some examples of how to provide structure without scripting and does wonders to help develop individual skills along with teamwork and collaboration.
However, even without structure or guidance, we ALL now have access to the most powerful tool humanity has ever seen to help us figure it out – AI.
You just need to be curious enough and use it the right way. Almost any question I get asked, you can ask ChatGPT and it will give you an answer that will probably be better than mine.
(On that note, I’ve been working with a partner on creating my own JB SalesBot GPT with all my training included and am looking for about 20 people to help me test it and provide feedback before releasing it to the wild. If you’re interested, all you need to do is respond to this email and I’ll give you free access for 2 weeks.)
If you’re a leader, I’m begging you to provide your team with some structure to help them figure things out without scripting everything for them. Turn your team into a Sales Lab and start testing different approaches.
If you’re a rep, I beg you to get curious. Before you ask your manager a question, go into whatever AI tool you like and ask the same question to see if you can get an answer and then go to your manager to get their feedback on the approach.
If we don’t collectively start improving our ability to figure it out we’re all going to get run over by AI faster than I think anyone expects.
One final note, I’m doing a webinar next week on identifying and refining your ICP (Ideal Customer Profile) to help people figure out where to focus their time and what approaches to use. Here’s a post I did about it on Linkedin for more context. Sign up today and help spread the word.
I’m also doing a Q&A for JB Sales Members right after the webinar so if you’re a JB Sales Member, make sure you go into the OnDemand platform and sign up in the “Live Events” section.
Let’s Make it Happen!
