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Talking About Learning and Growth in a Human Way WithChris Carolan

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Talking About Learning and Growth in a Human Way WithChris Carolan
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Most teams do not struggle because they lack information. They struggle because the way we package information creates friction, pressure, and overthinking. Then we call it “process” and act surprised when humans do not move.

In this episode of Value First Humans, host Chris Carolyn and I unpack something simple but deeply disruptive. Humans learn, develop, and decide in natural, non-linear ways. So when we force artificial stages, we do not create clarity. We create resistance.

And if you are building in HubSpot, leading a sales team, or trying to grow a company without losing your soul, this conversation gives you a better path forward.

Stop confusing control with progress. Build flexible paths that let humans explore in their own time. Remove gates that hold value hostage. Then watch trust do what pressure never can.

The moment that changed everything

Early in the episode, I describe a tension many leaders feel but rarely admit out loud. You can spend a whole day helping other humans and still battle the chasm of helping yourself learn and grow in the moment you need it. That is the real conflict. You want to serve. You want to scale. You also want to stay healthy and whole while you do it.

Chris frames our second Value First Humans commitment with sharp clarity: we will enable natural growth rather than force artificial processes. That one sentence becomes a mirror.

Because once you see it, you cannot unsee it.

When you build funnels, stages, and predetermined “qualification,” you are often trying to make humans behave like spreadsheets. And the moment you do that, you create friction where curiosity should live.

I said it like this, and I meant it. “Move with less friction.”

How they do the work in the real world

Here is what this looks like when you stop talking about it and start building it. Instead of demanding information in exchange for answers, you provide resources that support self-directed exploration. Instead of urgency tactics, you honor natural decision timeframes. Instead of pushing people through stages, you create adaptive pathways where humans can access expertise, schedule conversations, or explore solutions when they are ready.

That is not a theory for me.

It is how we operate at Sidekick Strategies. I share a real example: on our site, you can talk with our artificial intelligence coach that is trained to help with marketing, sales, business leadership, and HubSpot. The point is not to force a “conversion.” The point is to help you get unstuck.

  • You can get value without having to fill out a form.
  • You can get clarity without a sales call.
  • You can move at your own pace, in your own context, with your own questions.

Then I tell a story that reveals how deeply ingrained the old patterns are. When Chris shows an assessment experience that allows someone to “skip and view results without email,” his initial reaction is to resist it. Then he realizes that the skip link is the whole point. If it is truly valuable, the right people will return, share information, and raise their hands when they need to.

That moment matters because it reveals the shift. Let go of control. Lean into trust. And do not miss the human nervous system part of this. When someone sees “skip,” they feel relief. They feel safe. They feel respected. That emotional experience becomes part of the brand.

Later, we push into why teams keep recreating control. It feels measurable. It feels professional. It feels predictable. But when you design everything around control, you end up with a process that cannot represent the human condition.

That is why I say what I say about control. It hits a nerve for a reason.

We also talk about the trap of key performance indicators that require linear behavior, even though humans do not move linearly. If you agree it is not linear, stop using measurements that assume it is.

Then we make it practical with a signal-based example. If someone posts an article on LinkedIn and that signal matters, do not use technology to rush into a pitch. Use it to show up like a human. Read the thing. Add value. Appreciate something real. Be early. Be present.

“Ding, ding, ding, ding, ding, ding, ding. Winner winner. Chicken dinner.

In other words, do the human thing.

The lesson they want you to carry forward

If there is one idea I want you to carry into your next week, it is this.

Stop trying to force growth.

Enable it.

That means replacing qualification gates with recommendations. Turning “Are you in the market this month?” into “I thought this would be valuable.” It means choosing patience when your data says pushing harder does not work. It means building trust so deeply that people feel less resistance when you engage.

It also means being careful with artificial intelligence. Yes, it can speed everything up. That includes the speed at which you can ruin trust. If you make one “efficient” choice that stops feeling human, you can crash your brand faster than ever. Brand is everything. Trust is everything. Being human will be everything.

Then I land the plane with a moment of grace.

Give yourself permission to ask, “Is it possible for us?”

If the answer is yes, start removing what does not belong. There is going to be a lot of removing. And when you are ready, watch and listen using the embedded media near the top. Then take one simple action: find one place where your systems make it harder to treat humans like humans, and change it.

Frequently asked questions

What does “enable natural growth” mean in real life?
It means building flexible systems that let humans explore, learn, and decide in their own time, without artificial stages, pressure, or gated access to information.

Why are funnels and stages a problem for learning and growth?
Because humans do not move in a straight line. When you force linear stages, you create friction, resistance, and overthinking instead of clarity and trust.

How should teams use artificial intelligence without harming trust?
Use it to recognize signals and show up with real value, not to manufacture leads or automate pressure. Move faster only when it keeps the experience human.