4 Steps to Better Thinking for Your Business

There is nothing either good or bad, but thinking makes it so” – Shakespeare.

Here are four ways to provoke thought that work for my team that I’d like to share:

1. Start with Simple.

Understand the simple stuff deeply. Seek where you’re missing expertise, dig in to learn it, and learn it inside and out, and then move forward. In my business we have become so good at the simple processes that we have taken a process in social media that any business owner with the right motivation could certainly DIY themselves, but because it’s become so fluid, so simple and so efficient, we now add exceptional value. We spent the time on the things that our clients don’t want to. We offer innovative ways to approach every social media campaign from a different perspective. Learn the simple stuff and build on that. You can’t play a concerto without first knowing the scales.

2. Mess up.

Every so often we mess up, and that’s OK. Lately however I’ve been pushing myself and my team to color outside the lines intentionally. Empower your team to take risks and make small mistakes. This is the only way you’re going to learn and push the line of standard. Allow for your junior people to step up and take risks as well. Sheltering them in process and protocol only hurts their development and the innovation of your team. Trust them, trust that you’ve hired well, and allow for them to make mistakes. I find myself saying to my team “I trust your judgement” all the time.

3. Ask hard Questions:

Raise questions to clarify and extend your understanding. The right questions will help you see connections that you will miss otherwise. This is a tricky one. You don’t want to create an environment when everything is being questioned, but enquiring properly and from a pure place, and create an environment where asking “why” is accepted practice.

4. Glance in the rear-view.

When the new ideas start to pop up you need to step back, take a breath and see where they came from. Close your computer, sit with a piece of paper, and think about where the last innovative idea came from within your organization. Ask for help. Inquire internally and see if you can document the last time someone really cracked things open.

My most recent big innovation came while traveling. I was alone in my hotel room, reviewing our processes and challenging myself to improve, push, grow and expand the business beyond what I could conceive. I asked myself – “what would you do at Silverback if money was no object”, and it hit me. I began to roadmap my idea to extend the Westchester Digital Summit to other major cities around the globe. I pinged my team to bounce the idea off them, and we got to the business of making it happen. Now I try to calm my mind and ask that same question over and over and over “what would you do at Silverback if money was no object.”

I love what I do, and I’m lucky, but I find that thinking …real, deep, introspective thinking has become such a rare commodity that I have had to find a road map to become more efficient in my thinking, otherwise I drift off into unproductive daydreaming. I’m sure you feel the same way. We’re in the ever-constant mode ofdoing, and we rarely have the time to become introspective and really think about the issues that hold us back from over performing. Over the years I have become exceptionally proficient at this process. I shut everything down, pull out my notepad and think.

Transformative ideas means surrounding yourself with people that will challenge you, not by surrounding yourself with the same peers you’ve encountered in the past. Putting yourself in situations that challenge you and take you by surprise is hard. My friend Justin Brown is a business owner, and he challenges me every single time I sit with him. A few weeks ago he turned to me and said “do the shit that is hard.” Simple, right? Wrong. Seek difficult bumps in your business.

Identify the things that make you cringe and turn toward them. Do you have examples of how you’ve helped your business think better? Share them in the comments.

Photo: Shutterstock

@chrisdessi

 

Who’s the Coach?

I’m Chris Dessi.

Tech entrepreneur. Author. Talking head.
But before any of that—I’m a builder.

I’ve spent the last 20+ years helping companies grow:
From dot-com chaos to SaaS scale-ups to AI-powered everything.
I’ve sold software across continents. Closed $32M in deals using AI.
Built and exited businesses. Bombed a few too. All of it made me sharper.

Today, I run Torque AI, a marketing automation platform built for the 99%.
Small business owners. Solopreneurs. Operators with too much to do and not enough support.
We give them AI superpowers—without the hype, the jargon, or the BS.

I’m also the founder of AI Summit NYC, where real business owners come to learn how to actually use AI to drive revenue.

When I’m not building, I’m writing books, speaking on national TV, and coaching execs through reinvention—with a baseball bat in one hand and a meditation app in the other.

I believe reinvention is our greatest asset.
I believe AI isn’t the threat—it’s the test.
And I believe if you’re not adapting, you’re eroding.

Let’s build something that matters.

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