Keeping an Outside-in perspective
They say hindsight is always 20/20. Using "20/20" (perfect vision) as a metaphor for this clarity. Sometimes this is also true, "Can't see the wood for the trees" the idiom meaning someone is so focused on small details that they miss the big picture or the overall situation.
I've watched this play out in real life where I've worked and where I've been working with a client to drive transformation. Being a company guy was part of the culture and meant that you were all in along with all the other all-inners.
I watched in 2025 as the all-inners were retrenched across the Tech Industry and remembered the time I was retrenched and had to find a new role in the company I worked for. My heart goes out to all these colleagues who go the extra mile for the companies they work for. And then change happens and you simply become a number of an Excel Sheet.
That one time woke me up. I looked outside the company I worked for and what the skills the market was looking to buy. I had very few of what they wanted. This market my pivot to actively keeping an Outside-in perspective on everything that I do.
Keeping an out-in perspective on your skills
When I realized that I didn't have what the market cared about I was shocked. After all I was the CTO at a large global Tech Company. The challenge was I knew more about my tech company that I knew about what our customers wanted to buy. Here's an example. Of course I knew all about Cloud Computing. I was close to Microsoft and AWS, even heavily involved in our partnership with them and how we drove that for success into our company. I knew about all the challenges of adopting Cloud Computing. I was made to be acutely aware of our Cloud Services since that was what we were selling to the market. But when it came down to configuring a cloud landing zone from scratch and configuring the billing account and the commercials I was One-Click Steve. I could ramble on for 30 minutes about our Cloud Managed Service of course, but the customers were not buying that.
I woke up!! Going forward I made it a key task to spend at least 2 hours a week focused on the actual market and what was going on it. Thankfully so.
This gave me cause to realize the AI wave way long before it became "main-stream" giving me the confidence to give up my global CTO role and become a founder and director in Strideshift.ai. And as they say in the classics the rest is rapidly becoming history.
Keeping a Customer Centric perspective on your offers
If anything this is probably the more important lesson of this post. The reason for that is you will always have a job if you understand your customer and their market better than any of your competition, which as you will discover is not that hard to do.
As a seller engaged with customers their single most highlighted frustration is simply this, "Your sellers do not understand my business". Of course we all know that understanding the customers business is critical right? Wrong! Just look at the amount of time an organization spends teaching their people about their products and services vs teaching them about discovering and illustrating customer value. There's your answer.
On of the ideas behind the why for www.ideas.com was simply this. At the time I called it Expert Selling. The idea being that if we could create a group of expert sellers to engage on our key accounts we could win more, because the experts would demonstrate deep domain expertise about the customers business we would be more compelling.
Sadly the company never bought the idea and they are still struggling to make their numbers.
I went on to collaborate my my great friend Alison Jacobson, who is an expert on Customer Outcomes and together we built the Strideshift.ai POV (Customer Point of View) Solution which turns all sellers into customer experts though the Precision Selling AI Insights and Reasoning Engine.
We are winning deals and transforming the way that sellers engage their clients.
