WHY ASKING THE RIGHT QUESTIONS CAN MAKE A DIFFERENCE: A CAUTIONARY TALE
NOVEMBER 30, 2016
When I began my entrepreneurial journey, I was given bad advice.
Full of questions (what to do next, who to talk to, what to focus on), I asked anyone who would listen for advice. As such, a been-there-done-that business owner I admired advised me to focus on earning an income at this early-stage in my business. As an unknowing 20-something bootstrapping to bring my vision to life, I took the advice and ran with it.

And for many years, that’s exactly what I did. Enamored with income, my focus was on getting dollars in my pocket. Fast-forward to today: if I could go back, I would have structured my business differently from the beginning.
I’ve come to realize that I was focused on short-term returns for far too long. I realized much later in life that that advice encouraged me to view my practice as just that – a practice, rather than a business. I made decisions based on income maximization versus investing in people and systems to create intrinsic value in my business.
Once I had enough money to sustain my lifestyle, I needed to think about making investments in my business that increase the value of the business in terms of long term sustainability, versus short-term maximization of income.
And it can happen that quickly.
My journey is similar to most entrepreneurs – it wasn’t easy. Starting a business never is. If anything, I think my story is another cautionary tale of “If I could do it again, I would change XYZ.”
The reality is there’s always hard work involved when starting a company. But your journey doesn’t have to be as rough/frustrating/painful as mine was.
WHERE I WENT WRONG
Early in my journey I made the mistake of asking the wrong people the wrong questions. That, in turn, took me down the wrong paths.
Through my early growth stages, I continuously asked for business insights and advice. Mentors, family members and friends provided guidance that undoubtedly came from a good place (these were people who cared about me and wanted to see me succeed). And it wasn’t flat-out bad. The advice was cyclical, for a moment in time, on the scope of what I was facing that day/week (rather than using the entire scope of my business and life needs). But the real issue is that I simply handled the advice I was receiving haphazardly.
Hindsight being 20/20, I have come to realize that I was lacking process. I needed to catalog my thoughts, questions and actions to make the advice more valuable.
IF I DID IT DIFFERENTLY
Asking the right questions can ease the heartache (and could hit to your wallet) of the “common mistakes” entrepreneurs face. We see the challenges entrepreneurs routinely make time and time again, and almost all of them are unnecessary!
The first step is to have a process around what your questions are, who are you asking and how you are weighing those responses you’re getting. It all matters.
To start asking the right questions, explore
this new tool to see what you’re missing in the planning process. Looking back, if I knew those questions sooner in my journey, I could have grown faster and I could have grown much more profitably that I did.
But the questions likely don’t end in
this guidebook. While it’s important to establish a proper process for the advice you’re seeking in the first three years of business (when it matters the most), it doesn’t stop there. Entrepreneurism is driven on innovation and constantly seeking out the answers to questions you don’t know. There are always more questions you should be asking.