Why entrepreneurs hate the question "How are you going?"

Want to upset an entrepreneur? Try asking how things are going.

This seemingly simple question could mean a thousand things.

This is the fourth in a monthly series where I share my personal entrepreneurial journey. Month one: Making the leap from employee to founder. Month two: How to be a better decision-maker. Month three: How to steer your start-up through online critics.

This month I talk about how to answer some curly questions. The big one: “How are you going?”

It has been more than three years since I left a safe, full-time corporate role and started my own venture, iFLYflat. When I catch up with my network, past or the present, I commonly hear the question, “So, how are you going?”

I dislike that question. It may be a simple one, it might be a figure of speech, it might be a genuine question about my wellbeing – but I never know how to start.

It could mean a thousand things.

It may be a question about whether we are still in business – but it is too open-ended when speaking to an entrepreneur. It drives me crazy. Here is what I mean.

In the start-up world, everything moves fast

Each fortnight represents 14 days of events. Some are good, some are great and some are crap.

Notice how I said 14 days? That’s because I am working every day to some degree. If I’m not actively working, my mind is thinking about iFLYflat. The to-do list is as long as a piece of string.

Some of the things that keep me up at night:

  • new ideas for marketing, lead capture, PR, website copy and functionality
  • new and/or improvements in what we offer
  • new services we could commercially deliver
  • staff utilisation and happiness
  • planning for staff gaps and growth
  • on-boarding new customers and new staff
  • managing cash flow, profitability, funding
  • expanding my networks, nurturing relationships
  • preparing slides for presentations, preparing for TV or radio interviews
  • developing referral and partnership programs
  • measuring customer satisfaction, ways to deliver a better service and building more expertise in finding flights...
You get the idea.

“So, how are you going?”

I have no idea where to start.

Do they mean…?

How is the business going? We are profitable and self-funding, but I’m not yet Mark Zuckerberg. We have redeemed 85 million frequent flyer points to date, but I want to be redeeming 200 million points per year.

Do they want to know that we now have 10 staff, or that we were on Sunrise TV last month, and on ABC radio and news.com.au last week?

Are they interested in knowing that we have customers in diverse industries, from the real estate agent who may have sold your friend’s house, to the restaurant you dined in last month while celebrating a happy milestone or the car dealer that serviced your colleague’s car, to the farm where the corner café gets its broccoli and the company that is employing the security guy guarding the building site on the way to your office?

(Wow! This is surprising to me, even as I write this).

Are they interested in knowing that we finally learned how to send automated emails from MailChimp, which are triggered from whether you open, or don’t open, or click, our emails? We’re excited but it’s nowhere near as cool as how company X does it.

Or could it be interesting that we are partnering with a truly inspirational movement that would put us in front of more than 30,000 people globally?

Perhaps they are asking about my day yesterday, about how we hired someone in Hong Kong, how our team found three seats for a customer, and when given the okay to book, saw the seats disappear – and had to break the bad news to them (not happy, by the way) and resume searching, all the while receiving a kind note of appreciation from another customer who just arrived back from a trip?

Side note: Those same seats reappeared three days later and we finally booked them (very happy).

Why growing a start-up is like raising a child

There is so much going on in my mind, and so much action, that I often have no idea how to answer. My start-up is like a little child – it needs total care to grow up and survive by itself.

Steve deep in thought - probably thinking about how to improve his customer on-boarding process I am seduced and jealous by every other start-up getting funding, doing deals and hiring 20 staff with new offices that are splashed across the newswire. But mine is running its own race, along its own timetable; we are in our own market – everything is building.

Until we are able to help at least 100,000 people and their families to fly business class who have never been able to regularly do so, and help them experience the true joys and comfort of travel, we will keep building. The rewards points business is really just the most effective mechanism to do so.

Friend Q: “So, how are you going?”  

Me: “Yeah, it’s coming along. I still love it, we are helping people to fly business class for cheaper than economy, helping them to fly more frequently and giving those who never had the opportunity to fly flat before.”

Friend Q: “Okay, cool. You are still doing it. Let’s grab a beer.”

Our entrepreneurial minds are forever active, forever analysing, exploring ideas, thinking, and perhaps over-thinking every question…

Next month: Entrepreneurial freedom – is it all that different from a 9-to-5 job?


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