The One Question Every Entrepreneur Dreads

If you’re like me you get this one at least once a day. And when it comes from a total stranger or casual acquaintance it’s no big deal.

But, when it come from someone you know well, someone who actually wants and deserves a real answer from you (like a family member, close friend or trusted colleague) then it’s the most loaded question in the world. And it sounds so innocuous…

“So, how’s it going?”

Often it’s asked with just the slightest hint of concern, as if you are really being asked “So, I haven’t seen you featured on TechCrunch/Recode/The Wall St Journal yet… it must really be going badly, huh?” Now, maybe this is just my own insecurities and neurosis being read into a completely innocent question, but I don’t think so. Either way, let’s look at a number of possible answers to this question and see how they play out.

1) The basic — “It’s going great” — simple, direct, to-the-point; a conversation ender not a conversation starter. This works perfectly with the stranger/casual acquaintance group, they’re likely just trying to make conversation and probably don’t care about the real answer anyway. But a real friend deserves more.

2) The harsh reality — “Well product development is like a month behind, our competition has way more active users than we do and our marketing seems about as effective as a billboard outside The Braille Institute… of course we’re about to run out of money anyway, so none of that really matters.”

- This will definitely get you sympathy, but that’s not really what you want (I hope). After all the original question itself is already lightly dusted with pity and pity is the absolute worst. And while this answer is a definite conversation starter, it’s not the conversation you’re looking for. The person asking the question will feel bad for you and potentially embarrassed, they’ll likely offer a solution- “You know my cousin has a business cleaning port-a-potties with a toothbrush. I could ask him if he’s hiring.” Or a fix for your business that is so incredibly simple that you would have had to have been an idiot not to already have thought of it- “You know people really seem to like websites, maybe your business should have one of those.”

3) The CEO spin — have a quick stat or two ready about how you’re killing it (“Revenue is up 50% quarter-over-quarter and our latest new feature has seen the greatest uptake yet.”)

- This is how (almost) every CEO answers this question, and I know why — as CEO you’re the face of the company, setting the culture, captain of the ship. If you’re not positive on the company’s outlook, then no one is. But to me this has always felt disingenuous, after all I’m talking to someone who knows me well here. I feel like they deserve to know the truth and it also might help explain why I’ve been so stressed, haven’t returned their last 5 texts, missed their birthday and generally have been the worst person in the world toward them the last several months.

- Plus, when my business goes under in 3 months and I have to beg them for an introduction to a contact who just might know someone, who knows someone, who might be able to help me land a “real job” (with an actual salary), I feel like they’ll be more likely to help if I wasn’t lying to them through my teeth just a few months ago about how my company was killing it and how we were going to be the “Uber of Google.”

4) The (sort of) truth — here’s what I feel like we all should be answering with. A quick concise summary of the good AND the bad. “Well, we’re growing new users nicely, but our retention sucks and we need to fix that ASAP if we’re going to survive.”

- Note, this is definitely not the answer for everyone. The strangers/casual acquaintances don’t care and may not understand anyway. You’ll end up in a 20 minute conversation explaining what your business does (“So they have the Internet on phones now… wow, what’ll they think of next”) and ain’t nobody got time for that.

- However, with your close friends and trusted acquaintances this type of honesty will be refreshing. They’ll understand you and what you’re going through a little better, and if you really lucky they may even have a piece of useful advice for you (“You know my friend Lisa led all the user retention efforts for Slack, and she’s looking for a new gig… would you like me to introduce you?”).

- So that’s my recommendation, have #4 loaded and chambered at all times (just like you’re elevator pitch). Feel free to even practice it in front of the mirror a few times.

And now the next time someone asks the dreaded, “So, how’s it going?” You’ll actually have a good answer, and hopefully even be able to start a productive conversation from it.