by Kathryn Minshew  |  11:00 AM May  6, 2013

It’s happened to every founding CEO. You’re in a meeting — with
fellow founders, potential partners, VCs, or even just friends — and
you’re asked that simple question that often feels like the hardest one:

“How are things going?”

“Great!” you respond

Cue, awkward pause. Where do you go from there? As a CEO, I have to
answer a lot of tough questions: What’s our 5- and 10-year vision? Where
do we hire next? Should we focus on existing products, or launch our
next one? But for the open-ended “How are things going?” there’s no
perfect answer.

The best response obviously depends on your audience, but I’ve found
there are four different ways you can tackle this question that will
most likely to lead to a productive conversation.

Highlight two recent accomplishments. In most
conversations, you want to communicate that things are going well — not
abstractly “well,” but that your team has been accomplishing awesome,
concrete things. To convey this, I find it’s most helpful to highlight a
few (usually two) specific recent accomplishments. For example: “Things
are great! We just crossed 900,000 monthly active users and brought
Facebook on as a hiring partner.”

Why two? Because if you name more, you sound like you’re listing off a
memorized litany of accomplishments, and that’s annoying. And if you
only name one, it comes off like you want your audience to be impressed
by that one achievement. Whereas when you name two successes, they can
choose which one they want to react to, and you come off less like
you’re baiting them to compliment any specific aspect of your business.

Talk about one problem you’re working on. An
alternate strategy, especially useful with people who are familiar with
your accomplishments, is talk about what you’re working on next. For
example: “Things are great! Right now we’re building out the ability for
applicants to upload a resume and cover letter to our site, so they can
apply to a job without ever having to leave.”

Bonus points: Slip in a good ask. For example, “We’re considering
whether to integrate with applicant tracking systems like Resumator and
JobScore. I’d love to talk to the teams over there at some point.” Here,
you’ve given the other person an opportunity to be helpful, and if he
recognizes a useful introduction he could make he’ll often be more than
happy to offer. And don’t judge too quickly whether the person you’re
talking to can help: When it comes to networking, you’ll often be surprised by who’s able to help out.

Talk about what’s different than 3 or 6 months ago.
This is a great approach for people who you haven’t seen in a while and
want to catch up on your progress, and is essentially a variation on the
“two recent accomplishments” approach. But instead of highlighting the
great deals you closed last week, take a step back and think about how
your company has evolved since you last spoke to this person.

For example, “Things have been moving very quickly for us! When we
first launched our product, we had a one-size-fits-all model, but we now
have a really great tiered offering — we launched a lower-price-point
‘simple’ version aimed at small businesses, and we’re also building out a
premium product designed for larger enterprise clients.” This tactic is
very useful in guiding your audience to reshape their perception of you
and catch up on where you’ve grown, as well as to shake off any
stereotypes you suspect you and your company got pigeon-holed into
earlier on.

Ask for advice. Finally, when you’re speaking with
someone who has expertise you could use, “How are things going?” is the
perfect segue into asking for it. Start by sharing a relevant update,
then transition to your question. “Things are great! We’ve been selling
quite a bit and are growing our sales team, which is exciting. I know
you guys did a fantastic job with expanding sales last year — can I
actually ask your advice sometime on the best way to interview and hire
sales people?”

To avoid putting people on the spot, you can smooth the conversation
by suggesting you’d like to talk “sometime” about your question. In many
cases, that “sometime” will turn into now, and your conversation
partner will dive into giving you advice. But, by giving her the option
to say, “Sure, shoot me an email and we can talk about it,” you avoid
putting anyone on the spot (and can set yourself up for a better and
more in-depth conversation than you could have at the post-conference
happy hour you’re standing at).

When you run a business, summarizing “how things are going” is more
or less impossible. But the secret to answering this question is
realizing that your goal isn’t to summarize — it’s to set the
conversation in motion along a productive path that generally relates to
how you’re doing and what you’re working on. Have a couple good answers
prepared (and update them regularly), and when someone asks how things
are going, you’ll find yourself ready and poised to guide the
conversation down the path you want it to go.