“How Are Things Going?” Four Dreaded Words for an Entrepreneur

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“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.”

By Rachel Lehmann-Haupt (Editor, Women 2.0)

It’s a natural question when you’re having lunch with a friend, but when it comes to your fledgling startup, it’s often the last one you want to hear. In a recent post in the Harvard Business Review, Kathryn Minshew, the CEO of the Muse and the Daily Muse explains her four point strategy for getting through it.

1. 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.

2. 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.

3. 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.

4. 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.

Women 2.0 readers: How do you talk about your business when someone asks “How are things going?”

Rachel Lehmann-Haupt ([email protected]) is an editor at Women 2.0. She also works with companies on the art of storytelling. This includes content strategy and creation of  blogs, web articles, contextual commerce, e-books and e-magazines – with the goal of better influencing and engaging audiences. She was a founding editor and multimedia producer for TED Books and has published and edited numerous articles and books. Her interests include gender politics, working motherhood, urban innovation, health, and fashion. Her work has appeared in The New York Times, the Daily Beast, New York, Vogue, Self, Outside, and Wired. Follow her on Twitter at @rlehmannhaupt.

Photo credit: Miriam Berkley