Inside the Office
It’s the beginning of a new school year, and one of my favorite parts of September is welcoming back young entrepreneurs. I get to hear what happened to their ventures over the summer, what worked, what broke, and what new questions they’ve been carrying around. And since a good bit of that tends to show up via email, I thought I’d would share one that landed in my inbox this week.
The subject line was the title of this issue: “URGENT! Action Required!”
That subject line is usually reserved for spam or a billing notice. So I opened it. It was from a student entrepreneur I’d never met, and the venture appeared to be a few weeks old. The founder wanted to meet with me as urgently as possible… preferably in the next day or two.
But it didn’t really read like a request. It read more like a demand, which made me want to sit with it for a minute. I’m always curious and always willing to help, so I wrote back that I’d be glad to meet. But then I asked a question. Was this urgent for me, or urgent for them? I intended a little humor. The reply made clear that it was urgent for me to meet with them.
It reminded me of something I said to my management team at Shindigz for thirty years: Your lack of preparation and planning does not constitute an emergency on my part.
I wasn’t trying to be rude or uncaring when I said it. Instead, I was trying to teach discipline. When something arrived on my desk marked urgent, the first thing I did was ask how it got there. Almost every time, the emergency had been visible for weeks. Someone hadn’t asked the right questions early enough, or someone had hoped a problem would resolve itself, or — more than I would have liked — someone simply didn’t do the work. In other words, the urgency was real, but it just wasn’t mine.
That’s why I’m sharing the email I received. And, as we start a new semester and/or a new stretch of our respective entrepreneurial journeys, it’s a lesson worth sitting with.
Have you done the work before you ask for help?
Every founder should be able to answer a few questions before they walk into anyone’s office:
Have I identified the assumptions in my plan that, if wrong, kill the business?
Have I anticipated what the team and the business will need in the next ninety days, and do I have a contingency for each of those needs?
Am I asking for help at the right moment?
Am I approaching people in a way that makes them want to help me?
By the way, in case you couldn’t already tell, that last one is where this particular student’s email failed, and it’s also where I see the most room for improvement with founders of every age.
After all, time is the most valuable resource we all have We can raise more money. We can hire more talent. We can rebuild products. But time is gone the moment it passes, which means, when you ask someone for their time, you are asking for the one thing they can’t replace.
And because of the value of people’s time, the tone of an ask matters. A “must do” puts the other person on defense. In contrast, a “want to do” invites them in. The way to establish the latter is usually with a little humility.
For example, compare these two:
“I need to meet with you tomorrow about my venture.”
…versus…
“I’m a sophomore working on a venture in the campus food delivery space. I have hit a wall on unit economics and have done my homework on it. I am having trouble getting my CAC/LTV to pencil and I would value thirty minutes of your time in the next couple of weeks if you have it. Here is what I have so far.”
The second one tells me you’ve done the work, and it tells me what you want, and gives me a decent idea of how long it will take. These things make me want to say yes. Or at the very least, it makes saying “yes” easier.
And just to be clear, it’s OK to ask for help. In fact, asking for help is an important part of how entrepreneurs learn, and the best founders I’ve coached are relentless askers. It’s just that the people who ask well share a few important habits.
They ask specific questions. “Can you look at my pricing model?” gets a better answer than “Can I pick your brain?”
They show their work. They bring what they have tried, what they have learned, and where they are stuck. They make it easy to say yes. They close the loop. They come back and tell you what happened. Nothing makes me more willing to help someone a second time than hearing what they did with the first conversation.
Most importantly, they build a relationship before they need it. In other words, the founders who get the fastest help in a real emergency are the ones who did not wait for the emergency to introduce themselves.
That’s not to say if you don’t have a preexisting relationship with someone, you won’t be able to get the help you need. For example, I’ll meet with the student who commandingly emailed me. And when I do, my first piece of advice will be about about that subject line. And then we’ll get to work.
-Shep
Worth Your Time
Almost every conversation in my office hours eventually circles back to the same request — give me a sure answer: tell me my idea is going to work; assure me that I can land my “dream job,” paint the path for how I find happiness.
Everyone is seeking certainty. And honestly? I want those answers too.
Which is why I appreciated Simone Stolzoff’s new book, How to Not Know. How to Not Know follows people facing problems with no easy answers, like an economist trying to forecast the next market crash and an island nation confronting climate change.
If you’ve sat with the anxiety of wanting a response or lain awake craving someone to tell you how it ends, this book will feel uncomfortably familiar. It also offers practical ways to get better at not knowing.
Entrepreneurship is a daily exercise in not knowing. So is life.
