The Question Before the Question

In late 2012, I sell my company. I’ve worked hard, put my heart and soul into it, birthed not only a company but also two children in the process, and navigated a new business during a pivot. But I’m tired and have decision fatigue.

I’ve been responsible for a lot of parties, employees, investors, newborns, and had to make a lot of choices, often difficult ones. So I stay with the acquirer a year, and have my third (and last) child.

But I also start to ask new questions about my career.

Deep down, I seek validation from others, validation that I am still relevant. So for two years I do what I thought would make me feel more credentialed on paper. But in hindsight, I am becoming less fulfilled and less interesting.

I professionally dabble full-time, including as an Entrepreneur in Residence at a VC a day a week, advising private equity, guiding big data analytics CEOs, and looking for someone or something that inspired me.

I stumble upon a prestigious C-suite role at a Fortune 100 company that will fund plenty of private school education and therapy for my children.

Great, right?

Well, I stop. I realize I am limiting my options to the things in front of me instead of thinking about what I’m not considering. What was my passion? How could I find it? Was I fully exploring my options?

I am letting my options guide me, not me guide my options.

So a year ago, I realize I need to ask for help. I contact a number of people who have inspired me. This includes Wok, a developer who turned out to be my co-founder, someone I met at the VC.

One day, Wok cooked pho for all of the company, yet he only brought four bowls. Strange, right? Well, you know why he did this? So you could meet someone else as you washed yours.

He’s a guy with a terrific sense of community, but also with a great vision about human relations and, here’s the interesting part, where we are heading as a society. We share thoughts and I eventually learn that we also share similar values, and this is why I trust his judgment when I have to make the decision about where my daughter should go to kindergarten.

Wok is a big thinker who connects with people. And as I learn when we catch up, he had also been dabbling since we both left the accelerator, most recently on a sabbatical in Prague. But he is also yearning for something more meaningful, to build something that supports people.

IMOco-founders should share values and goals, because it provides a good foundation for decision-making in good times and in bad.

We find we click. So I explained my dilemma, and that over time, as I had more responsibility, and more people relying upon me (be that making payroll at a start-up, or planning play dates) my life was filled with more and more small decisions. And this wasn’t making me happy at all.

And of course, let’s not forget the “social” fatigue. I am getting so many emails, texts, slacks, whatsapps, facebook messenger posts, and it’s impossible to keep up across so many channels. OMG.

Not only am I drowning in “administrivia”, but the urgent is crowding out the important. And you know what? I am spending less time on the things that matter.

But am I focused on the right thing?

I remember Oprah writing:

“Life is about recalibrating. About continually asking yourself: ‘What do I have to do to get where I need to be?’ ‘How do I create the life I want?’”

Was the endless stream of social media keeping me from thinking about the bigger questions in life?

Aha!

We land on the power of asking for help on questions. Big ones. Little ones. Little ones that add up to big ones. Decisions that you make alone, decisions that you make with input from others, decisions that you make as a group.

Questions, options, decisions.

Yes: questions, options, decisions. I mean, how many people were waiting on decisions from me, and how many people was I waiting on for decisions? Could we as a society do a better job of asking?

We work really hard to find a great team. We realize that when we are thoughtful and ask good questions, we can make better decisions on people and product.

Armed with great feedback from an MVP, and the realization that we had a team that could execute well, we start to build out our product in earnest in August. After a few sprints, I realize we too were falling prey to the cycle of urgent crowding out the important.

We are focusing on delivering against features in our Beta, rather than thinking about how could critically use the product ourselves.

In a world of unlimited options yet limited resources, and consumers being inundated with the “next great thing”, how can we “dog food” our own product to ask better questions, generate better options and ultimately make better decisions?

How do we not let the things that command our attention, the bug fixes, the investor pitches, the submission deadlines, in other words, the “urgent”, crowd out the important? How do we not let customer interviews generate so many options that the product vision becomes diluted?

I now think about how we ask questions of ourselves everyday to make us great.

A decision is a response to an ask in response to a need for help. As a company that focus on asking better questions, generating better options, and eliminating those options to get to better decisions, we believe the answer for others can be found using our own tool.

By asking better questions, generating better options, and getting those we trust to help make better decisions, as a company can we be more:

• Innovative? While CEO of Google, Eric Schmidt[1] was interviewed by Time magazine. “We run the company by questions, not by answers. So in the strategy process we’ve so far formulated 30 questions that we have to answer. I think you get a better innovative culture if you ask it as a question.”

• Productive? In the morning, Ben Franklin would ask himself: “What good shall I do this day?” In the evening, he would ask himself: “What good have I done today?” In fact, Franklin founded an entire organization that he ran by asking his members questions, time and again.

• Focused? Steve Jobs asked Apple’s Design Chief John Ivy almost daily, “How many times did you say no today?

We won’t rest until we have a product people love, and until we have a competitive advantage as a company and as people because we’re using our own products.

[1] Schmidt’s fund Tomorrow Ventures was an investor in my last company and given this and many other reasons I consider him to be brilliant.