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Seven Questions All Startups Should Ask

If you want better performance, ask better questions.

Evidence shows that reframing the questions you ask inspires the kind of productive and insightful ideas that animate the most resilient and successful startups.

And by questions, I don’t mean questions like:

• What’s your business model? • What do your customers expect? • Who is your competition? • What is the cost of acquiring new customers?

These are important “tactical” questions and angel investors expect you to have the answers. Every startup can’t help but engage with these questions in the normal course of every business.

Pick Your Questions

The questions angels really want you to answer are “transformational” questions.

Questions such as “Where are you possibly wrong?” These questions are transformational in that the answers will make you question practices that you assumed were settled. It’s in the struggle with transformational questions that the most dramatic innovation is possible.

In a world where startups are expected to display supreme confidence, asking entrepreneurs to consider their fallibility is a nod to humility. Framed this way, the question acknowledges that every entrepreneur, no matter how well prepared, can’t be right all the time. (By the way, that’s true of angel investors, as well.)

There’s no shame in an entrepreneur being wrong. But there’s no excuse for refusing to consider the possibility.

In a fine book called Change Your Questions, Change Your Life, author Marilee Adams suggests that a good way to approach a problem is to ask better questions. Changing the questions inspires completely new ways of thinking about life’s challenges. Where roadblocks existed, new solutions emerge. Where blame and self-doubt clouded the team, new possibilities materialize.

Marilee Adams points out that most decision-makers get the questioning process wrong. She says that decision-makers should focus 80 percent of their deliberations on asking questions, and 20 percent on answering them. For most startups, the priority is the other way around. I encourage all startups to change the questions they ask themselves. If they don’t, I will. There are an infinite number of great questions. Here are seven questions for entrepreneurs to start with:

1. Where might we be wrong? Most teams are invested in demonstrating they are not wrong. But that process breeds arrogance and the temptation to discard evidence inconvenient to the premise. Growth and learning are best fortified in an attitude of humility.

2. How do we want the world to be different because of our startup? Framed this way, the question reminds the team that their initiative is a moral choice and requires them to consider how their startup advances the team’s deepest values and hopes for the world.

3. What rules/practices are we still reluctant to disrupt? The best startups are disruptors. But are there still traditions, assumptions, and practices that remain off-limits? Maybe there’s a good reason not to disrupt them, but you won’t know until you ask the question.

4. Honestly, is this what I really want to be doing right now? It’s a terrifying question because it confronts us with the fact that we only get one life to live and there are no do-over’s. The most important decision we all get to make is what to do right this minute.

5. What is our “meaning” metric? Every startup needs to track certain metrics and the selection of those metrics is critical to the long-term health of startups. A startup can focus on only so many metrics. Complicating the issue is that those metrics constantly change. The revenue metric is always important, but the meaning metric can be revealing. It differs for each startup. The meaning metric goes to the underlying purpose of the startup, the impact that the founders hope to have on specific people and their lives. The clearer an entrepreneur can be in articulating this metric, the clearer his or her path to executing against this metric becomes.

6. What should we stop doing? Most startups have an action bias. They focus on what they should start doing right now. But the harder question goes to what they should stop doing—what tasks they should eliminate. Without stopping to ask that question, opportunity costs go up as the team sucks up resources doing what may no longer be relevant and starving resources from what’s more important. The question becomes harder to ask as the practices being challenged appear to be been successful or profitable.

7. Whom do we serve? It’s important to see the startup as an opportunity to serve. But to serve whom, exactly? Customers? Investors? Peers? The profit motive? Those who seek to serve others before being served will tend to go the furthest because service to others is the only reliable path to cultivating relationships and relationships are the only reliable path to sustainable success.

What other questions do you regard as transformational?

Change Your Questions, Change Your Life.

Change Your Questions, Change Your Life.


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