Skip to content

2,400+ Clients since 2001 • $4.3+ Billion Raised

Challenge Stale Startup Assumptions

Ask Questions to Challenge Stale Startup Assumptions

I’m a big fan of the old adage “There are no stupid questions, only stupid answers.” We have all heard questions that begin, “This may be a dumb question, but…” used effectively by smart people who are not afraid of risking ridicule by challenging a questionable assertion from an intimidating speaker.

Most people in business seem to expect their leaders just to give orders. According to Gary B. Cohen in his book, Just Ask Leadership: Why Great Managers Always Ask the Right Questions, as leaders advance, they tend to oblige by asking fewer questions and providing more answers. This is precisely the wrong approach.

Entrepreneurs and business executives have to keep reign over a very broad domain. They need to ask the right questions in the right contexts to stay ahead of the game and to empower coworkers to find solutions, embrace responsibility, and become accountable.

Cohen provides specific insights to seek in particular situations, while also explaining how to create a culture of question-based leadership. I agree with his outline of five critical areas:

  1. Improving vision. Good vision requires insight from all levels of the organization. Forward-leaning questions can illuminate the values of both the leader and the team. This, in turn, will enable employee buy-in, and good choices with regard to interacting with customers and future goals.
  2. Ensuring accountability. Having coworkers solve their own problems is critical to building their accountability, and it increases team performance. When job descriptions are clear and people are encouraged to act in good faith, it’s easier to see who made the mistakes and who’s to blame. Failure must be used as an opportunity for learning, not an excuse for punishment.
  3. Building unity and cooperation. It’s important to listen respectfully to coworkers’ questions and opinions since they’re all a part of the team. This creates a culture of trust. It requires asking good and fair questions – not “gotcha” questions. Getting everyone to participate isn’t always easy, but when coworkers realize their ideas have value and the organization is receptive to them, they’re more apt to share.
  4. Creating better decisions. Most leaders make too many decisions and fall into the trap of doing others’ work. The best decisions are often made by those down the chain of command, not up. Get the right answers by asking the right questions. In order to avoid the blame game, it’s important to know who is responsible for specific problems.
  5. Motivating to action. “Because I said so,” is not a phrase that will inspire the team. Ask for success. Create a sense of urgency, appeal to people’s desire to be remembered, and energize coworkers by using shared responses – such as asking a group to say, “Agree,” after consensus is reached.

If you tell coworkers how to do their jobs, you are essentially limiting their options and stifling their initiative, says Cohen. You are not leading. Asking questions isn’t just about not knowing the answers – these questions lead to fresh ideas, committed action, and the creation of a new rank of leaders.

Socrates was the early master of asking the right question, He taught that when you ask questions, you show respect, and you are respected in turn. Of course, even the best question is moot if you don’t listen to the answer. Ask. Listen. Learn. Lead.

Marty is Cayenne's Chief Knowledge Officer and the Founder & CEO of Startup Professionals. His passion is nurturing the development of entrepreneurs by providing first-hand mentoring, funding assistance, and business plan development. He has over 30 years of experience in big businesses, as well as startups. View details.

This article was last updated on
Back To Top