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What Does Shark Tank Teach Us About Asking Dumb Questions?

Jun 21, 2024

I enjoy watching Shark Tank, though I particularly admire Mark Cuban. Unlike his more ruthless co-hosts, Mark often helps the entrepreneurs, even if he doesn’t invest. He’s tough, asks hard questions, and offers unsolicited advice, but business owners benefit from his feedback whether he invests or not.

One day, watching the show, I thought, “This seems like a simple process for effective consulting: Business leaders work hard to identify their problems and pitch their strategies while experienced experts provide honest, direct feedback.” Simple.

However, consulting often feels more like American Idol. Like contestants showcasing their talents, consultants put on a show to impress clients, focusing too much on themselves and taking too much responsibility for the client’s problems. If results don’t come, the consultants are easily blamed. At worst, clients are left with only recommendations, presentations, and an emptier budget.

Instead of this approach, I believe we should adopt the Shark Tank method: ask tough, simple, and sometimes obvious questions right from the start to set the tone. We’re not selling a methodology; we’re striving for transformation. Like Mark Cuban, we need to determine if we should invest our energy in these organizations. We must assess the leader’s level of buy-in and ownership of their organization. If these aren’t confirmed, it doesn’t matter how good we are as consultants—without the leader’s support, most changes will revert like a bungee cord.

As I consider the Shark Tank approach, here are 3 “dumb” questions I strive to ask more often when I meet leaders and clients for the first time:

Question 1:  What’s the problem? What are the core issues you are trying to address?

This sounds like a very obvious question. But it’s as powerful and important as it is simple. The initial answer will likely be a long list of symptoms. But defining root problems is a key

 responsibility of leadership and we can’t take that away from them or shield them from that

tension. Is it their process? Do problems revolve around key personnel? Is it a bad strategy? Is it ‘no strategy’? What’s the root? We can’t answer this question in one conversation. But it’s good to start the tone off right by asking the hard questions.

Question 2: What are the possible solutions? What have you tried so far? How’s that working out for you?

This question might spark a reaction like the first one. Some might say, “Everything!” Some might say, “Nothing…we called you.” Some might be swiping at the problem and ‘trying’ a variety of things. But this question is important to get a sense of the context. One client I worked with had hired 6 previous consultants before talking to me! When they offered to hire me, I accepted

under one condition, “I will be your next consultant if I can be your last consultant.” Meaning if I couldn’t be a part of a lasting solution I didn’t want to just join the recurring cycle of misfires. I

wanted to be a part of the solution, not just another excuse to blame in light of the chronic problems.

Question 3: How can we help?

If we ask this question, often future clients will say, “I don’t know…you tell me.” But there’s no better time to be very clear about expectations. Sure, we can fill in the gaps and lead them through the process. But we can never let them off the hook. Before, during, and long after our engagement, organizational health is their job, not ours. Our job is to help them do their job.

What we call “dumb questions” aren’t traditional dumb questions. We define dumb questions as simple questions that might need to be asked in order to create more clarity, insight, and growth. However, these types of questions also run the risk of sounding dumb. Though to a naked consultant, this is a worthy risk.

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