How To Ask More Powerful Questions

“I got this.”

This was my go-to line when I knew what I was doing and wanted to get my boss off my back. What I couldn’t see was how it highlighted a major mistake. I wasn’t evaluating the situation, I wasn’t asking questions. I assumed I knew all the answers, and I was usually wrong.

I didn’t realize the error in my ways until a major client rollout flopped and I had no one to blame but myself — my own stubborn belief that “I got this,” even though I clearly didn’t.

In a debrief with my boss, he said, “Aaron, when you say 'I got this' and have no concerns about a situation, that is when I get concerned.”

What he meant was that as soon as I stop asking compelling questions, I assume I know what’s going to work and stop evaluating potential outcomes and solutions. It’s a tendency we all have when we want to take the quick route. It’s what holds us back from being powerful leaders.

Why is asking powerful questions an essential leadership habit?

It provides leaders with a means to mitigate their confirmation biases and dive deep into the evaluation of a situation, a person or their team as a whole.

I had biases for how the rollout was going to play out. I’d done this before; I knew what was going to happen, so why should I look further into it? I wish I could say this was unique to me, but we all do this. Our brains are wired to jump to outcomes, to look for shortcuts.

Not sure if this relates to you? Watch this quick video to test yourself.

Daniel Kahneman, Nobel Prize-winning behavioral economist who was the first to highlight these biases, states, “Confirmation bias comes from when you have an interpretation, and you adopt it, and then, top down, you force everything to fit that interpretation.”

This bias can be disastrous for leaders; it can hinder their decision making ability and blindside them completely. Asking powerful questions is our way around it. It can help us avoid this common miscalculation.

What does a powerful question look like?

I’m going to share a definition of and the criteria for a powerful question, but I also want to be clear there is no script for asking a powerful question. Powerful questions evoke clarity, create greater possibility, reveal new learning and generate action. Here are a few ways to determine if a question is powerful or not.

A powerful question …

• Is open-ended: Ask what, when or how instead of asking a yes or no question.

• Comes from a beginner’s mindset: Start by telling yourself, “I don’t know the answer.”

• Is clear and succinct: Keep it simple, don’t use too many words.

• Is impactful: It’s important to remember that not every question in a conversation should be powerful. In a 30-minute conversation, aim for 2-3 powerful questions.

• Happens in the moment: Here is probably the most crucial point to remember about powerful questioning. You can’t plan it! Formulaic questions outlined before the conversation won’t work. You have to be in the moment.

There is no script for asking powerful questions. There is, however, an often-overlooked trait that will set you up to ask powerful questions in any situation.

What’s the trait?

Curiosity. Want to discover a master of curiosity? Find any 3-year old and watch them for an hour. They ask what, why and how to nearly everything they see in the world around them. They want to know more and do not limit themselves to the societal expectations of what’s right or wrong. They just ask.

As we get older, we are trained to lose our curiosity when it becomes clear it’s not acceptable to ask all the questions that come to mind. Instead, we go about our days having surface-level conversations, rarely digging more in-depth with a co-worker, client or even a friend.

The secret to asking more powerful questions is digging deeper. It’s triggering our 3-year old selves and reconnecting with our curiosity.

I found it hard to come up with a way to share this concept with you. I realized it’s so hard to explain because, as adults, there are very few situations where we are curious. Then I remembered riddles. They are a great way to bring the curiosity right back. Try this one out.

“What has a head, a tail, is brown and has no legs?”

As you are reading this, trying to figure out the answer, your mind is swirling with questions and possibilities.

What kind of animal has no legs?

Is it an animal?

What else could it be?

What sorts of things have tails?

The series of questions running through your head is your curiosity showing up. It’s the little kid inside of you wanting to understand, to know. Curiosity is the genuine desire to learn more -- to explore.

To be able to evaluate people, teams or situations with greater fidelity, go back to the curious part of you that wants to explore. Instead of restricting yourself, open yourself up and allow your mind to ask any question.

Allow yourself to ask the powerful questions. You already have them in you.

Sometimes it may take priming yourself with a riddle to get you there.

“What has a head, a tail, is brown and has no legs?”

A penny.

10 Questions to Ask a Financial Advisor

Before you commit to a financial advisor, you want to make sure you’re hiring the best person for you and your situation. Start by asking yourself a key question, then check out the ten questions you should ask an advisor before hiring one.

First, what type of financial help are you looking for?

1. I just need to get started investing for my financial goals: A robo-advisor may be the best fit if you're just starting out or only need investment management. For a low fee, these computer-based services choose and manage an investment portfolio for you. Some also offer access to financial advisors if you have questions about your investments or your goals. Robo-advisors often have low or no account minimums, so it's easy to get started.

2. I want personalized financial advice but don't need to meet my advisor in person. There are many services that offer online financial planning for less than you'd pay a traditional in-personal financial advisor or financial consultant. These companies provide complete investment management and holistic financial planning; the major difference is that you'll meet your advisor virtually — by phone or video chat — rather than in a local office. Most services pair you with a dedicated advisor or certified financial planner; some less-expensive options offer access to a team of advisors.

3. I want a local advisor or a wider array of financial advice: On the other hand, if you want in-person financial planning or have a more complex situation, you may decide a traditional local financial advisor is right for you.

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10 questions to ask financial advisors

If you think exploring a relationship with a traditional financial advisor is the right move, be sure to ask these ten questions during the interview process.

1. Are you a fiduciary?

A fiduciary works in the best interest of the client and only recommends investments that are the best fit. Nonfiduciaries, such as broker-dealers, need only to recommend products that are “suitable” — even if they're not the lowest-cost or most ideal for you.

2. How do you get paid?

Advisors can use a variety of fee structures. To keep it simple and avoid conflicts of interest, focus on fee-only advisors. They don’t get commissions for selling products.

"Make sure it’s fee-only — those particular words," says Alice Finn, founder of PowerHouse Assets and author of "Smart Women Love Money," a guide to investing. (Some of the questions here are from her book.)

Fee-only advisors might charge a percentage of the assets they manage for you (1% is common), a flat fee for services or an hourly fee. If cost is a concern, you may want to go with a low-fee robo-advisor or an online planning service like those mentioned above.

3. What are my all-in costs?

In addition to paying the advisor, you’ll face other fees — and you'll want to know what they are. Fees can decimate your savings over time. "You can lose half your net worth without even knowing it," Finn says. "You want to be vigilant."

4. What are your qualifications?

Financial professionals can have a confusing list of initials behind their names. And whether a finance professional goes by "investment advisor" or has a certified financial planner designation, it's your job to vet them. The Financial Industry Regulatory Authority's professional designations database will tell you what they mean; if there are any education requirements; if anyone accredits the designation; whether there's a published list of disciplinary actions; and if you can check professional status.

You can also use a Form ADV to check an advisor's record.

5. How will our relationship work?

Put another way: How much access will you have to the advisor? You want to know how often you’ll meet and whether they're available for phone calls or emails outside of scheduled appointments. (Learn more about what financial advisors do and what you can expect from the relationship.)

6. What's your investment philosophy?

It’s important to ensure you have the same investment management philosophy. Here’s why: “You have to believe in what they’re doing to stick with it,” Finn says. “When financial advisors really do their job is when the market is down and they can convince you to stick to the same page,” she says, so you don’t sell at the bottom of a market cycle.

It's also important to make sure you and your advisor align on investment style. For example, if impact investing is important to you, you may want to ask whether or not your advisor will be able to help you create a portfolio that aligns with your values.

Also ask: Who are your typical clients? Find an advisor who is used to a situation like yours and able to help you meet your goals.

7. What asset allocation will you use?

You’ve heard how important it is to be diversified, right? Your asset allocation is how you create a diversified portfolio. “It drives most of your returns,” Finn says.

“You don’t want someone who is just going to pick U.S. large-company stocks,” Finn says. Your portfolio should include domestic and international stocks, and small-, mid- and large-cap companies.

8. What investment benchmarks do you use?

Advisors should use benchmarks that directly relate to what they’re invested in, or be able to explain why they don’t.

Some managers will use a “straw-man benchmark,” Finn says. For example, the advisor says: “My goal is to beat the Standard & Poor's 500.” But if that advisor is investing in a diversified portfolio beyond simply large-cap U.S. companies, that benchmark is a mismatch. “Over time they should beat the S&P 500 because they’re taking on more risk,” Finn says.

9. Who is your custodian?

Ideally, your financial advisor has hired an independent custodian, such as a brokerage, to hold your investments, rather than act as his or her own custodian — à la Bernie Madoff, the notorious financial advisor who defrauded clients through a multibillion-dollar Ponzi scheme.

That provides an important safety check. “If I send my clients performance information … and it tells them how much I say is in their account, they can go online any minute and double-check,” Finn says.

10. What tax hit do I face if I invest with you?

This helps ensure the advisor has your tax bill in mind when making financial decisions. And asking about taxes and fees is a way to explore what your estimated net return might be. “What you want to know is: What do you get to keep after fees and after taxes?” Finn says.

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