How to Ask Great Questions

A Better Discovery Framework

Do you remember Mikhail Gorbachev? He was the last leader of the Soviet Union, and also played a pivotal role in dismantling the Cold War. In 2008, Gorbachev engaged in a U.S. tour to talk about nuclear weapons.

After a full day of interviews, many of which repeated the same tired questions, Gorbachev’s publicist decided to slash the last interview from one hour to 10 minutes. The journalist conducting the interview knew he’d needed to get Gorbachev’s attention quickly, so he opened with an unexpected question:

“What is the biggest lesson you learned from your father?”

The question was unlike anything that Gorbachev had been asked that day and it got him to think. He likened it to a movie playing in his mind. Gorbachev started telling the journalist a story about the day his father got called to fight in World War II.

It was a story full of intricate detail, describing the flavour of the ice cream and even the aluminium cup the ice cream came in. And every time Gorbachev’s publicist interrupted to say the time was up …

“I want to speak to him”

Gorbachev said, waving his hand and pointing at the journalist.

The lesson here is clear: when asking questions, first aim for the heart, as this leads you on a pathway to the soul

In our role as financial planners, there isn’t one magic question we can ask to get to our client’s hearts.

But there are hundreds of winning questions which will definitely get us closer to that goal. If you can make someone feel that you are genuinely curious about a subject that they are passionate about, there’s a good chance they will open up to you.

I’ve developed a framework to develop more meaningful conversations with my clients through asking better questions that I believe other financial planners can apply in their own firms. It is my personal goal to see that we, human financial planners, create social value in a way a robo-adviser algorithm never could.

Make the Conversation About Them

At the initial meeting with a client, it’s tempting to list all the reasons why you should be the one to help them.

But rather than going straight into salesperson mode, I begin by asking this valuable question:

  • “What prompted you to contact a financial planner?”

Your prospect will have the opportunity to explain what they need help with – and you’ll have a chance to actively listen.

Some of my favorite follow up questions to this are:

  • “What would be a great outcome for you in working with a financial planner?”

 And this one:

  • “What would be a great outcome for you from this meeting today?”

I love these questions because they let the client set their expectations for the process, which gives you an opportunity to deliver on and exceed their expectations. It’s a direct path to alignment and ensures they’ll leave the meeting feeling valued and understood.

Listen to the Answers

If you’re not actively listening to the responses that your client or prospective client is giving you, then it really doesn’t matter how good your questions are.

Active listening gives you the pathway to see solutions grow naturally out of the conversation with the client. Believe that your next question will depend on what the client just said.

Active listening is a skill. It doesn’t come naturally for many of us. Some tips for improving your active listening include:

  • Be quiet and actively encourage the other person to talk, through head nods and guttural sounds
  • Avoid interrupting the other person when they’re speaking
  • Avoid starting to think about your answer when the other person is speaking
  • Don’t finish their sentences or fill in the blanks… no matter how tempting!

In the end, good listening is all about promoting your client’s or prospective client’s willingness to communicate; so you need to be comfortable with silence.

Staying silent gives you time and the opportunity for them to share extra information with you. It may feel odd initially, but you will be amazed how often more information emerges after a moment’s silence.

Have Patience

The answer you’re looking for rarely comes from your first question. That’s why it’s important to have a series of questions that progressively get your client to open up about their goals. From there, you can start to position your services accordingly.

Imagine your questions are a shovel digging for gold. The more effectively you use your shovel, the closer you’ll get to the gold. If you’re only ever scraping the surface or digging your shovel in once before moving on, you may never get the treasure!

Prepare to Improvise

Perhaps the hardest part of having deeper conversations is that they’re different for every client. This means asking different questions and knowing how to improvise.

In my early days as a Financial Planner, I used to write out all the questions that had the biggest positive impact in my meetings. Then I’d review that list prior to all my client meetings and store it away for later, kind of like records in a jukebox.

I would observe the flow of the meeting to activate the appropriate ones. In other words, I was prepared to ask the question, but I was improvising on the best timing to release it based on the flow of the conversation.

This approach makes the back-and-forth between you and the client more spontaneous and builds on the sense of trust you’ve created because you’re involved in a conversation – as opposed to an interview.

Here are a few of my favourite questions to help you start building your own question bank:
  • “What does retirement mean to you?”
  • “What are your biggest concerns right now?”
  • “What changes or challenges do you expect to happen in the next five years?”

Remember, your goal is to start a conversation, not to interview

To do this requires active listening, patience, and a willingness to improvise.

By listening to what your client is saying about their goals, concerns, and dreams, you’ll be able to deliver a sound financial plan that will get them to where they want to be. And by connecting with them on a personal level, you’re more likely to build a solid long-term relationship with them, too.