How to Ask a Question

In 2010 I was riding the Metra in Chicago, as usual, making my way to the office near Monroe and Wacker. Although this train ride required me to be "that guy". You know... that guy that gets on their phone and talks like they own the train. So annoying. And I knew that I had little choice.

I had been doing a slow building of engagements for a well known brand for about year. One small engagement after another with a vision for where it was all going. We had done some great discovery and analysis at their retail locations as well as at their corporate headquarters. We had come to some final conclusions that included a high-confidence estimate on what was financially on the table. You could call it ROI, but everyone filters ROI into whether they "believe it" or not so forget ROI. It was how many dollars were at stake. It was over $1B.

My role in this has been consistent over time across roles, across organizations. I had revenue responsibility, which was where I am most comfortable. My job was to connect my team's consulting expertise, in situations where there was a sizable amount of money on the table, with a client that wanted our help to go capitalize on the opportunity. And this conversation was about to happen as my cell phone rang on the Metra.

I grabbed my bag, and got on my feet as I answered the call. I figured, what's the best version of "that guy"? I think it is "that guy" that is moving from car to car so he only annoys me in small 30 second segments. That was the best I could do. This call was literally MONEY.

We talked to customers all over the US for this client. We met with their retail teams. And the environments my team endured to talk to these customers and meet with their teams was actually legendary stuff. To this day, I feel like some of the insights we pulled out of their clients and staff are gold they never knew of before and have already forgotten. There were intense confrontations, situations that actually felt dangerous, and my favorite one... a bird flew over me and crapped on my sport coat as I walked in at 8am for my first retail visit. I started that engagement off with a message from the gods.

The client is a publicly traded firm and had lost about $1.5B in marketshare in the past year (2009-2010) so they had that kind of feeling in their headquarters of "what's going to happen now". I had been a badged contractor in their building, hanging out in their cafeteria at least once a week to be available for their leaders, answer questions, and just get the feel of the culture. With this kind of backdrop to the work I was doing as their stock price was falling like the bird crap that landed on my shoulder, my call had some potential to be full of landmines.

My client's question to me on that call, on that Metra train, was...

"What could you guys do for us that is free?"

What would you say?

Maybe...

"You get what you pay for."

"When is the last time you got something valuable for free?"

"Why would you think I offer free things?"

"Are your products free?"

"Why did you waste all of my time?"

"What is happening right now?"

What did I say?

I said...

"Explain"

I said no other words. I calmly said, "explain."

They answered like this:

"As you know, we aren't doing very well. In fact, you could say, everything that could go wrong is going wrong. Nothing is actually working. At our organization, we don't take big leaps... so we'll try something, then if it works, we'll try a little more. We slowly see what works and what doesn't and then we'll go all in."

I said, "Great, I'll come to the office tomorrow with the contract ready to sign."

Their response was a little laughing and a "What?"

I explained... "You said you guys like to try things, do a little more, see what works and what doesn't and then go all in. Well, you just lost $1.5B in marketshare. So you've done it. You've proven that what you're doing isn't working so it is time to go all in. We know what to take action on to get that value back. I'll have it laid out in the contract."

I signed that contract an a couple other multi-year, multi-million dollar contracts with them following that conversation.

You can make your own conclusions and commentary about that situation, that client, my approach, and how it ended.

The point I want to make here is my one word question: "Explain"

And how I came to ask that question and asked other questions of other clients. As I have learned over time that this is my superpower.

How to ask a question.

First, I'd like to answer an unasked question from you, the reader (although it could become and asked question in the comments later).

Why should I listen to Rolly?

Because I might ask that same question. Well, I have a pretty consistent track record and some scientific evidence of why you should take what I am saying to heart.

For the scientific evidence category, here are some descriptions of me from talent profiles of me over the years:

• "Chances are, Rolly probably started asking people questions as a child. Others quickly notice that he is genuinely interested in what they say."
• "Rolly poses never-before-asked questions."
• "Language has fascinated him since childhood"
• "Rolly's mind allows him to venture beyond the commonplace, the familiar, or the obvious."

Of course, that is great to see in terms of what you would expect from me in how I behave and interact. Now, it still doesn't matter unless I get results. So what kind of results have I seen (now that I'm 50 years old, I have a few things to look back on)?

• My 1st year in college I was hired as an Resident Assistant and within the next year became the Head of Training for the staff of 100+ RAs
• My 1st year playing college volleyball became the President of the club and secured the largest budget (by more than 100%) the club had ever been given
• My 3rd year in college I switch from player to Head Coach of the team
• In my 1st year as a player, became the Secretary of the conference we played in (SIVA)
• In my 2nd year as a player, became the President of SIVA
• My first job out of college was with the US Olympic Volleyball Teams
• In my next job, close the largest deal in the history of the firm
• In that same job, a few years later, closed the most profitable deal in the history of the firm
• In my next job, closed the largest strategy consulting contract in the history of the firm
• Got my Kellogg MBA
• Had many other big wins, less historic in nature, worth many millions of $$
• I have 6 kids that ask great questions and need me to ask them even better ones

I know that I didn't solve world hunger, but hopefully that gives you a few things to at least say, "This guy might know some things that are helpful."

And I could detail in a long article each one of these bullet points and how those outcomes started with me asking a question, a series of questions that led to that outcome. That is really why this is important to pay attention to. What did you ask in the most critical moments? That determines the outcome.

To me, this is why you need to understand how to ask questions.

And also, I have bad news.

Odds are, you are not very good at asking questions.

Don't feel bad about it. Most everyone I know is bad at asking questions. And that is why I am writing this. That is why I did a speaking engagement in 2019 at Kellogg about it. It is a life-changer to understand, and almost no one does it well. It is like an eclipse. I get to witness it very rarely in my lifetime. And when it happens, it truly is a sight to see.

For me, asking good questions in business is great. I move my business forward by helping clients move theirs forward. Tense contract negotiations become a series of what looks like "cheat codes" for me as I navigate conversations with executives and business leaders, responses, non-responses, and aggressive tactics by large procurement teams. And that's all good. Supporting myself and my family is great. Creating jobs for others, creating new opportunities for others, and maintaining an engaging environment for my colleagues at work by bringing in money to pay everyone and pay for everything is rewarding.

However, that isn't what gets me motivated to talk about asking questions.

It is about your family. Those that you love. Your friends. It is about your life.

When my teenager came to me and said, "I am feeling really depressed and I don't know what to do."

What was my first question? Second question? Should those questions be decent ones? Good ones? Great ones?

I say, it better be one of the best questions you've ever asked in your life. And I am not exaggerating. You need to be ready for that. If you are not ready, the outcome could be tragic.

If your dog is diagnosed with a terminal illness, what do you ask the vet? Who would be affected if my dog is that sick? All the kids, me, Veronica, and of course my dog. I better ask some really great questions.

That's where all my power comes from on this.

Business Smidgeness.

This is about your life and those you love.

Now for the fun part… I’m going to give you some things you can take away today, start using tomorrow, and if you have enough courage to really use the language I’m going to give you, you’ll see immediate changes in outcomes.?

Here we go.

Here are the 3 reasons I ask any question… the 3 guiding principles of what I ask, how I ask it, when I ask it, and who I’m talking to.

• I am not afraid
• I care about you
• I live to serve you

As a way to remember, I'll just give them one-word names and explain myself more...

• COURAGE (I am not afraid)
• CARING (I care about you)
• SERVING (I live to serve you)

COURAGE

I am not afraid of answers I might get from the questions I ask. I get clarity in the moment. With the answers I receive, I name problems and obstacles in the moment.

CARING

I care about you more than you probably can imagine. I nurture every question so you can best answer it. When it comes to building trust between us, I own that.

SERVING

I spend my life in service of others--I serve you. I always plan with you, together, not by myself. I see success that we want to achieve as something without excuses. We'll get what we plan for, and if we fail, it is our fault.

What are some questions you can ask based on these guiding principles? Here are some of my most used questions...

COURAGE (for clarity)

• Why are we here?
• What do you get paid to do?
• Where is the business going?
• Who is this product for exactly?
• Why are you in your role?

COURAGE (for problems/obstacles)

• What is the current state/future state/what's in the way?
• How high is up?
• Tell me more.
• Explain.
• Who makes that happen?
• Why make the effort to change?

CARING (nurturing/trust)--I put these things in front of questions to get the best, most precise answers

• Help me with something
• I'm going to ask an awkward question
• This is going to sound rough
• Are you ready?
• We've not worked much together so help me here

SERVING (plan together)

• What would you like me to do?
• How do we connect this conversation to ...?
• Walk me from today to us succeeding together
• What needs to happen to reach this goal?
• When you and I build something together that you can sign, I'll sign it with you.

Now, I'll head off another question here that is common... and I'll quote a CEO I talked to about this topic. Their question...

"It seems like attempting to say some of these things, asking some of these questions is strongly connected to being comfortable and genuine when saying them. So would you say that we shouldn't ask these things, say these things if we aren't comfortable with them?"

My response...

"Correct.

However, I think you're also asking if it is okay to not ask these categories of questions and ask other questions.

The answer to that is no.

Your comfort level isn't a good excuse for asking ineffective questions."

So (in a business context) if the person that will be doing the questioning, having the interactions with clients is not comfortable with these questions, they are in the wrong job. You need someone else in that role.

Of course, in your life, you can't hire someone to take on your role as father, mother, brother, sister, son, daughter.

So like I said, I am not exaggerating.

You need to be ready.

My first question (with some nurturing) to my teenager who said they were really depressed... "Ok. I am going to help you. I believe I can help you. I am here to help. It takes a lot of courage for you to come to me and say this. Let me ask you some things and I want you to just answer. Don't worry about your answers. This is just you and me talking. You will determine together with me what we do next. Ok? My first question is a tough one but important. Are you thinking about suicide."

That is a critical moment.

I am not afraid.

I care about you.

I live to serve you.

I want you to be ready to ask the right questions at critical moments.

There is too much at stake.