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Landon Calabello

By Landon Calabello

Oct 19, 2017


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IMPACT Stories  |   Coaches, Consultants & Strategists

How Asking Questions Can Avoid $10K Mistakes & Build Better Relationships

Landon Calabello

By Landon Calabello

Oct 19, 2017

How Asking Questions Can Avoid $10K Mistakes & Build Better Relationships

Many people possess the innate ability to simply carry a conversation and ask questions relevant to the person they’re speaking to. For others, developing these skills takes practice.

But if I’ve learned anything in my life, it’s that knowing how to ask powerful questions will change your life, both personally and professionally.

Let me share with you my story on how I thought I understood it all, and how that cost me $10K of my customer’s money.

Falling in Love with Marketing

I began my journey at 13 when I designed and developed my very first website on Geocities. By 16, I was fully immersed in my own freelance business, but creating websites alone wasn’t good enough for me, even then.

I wanted to know what happened when users came to a website, what they looked at, and why they left. This was well before Google Analytics existed, which made website analysis very difficult. That’s when I became obsessed with understanding the analytics and psychology of why people take the actions they take on websites and in marketing.

What started as helping some of my dad’s business friends create their first digital footprint turned into opening up the door to join a team at one of the world’s largest digital marketing research firms.

At 18, it was at this firm I had the amazing opportunity to help design and develop campaigns for companies like 1-800-Flowers, Encyclopedia Britannica, Reuters, and many other successful businesses.

Perhaps the most exciting project was working with The New York Times, testing their home delivery subscription process and creating strategies to increase home delivery revenues.

This was during a time where digital subscriptions on the Internet were gaining popularity, while the economy was also taking a turn for the worst. So, our job was simple… discover what works in driving users to purchase home delivery subscriptions.

We tested headlines, buttons, calls-to-action, short vs long copy, web forms, and numerous multivariate objects. After running many tests, we were able to get a 1,011% cumulative increase in conversion on the subscription path and a 541% increase in conversion on the offer page.

With so many huge successes under my belt, and after working with so many world-renowned companies, I thought I had it all figured out – but I was wrong.

How I Failed… Big Time

Fast forward many years, I had an opportunity to help manage a company’s entire digital strategy. We were excited and knew the customer was keen on generating new qualified leads quickly. Because the customer wanted to move so quickly, and despite my better judgment, we decided we would run Pay-Per-Click (PPC) ads immediately to increase lead generation.

We didn’t ask any questions. Instead, we got right to work without truly understanding the customer’s business and who their target audience was. We didn’t even know what keywords their target audience was using to search for our customer’s solutions.

We built their ads based on what we understood about their complex business, not their complex customer. We put $10K of our customer’s money into their account and launched the campaign.

If this section header didn’t give it away, the campaign failed, and though we generated significant leads for their business, they weren’t the right leads.

Since that day, I’ve never launched a single campaign without asking, not just questions, but the right questions needed to truly understand my customer’s business and their primary goals.

How I Overcame by Asking Powerful Questions

Ever since I decided to never launch a campaign without having all the details, I’ve used a simple, yet effective process to always ensure we are set up for success in driving results for customers… asking powerful questions.

In other words, You MUST ask questions that help you understand OMV (Objectives, Metrics, and Value).

For example:

Establishing Objectives

  • What is the ideal outcome you’d like to experience?
  • What results are you trying to accomplish?
  • How much would you gain on the competition as a result?

Establishing Metrics

  • Who or what will report on our results (against the objectives)?
  • Each time we talk, what standard will tell us we’re progressing?
  • How would you know it if you tripped over it?

Accessing Value

  • What will these results mean for your organization?
  • How will these results impact the bottom line?
  • What if this fails?

Understanding OMVs is absolutely critical in ensuring you drive success for your customers, and in a world where ethics in business are so rarely practiced, it’s the right thing to do for your customers.

One project this particularly came into play for was with Palace Resorts, the sister company of Hard Rock Hotels (and one of my favorite projects to date). Our goal was to help increase qualified leads for their MICE segment.

So, obviously, we made sure we had all the right information and asked all the right questions. Our team followed the OMV process with the owners, Vice President of Sales, and the Director of Marketing, essentially asking them 3 powerful questions:

  • What are the objectives?
  • How will we measure this together?
  • What value will these results bring to your organization?

Ultimately, this helped us determine that we needed to design and develop an entire digital strategy which included a website redesign, SEO, live chat, marketing automation, PPC ads, social influence, and many other strategic initiatives.

We worked hard for 12 months to implement, test, and improve on all the campaigns we were running for their business and we generated $61M worth of qualified leads for their business.

By far one of the most successful and exciting projects I’ve had the pleasure to be a part of.

We didn’t stop there, however.  We asked more powerful questions like: “If you closed just 10% of these opportunities, what would that mean for your business?”

I’m not awesome at math, but I know that’s a $6M increase to the top line.

That question alone granted us the opportunity to help their business, not just in marketing, but in helping optimize their sales process as well. That’s important to note because we built incredible trust with this customer by asking powerful questions and generating awesome results.

What Questions Should You Be Asking?

Alan Weiss from Summit Consulting Group, Inc. has developed a list of powerful questions in his article: 101 Questions for Any Sales Situation

Though Alan’s questions are primarily designed for sales consultants, they serve to help you understand exactly what your customer wants and what they need, regardless of what industry you’re in.

More importantly, I’ve found these powerful questions critical in establishing the objectives, metrics, and value for any marketing strategy.

Check them out below, organized by common sales hurdles or experience:


  • Why do you think we might be a good match?
  • Is there budget allocated for this project?
  • How important is this need (on a scale of 1-10)?
  • What is your timing to accomplish this?
  • Who, if anyone, is demanding that this be accomplished?
  • How soon are you willing to begin?
  • Have you made a commitment to proceed, or are you still analyzing?
  • What are your key decision criteria in choosing a resource?
  • Have you tried this before (will this be a continuing endeavor)?
  • Is your organization seeking formal proposals for this work?

Finding the Economic Buyer

  • Whose budget will support this initiative?
  • Who can immediately approve this project?
  • To whom will people look for support, approval, and credibility?
  • Who controls the resources required to make this happen?
  • Who has initiated this request?
  • Who will claim responsibility for the results?
  • Who will be seen as the main sponsor and/or champion?
  • Do you have to seek anyone else’s approval?
  • Who will accept or reject proposals?
  • If you and I were to shake hands, could I begin tomorrow?

Rebutting Objections

  • Why do you feel that way? (Get at the true cause.)
  • If we resolve this, can we then proceed? (Is this the sole objection?)
  • But isn’t that exactly why you need me? (The reversal approach.)
  • What would satisfy you? (Make the buyer answer the objection.)
  • What can we do to overcome that? (Demonstrate joint accountability.)
  • Is this unique? (Is there precedent for overcoming it?)
  • What’s the consequence? (Is it really serious or merely an annoyance?)
  • Isn’t that low probability? (Worry about likelihoods, not the remote.)
  • Shall I address that in the proposal? (Let’s focus on value.)
  • Why does it even matter in light of the results? (The ROI is the point.)

Establishing Objectives

  • What is the ideal outcome you’d like to experience?
  • What results are you trying to accomplish?
  • What better product/service/customer condition are you seeking?
  • Why are you seeking to do this (work/project/engagement)?
  • How would the operation be different as a result of this work?
  • What would be the return on investment (sales, assets, equity, etc.)?
  • How would image/repute/credibility be improved?
  • What harm (e.g., stress, dysfunction, turf wars, etc.) would be alleviated?
  • How much would you gain on the competition as a result?
  • How would your value proposition be improved?

Establishing Metrics

  • How will you know we’ve accomplished your intent?
  • How, specifically, will the operation be different when we’re done?
  • How will you measure this?
  • What indicators will you use to assess our progress?
  • Who or what will report on our results (against the objectives)?
  • Do you already have measures in place you intend to apply?
  • What is the rate of return (on sales, investment, etc.) that you seek?
  • How will we know the public, employees, and/or customers perceive it?
  • Each time we talk, what standard will tell us we’re progressing?
  • How would you know it if you tripped over it?

Accessing Value

  • What will these results mean for your organization?
  • How would you assess the actual return (ROI, ROA, ROS, ROE, etc.)?
  • What would be the extent of the improvement (or correction)?
  • How will these results impact the bottom line?
  • What are the annualized savings? (The first year might be deceptive.)
  • What is the intangible impact (e.g., on repute, safety, comfort, etc.)?
  • How would you, personally, be better off or better supported?
  • What is the scope of the impact (on customers, employees, vendors)?
  • How important is this compared to your overall responsibilities?
  • What if this fails?

Preventing Unforeseen Obstacles

  • Is there anything we haven’t discussed which could get in the way?
  • In the past, what has occurred to derail potential projects like this?
  • What haven’t I asked you that I should have about the environment?
  • What do you estimate the probability is of our going forward?
  • Are you surprised by anything I’ve said or that we’ve agreed upon?
  • At this point, are you still going to make this decision yourself?
  • What, if anything, do you additionally need to hear from me?
  • Is anything likely to change in the organization in the near future?
  • Are you awaiting the results of any other initiatives or decisions?
  • If I get this proposal to you tomorrow, how soon will you decide?

Increasing the Size of the Sale

  • Would you be amenable to my providing a variety of options?
  • Is this the only place (division, department, geography) applicable?
  • Would it be wise to extend this through implementation and oversight?
  • Should we plan to also coach key individuals essential to the project?
  • Would you benefit from benchmarking against other firms?
  • Would you also like an idea of what a retainer might look like?
  • Are there others in your position with like needs I should see?
  • Do your subordinates possess the skills to support you appropriately?
  • Should we run focus groups/other sampling to test employee reactions?
  • Would you like me to test customer response at various stages?

The Most Critical Question

  • Do you believe it yourself?

Why Asking Questions is Important for Any Relationship

It’s pretty simple…

They say, in sales, the person asking the questions is in control of the conversation, but in marketing, it’s more granular than that.

As leaders in marketing, it’s our obligation to understand exactly what our organization or customers need in order to help them drive dramatic results and we do that by asking questions.

Asking powerful questions:

  1. Shows that you care about the other person (and their business).
  2. Shows that you understand what it takes to get the job done.
  3. Helps you establish what’s important to your customer and why.
  4. Helps you and your customer succeed more often and with higher returns.
  5. Drives the conversation for building amazing relationships.

Zig Ziglar says it best: “You were born to win, but to be a winner, you must plan to win, prepare to win, and expect to win.”

When you ask the right questions, you will win more often in life and in business as well as be more likely to arrive at the right answers and achieve amazing results.

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