5 Questions Costing You Money

Screenshot from 2023-02-15 07-46-42

If you aren’t asking them

Roughly 10 years ago, a consultant shared with me the questions he asks his clients every year.

Not 6 months after they sign up.

And not just at the renewal of a contract.

Every year.

Since then, I’ve asked them of clients (though not as often as I should’ve).

When I was an executive in companies, I asked them about customers and channel partners.

And as a trainer and coach, I’ve taught them to clients, who have used them to varying degrees of success.

They are questions:

  • CEOs need to ask a few customers each year to understand their customers and protect relationships;
  • CFOs need to ask customers and/or channel partners to better grasp the marriage of qualitative and quantitative;
  • CROs, VPs of Marketing and/or Sales, and sales managers should ask some customers to ensure they are selling the right products or services;
  • Account managers want to ask to increase lifetime value and reduce churn;
  • Heads of customer success want to ask to improve customer satisfaction scores;
  • Product managers should add to their arsenal to better perceive what customers will want next, or want removed;
  • Heads of strategy can be asked to better pull together the intersection of competition, customers, and costs.

So what are they? I’ll tell you…..

But first, why ask these?

We either give too much lip service to understanding or caring about customers or simply don’t know to ask them what they want.

Senior executives sit around debating what product to roll out, or what changes to make to marketing or the channel strategy, but without the customer’s voice in the room. Someone from sales will often say, “What is going on?” but they’re usually operating under their own biases, fears, or misconceptions, so even if they’re heard, they’re not bringing the most accurate intel.

I’ve seen it operating IN companies; I’ve seen it as a consultant who pressed CEOs and heads of sales to ask these questions; and I’ve made the same mistake myself in my own businesses: we think we’ve got Steve Jobs’ clairvoyance on what our market or customers want or need from us.

Or we allow fear to keep us from going directly to those customers. Fear we’ll upset them, or lose the business, or look incompetent.

But fear shouldn’t trump getting it right.

So, the questions. Be warned – they’ll change your world, but only if you use them.


Number 1: Why’d you hire us/me? OR Why’d you buy from us/sign up with us?

We have our beliefs about why people spend money with us. Maybe it was our initial hypothesis that we believe is being validated. Maybe we heard a customer make a comment in passing, or they told us something in the buying process, or the sales team relayed to us what they think.

However, we don’t always really know.

This is a pro question because customers will tell you something different AFTER they’ve agreed to buy from you than they did BEFORE they spent money. They’re less guarded. They trust you more.

And you’ll now know their real reason for choosing you. That information can (and should) be used in marketing; in sales; in product development.

Another benefit to this question is that it often reminds customers or clients of the problem they had before you solved it, which is crucial to drawing out the information in the subsequent questions.


Number 2: How are we doing there?

There’s our measure of success for customers, and there’s their measure of success.

Yes, we can survey them, but there’s something really powerful in listening to a customer talk about how we’re doing, from their perspective.

It takes guts to ask this, knowing that 1) we may have missed something in why they hired us leading us to solve the wrong problem and 2) we may not be killing it for them.

But if either one of those is true, wouldn’t we want to know why?

If we’re doing well, don’t we want to understand what it is we’re doing well that delights them, so we can invest in it more?

Scary thought: what they value in our services MAY not be what we think they care about. We might have a different business or value proposition than we believed.


Number 3: Where else would you like our help? OR What are we not doing that you wish we were?

This one may take some A/B testing to find the right framing to be effective. Sometimes a few words change the answer we get, like when we ask someone what they think vs. what they feel. Those questions resonate with different areas of the brain and draw out different responses.

This question has enormous potential for anyone managing a relationship, or thinking through products and services for their existing or potential markets.

In effect, we’re asking, “What are we missing? Where are we letting you down?”

The pessimist sees this as a signal of failure; the optimist hears the answer to this as a cash register, birthed from new opportunities with the same customer.

A corollary question I got from Ray Green is this: “What if we removed _______________?” Think about a feature, product, or service whose value you’re unsure of. Maybe it’s the cost to deliver, or the utility to a customer. Let’s ask them to pretend it’s no longer available: would they care. Put that one in your back pocket when you’re wanting to go deeper in cost savings, customer understanding, or product development.


Number 4: What would get us fired?

Ready to unlock some magic? And keep customers longer? Ask this one.

Clients have told me about customers really opening up around this one. The other questions led to expected answers (by industry), but asking this led to a deeper understanding of and connection with clients.

Companies can also build plans around accounts based on this feedback. Why? It tells you the customer’s boundaries, some of which are unknown to those doing delivery.

Having asked this myself, I’ve learned that not everything sales touts as gospel is what really matters to a customer.


Number 5: Whom else should we talk to?

This can be internal, meaning an introduction within the company. Think about a manager purchasing from your firm. At some point, they’re likely to get promoted. You must be introduced to the person who will get promoted into the purchaser’s role, and well before the promotion occurs. Too many small businesses look at the customer they have, not the ones they’ll want and need 2-3 years from now.

This can also be external. No one can sell your company like a satisfied customer, and they typically know other potential customers you need to be talking with. But you have to ask. Regularly.

And after listening them to tell you the good, bad, and ugly of how you’re delivering, they’re often MORE likely to want to help you connect with someone else.



Is there more you can ask? Yes. These, though, are enough for now.

A few thoughts before you start lining up these interviews:

  • It’s not a checklist to be run through. Each of these is their own conversation, entailing several (more than 3) follow-up questions.
  • Because of that, the posture of the person asking needs to be one of genuine curiosity.
  • Someone must log the responses. One place to start is logging the answers in the CRM for anyone touching that customer to know and understand. Another application is to aggregate all of the answers from various customers. It’ll help you identify patterns.
  • Finally, it’s critical something is DONE with the responses: training of people; reviewing of policies; marketing tailored based on responses; product improvement. It depends on the actual responses you get, but these questions and their answers only hold value if someone takes them seriously enough to fold into the business’ DNA.

With that, you’ve got the questions my clients use to build better businesses. Get after it, and I look forward to hearing what you learn (and do) when you ask them.




Adam Boyd