The most valuable new year’s (business) resolution

Do you want to de-risk implementing business ideas, drive better decision making, and give your company an advantage over the competition this year? If so, there’s one resolution you need to stick to this year. And I’ll help you do it…

Over the last few weeks we’ve all been thinking about this past year, reading all the “best of” and wondering how we can make this year even better for our businesses. If you’re like me, you’ve spent a lot of time contemplating how to improve overall growth and profitability. And, if you are like me, you also know there are a ton of ways that you could potentially to do that…but there is one ultimate question you want answered before investing any time or money into a strategic growth or profit building effort.

That question is: How can I guarantee it will be successful?

Answer is: You can’t.

You can’t guarantee any of your efforts will be successful. I know…that’s not what you expected me to tell you. But here’s the thing…I don’t have a simple, yet brilliant piece of advice to give to you that would guarantee success. To be honest, I’m not sure there is, or ever could be, one single piece of advice anyone could ever give you that would guarantee that the new fiscal year will be better than the last.

But, even though you can’t ever guarantee success, you can come pretty close by removing as much risk from those efforts as possible before you take them on. If you de-risk them enough, you can get to a point of almost guaranteeing success. But you know this already and are actively trying to de-risk each effort you take on…right?

So, what I’m going to do is give you something better than a piece of advice. I’m going to give you a challenge. It’s a big one. But this challenge could end up being the most valuable thing for you and your business. Realistically, it could lead you to having one of the most successful years ever. If you accept it…and actually do it.

Ok, enough build up…here’s the challenge: Have one-on-one conversations with 5 of your customers every month… for a year.

You might not realize it yet, but what I just challenged you with is gold. Here’s why:

Having regular conversations with your users help you understand:

  • Their wants and needs
  • The pain points and frustrations they experience
  • Why your customers do the things they do

That last one is a big one.

What you are doing now with on-line chat, surveys, and “big data” play an important role in shaping the success of your business. But those tools can only help you understand your customers in broad brushes. Basically they help you understand what they are doing and some of their behaviors while they are doing it. What it doesn’t help you with is understanding their motivations, the context of their situation or most importantly “why” they are doing something. If you truly understand “why” your customers do the things they do, then you can quickly figure out what growth or profitability effort will have the best chance of success.

But don’t just take my word for it…do a little research. You’ll find the most successful innovators consider the simple action of routinely talking to their customers a critical part of doing business.

I realize this challenge seems a little daunting if you haven’t ever done it before. But just like everything else, starting is the hardest part. The good news is once you’ve done it a few times and uncovered a key insight or two, you’ll feel like a pro and may even integrate it as a critical business practice too.

Here’s some help to get you going…

Just like any resolution, the likelihood of failing increases when you set out to do too much too soon. So to help reduce the risk of failure, here are a few small, yet easily achievable goals you can do each month as you take on this challenge:

Goal 1: Pick an important topic you would want to know more about

If you’re not sure what topic you should start with, I would suggest “Customer Satisfaction”. In my opinion, digging into the current level of customer satisfaction is one of the best ways to understand how your business is doing. For example, if your customers aren’t satisfied with your product or service, why would they continue using it? If you truly understand how your customers feel about your product or service you’ll quickly be able to identify areas of improvement.

Goal 2: Create a discussion guide that has a few questions or prompts that’ll help you dig into that topic

Sometimes identifying the question or prompt you might use to uncover insights is the hardest part. Here are few different types of questions and examples you could consider:


  • e.g., Can you tell me about the last time you used our product?

Behavioral questions are great because they help kick start a conversation and typically open the door to discussing things they really like or issues they have recently experienced. And if you are able to be in person, modify this question a little bit and have them show you the last thing they did with your product or service.

Measurement & Follow up

  • e.g., On a scale from 1-10, how satisfied are you with our product? Why did you rate it that way?

The measurement question is a great way to gather data you can use for a business metric, but the power of this question comes from the follow up question: “Why did you rate it that way?”. The follow up question is a great way to really understand how your customers feel about your product. Numbers are good, but meaning behind the numbers is what really matters.


  • e.g., If you could wave a magic wand and have our product do anything, what would you have it do?

Hypothetical questions are a quick and easy way to get an understanding of how to improve your product or service. It might seem silly, but the “magic wand” question allows your customer to open their mind and remove all constraints. It can also help loosen up the conversation if it feels a little too formal.

Goal 3: Conduct a practice interview

Practicing with someone you know will help you figure out what works and what doesn’t work about the discussion guide without worrying about doing something wrong. I would also recommend timing the practice interview. This is a great way to get an idea of how long the discussion might take and see if you need to remove a question or two.


Goal 4: Contact 7-10 people that represent your customer base

I know I said to talk to 5 people, but recruiting for more than you need is a good way to insure you’ll get the number you are aiming for.  And if you’ve never personally contacted your customers before, it can be hard to figure out what to say and how to ask for the conversation. Here’s an email template you can use to get started:


Have time for a quick chat?


Hi {name},

We’ve been working hard to make {product/service} the best we can for you, but we want to make it even better.

Over the next year, my goal is to have a conversation with as many customers as I can in order to understand the experience you are having with {product/service}. I want to intimately know what you like, love, hate and want us to improve but haven’t had the chance to share it with us.

If you are willing to give me 15-20 minutes of your time, I would sincerely appreciate it. The best part is you will be a big part in making {product/service} the best it can possibly be.

If you are interested, reply to this message and I’ll we’ll schedule a time to chat.

Thank you so much for being a great {product/service} customer!

{your name}

{you title}

Goal 5: Schedule your first discussion

Find 30 minutes that work for both you and your customer and get it on the calendar asap! My suggestion is to schedule time for a little more than what you’ve originally planned for. This way if the conversation goes well, you have time to continue the chat. Otherwise, this will give you time to review what was discussed and make notes that could influence the next discussion.

Goal 6: Have a good conversation

A wise person once told me: You have two ears and one mouth for a reason…listen more than you talk! Yes, you need to ask your questions and get information, but make sure to pause in-between questions and their answers so they can finish their thoughts. A little uncomfortable silence for you is a perfect opportunity for them to give great insights!

Goal 7: Share what you heard

Unless you are a team of one, don’t keep the conversations you’ve had with your customers to yourself. Your team will really appreciate that you are sharing what you’ve learned and ultimately the insights you gathered will help inform design and development decisions.

Now do it all again… every month!

One last thing

I want to know how the challenge is going for you! Get in touch and let me know:

  • What’s difficult about this challenge?
  • What’s easy about this challenge?
  • How I can help you be successful during this challenge?

Good luck!


About Handrail

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Mat Winegarden

Product manager at Handrail. Sometimes I have ideas...other times I am brilliantly late to the party.


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