One of the biggest mistake I made as a product manager? Thinking I could understand customers without, you know, actually talking to them. Everything I did was based on input from colleagues who had direct contact with customers—customer success, support, and sales. Many of these inputs addressed real needs and problems. However, the issue was that I often didn’t get the complete picture. For example, when did this issue occur in the user’s journey? How significant was the pain point? Was this need perceived as more or less urgent compared to others?

Your colleagues will answer these questions happily and to the best of their capabilities. And you get the feeling that this approach might work, for a short while at least. But eventually, you’ll hit a major roadblock—the moment you’re asked to define a roadmap or, worse, a product strategy.

Without the big picture, a comprehensive understanding of your target customer’s needs, or a sense of how solving one problem could lead to better outcomes, you’re left with fragments. Imagine trying to solve a puzzle, with half the pieces missing, and a cat knocking them off the table. This makes it impossible to plan ahead. What happens next? You create a roadmap based on the most requested features—a strategy as effective as deciding lunch plans by asking, What’s everyone in the office craving today? And since most product-related books and articles will tell you that a feature-based roadmap is a bad practice, you’ll try replacing some features with superficial problem statements or assumed outcomes.

Here’s the “kicking in an open door” advice that every new product team or founder should take to heart: TALK directly to your customers regularly. And by regularly, I mean weekly—not monthly or quarterly, but at least once or twice a week. Founder teams won’t have the following issue, but product managers that join at a later time might face pushback from senior customer-facing colleagues. You may hear things like, ‘Don’t you trust our input?’ or ‘We know our customers better; let us filter out the useless information. Translation: Let us be the gatekeepers of knowledge. These remarks usually come with the best intentions, but it’s crucial to understand where this is coming from and kindly explain why regular customer interaction is essential for the company’s and your personal growth.

Automating Customer Conversations

Once you’ve achieved buy-in, the next challenge is scheduling these conversations. Should you pick up the phone and start calling customers until you have a couple of appointments for the coming 4 to 5 weeks? It’s not a bad start, but it’s often not sustainable. With so many competing priorities, calling customers often falls to the bottom of your to-do list.

The solution: automate your interview scheduling process. This advice, encouraged by Teresa Torres, is invaluable. My personal approach is to automate an email campaign to introduce yourself and request a digital meeting or an in-person visit at their office. Reduce barriers further by including a booking link (e.g., Google Calendar or Calendly) so customers can choose a time that works for them.

You don’t need fancy marketing or CRM tools for this. Personally, I use a Google Script, generated with help of ChatGPT (although I think Claude would do a better job nowadays), to send personalized emails to selected customers. All you need is a Google Sheet with your target list, Gmail, and the script. Below is an example script you can use. Make sure you test the email first. Trust me, you don’t want to send out a mass email with [FirstName] placeholders. Unless your goal is to become the punchline of a meme shared in company Slack channel.”

So, here’s the deal:

• Talk to customers weekly—no excuses.

• Don’t let secondhand insights replace firsthand conversations.

• Use automation to make scheduling easy and sustainable.

Remember: customer conversations are the foundation of great product strategy.