When was the last time you or members of your leadership team had an intentional conversation with a customer? A conversation you sought out with the customer rather than the other way around. Calling on the customer to upsell them doesn’t count.

My version of this was to take a client to lunch every other week. I’m sure that skewed the results somewhat, but since I had a digital agency, my client list was small. To compensate, I’d often bring different client team members to lunch rather than the primary contacts. Doing so gave me insights into my company and a better understanding of the client’s team dynamics.

In Scaling Up, we have this concept of a Weekly 4Q Conversation. Four basic questions to ask one client every week.

  1. How are you doing?
  2. What’s going on in your industry?
  3. What do you hear about our competitors?
  4. How are we doing?

Truthfully, I would suggest a minor rewrite of these questions to help frame a better response.

  1. How are you today? — It’s a subtle shift, but the swap from “doing” to “today” is more specific and constrained. Thus it’s easier for them to tap into how they are at that moment.
  2. Have you seen any new trends in your industry? — Again, it’s more specific and less generalized.
  3. Where could we be doing more for you? — I explicitly avoid the competitor question. Great companies don’t emulate their competitors; they innovate to serve their customers better.
  4. What was your last interaction with us like? — By being specific, the customer has a timeframe to consider. They recall the latest memory and often a few memories prior, sort them in time and reflect on the experience. This one produces excellent information to take back to your team.

Give these questions or a variant of them a try. I promise that the exercise will yield incredible insights and engaging conversations about your business after three weeks of asking these questions once per week.

Don’t stop there; take it internally. Go to your employee team, and ask someone new these four questions once per week.

  1. How are you today? — Similar to above, be timeframe specific.
  2. What’s going well for you at work this week? — For most people, it’s far too easy to highlight negatives. This is an opportunity to highlight what’s working well within the organization, do more of that!
  3. What three things should the company start, stop, and continue? — Again, we’re balancing the critique with praise. The goal is to gain insights, not to have the employees focus on all that is broken in the organization. This question solves that.
  4. How do you know you’ve had a productive day? — The typical response to this is, “I had no crisis or emergency.” It’s often the absence of negative factors rather than the accomplishment of positive contributions. Your goal as a leader is getting the whole team to focus on their positive contributions; anything less indicates that your processes and communication practices within the company require work.

Ask these questions of one member of your team once per week. It shouldn’t take more than 10 to 15 minutes of your time. In fact, in a large organization with varying departments, ask the questions to someone outside your department. Their “outsider” perspective might yield fresh insights.

If you find better questions to ask customers and employees, please share them with me; I’d like to hear what works well for you.

About the Author

I use my 20+ years of entrepreneurial experience and training to coach businesses on scaling up rapidly using Verne Harnish's Scaling Up framework. By doing so, my clients are more efficient and profitable, giving them the ability to make bigger impacts in the world.

I deeply believe entrepreneurs are the best equipped to be the vehicle for meaningful change, and in the decade ahead, we'll see a substantial shift in how business is done. We'll move to a model where company purpose, impact, curiosity, and team health will be differentiators in overall business success. As Simon Sinek has pointed out, the finite games are the legacy of the past; we're moving to an infinite game.

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