When I’m not consumed with my full-time job of running a technology startup, I enjoy producing a barrel of my own wine every year. For me, wine-making is a great reminder about what it takes to be an effective leader because it moves at its own speed, and it requires a lot of patience and faith. If you have enough persistence to keep at it, and continually make small adjustments as you go, you’ll eventually find yourself with a nice bottle of wine. But if you try to force it too quickly or don’t heed some of the signals along the way, you’ll end up with something no one will enjoy.
There are many parallels between making wine and running a technology startup, including starting out with a vision, working to get it just right, making many pivots and adjustments along the way. But perhaps the most important similarity is that both pursuits require the ability to ask the right questions.
Leading a high-performing, resilient organization in today’s competitive business environment requires a mix of confidence and humility. In a climate marked by constant change and disruption, no single person can pretend to have all the answers. So, in order to be a good leader, you need to acknowledge that you don’t know everything and recognize that you need to constantly draw upon the wisdom and expertise of others to navigate challenges as they arise.
I’ve learned most of what I know about wine-making by asking questions of people who know more about it than I do. Most of the time, I wasn’t sure of the right questions to ask until I was right in the midst of the process. But when I was going through my first fermentation, I asked a lot of questions about fermentation. When I was going through the steps of clarification, aging and bottling, I asked plenty of questions about those processes, too. The answers I received to those questions informed and improved the results of each step I took.
As a founder and CEO, I’ve found that the same dynamic holds true. I do a lot of my own research, but some of the most valuable insights come from peers, colleagues and thought leaders. This is why asking the right questions is critical.
In today’s competitive business environment, successful leadership is based on the ability to ask the right questions at the right time about the specifics that pertain to the business. Although the questions might vary from industry to industry, there are a few key topics that pertain to any organization. You should continually discuss these topics with and ask these questions to your entire team (and yourself) on a regular basis:
1. Vision: Are we clear about where we are going? Do we understand how we will get there? What’s something that inspires you personally about our vision?
2. Execution: Is your team working efficiently as it progresses toward achieving its goals? Do you see how your daily work connects to our vision? What’s one thing your team could do that would increase your confidence in our ability to achieve our goals?
3. Employee experience: Are we creating a great experience for our talent? Are we creating an environment that will attract top talent and make people want to stay? Can you name one thing that would improve your experience here as an employee?
4. Culture and values: Are we working well together? Do people treat one another with respect? Do you feel your work has meaning?
5. Change: Do you understand the change that is occurring? Do you feel we are agile enough to thrive through this change? Can you name one thing you need to be successful with this change?
These are the universal topics that matter to employees and employers across all industries and organizations. In order to sustain long-term success, leaders need to ask questions to their entire organization and tap in more frequently to the voice of employees around these topics. Learning how to ask the right questions is the key step to tapping into the collective wisdom that leaders need to propel their organizations forward.