The 5 Coaching Questions Every Leader Needs To Know

Command and control leadership has been replaced with the coaching model in forward-thinking companies, allowing for greater flexibility in creating new results. According to the Harvard Business Review, rapid change has disrupted the traditional top-down management model. “Managers going forward are going to be less technical experts and more social-emotional experts, to help employees navigate the culture of the organization,” according to Brian Kropp, chief of human resources research at Gartner, in the Wall Street Journal. Business is moving too fast for yesterday’s strategies of pattern-matching – today’s innovators have to coach to new levels of performance. Consider that the coaching model provides true opportunities for maximizing job performance, improving retention, accelerating goal-setting and building employee loyalty. Here are five coaching questions every leader needs to know:

1. Where are you, right now? In the coaching conversation, what you don’t know can help you. Coaching, to borrow from Steven Covey, seeks first to understand than to be understood. If the coach thinks that she knows where someone is coming from, she is responding to her own preconceptions. What happens if you coach from preconceptions? Not much. “It’s not what you don’t know that can hurt you,” Mark Twain famously said, “It’s what you think you know… that just ain’t so.” Coaching deals with what is, not what just ain’t [or isn’t] so. Coaches are at their best when they start with these three powerful words: “I don’t know.” If you don’t know what someone is facing, if you don’t know their challenges, if you don’t know where they are in their progress, you will actually become a better coach. Because you will come to the conversation with curiosity, not preconceptions. Curiosity is the key to listening more deeply, and looking in the direction of new possibilities – not old preconceptions. Is that where you are, right now?
2. Has anyone ever solved this problem before – and if so, how did they do it? The story in our minds is almost always tougher than the problem itself. We fall into a false narrative that the challenge in front of us has never been solved by anyone, anywhere, ever. The trap of inadequacy or imposter syndrome robs us of our true problem-solving abilities, keeping us from seeing that the impossible might just be do-able. And, while new advances in AI and other technologies present challenges for every business, it’s important to remember that we all have the ability to figure things out. Even if the entire problem hasn’t been solved before, what work or research or history or TikTok videos or AI prompts could help us to figure this out? Coaching looks in the direction of collaboration and reinforcement. How does it feel when you face a challenge, knowing you are not alone?
3. What else could this mean? When faced with challenges at work, it’s only natural to gravitate quickly towards solutions, right? Especially in the meeting, when the subject matter expert says, “Team, there’s only one way to solve this problem!” As any good coach will tell you, there’s never just one way to win. In sports, when the play breaks down and doesn’t go as planned, we see the true champion emerge. Because that’s when the team has to find another way to win. Asking “what else could this mean?”, or “what else could this be?”, allows us to step outside of what it is that we are telling ourselves about a situation. And then, we find new ways to win.
4. What’s good about this? If you find yourself inside a complaint conversation, flip the script. Unlike command and control structures, coaching doesn’t focus on criticism or complaint. Coaching is collaboration. In my work with the team that won the Rice Business Plan Competition this past spring, my approach was always the same: I wanted to encourage them to win. As a coach, are you catching your team doing something right? Are you seeing the good, reflecting on strength, and identifying progress? Are you using collaboration to create confidence – or criticism to create self-consciousness? You can still correct, but from strengths, not scolding.
5. What Could Make this Easier? Lots of coaching conversations focus on goal-setting. Inside any pursuit or journey, consider that easier always exists. Easier is a powerful place – because easier is empowering. If something is easier, it’s do-able. It’s not impossible. The journey from struggle to success is characterized by finding an easier way. Can you coach towards a path that enables new results?

Of course, nobody really needs coaching. Eventually, you will figure things out. But why wait? And what if you’re trying to access a complex process, or discover ways to turn soft skills into hard results?

If your company has the patience and the budget to fund your learning curve, while you are “getting a feel” for leadership, then congratulations. But if you don’t want to wait to get good at something, and your company doesn’t have the appetite to fund your missteps, coaching is the fastest way to accelerate your results. A good coach can allow you to discover in days, weeks, or even a single conversation, what might otherwise take a lifetime. What would that kind of acceleration mean, for your team?