Written by
Dan Guglielmo
Founder & CEO
May 21, 2023

Context Matters

When I’m coaching a CEO, the approach I use and the questions I ask—and the energy in the exchange—is dramatically different from a one-on-one I might have with a soon-to-graduate college student who is grappling with his or her future options.

The context—everything from the stakes to the pieces on the chessboard—is different. 

Let me explain why this matters and when it doesn’t.

Good questions (and good coaching) don't exist in a vacuum. It finds its meaning and utility because it helps a particular coachee with an issue they’re facing. Context matters, but coaching as a tool is wonderful because it is context-dependent but useful in virtually any scenario.  

Expert coaching works with people who work on your team. It works with peers, vendors, customers, and potential customers. It works with your significant others, friends, and children. The skills you develop as a coach—including the skill of identifying and exploring relevant context—are universally applicable. This weekend, I was watching my son play on the floor with my granddaughter, and they were working together on a puzzle. She was holding a piece in her hand and my son asked, “What if you turned it over?” When she did, her eyes lit up, and you could see the possibilities just expanding in front of her. 

That’s coaching in its purest form.

He didn’t take the piece and place it for her or tell her how to do it. He asked a question that triggered a journey of discovery. 

Context refers to the circumstances, conditions, and environment in which something exists or occurs. It encompasses the various factors that surround a particular situation or event, providing a framework for understanding and interpreting its meaning. Without considering the context, we are reacting in the dark.

Why is this important for CEOs and other leaders to hear?

Because one of the comments I hear from those who have some reservations about the concept of learning how to coach goes along the lines of, “Sure, it’s one thing to coach me personally as an outside consultant, but that’s fundamentally different from me coaching the people on my team. Those are different skills.”

They aren’t! The skills are the same. It’s just the context that's different.

The most dynamic leaders of today understand that the ability to coach others is an incredibly powerful developmental tool. It does far more than just promote growth in your leadership team. It gives those leaders the tools to develop their teams. Developing a culture of coaching infuses an entire organization with the responsive, adaptive DNA that can’t exist in a place where top-down solutions and directives are the name of the game. 

What does this look like in real life?

Judy is the IT Director at a large water management organization. Despite her impressive credentials and comprehensive professional background, she struggled to create a slate of KPIs for her direct reports. Colin, the CEO, needed those metrics urgently to pitch a new line of business to potential investors. He asked Judy how she was progressing on the task, and she answered that it was coming along slowly. 

“What’s holding you back?” he asked. 

“I need more empirical data,” she said. “I have to get more clarity on what each team member does to deliver financial results. That’s going to take some more research.”

Colin asked if a set time with him to map out those details would help her. She said it would, and Colin’s response might seem simple, but it is very powerful.

“May I please make a request?” he asked, and Judy immediately said yes. “Would you please find a half hour for us to get on a call tomorrow? And could you please set aside an hour ahead of the goal to outline the full scope of the research you need?”

Colin knew what he needed from Judy, and he knew that Judy needed a nudge. But instead of coming to her with a demand or an ultimatum, he got curious. He slipped into a coaching mode, and asked questions that would elicit where the hesitation was coming from. Colin understood the context of the situation, and his approach to Judy acted as an accelerant. 

Judy came to the meeting overflowing with research and incisive questions that went far beyond what Colin had even considered. He left with a set of KPIs that not only reinforced the strategic points he needed to make with the investors but also formed the basis of a vastly improved internal dashboard that could help other teams get the important information they needed at a glance. 

There’s a reason learning through self discovery is becoming an important part of the curriculum at some of the best colleges and universities in the country. It’s because this approach works so well when issues are complex and open-ended. If you need a pipe fixed at your house, you need a technical expert to come in and solve your problem. You hire a plumber. When you feel persistent pain you can’t identify in your stomach, you go to a doctor for a diagnosis and treatment. But in those cases, you’re a passive participant in somebody else’s expertise. In the case of an open-ended, complex problem that needs to be solved on an organizational level, learning through self discovery and questioning distributes the problem-solving power to the entire team—not just the leader. It fundamentally changes the power dynamic between “boss” and “employee” and puts everyone on the same side of the problem-solving table. 

When we deconstruct the conversation between Colin and Judy, we find that there are several questions from Colin prompting dialog and discovery, followed by a suggestion. The questions demonstrate the leader as a coach, while the suggestion is directive leadership. Colin’s ability to fluidly shift between the styles is clear evidence of his grasp of the context and is a wonderful example of the power to coach in the corporate setting. 

Want to learn how to use this different kind of leadership “flow” to supercharge your own teams? Let’s talk.

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