How Executive Coaching Changed the Way I Lead
Executive coaching has been gaining traction in leadership circles for years, yet it’s still often misunderstood. Is it mentoring? Is it therapy? Is it just another trendy workplace perk?
To bring clarity to the topic, I sat down with seasoned professional coach Sandra Cain for an honest and thoughtful conversation about what executive coaching actually is—and what it definitely is not.
Sandra has more than 20 years of experience as a professional coach and previously held leadership roles at American Express and the Co-Active Training Institute. I’ve worked with Sandra personally and credit her with helping me navigate some of the most challenging moments in my leadership journey.
If you’re curious about what executive coaching can offer, whether you’re a leader, an HR professional, or someone considering coaching as a profession, this conversation is for you.
What Is Executive Coaching?
The term “coaching” gets used in a lot of different contexts. From sports to agile teams to personal development, it can mean anything from motivational cheerleading to offering tactical advice. But true executive coaching is something distinct.
According to Sandra, professional coaching is a collaborative relationship that helps leaders explore their own thinking, gain clarity, and move forward in alignment with what truly matters to them. A professional coach doesn’t come in with an agenda or a list of answers. They’re not there to fix people. They’re there to support exploration, insight, and growth.
As Sandra puts it: “I don’t have an opinion about [what’s right for you]. I don’t have an agenda. I’m all in on supporting you to come up with your own solutions.”
That’s a fundamental difference from what many people expect. Coaching isn’t about giving advice or telling someone how to lead better. It’s about creating the conditions for the leader to see themselves—and their situation—more clearly and move with purpose from there.
Dispelling the Myths of Executive Coaching
Years ago, before my time with Sandra, I worked with a coach. At the time, I wondered if the coach had been brought in to subtly help me exit the company. That suspicion stuck with me for years, and it’s one of the reasons executive coaching can still feel misunderstood or even mistrusted.
I asked if she’s ever been asked to coach a leader out of an organization. Sandra is clear on this point: “I’ve never been asked that. If I was, I would say no, because that’s not what coaching is.”
Real coaching doesn’t serve a hidden agenda. It’s not performance management in disguise. It’s not a covert HR strategy. And it doesn’t exist to help leaders “get fixed.” It exists to help leaders become more fully themselves, with more awareness, confidence, and clarity.
The idea that coaching is only for people who are struggling is another common misconception. More often, Sandra says, organizations bring in coaching not because someone is failing but because they see potential for growth or because a leader is taking on a bigger role and needs support navigating the complexity that comes with it.
How Executive Coaching Helped Me as a Leader
My experience with Sandra is a case study of what executive coaching can look like when done well. During my time leading a business through a turbulent period amid organizational challenges and the chaos of COVID, Sandra served as my coach.
Now, I admit that I’m a strong personality with a tendency to talk my way around things. Sandra didn’t let that slide. She wouldn’t let me weasel out of answering a question. Even if the answer was, “I don’t know,” it had to be real.
That kind of accountability and reflection made a difference. Over time, I began to shift how I approached leadership, stress, and decision-making. Coaching helped me gain insight into my own patterns and realize which assumptions needed to be challenged.
Sandra’s style, grounded in curiosity and partnership, helped me feel supported but never coddled. She asked hard questions. She made space for the truth. And she always did it in service of my growth, not her own opinions or outcomes.
Why the Right Coach Matters
Sandra emphasizes the importance of chemistry in a coaching relationship. Coaching is personal. It only works when there’s mutual trust and a willingness to go deep.
Sandra encourages leaders or organizations looking for a coach to meet with two or three people to find the right fit. That first conversation matters. It should feel safe, constructive, and energizing. If the connection doesn’t feel quite right, that’s okay. A mismatch can slow down progress or prevent meaningful work from happening.
It’s not about being comfortable. It’s about the right kind of challenge. You want someone who pushes you in a way that helps you grow.
What Executive Coaching Offers Organizations
Executive coaching isn’t just valuable for individuals, but it can have ripple effects throughout a company. When a leader gains clarity, their team often benefits. Communication improves. Decision-making becomes more thoughtful. Reactions are more intentional. And alignment across leadership becomes more attainable.
Sandra explains that for organizations, one of the biggest benefits is giving leaders a neutral, outside partner. Executives often feel isolated or under pressure to perform. Having a space where they can speak openly without fear of judgment or internal politics can be transformative.
She’s also quick to note that individual coaching often highlights patterns that extend beyond one person. Sometimes, what seems like a single leader’s challenge is actually a reflection of broader team dynamics or cultural friction.
That’s why Sandra often blends one-on-one coaching with team coaching or facilitation. Starting with individuals allows for personal awareness and growth, but bringing leaders together can create breakthroughs in how they relate and collaborate.
Executive Coaching Isn’t Just for the C-Suite
While the term “executive” suggests top-level leaders, Sandra believes coaching can be incredibly valuable at the mid-management level, too.
Mid-level leaders are often under immense pressure. They’re being pulled in multiple directions from senior leadership, their peers, and the teams they manage. And they’re often the ones shaping the everyday experience of company culture for employees.
Yet, they’re also the group that tends to receive the least amount of support or professional development. They have the most line of sight and direct impact to team members. They’re the culture influencers and the culture killers.
Executive coaching—or leadership coaching, or simply coaching—can offer mid-level managers the space to step back, reflect, and grow. It helps them manage change, navigate uncertainty, and lead with more intention, even when the ground is shifting beneath them.
What to Look for in an Executive Coach
If you’re in an OD (Organizational Development) role, HR, or part of a leadership team considering executive coaching, Sandra suggests asking a few key questions before hiring someone:
- What kind of professional training do you have?
- How many years have you been coaching?
- Do you have experience working with leaders in similar roles or industries?
- How do you approach conflict resolution or team dynamics?
- Can you facilitate sessions, not just individual conversations?
Beyond credentials, it’s important to understand how the coach approaches the work. Do they listen more than they talk? Do they show up with curiosity instead of advice? Are they comfortable challenging assumptions in a supportive way?
A good coach should also be clear about what coaching is and what it isn’t. Sandra is especially passionate about this point. She believes the coaching profession has struggled at times because the word “coach” is used so broadly.
“It’s really us partnering and looking at this and me kind of helping you get curious about what do you want and what’s next,” she says.
Timing: When Is Executive Coaching Most Helpful?
So when should a leader or organization bring in a coach?
Sandra says there’s no single answer, but a few moments often signal a good time:
- A leader is stepping into a bigger or more complex role
- Communication issues or team tensions are starting to escalate
- There’s organizational change creating confusion or resistance
- A promising leader needs help shifting from tactical to strategic thinking
- Someone is struggling to find their footing or confidence
But it doesn’t always have to be a crisis. Sometimes, coaching is simply the right investment at the right time, an opportunity to support growth before issues emerge. The biggest surprise for me was how lonely leadership can be. Coaching gave me a place to talk about what I couldn’t say anywhere else.
Coaching vs. Consulting: Know Where You Land
What, then, is the difference between coaching and consulting and why it’s important for aspiring coaches to know where they naturally land?
For me, consulting comes more easily. I like solving problems and being the expert in the room. Coaching, on the other hand, requires slowing down, asking instead of telling, and being comfortable with not having the answer.
Sandra agrees. Many people trained to solve problems find the coaching stance challenging at first. But when done well, coaching doesn’t remove the need for consultants but complements it. It builds leaders who are more capable, self-aware, and able to bring the best out of others.
Executive Coaching as a Trusted Partnership
The relationship between Sandra and me is a clear example of how powerful executive coaching can be when done right. It’s about partnership rather than quick fixes or top-down advice. Trust. Honesty. And a willingness to explore the hard questions.
As Sandra puts it, coaching is shoulder to shoulder. It’s about partnering to look at your life together, not telling you what to do.
Executive coaching doesn’t need a new label, but it does need clarity. It’s not for broken people. It’s not a shortcut. It’s a space for real growth—personal, professional, and organizational.
If you’re curious to hear the full conversation, we invite you to watch the video above. The right coaching partnership can unlock a new level of clarity and effectiveness for individuals, teams, and the culture as a whole.
