What is Leadership Coaching?

Man on leadership coaching call with client

“Everyone needs a coach.” — Bill Gates, Microsoft

Being a leader is hard. 

Whether you’re leading a department or you’re the CEO, Leadership can be really challenging.

  • You might feel frustrated with the performance of your team but also feel uncertain about how to help them excel.

  • You might race from task to task without feeling like you have time to reflect on the bigger picture.

  • You might feel burned out, lacking balance between your life at work and your personal life.

Even when you see these issues clearly, you may not know how to fix them. You want to be the best leader you can be, but you may not know exactly how. 

Leadership coaching helps you be that better leader. 

The most successful business leaders on the planet—people like Steve Jobs, Sundar Pichai, Bill Gates, Larry Page, Sergey Brin, and Sheryl Sandberg, Eric Schmidt—have found great value in leadership coaching. Each of them recognizes that to be at the top of their game, they need the feedback and guidance a coach can give. 

Leadership coaching has proven to provide significant value for modern business leaders. 

What is leadership coaching?

Leadership coaching is a personal, tailored approach to developing your leadership skills, expanding your capacity, and building a successful company that you love. It’s about intentional change: coaches help you set productive personal, professional, and organizational goals and then develop the skills and resources you need to accomplish them. It’s practical and focused on results. 

Leadership coaching involves:

  • Critically and compassionately reflecting on and evaluating your actions

  • Unpacking the mental models you use for decision-making

  • Engaging in deliberate practice of critical leadership skills

Want to see what leadership coaching is like first-hand? Book a trial session and try it out.

What is not leadership coaching?

Leadership coaching is not life coaching or therapy. Life coaching and therapy focus on overcoming barriers in one’s personal life. Leadership coaching may include some discussion of one’s personal life, but the focus is squarely on leadership skills in the workplace and business outcomes. 

Leadership coaching is also distinct from advising and consulting. There is some overlap, but advising and consulting are more focused on providing a solution to a specific business problem. Leadership coaching is about developing the capacity of leaders to solve a variety of business challenges. 

Who can benefit from leadership coaching?

“Without a coach, people will never reach their maximum capabilities.” — Bob Nardelli, CEO of Home Depot

Every leader can benefit from a coach, regardless of position or seniority. Coaching isn’t a sign something is “wrong”—it just signals a desire to grow (and everyone has potential for growth). Some of the best coaching results come from high-performers that want to perform even more highly.

Here are some signs that a leader could benefit from a coach:

  • They want to become a more confident leader 

  • They feel like they need an unbiased sounding board

  • They’re juggling a lot and need to clarify priorities

  • They want to enhance their self-awareness and their understanding of their teams

  • They want to be better at navigating difficult conversations

  • They want to better balance their professional and personal lives

  • They know something needs to be fixed, but they aren’t sure what

  • They’ve recently stepped into a new role and feel unprepared

  • The growth of their company or department is stretching them to new levels of leadership

Not sure if Leadership Coaching is right for you? Book a free trial session and get a feel for the kind of value it can provide.

What value can coaching provide? 

“The one thing that people are never good at is seeing themselves as others see them.” — Eric Schmidt, Google

Coaches function like a mirror; they help leaders see themselves clearly. 

Coaches use thoughtful questions to uncover core beliefs. They remind leaders of their commitments to keep them accountable. They provide feedback, facilitate learning, and help leaders deliberately practice new skills.

Coaching provides the following:

  • Perspective. A coach can help a leader clarify what’s most important. Coaches also help leaders understand how others perceive them and how their style impacts morale and, ultimately, business outcomes.

  • Accountability. Coaches help leaders follow through on the things they say they’ll do and stay committed to their own goals. 

  • A trusted partner. Coaches are confidential, trusted, unbiased listeners. They give leaders a place to share their dilemmas, worries, frustrations, and doubts—and make a plan to move through them. 

  • Experience. Coaches are able to see patterns over a wide range of clients. They can tell leaders what’s normal for their situation—and what isn’t. 

  • Empowerment. Coaches help leaders solve their own problems. They give tools to help leaders overcome overwhelm, procrastination, and self-sabotage.

  • A long-term view. Coaches focus on root causes instead of reacting to the immediate problem. They help leaders make lasting changes. 

What are common leadership coaching topics?

Coaching is flexible by nature. It’s aimed at helping leaders overcome the particular and unique challenges they face. Some of the most common leadership coaching topics we work with at HabitStack include:

  • Leadership skill development

  • Strategic decision making

  • Time management and prioritizing

  • Goal setting

  • Effective delegation

  • Management style and managing people

  • Self-awareness and emotional intelligence

  • Managing conflict and having difficult conversations

  • Delivering and receiving feedback

  • Maintaining work-life balance

Book a free trial session to see if Leadership Coaching could address the particular challenges you face.

Has coaching been proven to work?

The research indicates that coaching works. If you are interested in the studies, see:

Several studies have estimated an ROI of 5 to 7 times the initial investment in coaching:

Many major companies use leadership coaching, including Hewlett-Packard, eBay, IBM, Google, Microsoft, Motorola, and Facebook. 

When does coaching fail?

The following factors can reduce coaching effectiveness:

  • Lack of motivation. Coaching relies on the engagement of the leader. Leaders that aren’t motivated or engaged may not see results.

  • Unrealistic expectations. Coaches are sometimes used to try to “save” a poor performer. Coaches can help improve performance, but if the leader is unwilling or unable to make changes, coaching is unlikely to be successful.

  • Bad fit. The chemistry between a coach and a leader is crucial. Without trust, respect, and rapport, the coaching impact may be limited.

What should leaders look for in a coach? 

There are many coaches out there. How can leaders know who might provide real value?

The most important characteristic is fit. For coaching to work, there needs to be chemistry between the leader and the coach. A leader buys into who their coach is as much as what they do

Beyond personal fit, the following characteristics can signal a competent, effective coach:

  • Certification. The main certification body for leadership coaching is the International Coaching Federation. A certification doesn’t guarantee quality, but it does indicate that the coach has been trained.
  • Real skills. A good coach offers new skills, awareness, and knowledge. They’ll help define a leader’s core challenges, ask hard questions, and hold the leader accountable.
  • Experience. An effective coach should be able to point to good reviews from past clients—real successes that they’ve had coaching others. Ideally, those positive past experiences will come from leaders who faced similar challenges.
  • Methodology. Leaders should look for a fit with methodology as much as a personal fit. Skilled coaches will walk leaders through how they work. They’ll describe how leaders will learn new skills and the support they’ll provide. 

Our recommendation for finding a great leadership coach: meet with a prospective coach and ask them to help you work on a specific challenge. In other words, try to experience them coaching as opposed to having a conversation about coaching. 

HabitStack’s Methodology

Methodology—how your coach works—is one of the critical factors in picking a good coach, so let us explain ours at HabitStack. Our coaches start by understanding your goals—what you’re trying to accomplish and how successful you typically are at achieving them. We make sure you’re setting productive goals and making them specific and measurable. 

We start with goals because it connects our conversations to the real world and lets us dive into the business problems you’re facing. It also gives us an opportunity to see you in action. A golf coach wouldn’t correct your swing without seeing it; similarly, we need to see how you approach your work before we can know where you need to adjust.

Once we understand your challenges and what may be undermining your performance, we go a little deeper. We examine some of your other “Doing” habits—the routines you have at work and your skills. We help you tweak or develop those so that they support you in accomplishing your goals.

Over time, we’ll explore what we call “Being” habits. These are things about the way we are that can affect our work outcomes.

HabitStack's Methodology tree diagram


Imagine a person with imposter syndrome (hint: everyone has it) that has a frame like, “I don’t belong here and people are going to find out.” Perhaps that insecurity makes them prickly in response to feedback. That, in turn, makes their team hesitant to provide feedback. Without collaboration and feedback, they’re more likely to set vague goals or to focus on the wrong things. Ultimately, the frame they have makes them less likely to succeed at their business outcomes.

In this example, our coaches would seek to uncover that frame that’s at the root of the issue. Then we might try to reframe it, and also work to help the client receive feedback in a way that isn’t threatening. Ultimately, that could help them perform better on their work objectives.

Our methodology is centered on achieving concrete outcomes for the business. Sometimes that means we attack deeper, more personal barriers that are holding you back, but it’s always in the context of becoming a higher-performing member of your team. 

Want to learn more about HabitStack’s approach to coaching? Book a trial session and try it out.

How do we hire coaches at HabitStack?

We offer one-on-one leadership coaching at HabitStack, so we regularly select high-quality, effective coaches. Here’s how we ensure our coaches are effective: 

  • We look for training from a credible institution with a reputable certification

  • We look for several years of coaching experience

  • We look for several years of experience leading teams 

  • Most of our clients are leaders in tech startups, so we prioritize candidates with experience in technology startup contexts

  • We look for coaches with great references and testimonials from previous coachees 

When is coaching the wrong solution?

Coaching isn’t the solution for every problem. Here are some problems for which coaching may not be effective. 

  • An employee needs remedial help. Coaching can improve performance, but it’s often not the right solution for an employee that is performing very poorly. It’s much more effective for improving the performance of those already performing well who are motivated to level up even further.

  • A company strictly wants business advice. Coaching isn’t the same as advising or consulting. For example, If what a company needs is new marketing tactics, a marketing consultant is more appropriate than a leadership coach. 

  • A leader needs therapy. Although it’s holistic, leadership coaching isn’t therapy or treatment for mental health conditions. If mental health is the concern, a therapist or clinical psychologist may be more appropriate.

  • A leader isn’t interested in introspection. Coaching works best when it helps a leader reflect on their behaviors and uncover patterns in thinking. If a leader doesn’t want to engage in that kind of reflection, coaching may not be very useful. 

  • A leader doesn’t want to change. Leaders have to want to invest in themselves and grow. Coaching may not be effective when it’s pushed on a leader without their buy-in.

Not sure if coaching is the right solution for your challenge? Book a free trial session and a HabitStack coach will help you understand whether we can help.

What is involved in coaching week-to-week?

In practice, coaching usually entails a weekly or bi-weekly virtual meeting. Sessions are about 30-60 minutes. Most coaching programs last anywhere from three months to several years. A typical session may involve:

  • The leader brings up a problem they’re having that week. The coach may then help them think through possible solutions. 

  • The coach may follow up on previous sessions or discuss progress on skill development. 

  • The coach may encourage the leader to engage in particular activities or actions to develop their skills. 

The content of sessions is usually guided by the coachee—the leader—and varies from session to session.

Higher performers have coaches for a reason

“Everybody needs a coach.” — Eric Schmidt, Google

It’s not a coincidence that well-run companies supply coaches for their leaders. They do it because coaching works. 

Coaching helps leaders see themselves and their teams more clearly. It helps them define their challenges, recognize opportunities for growth, and guide their skill development. The right coach can improve a leader’s performance, clarity, and ultimately their business outcomes.

Every world-class athlete and every successful performer has a coach. They invest in coaching because it makes them better at what they do. 

Business leaders and executives benefit from coaches in the same way—to perform at their best, they need a coach. 

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HabitStack Leadership Coaching helps you reach your potential

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"I’m more focused, energized and disciplined. I’m enjoying my work more. And my health and relationships are better too. HabitStack's coaching definitely helped me raise my game."
— Gabriel Padva, CEO at RevenueAccelerator.io

Our 1:1 leadership coaching offers a growth-focused, results-driven approach to leadership development. Chat with us and see how you can accelerate your leadership journey

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