In cybersecurity leadership, experience matters. CISOs operate under relentless pressure, making high-stakes decisions that shape the security and resilience of organizations. Many CISOs feel drawn to coaching, wanting to support others facing similar challenges.

But coaching isn’t just about talking through problems or offering advice. And not all coaching is created equal. There’s a significant difference between a current CISO who coaches as a side gig—without formal training—and a former CISO who has dedicated themselves to coaching as a full-time profession.

Understanding this difference matters, especially for security leaders looking for real growth. The right coach can mean the difference between a leader who simply solves today’s problems and one who evolves into an executive who transforms organizations.

Coaching Isn’t Just Talking

At first glance, coaching can look like a conversation with a plan—a seasoned leader sharing insights with someone looking for guidance. But great coaching is much more than that.

Coaching is intentional, nuanced, and expertly structured. It’s not casual dialogue; it’s an expertly calibrated process designed to bring out the best in people.

A skilled coach isn’t just reacting to what’s being said. They’re listening for what’s beneath the surface—the unspoken fears, assumptions, and potential waiting to be unlocked. They don’t just apply a single technique or approach; they understand that coaching requires a vast toolkit, just like cybersecurity itself. Using only one or two coaching models for every client would be like trying to cut a diamond with a chainsaw—ineffective at best, destructive at worst.

This is where the difference between a CISO coaching as a side pursuit and a trained, full-time professional becomes clear.

The CISO Who Coaches on the Side

A sitting CISO who offers coaching informally brings invaluable experience to the table. They’ve navigated the pressures of the role firsthand and can provide practical, real-world guidance to those following in their footsteps. Their insights can be a powerful resource for rising security leaders.

However, coaching as a side activity has natural limitations. Without formal training in coaching methodologies, the approach often leans more toward mentorship or consulting rather than structured coaching.

Some common characteristics of a side-coaching CISO include:

• An advice-driven approach: Many untrained coaches naturally default to sharing their own experiences and solutions rather than guiding clients to develop their own.

• A limited coaching toolkit: Without deep exposure to coaching models and techniques, they may not have the structured frameworks that create lasting transformation.

• Personal perspective as a primary lens: Their insights are shaped by what worked for them, which may not always align with a client’s unique challenges and leadership style.

• A balancing act between roles: Coaching is secondary to their primary job, which may limit the time, focus, and energy they can dedicate to each coaching engagement.

That said, side-coaching CISOs play an important role in the field. Their willingness to invest time in developing other leaders speaks to their commitment to the profession. Many provide invaluable mentorship and help shape the next generation of security executives.

However, for those seeking deep, transformational coaching, working with someone who has made it their full-time focus can make a significant difference.

The Former CISO Who Is a Trained, Full-Time Coach

A CISO who has transitioned into full-time coaching—and invested in professional training—brings a completely different level of impact. They combine deep cybersecurity leadership experience with proven coaching methodologies, making them uniquely equipped to help leaders navigate challenges beyond technical expertise—focusing on leadership, mindset, and growth.

What Sets a Professional Coach Apart?

• Mastery of coaching models and techniques: A trained coach has studied and practiced dozens (if not hundreds) of coaching approaches, knowing when and how to apply them effectively.

• Listening beyond words: They don’t just hear what’s being said; they notice patterns, hidden fears, and underlying beliefs that shape decisions.

• Guiding, not advising: Instead of handing out solutions, they ask powerful questions that help leaders develop their own solutions, tailored to their strengths and context.

• Commitment to coaching as a craft: They’re not juggling two jobs. Coaching is their full-time focus, allowing them to dedicate themselves fully to their clients’ growth.

Why This Difference Matters

Cybersecurity leadership is evolving. The pressures on CISOs are growing, and the challenges are too complex for one-size-fits-all advice. True coaching isn’t about handing down wisdom from experience—it’s about guiding leaders to unlock their own.

If you’re seeking coaching, ask yourself: Do I want someone who shares advice based on their past? Or do I want someone who can help me develop the leadership skills I need for the future?

Both side-coaching CISOs and full-time, trained coaches have value. The key is knowing what kind of support you need. If you’re looking for mentorship, someone with deep industry experience can offer invaluable guidance. But if you’re seeking real transformation—coaching that helps you shift perspectives, unlock new insights, and grow into your next-level leadership—you may benefit more from working with a trained, professional coach.

A great coach doesn’t tell you what to do—they help you become the leader who already knows what to do.

Now that we’ve explored the difference between a side-coaching CISO and a trained, full-time coach, let’s examine how this impacts leadership growth.

Not all coaching delivers the same results. Some differences are easy to spot, while others fundamentally change the effectiveness of coaching.

1. More Obvious Differences in Value – The clear distinctions in availability, depth, and structure.

2. Subtle Yet Powerful Differences in Value – The hidden factors that determine whether coaching leads to minor improvements or fundamental transformation.

More Obvious Differences in Value for Clients and Companies

These differences are easier to see, but they still have a significant impact on the effectiveness of coaching engagements.

1. Depth of Leadership Growth

• Side-Coaching CISO: Offers tactical guidance based on personal experience. Clients may get quick wins—advice on board interactions, crisis management, or navigating internal politics—but the growth is often surface-level and situational.

• Full-Time Coach: Helps leaders achieve deep, transformational growth by shifting mindsets, strengthening leadership presence, and refining decision-making. The focus isn’t just on what to do next, but on who the leader is becoming.

💡 Value to Clients & Companies: Leaders coached by a trained professional experience sustained improvement in leadership effectiveness, not just immediate problem-solving.

2. Long-Term vs. Short-Term Impact

• Side-Coaching CISO: Sessions often center around immediate challenges, like handling a security incident or preparing for a board meeting.

• Full-Time Coach: Works with clients over time to develop strategic self-awareness, resilience, and adaptability—key traits for long-term leadership success.

💡 Value to Clients & Companies: Organizations investing in full-time coaching see lasting improvements in executive leadership, rather than one-off solutions to today’s problems.

3. Internal vs. External Growth

• Side-Coaching CISO: Typically helps clients navigate their current role, with insights drawn from personal career experience.

• Full-Time Coach: Helps leaders expand beyond their current roles, preparing them for broader executive responsibilities, future career moves, and increased influence.

💡 Value to Clients & Companies: Companies get leaders who are future-ready, not just effective in their current role.

4. Customized Coaching vs. One-Size-Fits-All Advice

• Side-Coaching CISO: Often applies a mentorship-based approach, meaning clients receive advice based on what worked for the coach personally.

• Full-Time Coach: Uses a customized coaching approach, drawing from multiple coaching methodologies to suit the leader’s specific needs and organizational context.

💡 Value to Clients & Companies: Leaders receive coaching that is specifically tailored to their unique challenges, strengths, and leadership style, leading to greater personal and professional breakthroughs.

5. Ability to Navigate Leadership Beyond Cybersecurity

• Side-Coaching CISO: Primarily helps security leaders grow within the cybersecurity function.

• Full-Time Coach: Helps security leaders develop the skills to become key members of the CEO’s team or the Senior Leadership Team (SLT), expanding their influence and applying systems thinking, risk mindset, and leadership perspective beyond security into broader executive leadership.

💡 Value to Clients & Companies: Organizations benefit from leaders who can bridge cybersecurity with business strategy, making them more effective at influencing C-suite decisions.

Subtle Yet Powerful Differences in Value

These distinctions aren’t always visible at first glance, but they fundamentally change the effectiveness of coaching.

1. The Power of Inquiry vs. The Power of Experience

• Side-Coaching CISO: Relies on personal experience to guide clients, often saying, "Here's what I did in that situation."

• Full-Time Coach: Leverages skilled inquiry—knowing how to ask the right questions to help the client uncover their own best answers.

💡 Subtle Impact: Tactical advice is useful, but it’s limited to the coach’s career path. True coaching builds the client’s own decision-making ability, leading to lasting growth.

2. Addressing the Present vs. Rewiring Thinking for the Future

• Side-Coaching CISO: Helps with current leadership challenges—board interactions, reporting structures, team management.

• Full-Time Coach: Works at a deeper level to help clients reframe their leadership identity, ensuring they approach future challenges more effectively.

💡 Subtle Impact: Tactical problem-solving helps today. Changing how someone thinks transforms their entire career.

3. Recognizing Patterns vs. Offering Solutions

• Side-Coaching CISO: Provides solutions based on personal experience.

• Full-Time Coach: Helps clients identify and break leadership patterns that may be holding them back.

💡 Subtle Impact: A solution fixes one problem. Breaking a pattern prevents future problems.

4. Leadership Adaptability vs. Leadership Replication

• Side-Coaching CISO: Helps clients model their own leadership style.

• Full-Time Coach: Helps clients develop a unique, adaptable leadership approach that works in any context.

💡 Subtle Impact: The best leaders don’t just imitate—they evolve into their own authentic leadership style.

5. Managing Challenges vs. Shifting Mindsets

• Side-Coaching CISO: Helps clients navigate difficult situations with strategies and war stories.

• Full-Time Coach: Helps leaders shift their mindset, making them more resilient and adaptable.

💡 Subtle Impact: Tactical guidance helps now. Mindset shifts continue to pay off for years.

6. Supporting the Leader vs. Challenging the Leader

• Side-Coaching CISO: Provides encouragement and guidance.

• Full-Time Coach: Challenges the leader, pushing them past assumptions, blind spots, and limiting beliefs.

💡 Subtle Impact: Real growth happens when leaders are challenged, not just supported.

7. Providing Advice vs. Elevating the Client’s Self-Trust

• Side-Coaching CISO: May unintentionally create dependency, where the client seeks external validation.

• Full-Time Coach: Builds the leader’s self-trust, so they make decisions with confidence.

💡 Subtle Impact: The best coaching doesn’t just give answers—it makes leaders trust themselves more.

ROI: The Business Case for Coaching Investment

Many companies invest in coaching, but not all coaching delivers the same ROI.

• A side-coaching CISO can provide industry-specific insights that help security teams perform better. However, the coaching is often more tactical than strategic.

• A full-time, professional coach helps organizations build stronger, more resilient leaders who drive better business outcomes, improve team performance, and enhance executive effectiveness.

💡 Value to Clients & Companies: Companies get leaders who not only solve today’s security challenges but who also elevate the organization’s overall leadership culture.

The most powerful ROI doesn’t come from short-term tactical wins—it comes from leaders who think, lead, and inspire at a higher level for years to come.

Final Thought: The Depth of Coaching Matters

Both a side-coaching CISO and a full-time, trained coach offer value—but the difference is how deep the impact goes.

For companies investing in coaching, the question isn’t just:

👉 "Who has industry experience?"

It’s:

👉 "Who will drive the greatest leadership transformation?"

A coach who is only sharing their own experience may help leaders today. But a coach who fundamentally shifts how leaders think, decide, and grow will elevate the future of an entire organization.

The right coaching doesn’t just improve performance. It builds leaders who change the game.