Last week I facilitated my last international leadership workshop for 2023. Three days of great conversations and great learnings with a group of 35 mid-senior level leaders from around south-east Asia. 

At the end of any of workshop like this, I always conduct a reflective session where participants can share their key take-aways along with what actions or experiments they will commit to taking back to their businesses. In addition to the 45-minute group re-cap, delegates are also sent a link to a more detailed survey where they can share more of their reflections and thoughts confidentially. 

As I sat on the plane coming home reading through every single response, I noticed one very common theme. Every single attendee (all 35 leaders) wrote that they wished their executive leadership team (also referred to as ‘the C-Suite’) would attend this type of training. 

Interesting that they had all included this ‘suggestion’ in a confidential survey, but none of them had mentioned it during the 45-mintue face-to-face feedback session. What were they afraid of? 

As someone who does a lot of coaching with emerging and mid-level leaders, this is also something that often comes up in private sessions – the question around why the more senior leaders in the organisation aren’t taking part in coaching or professional development programs, too. However, as an executive coach I am also fortunate to be able to work with several CEOs and others in C-Suite roles, so I can confidently say that many do take part in such programs, but typically it’s the ones that should be working with a coach that aren’t. 

Why are these executives so quick to agree to coaching for their first-time leaders and middle management, but not nearly as open to having coaching themselves?

Within hierarchical structures and what I often like to refer to as the game of ‘snakes and corporate ladders’, introducing the concept of coaching to a superior, especially someone in the upper echelons of leadership like a C-Suite executive, demands finesse and strategic navigation. 

The idea of coaching at this level often encounters resistance, scepticism, or even apprehension due to misconceptions about its application. However, the potential benefits of coaching for C-suite leaders are vast, and delicately initiating this conversation can lead to remarkable results for both the individual leader and the broader organisation. 

Why do you think senior executives typically shy away from coaching? Surely it can’t just be a time commitment thing. 

While time commitment is often a significant factor, it’s certainly not the only reason C-suite leaders might avoid the idea of coaching. After all, executives at the top might feel they have reached a level where they no longer need guidance. There might be a sense of self-sufficiency or a belief that seeking coaching could imply a personal or professional deficiency, which could potentially clash with their self-image. In addition, for many in C-suite roles, admitting the need for self-improvement could be seen as a sign of vulnerability and when operating in a high-stakes environment, displaying vulnerability would surely be perceived as a weakness. 

Recognising some of the tell-tale signs that a C-suite leader might benefit from coaching is the foundational step.

When a senior executive exhibits a plateau in their growth, faces challenges in effective communication, or experiences strategic misalignments, these could signal an opportunity for additional support. However, rather than representing perceived weaknesses, these signs should be viewed as moments ripe for growth and development. Being proactive about coaching can prevent these issues from escalating and can significantly enhance the effectiveness and growth of a C-suite leader. 

Suggesting coaching to a C-suite leader demands a strategic, delicate approach.

Framing the conversation as a supportive measure rather than as a criticism is crucial. Emphasising the potential benefits for both the executive and the organisation is essential to set a constructive tone. Remember, the goal is not to impose but to suggest and encourage an open dialogue about potential professional development opportunities. 

If you are wanting to convince your leader that they should consider coaching, your goal is to present coaching not as a solution to a problem, but more as an opportunity for continual growth and development. Frame it as support, not criticism. Approach the conversation from a loyal place, highlighting that coaching isn’t about pointing out weaknesses, but about enhancing existing strengths to fuel their success. 

There’s no doubt that suggesting the benefits of coaching to your own leader takes guts.

Offering concrete examples of successful coaching experiences within the organisation or in similar industry contexts can serve as compelling evidence. References to specific instances where coaching resulted in enhanced leadership skills, improved team dynamics, or even your own personal coaching success stories can help substantiate the suggestion. 

Of course, respecting your boss’s position and autonomy plays a pivotal part in the courageous discussion. Advocating coaching as a tool to further leadership excellence rather than as a remedy for managerial deficiencies is crucial to ensuring true dialogue and fostering a receptive conversation. 

Your goal should be to highlight the overall organisational impact beyond the C-suite by discussing how their personal and professional growth through coaching could positively impact the entire company, fostering a more effective leadership approach and healthier work environment. 

Coaching isn’t only about the individual executive; it significantly influences the entire organisation.

Emphasising the broader impact of your leader’s personal growth through coaching on the organisation’s culture, the team’s motivation, and overall business effectiveness is key to your success in such a conversation. Encouraging your leader to invest in their own development sets a positive tone for the entire company, showcasing a commitment to growth and improvement at all levels. 

Addressing the elephant in the room by suggesting executive coaching to a C-suite leader is undoubtedly a delicate process. 

It demands a strategic approach, and a genuine desire to see both the leader and the organisation thrive. The goal isn’t to pinpoint flaws, but to open doors to greater potential and growth. When approached thoughtfully (and professionally, of course), this conversation can mark the beginning of a transformative journey, benefiting not just the leader but the entire organisation. 

Remember,  Hellomonday  can provide support to every leader – emerging, new and right up to C-suite – reinforcing habits through curated learning and impactful coaching, helping to equip, empower, and enlighten them to make a difference across the entire organisation.