Why is Coaching Difficult

Welcome back to Heylia’s coaching month. Last week we talked about the importance of executive coaching, and how even those who have been in the executive position for years can benefit from one form of coaching or another. We also touched on a few of the challenges that executives come across when facing the reality of their work environment (very little opportunity for mentorship, hyper-competitive peers, etc). This week, we’re going to take a look at how coaching can become challenging once the process begins.

It might sound like a diss (and maybe it kind of is), but the reality is that every good executive needs to have a solid foundation from which they can manage their company. That foundation should not aim to tower over others, but to meet them where they are in order to unlock potential and performance. This requires an abundance of self awareness on the part of an executive. Being self aware means you’ll be able to connect with your team on a more meaningful level, building more trust and a more honest work environment. This only happens when you're able to build an understanding of your own feelings, motivations, and weaknesses. 

This can become a challenge when many throughout the executive world look to the most successful business leaders and focus on seeing only the surface layer of success, might, power and influence. We often see executives emulating that external behavior, in an effort to not seem flawed or expose their areas for development. The pressure on executives is real. It is hard. They are a cohort who do not often earn empathy because of their earnings. Not only do most truly earn those earnings, but they do so under enormous pressure to never foot-fault on the job. The scrutiny is overwhelming, the hours long, empathy offered is very scarce and it can be a lonely place. The opportunity for self awareness, self scrutiny at the cost of hard earned confidence (real or not) is a powerfully vulnerable place to explore. The higher the position in the ranks, a potential fall from grace can seem fatal. Ironically, self awareness is the key for most of the successful leaders and executives, but it is the one attribute that many won't share openly and cannot be measured on a check list of accomplishments, revenue and goals. It is an individual journey that most don't recognize is needed for success, and many who try to embrace it, struggle with the difficult realities it represents.

Understanding one’s strengths and weaknesses is born from the kind of self-awareness we’ve just been talking about. This can be a journey many do not successfully take alone (hence having a coach). Navigating the self awareness journey can be hard alone. It can be daunting, you can lose sight of holding yourself accountable, you can lose sight of the strengths that got you here in the first place. The next challenge comes from understanding what is possible with your strengths and weaknesses, and embracing different paths. This might mean taking on-board feedback that is difficult to hear. It could also mean making choices about where you focus your career and figuring out how to close those gaps in your own performance.

Maybe you have been incredibly successful in your executive or leadership career thus far. Why change something if it ain’t broke? Maybe you have hit a wall and aren’t progressing to the next level. Maybe you took a new job and all the things that worked in the past aren’t working in your new gig? Maybe you got some feedback that your success is on the precipice and you need to evolve. Either way these are opportunities and the kinds of roadblocks that coaching can help remove. Sure, there are paths to improving upon your weakness. It’s important to work on something that you might not be very good at, and with enough time and dedication, you may be able to turn that weakness into yet another strength. At the same time you don’t want to develop yourself or change yourself into a mediocre version of you. There are some weaknesses to fix. There are some to embrace and solve for in your choices of where you work and what you do. Either way, self exploration via coaching can help.

Having strengths you have relied on, over and over again to be successful, can make you feel invincible. Complacency can set in fast, and you should never underestimate its degrading nature. In a blink, your strength can be your weakness. So, in these cases, coaching can enable you to utilize strengths in a way that keeps them sharp, and fresh and relevant. Chuen Chuen Yeo says it best in this Forbes article on better ways to lead rather than always playing to your strengths: 

“An overused strength might end up being your weakness. In leadership, it’s important to recognize the context and nuances in different environments. While you will still play to the same strengths, how you calibrate and use them will be different. It’s kind of similar to using the same knife for everything, and you know that’s not right from experience. Use the best instrument for the task it’s most suited for,” Yeo says, quite perfectly, if we may add.

So we know weaknesses can’t be brushed aside, and strengths can’t be overestimated. Self-awareness is key to identifying these things, but beyond just seeing, we have to do. The path before us involves striking a balance between motivation and being content. It’s only with that balance can you as a leader move yourself forward, and in turn, the rest of your team. 

Self awareness - we keep repeating, is the unlock. In our experience, it is the true differentiator between leaders who are able to evolve to new and different levels and path to success, and those that stagnate (even successfully stagnate - executive compensation can still mightily reward those who keep doing the same things over and over again with mediocre results). So if this is one of the first steps in progress, why is it so hard? Sounds simple doesn’t it? We have seen over and over again that a willingness to take a hit to the ego, to change your belief system about yourself, to address some of the foundational belief systems that you have built an entire career on - is extremely hard and even harder to do alone, without the support of someone who can help.

There is an intrinsic tension in growing through self awareness and a balance that enables the client to succeed. That balance comes from being able to maintain two mental models at the same time, two pictures of yourself that while contrary, need to coexist and thrive together. The one model that brutally owns the truths you need to hear. That examines yourself under the clear light of day and finds you lacking. The second model that believes deeply in your capacity for impact, that fuels the type of confidence that isn’t arrogance or complacency, but the confidence to tackle the hard stuff knowing you can actually successfully navigate the unknown, because you already have. This model examines yourself and finds you worthy. Then mash them together and that is where the magic of professional transformation can begin.

The challenge for coaches is to take this self awareness and build concrete actionable plans with their client, that build aspiration into action. It requires creating safety for failure, understanding the context of your client. Getting access to their day to day and feedback on your client through the lens of the people around them. Mostly at work, but sometimes at home too.  A coach aims to create a symphony from what they have worked to instill in their clients; helping their clients pick up every instrument and get comfortable with playing first, second or third seat, but playing and trying nevertheless.  With all of these practices put into action, the final test of moving forward begins. Think of it like an engine. All pistons begin firing, all parts working together to create the energy that moves the client through otherwise overwhelming obstacles.

It might sound like the simplest task of all; just move forward with what you’ve learned in coaching. Have an awareness of self that leads to a complete understanding of both the strengths and weaknesses that you can either lean into, or find a solution to. You want to ensure that your strengths don’t become weaknesses and weakness doesn’t spread to skills that are working.

…Simple enough?

That’s where we come in! Heylia offers a variety of coaching opportunities for wherever you are in the process. We’re here, we know the game, and we know how to play it. These challenges are fairly universal, so if you don’t think we’re ready for it, think again.