Consultant?  Mentor?  Coach?  However you might be trying to encourage someone who is already an outstanding professional do what they do better, what is most likely to get in your way?  It is quite possible that professional is not accustomed to being on the receiving end of good coaching.  Any leader who spends most of their time getting things done promptly, inspiring a team with excellence, may have forgotten or never have learned how to be open to quality feedback.  That may seem like the executive’s problem, but it is clearly a challenge any great coach should be excited to accept.

One of the key problems many executives face is the impossibility of getting honest, useful feedback, often until it is too late.  A study last fall from the Kellogg School of Management identified the Icarus Paradox as a particularly pernicious factor in the continuing success of accomplished CEOs.  Where top executives are often most in need of quality feedback, they are often at the disadvantage of their own nervous circles.  Exaggerated levels of flattery and opinion conformity are too often the norm within organizations, leaving the already exposed leader even more exposed than necessary, too often in the spirit of being well-meaning.  “My advice would be to remember that the higher you are, the more likely you are to be ingratiated, and therefore you should make sure you get advice from people who do not depend on you,” wrote Northwestern professor Ithai Stern, one of the authors of the study.

There’s some interesting advice — seek input from someone who has no reason to flatter you, but rather is 100% aligned with you objectively for success.  Sounds like opportunity with huge upside for the right person ready to provide that challenge in a manner where it is unfiltered, constructive, and uncompromised.  The goal is not so much self-enhancement of the individual as it is strategic enhancement of the individual’s mission, upon which so many are depending.

Sounds like an ideal place to be, but how do you get there?  Surely it’s possible for someone like Baseball Hall of Famer Sandy Koufax to return to his Dodger roots and offer a pointer or two to Cy Young Award Winner Clayton Kershaw, who is still early in his career and confident enough in his own pitching to know how to listen to a legend.  What if your experience is different from that of the person you are coaching — can you still be of high value?   Because I do this every day with world-class individuals who do things I could never do, I promise you that you can — but you do have some immensely hard work ahead of you.

Imagine you could help anyone in the world get better at what they do in a professional context, regardless of his or her area of expertise or your own.  Hey, this is for fun, pick anyone you want — an artist, an athlete, a headline corporate leader.  Great, keep that person in mind, and presume you are not renowned for the same things they are.  How are you going to get past the barrier of getting them to accept your insight?  That perhaps is a much bigger challenge than getting the fantasy assignment in the first place.

You might be saying to yourself your initial goal has to be to establish rapport, and that would be a good place to start, but what does it mean?  In the Executive Coaching Workshop I lead with John Vercelli at Coaches Training institute, we talk less about the notion of rapport, and more about the notion of empathy.  In the many exercises and role-playing scenarios we run, we have yet to find two individuals so disparate in life experience that they cannot find a path to empathy.  In this context, empathy is the basis of common understanding, an appreciation of shared aspirations and motivating factors, an interlinking of common goals outside the specifics of a work-oriented task.  No matter how far apart people begin, if they make the effort and commit themselves to finding reciprocal empathy, they can find common ground to break down a set of complex problems quickly and consistently.  The outreach that constitutes the task of discovering empathy leads to the bond of trust that is essential in any coaching relationship.  Find empathy, establish trust, and the process of being open to outside support is not nearly as hard as it seems.

Is it any wonder that this kind of trust is difficult for an executive to exhibit in the hyper competitive workplace?  Anyone in a position of leadership is constantly faced with endless conflicts of interest, mixed messages, hidden agendas, and far too much flattery.  When a coach can break through all that noise through the powerful act of focused listening, the next person likely to listen might be the executive.  That could constitute an unequaled breakthrough and the beginning of a powerful business friendship.

If Professor Stern and his colleagues are right about the Icarus Paradox, and senior business leaders can be set up for a fall by unrealistic levels of strategic confidence fostered by too many piled up compliments, then the smartest ones are going to look outward for the right kind of listening and more useful forms of feedback.  That’s a field day for the executive coach willing to step up and be honest, empathetic, and a confidential source of creative exchange.  With that kind of listening, flattery can be replaced with progress.