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Exec Coaching for Coachable Execs

Todd Gibby
Sep 2 · 6 min read

It is a good thing to be “coachable,” meaning capable of being easily taught and trained to do something better. It’s easy to understand why companies consistently seek to hire and reward coachable behavior in their teams. Based on this definition, I’d argue we all want to be coachable. Unfortunately, our egos often get in the way. This likely explains the countless books and articles that provide tips on how to become more coachable. These serve a valuable purpose; and I don’t have a beef with any of them. With one exception: their guidance seems to overwhelmingly focus on junior level professionals, and to largely ignore senior executives. At Lock 8, we strongly believe in the power of coaching to elevate the performance of executives and (correspondingly) the businesses they lead. This post shares some experiences and observations around coaching / coachability for people who need it just as much as anyone — seasoned senior leaders of small-scale businesses.

Contrary to popular belief, the need for coaching does not decrease as one’s proficiency / expertise / seniority increases. Elite performers of all types (e.g. athletes, performing artists, authors, painters, etc.) all tend to utilize more coaching, not less, as they advance in their respective fields. Want evidence: have you noticed the sideline of a big-time football game in recent years?

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And yet, an anecdotal sampling of articles about coachability in the workplace shows an overwhelming focus on the most basic aspects of the topic. One recent article from a highly respected publication offered five tips for being more coachable — and all five of them focused on responding well to feedback. Although requesting / receiving feedback is an undeniably valuable skill, I’d argue it is a necessary, but insufficient condition to being coachable. For executives aspiring to become more coachable as their careers progress, simply getting better about asking for feedback won’t move the needle.

This all has been top-of-mind for me lately: I recently resumed working with an executive coach, after a six-year hiatus from doing so on a formal and consistent basis. The experience has been really positive. And it has been a reminder that there are wide variations in these coaching sessions, with some being truly groundbreaking and others not so much. Reflecting on this, I’ve realized that the variations are largely of my own making. Certain behaviors elevate the results, while others undermine my efforts to be coached. In short, the outcome depends on how “coachable” I’ve been in connection to a particular session. Below are some observations around my recent exec coaching experience, in hopes that they will help other execs who are looking to optimize their own coachability.

1) Nike Rule: Just Do It. Seriously, a huge step toward execs becoming more coachable is making the commitment to formally work with an executive coach. This seems obvious, but it’s surprisingly hard. First, there is a lot of inertia against taking the plunge. Second, it can be expensive. Third, I personally have found it consistently challenging to find a coach I actually WANTED to work with (perhaps more on that in a future post). Finally, we tend to convince ourselves that receiving regular (or even irregular) feedback from various colleagues / employees / peers / board members is tantamount to coaching. It’s not –it’s just varyingly structured feedback that should be absorbed and internalized, but also viewed through whatever prism it’s being delivered. Conversely, establishing a formal exec coaching relationship (and paying for it), immediately fosters a coachable mindset in the person being coached.

2) Embrace vulnerability: Leaders generally are relied upon to provide guidance and strength to others. And while we’ve largely / thankfully outlived taboos against company leaders showing weakness, a complex dynamic exists for them across the concepts of vulnerability, safety, and competence (I made a quick video on this topic here). The result is that there are precious few situations where leaders can fully display vulnerability. Coaching sessions are that place. Let it all out — personal doubts, fears about the business, nagging weaknesses — they are all open topics, with no negative repercussions for raising them. If naming a problem is a first step toward solving it, then these sessions are the safest place to take that all-important first stride. Run to it.

3) Be Prepared: Aside from being one of my favorite musical numbers from The Lion King (1994), “Be Prepared” has become my new motto for these coaching sessions. It strikes me that there is a near-linear correlation between time spent on active preparation in advance of a coaching session, and the productivity of the session itself. My best results roughly reflect a 1:1 ratio (60 minutes of prep per 60-minute session). This generally falls into two buckets: (a) writing down thoughts as follow-up to topics / exercises that arose in the prior session and (b) codifying (and sharing with my coach in advance) a set of themes that I’d like to explore in the upcoming session. This allows my coach to optimize our time together and dig-in with real focus, while still leaving room for unscripted exploration. The less I prepare, the more I devolve into free-association without purpose — which strikes me as being in direct conflict with the definition of coachability above.

4) Talk More, Smile Less: With all due respect to Aaron Burr in Hamilton (“Talk less, smile more”), being coachable demands unapologetically open and honest voicing of one’s positions and beliefs. This runs counter not only to Burr’s advice, but also to what we are encouraged to do from a young age (“We have two ears and one mouth for a reason…). But talking things out is a necessary component of being coachable, especially for external processers like me. This guideline applies not just to our fears / concerns (per the vulnerability point above), but also to our hopes and dreams. Brazenly expressing our most ambitious goals, irrespective of how insanely audacious they may be, will spur a constructive discussion about the current realities, options available, and execution required to achieve them.

5) Ask to be Asked: As thoughtful coaches will assert, their role is not to dispense advice or impart gems of wisdom, but rather to ask provocative questions. This point is especially true in the context of coachable executives, since we don’t typically do this for ourselves. Left to our own devices, business leaders are adept at coming up with answers / solutions — it’s what we do. But we are less good at asking and holding ourselves accountable to answering deep questions. We are just too ____________ (pick one: busy / invested / scared / lazy / committed to the current path(?)) to do it consistently. That’s what executives should ask coaches to do for them. The less I expect my coach to tell me stuff, the more I empower her to ask tough questions, the better our results are. As a related aside, this point should help debunk the common misconception that a coach needs to be more expert at a given pursuit than the person receiving the coaching. Wrong. If this were true, how would Beyonce or Roger Federer or Simone Biles select a coach? Spoiler: They all have coaches whose role is to help these G.O.A.T.s challenge themselves.

6) Read, read, read: I find that my coachability rises on weeks when I’ve read a wide range of business-related books / blogs / articles. This one might also seem obvious; reading undeniably expands our knowledge base, which naturally improves our ability to learn. But I include it here for what might be an unexpected reason: Reading about the business challenges and successes of others reinforces just how unremarkable my own are. I find this oddly reassuring and helpful when it comes to (a) keeping things in perspective, (b) taking feedback less personally, and c) avoiding the pit of despair when things feel like they are running off the rails. Reading is a great reminder that someone is always tackling something much harder and much more effectively than me at this very moment.

To finish where we started, we all want to be coachable. Like anything worthwhile, it takes hard work and some intentionality to make material improvement. Meanwhile, I’ve been enjoying working out the kinks as I’ve re-entered the world of working with an executive coach. And it really is worth the effort. As we say at Lock 8 all the time: coaching’s impact effects not only the person receiving the coaching, but also the team they lead and the organizations they drive.

Made Not Found

In SaaS businesses, operating results are earned every…

Todd Gibby

Written by

SaaS operator-turned-investor | Founder of Lock 8 Partners | Sharing observations, thoughts, and lessons learned from the ever-educational journey.

Made Not Found

In SaaS businesses, operating results are earned every single day; and good businesses are made, not found. Writing here about building organizations, learning from the experience, and appreciating the ride.

Todd Gibby

Written by

SaaS operator-turned-investor | Founder of Lock 8 Partners | Sharing observations, thoughts, and lessons learned from the ever-educational journey.

Made Not Found

In SaaS businesses, operating results are earned every single day; and good businesses are made, not found. Writing here about building organizations, learning from the experience, and appreciating the ride.

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