After Conducting 1,000 Coaching Sessions, Here’s What I Learned

Inflection Point Partners has reached an inflection point of its own: one-thousand coaching sessions with executives and individuals wanting to accomplish something meaningful. 

As I reflect on this milestone, my mind gravitates towards the insights and lessons that I have learned from partnering with this talented and diverse group of people. While my (partners/relationships/clients) have different roles and work across industries, common themes emerge, which offer insights and lessons that can have meaning for others who also seek a deeper understanding of who they are, where they want to go, and what they want to accomplish. 

Here are some of the most compelling lessons I have learned from my time with a group of extraordinary people.  

It really can be lonely at the top

Behind the old cliché is a difficult truth that many successful people experience, often quite deeply, and especially when they reach the summit of their ambitions. I frequently hear executives say, “You’re the only one I can share this with. I can’t share it with my peers; I can’t share it with the people who report to me; I can’t share this with the board; I can’t share this with my partner.” 

This reflection is simply the harsh reality of their situation. With leadership comes responsibilities involving sensitive information, uncomfortable realizations, actions they may (or may not) be able to take, and decisions they cannot share with others, often for ethical, political or practical reasons. Most of us are naturally inclined to “talk things through.” When the usual avenues of communication are closed, leaders naturally feel isolated. If left unaddressed, this loneliness can it work against leadership goals and have a profoundly negative impact on how each individual leader feels on a daily basis. 

Fortunately, no one has to be alone in these situations. Mentors, trusted peers and executive coaches have lots to offer. I’ve been privileged to partner with these leaders to work through the loneliness that comes with the position, and witnessed positive inflections in their disposition and career trajectory. At the core, a beneficial relationship is about communicating and replacing isolation with safe connectedness. And it is this connectedness that leads to meaningful growth. 

Executive coaching clients now wear it like a badge of honor

Ten years ago, executive coaching held a stigma similar to psychotherapy years earlier: a beneficial private resource that many people nevertheless felt uncomfortable acknowledging in public. The preponderance of business leaders perceived coaching as an admission of insufficiency. Something remedial. Executives were inclined to keep mum about it.

That tide has turned. Dramatically. Executives - and non-executives - are enthusiastically raising their hands and jumping at the opportunity to engage with a coach. Organizations understand that high-potential employees perform disproportionately well, and therefore will take every effort to attract, retain and encourage future stars. Coaching is becoming a standard benefit to keep and develop top talent.

Today “performance coaching” is a public recognition that companies bestow on top performers. It represents a badge of honor that an organization investments in leaders who hold their greatest confidence. Instead of hiding their work with coaches, executives now wear that badge with pride. As one client shared with me, “Hey, if Serena Williams has a coach, I can benefit from this coaching partnership as well!” 

Thinking outside of the organization can make a difference

In coaching sessions, I’ve seen the most rewarding breakthroughs come when an executive drops her guard and lowers her defenses. It starts with trust, the essential ingredient for a successful coaching partnership. 

Privacy and confidentiality are prerequisites for that trust, and an internal coach may not foster the necessary environment for the kind of open, frank conversations that address root concerns and explore new possibilities. 

Even when offered with the best of intentions, a coach within your organization may require a leap of faith.. 

At the risk of sounding self-serving, having an external coach can yield a better outcome: a more powerful and beneficial partnership. I encourage executives to consider the advantages of external resources, who are devoid of interpersonal conflicts and are free to serve as an uncompromised ally.  

Allow the stars to shine

It’s true: talented people often get promoted beyond their initial competencies. (See The Peter Principle.) Star salespeople may eventually lead stellar sales teams, even though selling is a profoundly different skill than leading. Companies rarely anticipate that star performers will need development to succeed in new roles. 

As a consequence, the most promising people can feel exceptionally vulnerable when they are elevated to positions in which they feel insecure. More than once I’ve heard accomplished executives say, “I don’t really know what I'm doing. I’ve never done this.” 

You may be among the large tribe of leaders who have a nagging suspicion they’re posing as imposters - that they’re not who they’re “supposed” to be. The truth is, you’re exactly who you’re supposed to be. You secured the position because you are good. But moving into a new role requires development and often a re-examination of your attitude, outlook, and practice. Coaching can help you make a transition with confidence, applying new tools, methodologies, and information. It can offer a supportive partnership to prepare you for your next role, mitigate the risks, and maximize the results.  

Successful people control the controllables

The loneliness and isolation so common in leadership can turn reflection into brooding. Often the most intelligent and conscientious people become trapped in their own ruminating thoughts of projected anxieties and anticipated fears, especially about losing control. Leaders may feel they have to retain control, but in reality, there is only so much any human—even the most powerful—can control. Coaching can help you get out of your head and transform negative thoughts into focused energy.

I often ask my clients, “If this day is going to be successful for you, what are the three things you need to begin, advance, or complete today?” 

Converting vicious spirals into controllable steps, I’ve seen executives rise to the challenge easily by immediately swapping speculative fears for practical actions and simultaneously increasing focus, competence and confidence.

?Small steps lead to big changes

Large moves, fundamental change and significant adjustments can paralyze even naturally action-oriented people. At times, highly capable executives find themselves unable to act because they don’t know where to begin, and believe they have neither the time nor the energy to tackle big change. 

In effective coaching, the focus is always on the smaller—but significant—set of things you can control and the necessary specific actions to take, by grounding ourselves in the here, the now and the real. As Desmond Tutu once said, “there is only one way to eat an elephant: a bite at a time.”

Again and again, I have seen small, incremental and smart tweaks yield immense benefits. Think about fitness goals where committing to overnight lifestyle change doesn’t work; the more effective approach is often the ‘one push up’ rule. Try it out. Commit to doing one push up today. It’s highly likely that you will not only complete the task, but also you will go above and beyond. More importantly, you likely will repeat the process the following day, and the day after that. Executive after executive has report that incremental changes unlock the most meaningful results. In one example, stopping to talk to more junior team members for a handful of minutes a few times a week completely altered the vibe in the office and strengthened connections that paved the way for the entire organization to transform.  

I’m all in–and so are the most effective people I’ve coached

Coaching is a partnership that requires commitment from both parties, and embracing that truth is a common trait among successful executives I’ve worked with. You have more than my ear: you have my attention and the full benefit of my experiences and skills. I’m completely present. I am listening and I am hearing you. To get the most from our partnership, you need to be as well. 

Coaching can be a transformative experience. But as in so many meaningful things in life, what you get out of it depends on what you put in. I’ve been honored to play a role in helping people reach great heights and explore depths that reshaped careers - and their lives. Together, we set goals and objectives and co-created Game Plans that serve as the GPS to take them where they want to go. The people who’ve amazed me jumped into the process with both feet. If you’re ready to do that, you are poised to harness your greatest resource: you. 

Matt Spielman is the founder and Managing Partner of Inflection Point Partners LLC. (www.inflectionpointpartnersllc.com) Matt's work focuses on executive coaching and career transition. He gets energy from helping people realize their potential, and having a positive impact on careers and lives.