Executive Coaching

Know and go.

ABOUT YOUR COACH

Executive Coach Dave O’Connor sparks transformative action through the inner wisdom of senior leaders in knowledge-intensive industries such as law, healthcare, and marketing. Dave guides his clients through individual and team introspection and real-world experimentation that transforms them into confident, purposeful change-makers who lead fulfilling lives and cohesive teams. Dave’s clients describe their sessions with him as a combination of self-discovery and making real plans based on powerful insights.

Dave’s guiding principle is that the power to create the lives and teams we want comes from self-awareness, a clear vision, and a hunger for purposeful action.

Through online sessions nationwide and Chicago / North Shore in-person sessions, Dave helps private and corporate clients move from a state of craving change to looking back on lasting transformation.

COACHING PROCESS

On 60-minute dialogue-driven coaching sessions, I will help you grow your confidence, define life, career or leadership goals, and help you overcome roadblocks to achieving them.

  • You and I will meet by phone or video to discuss your context for coaching (goals, timeline, and coaching expectations) and my approach to serving clients (my coaching point-of-view, relational style, and client expectations).

  • I will send you my contract and pricing options, tailored to your needs; upon agreement, we will co-sign the contract, you will make your first payment, and we will schedule your first session.

  • We will meet virtually for all of your sessions within the timeframe agreed upon in your contract. During these sessions we will address the goals you stated in your Discovery Call, and new or urgent topics that arise in between coaching sessions. The direction we take in each session is ultimately determined by you.

  • The International Coaching Federation describes coaching as, “partnering with clients in a thought-provoking and creative process that inspires them to maximize their personal and professional potential. The process of coaching often unlocks previously untapped sources of imagination, productivity and leadership.”

    I define coaching as surfacing the inner awareness of my clients so that they may shape the life they want. My coaching philosophy is that through coaching we can have, and give, fun to a world that desperately needs it. We can be in partnership with loved ones, colleagues, and friends joyfully.

    Sometimes getting there takes a bit of work on ourselves first.

    While I am a coach, my starting point is as an enthusiastic fan; of any man eager to look inward in order to better engage outwardly.

  • Therapy sessions often focus on your past to help you understand why you are the way you are.

    Coaches are future-oriented, focusing on understanding where you are now, where you want to be, and what you need to do to get there.

  • You will benefit from coaching if you have:

    • A desire to better know yourself and your presence in the world

    • Upcoming life or career events you wish to handle with confidence and grace

    • A need to level-up your approach to relationships or decision-making

    • Crave new methods and mindsets for handling life’s ups and downs

  • I applaud anyone who seeks avenues for self-improvement. I welcome the opportunity to help any person over the age of 25, regardless of gender, or career status.

    If you choose to attend a Discovery Call with me and we find that we’re not a fit, I will reach out to my coaching network on your behalf to align you with someone who might be.

  • I help clients grow in one or more areas:

    1. Self-awareness and Self-confidence

      “I just needed to get out of my own way,” is a phrase that epitomizes the power of self-awareness, the foundation for self-confidence. Self-awareness creates space for you to know yourself better, know how you operate in the context of others and life events and helps you embrace exactly who you are, confidently.

    2. Purpose, values, and personal manifesto

      Much like a company, every individual can be steered by clearly defined and documented values, a purpose, and a personal manifesto that defines how values and purpose are brought to life.

    3. Career fulfillment

      I often hear people claim that work is not meant to be fulfilling, but rather an exchange of labor for income. I absolutely disagree. The challenge most of us face at least once in our careers is finding fulfillment despite being “stuck,” and catalyzing that stuck feeling as fuel to shape our next chapter in alignment with our purpose, values, and manifesto.

    4. Embracing vulnerability

      Ah, to never have to take a risk! Being vulnerable is risk-taking with those you trust. Vulnerability is almost never easy, especially for men. Vulnerability is where exceptional men come to life.

    5. Authentic communication

      Authentic communication starts with self-awareness and ends with embracing vulnerability. Even the most purpose-aligned, best-intentioned people have to be mindful of how they are present with others, and how they communicate.

    6. Being decisive

      To be clear, being decisive does not mean being a jerk. Being decisive does however require clarity from self-awareness, pointed towards a North Star of purpose and values, and authentically communicating our needs and desires.

      Are you ready to make it happen? Let’s talk!

  • Because I coach over Zoom it is essential to me that we connect virtually for the discovery call. However, if, for any reason, you are more comfortable meeting by phone, I welcome you to state this preference.

    The discovery call is a two-way street. This is your opportunity to interview me as a prospective coach and a chance for me to understand where you’re coming from as a prospective client.

    Specifically, we will discuss your immediate needs, my coaching approach, and expectations for the coaching relationship. Through this dialogue, we will begin to sense whether we are a fit.

  • My pricing is based on a service package tailored to your needs.

    Each package includes:

    • 60-minute dialogue-driven coaching sessions

    • Additional communication (via text or email)

    • Reference materials (literature, podcasts, video materials, etc)

    I understand the financial element of a coaching experience can cause anxiety, discomfort, and uncertainty. I, therefore, encourage you: if you need to discuss monetary costs, please speak up.

FREQUENTLY ASKED QUESTIONS

TESTIMONIALS

“The two most important days in your life are the day you are born and the day you find out why.”

Mark Twain

GET IN TOUCH

On our free 15-minute discovery call, you can ask any questions you have related to my expertise, coaching methods, and session structure.