Howard Gray
Seeking the groove.
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Coaching

Coaching isn't advice - it's structured space to discover what you already know but can't quite see yet. Whether you're scaling a venture, stepping into leadership, or navigating a major transition, the right conversations at the right time change everything.

As an ICF certified professional coach, I help creative entrepreneurs and executives turn uncertainty into strategy, ideas into execution, and challenges into opportunities.

Strategic coaching for creative leaders

Big-picture clarity, positioning, leadership development, and communication mastery

  • Best for: Founders, creatives, and executives navigating inflection points in their career or business.
  • Focus: Strategic clarity, identity, positioning, scalable growth, and executive presence.

Think of this as calibrating both your inner engine and how you show up - who you are, what you stand for, where you're going, and how you communicate it powerfully.

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Looking specifically for presentation and workshop development? Check out Groove Build for dedicated co-development of signature talks and workshops.

Who I work with

I specialize in working with creative professionals who are ready to level up:

  • Founders & entrepreneurs → From startup founders to independent creators, navigating growth, positioning, and business strategy
  • Creative professionals → From brand strategists to international DJs, scaling their work and increasing their impact
  • Executives & emerging leaders → From agency directors to tech VPs, stepping into leadership and communicating with confidence

How coaching helps

Working together, we can help you:

  • Clarify your positioning & messaging → Get crystal-clear on who you are, what you offer, and why it matters
  • Transform ideas into viable ventures → Turn what's in your head into something real and scalable
  • Master storytelling & communication → Elevate your pitches, presentations, and leadership presence to world-class level
  • Navigate leadership & career transitions → Step into new roles with confidence - without losing your creative edge
  • Overcome creative resistance & imposter syndrome → Stay in motion when self-doubt creeps in

How we work together

My coaching philosophy

I believe the answers you need are already inside you - my job is to help you access them. Great coaching isn't about giving advice; it's about creating the right conditions for breakthrough thinking. I provide structured space for you to think clearly, challenge your assumptions, and move forward with confidence.

What to expect

  • First session: We start with a strategic deep dive - understanding where you are, where you want to go, and what's really in the way.
  • Ongoing sessions: Each session is tailored to where you are in the moment. We might dive deep into strategy, work through a specific challenge, or practice a presentation. Between sessions, you'll have clear actions and accountability.
  • Format: 90-minute sessions via video call (or in-person if you're in NYC). Sessions are focused, practical, and designed to create momentum.
  • Most clients see significant clarity and momentum within the first month, with sustainable systems in place by month three.

Investment

Strategic coaching program

  • Investment: From $6,000 (3-month minimum)
  • Format: Strategic deep dive + bi-weekly sessions
  • Includes: Personalized action plans, accountability, frameworks to scale sustainably, and communication coaching

I only work with a small number of coaching clients at a time to ensure deep, high-impact sessions.

What makes this different

I've been in nearly every seat at the table

I'm not just a coach - I've been an entrepreneur, manager, freelancer, consultant, and employee. I've built ventures, led teams, and worked across startups, creative studios, and Fortune 100 companies. This means I don't just understand business and creativity - I've lived both sides of the equation.

I coach from lived experience

I've felt the highs and lows of launching a business, hitting frustrating plateaus, dealing with creative resistance, and navigating difficult leadership transitions. I coach from experience, not just theory.

Coaching is a craft - and I take it seriously

  • ICF-certified professional coach (Coaching for Transformation, Leadership That Works, NYC)
  • 300+ workshops designed & delivered for Fortune 100 companies, startups, and creative leaders
  • Continuous professional development because this work demands both solid foundations and ongoing growth

My approach is practical and results-driven

  • Practical & action-oriented → No fluff, no drawn-out introspection - just genuine insights and real action
  • Supportive but challenging → I'll push you when needed, always in service of your growth
  • Big-picture + tactical → I help you see the system, then act on it

What they say

I started working with Howard during a period where I was dealing with a whole new context and a lot of questions I was trying to work through. I started slightly skeptical about using a coach, but through Howard’s great balance, poise and wisdom, I felt quite safe in exploring these challenges.

Howard is great at asking the right questions in the right way, enabling me to talk my way through issues and nudging me through to these ‘aha’ realisations.

I’ve uncovered and discovered new things, changed thinking and realised that in fact the root of some of my challenges and questions originated from somewhere I did not expect.

Breaking down my next steps into easy manageable accountable actions hugely simplified what was overwhelming before.

– Alex F., Startup Founder, Sustainability

Howard is an absolute master at his craft when it comes to "workshop coaching”. His knowledge and suggestions are brilliant and his guidance has helped me refine and elevate my workshop content. I HIGHLY recommend you work with him - you will be very pleased with the results.

– Jeff Salzenstein - Keynote Speaker & Former ATP Top 100 Tennis Pro

Next Steps

FAQs

What is coaching?

Coaching is still a relatively nascent discipline and there are numerous approaches, methodologies, and types of coaches out there.

My preferred definition of coaching is as a powerful partnership between you and your coach that helps you focus, become more effective, and realize your visions and goals.

With a Professional Coach, you can develop the tools and gain the support to remove obstacles and facilitate the changes you want to see in your life.

As well as being a coach, I also work with a coach. It’s been a huge contributor in helping to clarify my thinking, see new ways of doing things, and make genuine progress in my life and work. And I get to learn new coaching skills too.

What are the different types of coaching?

You may have seen a few different types on offer – from life coaching to career coaching and leadership coaching. As the coaching industry is largely unregulated there’s nothing to stop just about any type of coaching being provided – this means there are all kinds of flavors and niches on offer, but as with many things it’s a case of a prospective customer/client being vigilant and taking steps to understand what they need and what they’re committing to.

Most good coaches will likely tap into deeper agendas around a particular topic, so while a focus may be on say careers, you shouldn’t be surprised if there are aspects of your personal or social life that come up in coaching sessions.

My particular focus is on the world of work, so I tend to focus on careers, leadership, and entrepreneurship as primary topics, but inevitably ‘life’ comes up regularly too 🙂

What are the reasons to work with a coach?

There are many, and again it depends on what you’re looking to get coaching on, but here are a few of the reasons my clients work with me:

  • focus your thinking
  • discover and connect with your core values and passions
  • create more balance in your life
  • make a transition or pivot in your career
  • focus your energy to finish or plan a project
  • launch or grow a new venture
  • develop and increase your leadership skills
  • set clear goals and build structures to help achieve them
  • enjoy life more

How can I get the most out of coaching?

  • Find the coach who feels like the best fit for you. It’s worth speaking to a few – most coaches (including me) will offer a free initial call to get acquainted. The personal fit between you and your coach is so important – take the time to have that initial conversation before committing.
  • During your first coaching session (likely a longer discovery session), set a small number of 3-month goals (maximum 3) that are worth accomplishing.
  • Make the most of your coaching time. Tell your coach what results you want and your coach will help you make it happen. However, it’s important to note that your coach can’t do the work for you. The progress to the goals you want to achieve will come about through your own work. Also, don’t be afraid to tell your coach if a particular approach isn’t working for you – the coach’s role is to ensure you get the results you want as a client.
  • Use the time between sessions to work on homework assignments and to deepen any new awarenesses you gain from a session. Share what you are learning about yourself and what changes are happening for you with the important people in your life. Provide updates to your coach (and any friends & family you want to bring along on the journey) on a weekly basis if you can – accountability is a powerful thing.

What do you do - and not do - as a coach?

  • Listen to you openly and actively
  • Reflect/mirror back to you
  • Offer different perspectives
  • Provide structure
  • Ask powerful and probing questions
  • Assist in setting goals, planning and strategizing
  • Hold you accountable for what you want to achieve
  • Trust you to make your own decisions
  • Have your best interests at heart
  • Tell the truth
  • Believe in you

I don't:

  • Do your work for you
  • Judge you
  • Give you legal or financial advice
  • Take responsibility for you or your actions

Where can I find out more?

Here are a few coaching resources I’ve found useful:

Ed Batista, a coach based in San Francisco who also teaches at Stanford University. Ed’s blog posts and slide decks are well worth checking out.

Presencing’s Theory U

Conscious Business by Fred Kofman – former coach at LinkedIn

Why do you do this work?

I’ve been doing this work for almost as long as I can remember, starting with coaching my brother’s football (soccer) team when I was 13.

It’s followed me throughout my career: the greatest pride I took from being a company founder was being able to provide a platform for a group of talented people to build their creative careers. I still love being able to cheer them on from the sidelines today.

But frankly I used to think the concept of ‘coaching’ was a bit weird – why would anyone need this outside of a sports team?

As I adopted more of a growth mindset in various areas of my life I realized there were so many things to explore and learn – about the world, about other people, and about myself.

I started to look at all the things I didn’t know rather than what I did.

Coupling that curiosity with an interest in what enabled successful people to do what they did led me towards what I do now (and yup you guessed it, a significant factor for nearly all these people was coaching).

Since 2019, I’ve more formally built my skill set in this field via an intensive ICF-accredited coaching certification, plus lots of facilitation, mentoring, learning design, and creative and entrepreneurial endeavors.

I’ve also experienced the successes, failures and valuable learnings that inevitably come with putting yourself out there and doing something new, so I’m well positioned to work with clients who are entrepreneurs or growing into leadership positions.