TRANSFORM YOUR CONFIDENCE.
TRANSFORM YOUR LEADERSHIP.
Are you ready to step into your full potential but feel held back by self-doubt?
Despite their achievements and ample evidence to the contrary, many women struggle with self-doubt and imposter syndrome, feeling like they aren’t as competent as others think they are. Learn to turn down the volume of your inner critic, embrace your strengths, and lead and live with confidence.
Do you feel like your hard work and contributions often go unnoticed?
If you’re struggling to gain visibility in the workplace, you’re not alone. Many women face the challenge of their hard work and contributions being overlooked or under-appreciated. We help you develop tools and strategies to increase your visibility, advocate for yourself, and build influence - all while staying true to your authentic self.
Are you ready for the next level of leadership but unsure how to get there?
Moving into new leadership roles presents new challenges and opportunities. With each level, the dynamics change - as do the mindsets and skills needed to thrive. Our coaching provides the tools you need to lead effectively, develop and embrace your own leadership style, and break through challenges that may be holding you back.
Do you hesitate to speak up for yourself when it comes to opportunities, recognition, or promotions?
Advocating for yourself can be a daunting task - whether it’s standing up for your idea in a meeting, pushing for new opportunities, or taking credit for your achievements. You don’t have to master the art of negotiation to be able to own your value and confidently advocate for yourself. Learn how.
It’s time to be the best leader you can be.
Our Coaching Approach
Our approach is grounded in the truth that who we are personally and what we believe impact how we lead professionally. Every leadership opportunity and challenge is influenced by our inner strengths and saboteurs. We are all unique, with different strengths and experiences. There are no quick fixes or one-size-fits-all answers.
Decompress
You won’t find the pressure to have it all together here. This space we create is a calm, confidential respite from the chaos and stress outside.
Discover
Do you have a complex world of thoughts hidden in your mind? Exhale and be your authentic self as you process out loud. You don’t have to know where to start or even where you want to go. We’ll figure that out together.
Develop
With an understanding of your goals and challenges, we will tailor a coaching plan. We may have a long-term plan or create a new one to address a pressing concern - or both. We’re flexible.
Dive In
Stop letting others, external circumstances, and your own fears hold you back. Regain control and confidence with the support, insights, and accountability of your coach.
Howard Cleveland, JD, CLC
Hey! I’m Howard:
I have always been fascinated by human behavior - particularly when it comes to understanding what is keeping individuals from reaching their full potential. Whether coaching youth athletes, leaders, or teams, I thrive on helping people get unstuck, gain confidence and clarity, and find a path from where they are to where they want to be.
I have been fortunate to serve as a coach, confidant, and trusted advisor for founders, executives, and leadership teams across five continents. My clients come from a variety of industries, leadership positions, and experience levels. While their circumstances and challenges are different, there are some common themes. They:
Have been very successful by outside standards.
Often have a strong desire to please others and add value.
Hold themselves to extremely high standards.
Are tired of letting others, external situations, or their own fears hold them back.
Have a complex, inner world of thoughts, fears, and wishes hidden in their minds.
Want to get to a point where they are courageously authentic.
Are struggling to gain traction and to be as effective as they want to be.
Are approaching or in the middle of a significant personal or career transition.
As a leader, there is constant pressure to "have it all together.” In contrast, our conversations are a space where you can exhale and be yourself. You can explore, think out loud, and meander as you talk - without judgment, without trying to maintain the appearance of having it all together.
My style is a blend of authenticity, humor, insight, and unwavering encouragement. Whether coaching individuals or teams, I strive to create safe, collaborative environments where leaders are empowered to grow and thrive. With over 25 years of personal, consulting, and coaching experience in leadership, I’ve faced and helped other leaders face leadership challenges at every level and every career stage.
The technical details:
I’m a recovering labor & employment lawyer and partner; founder of PeopleCap, a people strategy consulting firm; a certified leadership coach; a member of the International Coaching Federation (ICF), and an ICF Peer Coach. I am certified in the Leadership Circle Profile, 16pf, DiSC, and the Collective Leadership Assessment; trained in CliftonStrengths and the Five Behaviors; and serve as a mentor with Inspiring Rare Birds in Australia.
I am the co-author of Running the Gauntlet: Proven Strategies for High Growth Leaders; creator of the Confident Leading: Accelerator for Women Leaders; and a frequent speaker at national conferences discussing leadership effectiveness, leveraging your natural strengths, and elevating team performance. I have served as a leadership and culture expert with executives from Toyota, AT&T, Delta, Cox Automotive, 7-Eleven, and International Paper.
My Top 5 CliftonStrengths are: Strategic | Individualization | Learner | Relator | Restorative.
What Our Clients Are Saying
“Howard sees strengths in me I don’t always see and has helped me see and appreciate myself more fully. Sometimes, when I lose confidence in myself, I call Howard to borrow some of his.”
— Natalie, Director
“Howard is an excellent coach. His presence is of genuine partnership where you feel honored, respected, and supported. I’ve worked with a lot of coaches over the years as a leader. Howard is different. He can see things others haven’t. He has a sense of when there is something behind the something.”
— Gail, Founder
“It's been amazing. Howard is incredibly easy to talk to and asked really thought-provoking questions. I would recommend Howard 100% - a 1000 times over. He has helped me tremendously, and I can't thank him enough.”
— Merissa, Director
“I have worked with many coaches before, however, not one of them was able to listen to, understand, and truly see all circumstances from a Bird's-eye view like Howard does.
What I find most valuable is how he shows up very authentically, and most importantly for me, genuinely he wants to help and how much he loves his work, which is all priceless to me.”
— Julia, Entrepreneur
“Howard’s approachable demeanor and relatability stand out. He openly shares his own experiences—the highs and the lows—when relevant, offering valuable lessons from both successes and areas for improvement. This transparency adds depth and authenticity to the conversation.”
— Lynn, Manager
“In our sessions, I find the freedom to be unapologetically vulnerable, expressing myself without any fear of judgment. Howard brings a wealth of experience to the table. His guidance is grounded in real-world business acumen and life wisdom. His coaching has been an invaluable asset in both my business and personal life."
— Marissa, Founder/CEO
“What I appreciate the most about Howard is his balance between support and challenge, pushing me to stretch beyond my comfort zone while providing unwavering encouragement. Howard created a safe space for me to feel comfortable being open. Howard has the amazing ability to sense the right time to speak up and let me be in the moment with myself.”
— Elina, Executive Coach
“As a seasoned leader making a career shift was really challenging. Howard helped me see some of the stories and beliefs I was holding onto. Letting those go gave me a completely new perspective, built my confidence, and allowed me to see options I never would have let myself consider.”
— Teresa, Vice President
“Howard is excellent. Great listener. Very authentic and comfortable to talk to.”
— Ann, Director
"Howard’s partnership with our leadership team has been incredibly valuable. Howard created a space where we felt comfortable candidly exploring the issues most important to the team.”
— Lisa, President
“Working with Howard illuminated the unique value of my experiences. He helped me understand how to leverage these strengths to elevate my work, advance my career, and support others more effectively.
The time I spent with Howard didn’t feel like formal coaching sessions; it felt like genuine, meaningful conversations. Yet I always walked away with valuable insights and practical next steps that I could immediately apply.”
— Elif, Executive
“Howard’s questions inspire deep thinking. I could rely on Howard to offer insight as to what he was seeing and then pose a unique question that causes me to totally reorient my way of thinking about the situation in a way that was different than what I have experienced in other coaching experiences. He wasn't afraid to say the hard thing which invited exploration from a different lens.”
— Jessica, Manager
“You helped plant in my heart and in my head a new perspective. I am relieved from uncertainty and have gained confidence in what I know and what I can do. I hope you can help other people the way you helped me. It is priceless. It really is priceless.”
— Mihaela, Director