Lead with Confidence.
You’re capable and trusted — but you’re tired of carrying too much, being seen too narrowly, and holding yourself back through self-doubt. Strengthen Leadership helps you shift from over-doing and self-doubt to leading with confidence, clarity, and influence.
Are you the one everyone relies on, but others are tapped with more visibility and opportunities?
You’re the fixer. The person who holds teams together, absorbs the emotional toll, and quietly prevents crises. You’re known for your reliability and ability to “figure it out.” But while you’re stuck in the execution layer, others are being tapped for strategy, visibility, and next-level opportunities.
You’re proud of your work. But starting to wonder “Has my reliability become my ceiling?”
Are you ready to step into your full potential but keep letting self-doubt hold you back?
You’re really good at your job. You build and leverage relationships and have really high-standards. But in certain situations, despite your achievements and ample evidence to the contrary, you struggle with self-doubt and finding your voice. You begin editing what you say, waiting for permission, and hesitating to share your insights,
You play small to avoid conflict, judgment, and risk; and then you kick yourself later for not speaking up.
Are you over-owning responsibility?
You’re doing more than your role actually requires. You take responsibility for outcomes and potential problems that don’t belong to you. When nobody steps up, you do. You do it because you care; because you can’t sit by and watch a ball drop; or because you would rather do it yourself than deal with delegating it.
Whatever the reason, over-owning often leads to exhaustion and resentment - and prevents you from getting to use your strategic strengths,.
Are you ready for the next level of leadership but unsure how to get there?
Each new level of leadership comes with a completely new job description. The skills, and habits that made you successful in your current role can work against you and keep you from being effective at the next level. Then there’s the elusive “executive presence”.
Asking for feedback often doesn’t result in anything helpful. So, how do you know that you need to work on or develop?
If any of this feels familiar, you’re not alone.
While every leader’s exact journey is different, the challenges take on common themes and patterns. They come with a cost, however.
The hidden costs at work of being stuck:
Conflict Avoidance: You delay constructive feedback because you don't want to be seen as harsh or difficult. You avoid being direct, especially when correcting a peer or a senior leader. Problems fester. Resentment builds.
Overload: You become the default problem solver, and everything falls on your plate. The cycle is self-fulfilling: the more you do, the more others depend on you, and the less capacity you have for the work you're actually meant to do.
Missed Innovation and Solutions: You find yourself waiting for "right" moment to speak up, the perfect plan, or external permission that may never come. As a result of playing it safe, your ideas don’t get the attention they deserve and opportunities are missed.
Leadership Gap: As you push yourself to figure everything out, take on other people’s jobs - either out of habit, necessity, or conflict avoidance - you become so busy you don’t have the time to be a strategic leader.
The real costs TO YOU of being stuck:
Burnout and Exhaustion: Each of these patterns comes with stress, emotional depletion, and the impossibility of balancing work with the life you want to live.
Underutilized Strengths: You become known as the reliable fixer, not the go-to strategist. Execution is addictive because it is accompanied by crisis and achievement, but it can pull you away from what you’re capable of.
Identity Erosion: You’ve spent so much time being what your job needed and measuring your value by your work successes, that you’ve lost connection to who you are apart from your work role. A lot of times we don’t know it’s happened until we experience a major life transition and start looking around.
Career Stagnation: It’s possible to be incredibly busy and achieve every goal given, but not be moving your career forward. You’re managing, surviving, reacting, waiting, planning. and tolerating. And the clock keeps ticking.
How We Work Together
A new way forward:
Exhale
There are plenty of places where we feel like we have to have it all together. This is not one of them. The space we create is a calm, confidential respite from the chaos and stress outside - a place where you can exhale and ramble. You don’t have to know where to start or even where you want to go. We’ll figure that out together.
Clarify
We’ll explore your challenges, the world of thoughts hidden in your mind, what you need and want, and what you would like to stop carrying and what you would like to do more of. We’ll figure out how to be leverage our partnership to impact your happiness, confidence, and contentment
Develop
With an understanding of your goals and challenges, we’ll figure out the best path forward. We can set a long term goal or deal with a more pressing situation. There’s not a set template or format. This is your time and journey. Again, you don’t have to know exactly where you want to go. Often that evolves as we talk.
Dive In
This is where we get to explore. We’ll discover and lean into your natural strengths, your purpose, and your values to shine a light on the best path to your goals. We’ll explore the assumptions and beliefs inside your head that are holding you back, and those you can use as a springboard.
About Strengthen Leadership
Meet Our Founder
Howard Cleveland, JD, CLC
Hey! I’m Howard
Cliff Notes: I help high-achieving women leaders step out of self-doubt and over-functioning, reclaim their strategic identity, and lead with confidence and clarity — so they stop playing small, stop carrying everyone else’s work, and lead confidently at the level they’re capable of.
The leaders I work with don’t struggle because they lack ability. They are brilliant, high-achieving, and purpose-driven. Instead, they struggle because something significant has changed - either personally or professionally. It may be something tangible like getting a promotion, getting new team members, becoming a parent, starting a new business, or receiving direct feedback. But as often, the significant change is not visible from the outside. They’ve had a change in perspective, are burned out, are tired of holding themselves back by playing small, or are wrestling with their identity which has been defined by work for most of their lives
That’s where I come in.
My work is focused on leaders at these inflection points — moments when roles, responsibilities, and identity are shifting faster than confidence or certainty. I work with people who are trusted, relied on, and often over-functioning, who despite their outward successes. still question their voice, their authority, or whether they’re showing up the way they want to at the next level.
Coaching with me is not about quick fixes or surface-level performance tips. It’s about slowing down enough to see what’s actually driving your decisions — what you’re carrying that no longer serves you, what you’re avoiding, and what strengths you may be under-using or hiding.
Clients often come in feeling:
responsible for everything and unsure how to let go without dropping standards
hesitant to speak up in senior or high-stakes settings
clear on their competence, but less clear on their leadership presence
tired of proving themselves and ready to lead with more intention
Our work creates space to:
lead through others without losing momentum or control
move forward even when certainty isn’t guaranteed
speak with confidence that feels grounded, not forced
align how you lead with who you actually are — not who you think you’re supposed to be
I bring structure, challenge, and perspective — but I don’t have a cookie-cutter framework that I try to stuff every conversation into - and I don’t have a template of an ideal leader. The goal isn’t to turn you into a different kind of leader. It’s to help you discover and lean into your unique strengths and leverage your purpose and values to lead visibly, confidently, and sustainably as yourself.
If you’re standing at a moment where staying the same feels just as risky as changing, and you’re getting tired of tolerating the status quo, you’re at a significant inflection point, and I would love to work with you.
Enjoy!
Howard
The technical details:
I’m a former 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; extensively trained in CliftonStrengths and the Five Behaviors; and serve as a mentor with Inspiring Rare Birds in Australia.
I have worked with leaders from five continents and have over 2000 hours of individual and team coaching experience.
I am the co-author of Running the Gauntlet: Proven Strategies for High Growth Leaders; creator of the Confident Leading: Leadership Empowerment Program for Women Leaders; and a frequent podcast guest and speaker at national conferences discussing leadership effectiveness, leveraging your natural strengths, and elevating team performance. I have served as a leadership and culture expert on panels 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 Say After Working with Us
“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
“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’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, Founder & President
“Howard is excellent. Great listener. Very authentic and comfortable to talk to.”
— Ann, Director
“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
“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
“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
“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
“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 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
“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
“Working with Howard was exceptionally helpful. He intuitively understood my personality and my characteristics. Howard helped me see traits and strengths in myself that I have not been consciously aware of.”
— Todd, Director