What I do
I Help People
MAKE THE CHANGES
THAT will PROFOUNDLY IMPACT THEIR BUSINESSES, CAREERS, AND LIVES.
Through individually tailored sessions, we will work together to transcend limitations, harness potential, and leverage opportunity so you can not only achieve—but exceed—your personal and professional goals.
Areas OF Focus
Fuel transformation, one powerful step at a time.
Business
Whether you’re looking to spearhead a liquidity event, considering succession planning, or need to upgrade your bottom line, as a business leader who has walked in your shoes, I am committed to helping you develop a strategy to effect powerful and propulsive change.
Career
Not quite understanding why you continue to get passed over for promotion, or why that annoying teammate keeps taking credit for your work? Or even worse, why Monday mornings seem to be scored to a funeral march? Together we will create a plan to break through barriers in a way that is certain to make you shine.
Transitions
Transitions—even those we choose—are tricky little beasts. And far too often, the fear of moving forward can keep us stuck. Sometimes for years. Whether you’re experiencing a career upheaval, relationship changes, or living with the sense that life is passing you by, I am passionate about helping you achieve the mindset shift necessary to embrace the challenges ahead.
Leadership
Over the course of my career, I have witnessed the power of leadership. Excellent leaders enable businesses and teams to thrive, while weak leaders have even greater power to make talent run for the hills. Transcendent leadership begins with a commitment to transform yourself first—a journey that as your trusted advisor, I’m eager to help you begin.
Tell me more
The Process
Because the scope and complexity of every engagement varies, the process I use is tailored to each individual’s specific needs.
Okay, but in practical terms, what the heck does that mean?
There are times when one or two sessions may do the trick—when you’re preparing for a salary negotiation, a board presentation, or that critical interview for your dream job. Other situations may require a longer time-horizon to resolve—such as when you’re putting together a business plan for a new venture, or trying to get one you’ve started more fully off the ground. Still others are complex in nature and demand a more intensive approach—a company looking for liquidity, or one that is languishing and needs to turn itself around.
In every case, my goal is to help you create an efficient and timely path to success. Or more succinctly, my value-add is making you feel you’ve gotten the right bang for your buck. And the way we do that is not by prolonging our engagement unnecessarily, but by working towards a swift and successful resolution. But of course, that all depends on you, and your willingness to do the work and follow-through.
But perhaps the more important question is this: Why? Why would you choose to work with someone and not simply go it alone?
Sometimes we all—myself included—just need a little push.
You have a vision for your company but for whatever reason, you can’t seem to make it happen. Perhaps you’ve lost your enthusiasm for the venture you once felt so passionate about. Or maybe your team isn’t functioning the way you need it to and you’re too exhausted to give it—or yourself—the nudge required to get over the slump.
Perhaps you’re looking to chase a dream and start a side hustle, but you’ve never done this kind of thing before. Sometimes it comes down to the recognition that the things that are stopping you are within your power to transform, but you’re at such a loss on how and where to begin, that it feels easier just to give up. Maybe you keep getting the same negative feedback at work, and for the life of you, you can’t see the limitations that others believe exist. But maybe, just maybe, it really isn’t down to you—but the job you’re in—the boss you have—aren’t the right fit, and you’re too downtrodden to find what is.
There are times when we all need an advocate—a confidential advisor and thought partner, a champion who can give us the boost necessary to move through the messy parts and obstacles that prevent us from having the careers and lives we hope for—that prevent us from joyfully realizing our dreams.
What People Say
Clarity and Confidence
Diana has had a deep impact on my life and career. When I was at a very transitional point in my career, she not only gave me my confidence back but she helped bring out and identify my strengths and encouraged me to lean into those. It’s hard to find people that will lift you up while giving you direct and honest feedback in a way that is easy to receive. Thanks to her, I shifted my career and am on a much happier, more satisfied and financially rewarding path!
Jayla Siciliano
CEO, Atlas Vacation Properties
Host, Seed Money Podcast
Transformational Coaching
Diana is simply the best of the best! I’ve known her for close to twenty years and she’s been a mainstay in helping me create and build multiple business ventures and navigate some big life transitions. Her coaching expertise is second to none. She has a very gentle yet purposeful nature as a coach helping you dig deep and pull out your very best (and take action). I certainly wouldn’t be where I’m at in my business, and honestly my life, if it wasn’t for Diana’s expert guidance, support, wisdom, and dedication.
Shannah Compton Game
Transformational Money Expert
Host, Everyone’s Talkin’ Money Podcast
Leadership Expertise
Through her clear-eyed understanding of the power of EQ, Diana Wilson has cracked the code to effective leadership that simultaneously grows people, businesses and brands. She understands that empowering others begins first and foremost with a commitment to listen with intention. Listening lets people know you hear them; people that are heard feel respected; respect begets dedication; dedication causes people to ALWAYS go the extra mile; extra mile teams are deeply productive; high productivity builds great businesses and great brands. She’s cracked this code, now it’s perfected for us all to learn, and lean in.
Barry McGeough
Group Vice President of Innovation
AmericoGroup
There is a “fancy” version of About Me that involves a lot of corporate speak—you know the kind of thing I’m talking about—the detail you’ll find on my Linkedin profile, which as informative as it may be, doesn’t quite fit the picture I’ve included here. The one that was taken as a bit of a lark at the end of a personal branding photoshoot—and one I never intended to see the light of day.
But of all the photos taken during that session, this one has ended up being my favorite because it captures the more authentic version of me. And because it does, it is a better evangelist for the work I do now—work I’m not only passionate about, but that is a constant source of gratification. Work that is all about helping you find that same sense of personal authenticity, because I now know doing so is the key to bringing greater life satisfaction, success, and yes, joy.
Photos taken that day were intended to mark the transition from my last corporate gig to the life I lead now. The decision to leave was one I didn’t take lightly, nor was it without complications—including the forfeiture of an identity that had been part of my entire adult life. But I had a dream I wanted to fulfill—a dream that included exploring my own creativity which by necessity, had largely taken a backseat. (I write about that—and my experiences trying to get my debut novel published—via Wit & Wisdom on Substack.)
Throughout my 35+ years in business, I’ve experienced so many wonderful things—challenges that helped me grow, that led to dreams fulfilled. I’ve taken a company public, raised millions of dollars, and spear-headed a number of high-octane M & A transactions. I’ve held CFO, COO and CEO positions in a variety of industries. I’ve led companies through upturns, downturns, liquidity events and most recently, through a pandemic.
But I’ve also experienced career upheavals and disappointments—gone through periods of anxiety and paralyzing self-doubt in a time when there weren’t the resources there are today that could have helped me through. Which is why I have this driving desire to help others because I know what it’s like to go it alone, and how much easier it is when you don’t.
So if you’re looking to transform uncertainty into change, if you want to craft a life created by design versus circumstance—or if you feel you just need a little help to get you through—please know whether it’s me or someone else, there are countless excellent resources available to help you transcend and thrive.
FAQs
How are the sessions conducted?
Sessions are conducted online, ensuring convenience and accessibility for clients worldwide.
How are Business-centric engagements different from Career and Transitions Coaching?
While both are aimed at helping the client push through obstacles, leverage opportunities and maximize growth, Career and Transition work is typically more focused on the individual’s goals versus those of the business.
What commitment is required?
While I am here to champion your efforts, results are wholly dependent on your commitment to the process—which requires regular attendance to sessions, openness to self-reflection and change (that’s the key here), and a willingness to do the work.
How much does the coaching cost?
Coaching and engagement fees vary based on the program selected and its duration. For detailed pricing, contact me directly for a tailored quote.
What results can I expect?
With your commitment, you can expect enhanced clarity, improved decision-making, the ability to overcome limiting beliefs, and a proactive approach to challenges and transformation. This work often leads to increased confidence, greater bottom line results, and of course, progress in personal and professional goals. And the main thing? You’ll finally understand you don’t have to go it alone!
Ready to transform your business and your life?
Reach out to schedule your free consultation, and let’s explore how I can help.
Diana M Wilson 