Transferring Best Practices Into Action

“I made more progress with Jessica in two one-hour sessions than I did in a full year with a previous coach. I chalk it up to her style of helping me to tap into what makes me, ME and then leverage my unique strengths to help others and lead myself better. The secret isn’t to do more of what hasn’t worked, but to try a new way of listening and understanding.”
– J. Peirce, Coaching Client

Her Top 5 CliftonStrengths are Individualization, Maximizer, Connectedness, Developer, and Empathy.

We asked Jessica about her career and how she gets effective results for her coaching clients. Here’s what she shared:

1. How did you get into this career?

The Foundation: The common thread woven throughout my career is leadership development best practices for C-level executives. Shortly after graduating from college, I worked at Forrester Research for their Leadership Boards division. As part of the research interview teams with CIOs and CMOs of Fortune 100 organizations, I heard the firsthand accounts on how to motivate people and a workforce from those at the top of their game. One report on the Human Capital of IT was my first taste of the talent side of the business and it just made sense to me.

The Preparation: I had the distinct honor early in my career to support training workshops for Marshall Goldsmith’s coaching content. He is a NYT best-selling author on leadership and an Executive Coach to Fortune 100 CEOs. As the program manager, I learned his best practices for coaching, trained our sales teams on the content and products and introduced him at live workshops.

The Decision: I had been in the training and coaching industry for over a decade and decided the time was right to wear the hat of a formal coach after taking the StrengthsFinder assessment. The results were far more specific and accurate to me as an individual than any other tool I have seen. The application of CliftonStrengths is the essence of positive psychology and it aligned with my Individualization (#1) and Maximizer (#2) of being growth-minded and focusing on what is right with people. It’s a thrill for me to discover a client’s unique talents and motivators and help position them for success.

2. Who is your ideal client?

I specialize in mid-career executives who are in career transition – going from individual contributor to manager or director to VP. My style combines emotional intelligence with a simple action. I rely on my ability to spot talent and help clients move through the change—such as a promotion, new job, acquisition or organizational merger—in the most efficient way.

I use the William Bridges Transitions Model as a framework that helps people manage any change they are experiencing. Clients get a confidential and trusting conversation within the structure of a proven framework. I’ve been told that people are disarmed by my calming energy, and we often get to the root issues quite quickly.  I customize the right next step that is both simple and achievable. Adding up the simple steps creates positive momentum in the right direction.

3. Who is your favorite thought leader?

I often recommend clients listen to Peter Bregman’s podcast on how to become more powerful, courageous leader. I’ve relied on his HBR article, “Don’t Be Nice; Be Helpful”, as a go-to resource for managers. His tips are simple, actionable and they work. His book Four Seconds aligns with the CliftonStrengths philosophy of being intentional.

4. How do you use your own Strengths?

Richard Branson relies on intuition far more than data for business decisions and Steve Jobs said intuition is far more powerful than intellect. Knowing my CliftonStrengths has taught me how to intentionally fire up all my talents simultaneously and trust the path I see. I ask pointed questions that make clients stop and think about a situation in a completely new way. My preparation, communication, and influence is tailored for each conversation and always driving for new performance.

5. Who do you follow on Instagram?

Sara Blakely, the CEO of Spanx. I saw her speak at the MA Conference for Women in 2016 and was inspired by her humility and transparency. She shared how she trusts the universe and follows her intuition in business and always gives back. My favorite posts are her Monday Mugshots where she literally holds up a coffee mug to her face with an inspirational quote and then tells a story on how she uses it. Her posts about how life is crazy being a parent of four kids are real and hilarious.

During a podcast interview with Lewis Howes, she was asked about her biggest fear. She said it was to lose someone she loved because she had lost 11 people close to her in separate tragedies by the time she was 31. She learned that facing her own mortality at a young age had hidden gifts. She used it in a positive way fuel her courage. Her story shows how you never know what people have gone through or are going through on any one day, even a billionaire or public figure.  She is no stranger to hard work and grief and I am a huge supporter of all her success!

6. What experiences do you draw upon when coaching?

I know what the neutral zone of a transition feels like. It’s the unknown between an ending and when a new beginning starts to feel like normal. I can find the place within myself that holds the same feeling a client has—proud, motivated, frustrated, tired—not necessarily the same experience.

I was in my late 20’s when the recession of 2008 hit. We went from one day being business, as usual, to say goodbye to half of our workforce. It was traumatic. During that time there was no light at the end of the tunnel and no one had answers to when the pain would end. Our company used the Bridges transition model with internal employees to address the unknowns and refocus on daily work.

Personally, I turned to my areas of strengths that are externally focused on others and choose to run the Falmouth Road Race on Cape Cod as part of the Alzheimer’s Association team. My Grandfather was affected, so it was a cause that hit close to home. Training for the run and fundraising became a way to control what I could during the unknown of my grandfather’s disease and the economy. Being of service to a cause far greater than myself was a way to connect with others. That connection was healing and brought a positive focus to daily life during a tumultuous time.   

7. What don’t most people know about you?

I sought out positions in marketing management to gain practical experience to apply my content knowledge on how to get the best out of a team. I have training in product marketing from Pragmatic Marketing Inc. and was part of the first cohort of mentees to be formally assigned a cross-industry mentor as part of the Boston Product Management Association. I am most proud of being able to take the processes from the proven framework and apply it to service-based businesses.

8. Who is your mentor?

Sara Regan, my CEO. She is a force. She is generous and kind and brilliant. She started this company eight years ago and it has grown to a full demand strengths-based consultancy—the top in New England. She was in one of the first cohorts to be a certified coach by Gallup. She’s an amazing trusted advisor to global executives—such as Ellen Agler, #38 on Fortune’s list of the world’s greatest leaders.  Sara’s a mother of three teenagers and manages the ups and downs of daily life with grace, humility, and humor.

She is a strategic thinker who makes the right decisions. It’s not about quantity with her, but the big moves. I get the benefit of observing her business decisions, style with clients, and direct coaching. She lifts me up to a new level. She holds you accountable in a positive way that makes you want to step up to any challenge with full confidence. She lives a strengths-based life and practices what she preaches. If you haven’t met Sara yet, you must!

What do clients say about Jessica?

“In a world of infinite information, what we really crave is wisdom. You’ve read all the books, subscribed to all the blogs, listened to all the podcasts, even worked with other coaches, but you’re still not reaching your goals. You’re still not able to get out of your own way to become the person you know you could be. What you really need is someone who can give you the insight to discover what to do with what you know—that’s wisdom. Jessica doesn’t just give you the one size fits all leadership tips you could find in a google search. She listens deeply to understand how your strengths profile influences your motivation, your personality, and then helps you leverage your unique skill set and way of being to tap into new heights of confidence and success. I made more progress with Jessica in two one-hour sessions than I did in a full year with a previous coach. I chalk it up to her style of helping me to tap into what makes me, ME and then leverage my unique strengths to help others and lead myself better. The secret isn’t to do more of what hasn’t worked, but to try a new way of listening and understanding.”

– J. Peirce, Coaching Client


To learn more about working with Jessica at Strengths Now, please visit their website: