Faces of HR

Faces of HR: Ann McCloskey on the Value of Authenticity, Safety, and Taking Risks

Ann McCloskey has more than 25 years of experience working with executive teams to build organizational health with a direct tie to financial performance. Not only does she specialize in culture build, strategic talent management, executive team alignment, and executive coaching, but Ann has also helped transform talent practices for software and tech enabled businesses.

For our latest Faces of HR profile, we sat down with Ann to discuss how she got her start in the industry, her biggest influences, as well as the importance of making talent feel safe.

“While it is very important for people to feel safe, I think the purpose of this safety is to make it ok for them to actually feel uncomfortable,” McCloskey recently told HR Daily Advisor. “Work can be a powerful place for growth and transformation. That doesn’t happen if you don’t feel safe but, at the same time, it doesn’t happen if you’re too comfortable. I want people to be the best that they can possibly be and that only happens when we create an environment where they can safely experiment and try to new things.

“I worked for an organization that used the motto, “We will help you do things you never dreamed possible,”” she continued. “Being a part of helping people reach those goals is the most rewarding thing I could possibly do. I find the best way to create the environment is to put away corporate speak and bring your own authentic self to work. If I can demonstrate that it’s safe to make mistakes or to be learning, then it helps create the environment for others to take risks as well.”

Today, Ann is the Operating Principal, Leadership and Talent for Accel-KKR — a private equity firm that invests in mid-market software and technology enabled services businesses. 

In our latest Faces of HR profile, meet Ann McCloskey.

How did you get your start in the field? 

Earlier in my career I worked in financial services and was lucky enough to work with an executive coach who pointed me in the direction of Organization Development.  I went back to school to get my Master of Science degree in OD from Pepperdine University and made a complete career shift thanks to her.

Who is/was your biggest influence in the industry?  

I have had many positive influences in my career starting with the coach that helped me make my initial career change, Cathy Van Berkem. I’m inspired by people who understand the link between high performing talent practices and business success. Because of my role in private equity, I have had the privilege of working with a number of different executives and company leaders.   I have learned the most from the CEOs that I now describe as having “asked the first question.”  They demonstrate a vulnerability and willingness to learn without the need to be the expert.  I’m also a voracious reader and have learned from business authors like Jim Collins, Patrick Lencioni,  and Susan Scott as well as people like Byron Katie, Thich Nat Hahn, and Carl Jung.

What’s your best mistake and what did you learn from it? 

My best mistake was starting my career in Accounting and Finance. To this day I still wonder why we ask an 18-year-old to decide what they want to do with their lives, give them a degree, and expect them to be happy with that chosen career for the rest of their lives. But I wouldn’t trade my financial experience for anything. That knowledge and experience helps me speak the language of executives and to focus on high impact people related programs that make businesses more successful.

What’s your favorite part about working in the industry? What’s your least favorite part, and how would you change it?  

Currently my favorite part of working in the industry and my least favorite part are the same. The world of work has radically changed since the pandemic, and we are all charting new waters. These changes are creating new and interesting challenges and, at the same time, create a new humbling experience because so much of what has worked in the past no longer works. Where I once felt like an expert, I’m now having to bring a beginner’s mindset. I love that people are pushing the envelop about what they expect from their jobs and their organizations – from flexible schedules to more inclusive environments.  The old rules are changing and the organizations who can quickly adapt to those changes will be the most successful.

How can company leaders make HR a value within their organization?

I believe that HR leaders need to start this conversation from a different perspective. They need to learn about the needs of the business and connect the dots between people and their ability to help company leaders achieve their goals. Additionally, people related strategic initiatives need to be owned as business objectives and not HR initiatives. They need to be integrated into the organizations strategy and owned by every leader in the organization. 

Where do you see the industry heading in five years? Or are you seeing any current trends? 

Employees have more options today than they have ever had and the pandemic caused many people to take stock in what they expect from work and how it fits into their lives. The role of the talent leader will need to move even more to one of facilitator and creator. People in these roles will need to educate themselves on the changing needs and wants of the new generations coming into the workplace so they can be the voice inside the business of how to adapt. 

What are you most proud of? 

My true passion is leadership development and learning. Twice in my career I have had the honor and privilege to design and launch year-long in-depth leadership development programs for mid-level and senior leaders that focus on building both leadership skills and business acumen. Several of the graduates from these programs have moved on to become CEOs. But the most satisfying thing is the random messages that I receive from graduates letting me know what a positive impact I had on their life. My goal is to help make leaders better so that work can be better for all.

Do you have any advice for people entering the profession? 

The most important piece of advice I can give someone who wanted to enter this profession is to build out your business acumen. Learn how to read financial statements and understand the strategic objectives of the business. This knowledge will help you build a more compelling business case for any changes you’d like to make.

Is there anything else you’d like to add?

I have long had an aversion to the term “Human Resources” and while it is still widely used and understood, it harkens back to when HR leaders were focused on tactical compliance and rule following rather than creating robust cultures where businesses and people can grow together. We need to do more to elevate and professionalize this role as a key strategic lever. You can have the best strategy in the world, but that strategy must be executed by people who are clear, aligned, and accountable. Chief People and Culture officers need to always be wearing both hats and thinking about leading the way for others.

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