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“Find your voice and use it; Confidence is key” with Jason Hartman & Kathy Pickering

My advice for women in business is to find your voice and use it. Confidence is key for leadership but it’s something women may struggle with in their careers. For women leaders and others in positions of power, make sure you’re empowering women who are early in their careers to share their opinions and ideas. […]

My advice for women in business is to find your voice and use it. Confidence is key for leadership but it’s something women may struggle with in their careers. For women leaders and others in positions of power, make sure you’re empowering women who are early in their careers to share their opinions and ideas. The other piece is for executives to challenge their companies to create a culture of acceptance and belonging, where everyone is encouraged to share their ideas freely. Your employees and outcomes will be stronger for it.


As a part of my series about strong female finance leaders, I had the pleasure of interviewing Kathy Pickering.

Kathy Pickering is the chief tax officer at H&R Block. In this role, Pickering leads the relationship-management strategy with the IRS and state taxing agencies and is responsible for the strategic direction and management for a team of the nation’s top experts on tax issues. She oversees the enrolled agents, CPAs and attorneys who make up The Tax Institute and provide information and analysis on the real-world implications of tax policy and tax proposals.

Pickering serves on the boards of multiple tax industry associations, including serving as chair of the Council for Electronic Revenue Communication Advancement (CERCA) and co-chair of the Identity Theft Tax Refund Fraud — Information Sharing and Analysis Center (IDTTRF-ISAC). She represents H&R Block on the Security Summit, the public-private partnership of the IRS, the states and the tax industry, and is a member of the Electronic Tax Administration Advisory Committee (ETAAC). Through these organizations, she leads the way towards improving tax administration through industry and agency collaboration.

Pickering has more than 20 years of experience in tax operations. Prior to joining H&R Block, she was in information technology and worked with Sprint PCS, Olsten Health Services, Leprino Foods and various consulting firms where she focused on implementing large scale accounting and financial systems.

Pickering speaks about taxes and tax administration policy issues to policymakers, journalists, tax policy experts and tax preparers. She has appeared in broadcast and print news from FOX News, CNN, CNBC, the New York Times, Wall Street Journal, USA TODAY, HuffPost, the Los Angeles Times and more.

Pickering received her bachelor’s degree from The Catholic University of America and became an enrolled agent in 2017.


Can you tell us the “backstory” about what brought you to the Banking/Finance field?

Ithasn’t been a linear path. I’ve been with H&R Block for 20 years but actually started my career in information technology (IT). I was a psychology major who went into IT after graduating. I then joined H&R Block in an IT role leading various functions from tax software development to e-filing operations. I transitioned from there into product management and client experience work. For the past 10 years, I’ve led The Tax Institute, the team that our president and CEO Jeff Jones fondly calls “the Navy SEALs of taxes.” The Tax Institute studies the changing tax laws to support each of H&R Block’s myriad options for preparing taxes, whether that’s supporting our network of 70,000 highly-trained tax professionals, or helping to operationalize the requirements for our tax software or virtual tax preparation services.

Taking this winding path has allowed me to broaden my skills and experience in a way that have prepared me well for my current role as chief tax officer. My career advice for people is to get exposure to different aspects of the business that can make you more valuable and knowledgeable.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

When I first became the executive director of The Tax Institute, I told my boss I was ready to take on the role as long as I didn’t have to handle the media interviews. My boss said not to worry, I wouldn’t be serving as a spokesperson. Then, as soon as I took the role, I was told I was scheduled for media training.

Now, I do dozens of interviews with top media outlets. I’ve found I enjoy talking about taxes because I get to translate tax issues into something people can understand and inspire their own financial confidence. I love being a spokesperson but it still makes me nervous every time. Communication is one of the most important leadership skills and, although it may not have been part of the original deal, I’ve learned to grow as a leader and to be comfortable being uncomfortable.

Are you working on any exciting new projects now? How do you think that will help people?

One of the things we do at H&R Block is work with the IRS to reduce fraud and advocate for taxpayers’ rights. I chair CERCA, a committee dedicated to the relationship between the IRS and the tax industry, and am a member of ETAAC, a committee dedicated to the integrity of the e-file system that more than 90 percent of taxpayers use to file their returns. This work is extremely impactful to preventing identity theft and reducing fraud in the 150 million tax returns filed yearly in the U.S.

What do you think makes your company stand out? Can you share a story?

H&R Block is guided by its purpose to provide help and inspire confidence in our clients and communities everywhere. Nobody but us thinks about taxes outside of tax season. Our experts at The Tax Institute are researching taxes year-round to create the best experience for our clients. Whether you’re seeking help in one of our 10,000 retail offices, or you’re doing your taxes yourself online or with our software products, we want our clients to have a great experience.

Last year H&R Block was the first major brand to offer upfront, transparent pricing. This is different because the industry norm is to keep consumers in the dark by completing their taxes first, then figuring out the price. Or, surprising people with hidden fees at the end. H&R Block is leading the industry to change this. This level of know your price before you begin, increased our client satisfaction scores around price for value by nine points. We look forward to continuing this level of price transparency, and will continue to develop new, convenient ways for Americans to prepare their taxes and get the best possible outcomes.

Wall Street and Finance used to be an “all-white boys club”. This has changed a lot recently. In your opinion, what caused this change?

Wall Street is a proxy for what we are seeing across the country. With more focus on diversity, inclusion and belonging, we’re seeing changes including an increase of diverse leaders. We are feeling more comfortable, finding our voices and bringing our complete, authentic selves to work.

Of course, despite the progress, we still have a lot more work to do to achieve parity. According to this report in CNBC, less than 17 percent of senior positions in investment banks are held by women.

In your opinion or experience, what three things can be done by a)individuals b)companies and/or c) society to support this movement going forward?

For many years I found myself as the only woman in the room. It could sometimes be challenging to speak up and ask the uncomfortable questions or share new strategies. It took me time to find my voice and put my ideas forth confidently. When I began doing that, I found it encouraged others to share their ideas.

My advice for women in business is to find your voice and use it. Confidence is key for leadership but it’s something women may struggle with in their careers. For women leaders and others in positions of power, make sure you’re empowering women who are early in their careers to share their opinions and ideas. The other piece is for executives to challenge their companies to create a culture of acceptance and belonging, where everyone is encouraged to share their ideas freely. Your employees and outcomes will be stronger for it.

According to this report in Fortune, nearly two-thirds of Americans can’t pass a basic test of financial literacy. In your opinion or experience what is the cause of these unfortunate numbers? If you had the power to make a change, what three things would you recommend to improve these numbers?

Building financial literacy is like running a marathon — it takes preparation, persistence and a positive attitude. In fact, H&R Block data found two thirds of Americans want to make changes to their personal finances but obstacles like fear of failure (86%), lack of confidence (88%) and finances (88%) get in the way of making changes.

  1. Preparing to run a marathon takes time. You train for a marathon over many months. Building financial literacy also starts by taking small steps that build over time and overcoming obstacles.
  2. Persistence is important because there will be times when you want to give up. However, staying focused on the goal, such paying off your debt or buying your first home, keeps you focused and motivated to stay on track.
  3. Finally, having a positive attitude because feelings about money drive many financial decisions. If you feel deprived or ashamed of your situation, it’s easier to make bad choices. Staying positive and celebrating small successes reinforces good decisions.

You are a “finance insider”. If you had to advise your adult child about five non intuitive essentials for smart investing what would you say? Can you please give a story or an example for each?

I’m passionate about money, personal finance, and of course, taxes. That said, I know it can be daunting for some. Here’s my advice for being financially savvy about your taxes:

  1. Take your employer’s money. What I mean by that is take advantage of the health insurance coverage and, if offered, the health savings account. It can lower your taxable income and put more money in your pocket.
  2. Invest in your education. There are important education credits in the tax code to know about and take advantage of, whether you’re getting your degree or investing in lifetime learning opportunities.
  3. Invest in your retirement. Maxing out your 401k as quickly as you can is a really smart thing to do. Be sure to invest in whatever retirement plan your employer offers; that pre-tax money lowers your taxable income and typically comes with a match. That’s just free money.
  4. Invest in yourself. Know your tax situation and plan for your preference. This means updating your W-4 if you have life changes or surprises at tax time. Create an emergency savings account if you don’t have one. If you do, invest that money in your family or your community. Even small amounts contributed to local programs that you’re passionate about can make a difference and create stronger connections to your community.
  5. Get the help you need. If you have a complex situation or want to make sure you’re taking advantage of all the tax benefits you may be due, don’t be afraid to get help from a qualified tax preparer.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Irely on the concept that we each need to create our own board of directors. I have a small group of trusted friends and advisors that weigh-in on aspects of life including my performance and my overall well-being. I trust them to be honest, helpful and straightforward. I’ve got an executive coach, a personal trainer, a communications expert, my boss, my husband, my BFF, my financial advisor and others. Each helps with a unique dimension in my life and together they all help me be the very best.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Igo back to my earlier advice for women in business: “Find your voice and use it.” I wouldn’t be where I am in my career today without taking this advice to heart. Learning to speak up took time and practice. As I mentioned, when I first took the position at The Tax Institute, I wasn’t planning to become a spokesperson. Now, with coaching and help from colleagues, I can say I’ve done interviews on the floor of the New York Stock Exchange. I believed in my own confidence and even lobbied for my new role of chief tax officer, so you never know where your voice can take you.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be?

Ilove the African proverb that says, “when you educate a girl, you educate a nation.” Women have often stayed on the sidelines playing a supportive role and not taking the lead. When women have confidence and support, they can do amazing things.

I found my confidence through athletics. I started running marathons and now I do triathlons. The physical challenge helped me build the self-confidence to take on new challenges at work. I want to inspire a movement that challenges women to challenge themselves and learn they are capable of so much more than they even thought possible.

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