Women Of The C-Suite: Jennifer Mackin of Oliver Group On The Five Things You Need To Succeed As A Senior Executive

Candice Georgiadis
Authority Magazine
Published in
14 min readDec 3, 2020


Keep the balance in mind. There is much more to life than our work lives. There were many weeks where I didn’t focus enough on my family or friends and I wish I could get those weeks back.

As a part of our series about strong women leaders, I had the pleasure of interviewing Jennifer Mackin.

Jennifer Mackin (www.jennifermackin.com) is a ForbesBook author of Leaders Deserve Better: A Leadership Development Revolution, and a leader of two consulting firms — CEO of Oliver Group, Inc. and President and Partner of Leadership Pipeline Institute US. As an author and speaker with over 25 years of consulting experience, she is a recognized leadership development influencer, having worked with CEOs, human resources managers, leadership development leaders, entrepreneurs, and other senior leaders in all industries. She earned her BS in marketing from Indiana University and her MBA from Owen School of Management at Vanderbilt University.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I grew up in a family with an entrepreneurial spirit, with parents that chose to switch careers, mid-career, to start a new business. I was deeply involved, learning firsthand, as a high schooler, about what it takes to build a business — especially the challenges of the start-up phase. Even without experience my parents let me stay involved, sitting in on meetings, helping answer the phone, and typing letters. The dinner table business conversations were always interesting to me and provided an early education before the start of my formal education.

After college, I accepted roles in the airline industry and later worked for a large pharmaceutical firm, all of which prepared me to come back to the family business. I learned from those experiences that I love problem-solving, getting in the middle of challenging situations, connecting dots and making relationships that move ideas forward. Those experiences, and the insights they generated, have helped me lead my own business in positive directions.

Can you share the most interesting story that happened to you since you began leading your company?

There have been so many interesting and impactful stories gathered from my career helping clients develop their businesses and achieve success. It’s been exciting to hop on a client’s jet to talk to the leadership team. Or to attend the Kentucky Derby horse race festivities as a guest of one of the world’s leading spirits distillers.

But, in terms of impact, there was one particular client that taught me the most about this profession.This company was growing by leaps and bounds and they asked me and my colleague to put together suggestions to assist them in every facet of their growth. After working with them for 18 months, the president was able to credit part of their success — including tripling in size in less than 5 years — to their partnership with us. We were able to align their leaders around their strategic goals; prepare their leaders

to be ready for leading a much larger company; and help them hire the hundreds of people necessary to realize their vision.This experience confirmed for me the impact of our work and helped me to evangelize the range of assistance we can provide.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I don’t make mistakes. Ha, ha. Yea, right. The funniest situations always have something to do with me tripping and falling or spilling something on a white shirt.

One mistake in particular happened in front of many key community leaders. I was invited to join a high-powered chamber meeting where there were a lot of important community leaders. As you can imagine, I dressed for success! I was in a sharp business suit and high heels. As I was walking toward someone with my hand out to introduce myself, my heel caught on the carpet in an awkward way and I found

myself on the ground before I knew what happened. I was lucky that I didn’t hit the corner of the table in front of me, but I certainly hit my ego on the way down! I participated in that meeting and was able to laugh about the whole incident later. It wasn’t exactly the perfect first impression, but they didn’t forget me.

From this, and similar incidents, I have learned that I don’t need to try and impress people with the way I dress or how I look. When I’m more comfortable with myself, relationships are easier. I can’t say that I still don’t trip or spill, but at least I’m genuine when I do!

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?

My father will always be my strongest mentor, as he shaped my sense of self-confidence, work ethic and business acumen. He believed I could accomplish anything I set my sights on. He and I worked together for nearly 12 years before he passed away, and I still hear his wisdom when I need it most.

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high-stakes meeting, talk, or decision? Can you share a story or some examples?

I have at least two to three high-stress or high-stakes meetings scheduled per week, and it is crucially important that I am prepared for each one. Each week, I take the time to remind myself of what my goals are overall — not just for the week, but for the year as well. When it comes to high-stakes meetings, I’m a planner and often prepare ad nauseum to ensure my success. I give myself time to connect the dots between my goals and these meetings so that I’m best able to identify the important criteria for decision-making. Like a jigsaw puzzle, every piece must fit to help me align my goals and values to my end game.

I was invited to be a speaker for a significant group of CEOs on a topic I hadn’t spoken about, at least I hadn’t spoken about it in a large setting. My topic was “succession planning,” and my message to these CEOs included the proposition that the problem with a well-executed succession often resides with them. Of course, they can also be the solution. If CEOs aren’t in the center of driving the discussion around who will lead their organization into the future, their planning efforts won’t provide the necessary leader readiness. I wasn’t sure how they would initially take my message, but I knew it was an important one for them to hear.

I did a lot of preparation, thinking first about the audience takeaways and then envisioning the dialogue around this important topic. With any difficult conversation I often try to think about the audience point of view and run it by a trusted colleague.

As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

I have worked with hundreds of companies’ leadership teams, and the majority are still far less diverse than these leadership teams, or our society more generally, would desire. Most CEOs and their direct reports know that diverse leadership teams have much higher earnings results. They far outperform less diverse alternatives. In addition, they know diverse companies can serve their employees and their customers more successfully through their facility with different approaches.

I have seen companies attempt to create a culture of equality and inclusion such that they don’t just fix the problem at the executive team level, but also have a queue of rising, diverse leaders and an environment where all employees feel valued and important. It needs to be an environment where they have equal opportunity for building a meaningful career. That is how you become an employer of choice. If each company does their part, the United States will be in a different position.

As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.

I wish I had a societal answer. I don’t know if anyone recognizes all of the steps that will lead to an inclusive, representative and equitable society. What I’m heartened by is being surrounded by friends and colleagues who want to do their part in creating that environment in their communities. One by one, moving each of our communities toward a culture where everyone can thrive is how to seek change. It is about learning, engaging and trying to move the needle.

For example, in learning more about the lack of equity-building opportunities for African Americans in my hometown, Louisville, Ky., my husband and I are working with various organizations to redevelop an industrial building we own, in partnership with community organizations and local businesses, and use it as a vehicle to design an equity structure that allows tenants to be true partners and build wealth as part of that redevelopment.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

A CEO’s first and primary job is to guide the strategic-planning process and ensure its successful execution. They help integrate individual functional plans into a collective team plan that garners excitement, generating an outcome where their direct reports work together in a way that benefits the whole organization. They both set and exhibit the key principles that will build the right environment and culture and, from this, help establish principles that guide key decision-making.

CEOs are the drivers of all key initiatives, especially around development of their key resource: their people. CEOs are responsible to ensure the company has people throughout the business ready to take on different, advanced roles as they move along in their career path. When CEOs focus on people, they set the organization up for long-term success.

What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?

Myth #1: CEOs have all the answers.

I see that people look to CEOs as the “all-knowing” source of answers. I have had several CEOs say they don’t know if they are performing their role correctly, guiding the ship in the right direction or building the right teams. They don’t need to have the answers! They need to be able to guide their teams to the best solutions at each critical moment, knowing that the solution can change as circumstances change.

Myth #2: CEOs have glamorous, easy lives.

The CEOs I have met have gotten to their role for many reasons, including by being smart, working harder and longer than most, and being strong influencers in their space. Many have started with very little wealth and influence, and they rarely have easy lives in pursuit of their own — and their organization’s — success.

Myth #3: CEOs have all of their shit together.

I haven’t met one CEO yet that has a life where they feel it is all just “humming along.” As with any of us, each of them aspires to be healthy, to sleep well, exercise regularly, and eat right. Unfortunately, I don’t know many who reach all of those goals once they are CEO. Instead, I have found many of them to suffer from poor family relationships and the sacrifice of their personal interests in order to achieve success in their CEO role.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

Once women assume top executive positions, there are often less problems to navigate than those they combatted in order to achieve their position. That battle often furnishes them with earned respect. Having said that, women do face unique challenges, in large part because of the small percentage of women in these positions. Only 21% of the C-Suite is made up of women, and they often face more scrutiny than their male colleagues as a result. With fewer women present, the ones that are in the C-Suite are often required to demonstrate more tangible results.

Women often perform at a higher level than men because of a need to prove themselves or show that they aren’t just the “token female.” A female executive’s professional decisions are affected by personal circumstances at a higher rate than men. I think this is a challenge, but also what contributes to making us fantastic at our jobs. There is a perception that women can’t handle the pressure of these top jobs.

When a woman comes across as “strong,” it is often perceived negatively. And there is a societal norm that men are not as responsible for the family or household needs that arise daily. At a higher rate than men, women must carve out a path to having both a full career and taking care of a family at the same time — an underappreciated reality that often carries the additional stigma of making a woman choose between an outmoded sense of femininity and the modern demands of being the boss.

What is the most striking difference between your actual job and how you thought the job would be?

I had the opportunity to study and support CEOs for many years before I became CEO of my company. I coached many and guided them to best lead their teams. With that, I had better visibility into the actual job than most who become CEO. I didn’t realize the fun I would have developing the organization into the company I envisioned by supporting our employees and clients. My role is more about guiding other

leaders and building their abilities than being responsible for any day-to-day operations.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive, and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

Not everyone is cut out to be an executive, and not everyone wants that role for themselves in their careers. Those that make the most successful executives have a passion for developing people and seeing others succeed, as well as possessing a strong passion for their business. This combination allows them to build enthusiasm among their direct reports and the rest of the organization. It is important that employees believe in and support their executives. Additionally, I think it would be difficult to be an executive if you don’t handle pressure well. Executives are often in the line of fire where decisions have weighty consequences and can affect so many lives. Risk-taking is something that most executives tolerate, if not enjoy.

What advice would you give to other women leaders to help their team to thrive?

Teams get the best results when each team member brings different characteristics and viewpoints to the table. To avoid “group think,” make sure all individuals are heard and have a unique role to play that takes advantage of their gifts. Also, encourage your team to share information about their personal lives so that you can help each other when there is a need. If one team member is struggling, others can pick up the

ball. That is one of the main reasons to work collaboratively.

How have you used your success to make the world a better place?

There is always more to be done and I have learned that I can only make a small ripple effect if I, alone, give just my resources to improve our world. That said, my perspective is that those with even a small amount of success have a responsibility to give back to others who aren’t as fortunate. Perhaps more importantly than my individual effort, as CEO I have been able to enable our employees to all make a difference in the community by giving extra days off to volunteer or give their consulting time to a non-

profit. I encourage all team members to give time to causes important to them. Using some energy just to think about how we can make the world a better place will move the dial.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

1. You will disappoint someone every day because you can’t possibly return every call or reply to every request.

2. Be authentic and don’t try to be too formal. I grew up where it was important to “look the part,” which can come across as fake. I think we all choose to be around others that are comfortable in their own skin.

3. Listen more than talk. Hearing other ideas will lead to a better solution or decision.

4. Saying no is critical. Especially early in my career, I would say yes to most requests. Now, I make sure that I say no to appeals that don’t fit with my interests or goals.

5. Keep the balance in mind. There is much more to life than our work lives. There were many weeks where I didn’t focus enough on my family or friends and I wish I could get those weeks back.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

I observe that each medium to large city has its own non-profit organizations, with volunteers working hard to support the cause, whether it be helping with food shortage, housing challenges, or other serious needs in the community. Most of these non-profits have a passionate founder, a dedicated board, and a staff of workers and volunteers who support the mission and the people who depend on them. But I see many inefficiencies. I believe these organizations could combine and be even more impactful. Instead of four organizations feeding the hungry, with four buildings, four CEOs and four accounting departments, let’s have one where all fundraising and volunteer energy is funneled under one umbrella.

Can you please give us your favorite “life lesson” quote? Can you share how that was relevant to you in your life?

“We have never arrived. We are in a constant state of becoming.” I see myself on a never-ending learning journey and I often put myself in new situations, with new people. Recently, by writing my first book, Leaders Deserve Better, A Leadership Development Revolution, I was in unfamiliar situations every day for a year. I hadn’t shaken up my day-to-day focus in a while and it was long overdue! Changing my focus at work, especially during the pandemic, just made life extra crazy. “Never a dull moment,” my dad would say!

We are very blessed that some very prominent names in business, VC funding, sports and entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I would love to have breakfast or lunch with Michelle Obama. She is someone I greatly admire for her mix of proactivity, thoughtfulness and grace in so many difficult situations and times of opportunity.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.



Candice Georgiadis
Authority Magazine

Candice Georgiadis is an active mother of three as well as a designer, founder, social media expert, and philanthropist.