Struggling CEOs' Top 3 Challenges, Explained by an Executive Coach

Struggling CEOs’ Top 3 Challenges, Explained by an Executive Coach

Ask any CEO to complete the sentence, “Being CEO is _______.” You won’t hear anyone say the word “easy.” They’ll most likely say that being CEO is hard, lonely, or stressful – the list of negative adjectives goes on.

For many leaders, the weight of responsibility can be overwhelming. Left unchecked, burnout will eventually set in, and our mental and physical health can even be compromised. But I’m here to tell you it doesn’t have to be this way and it shouldn’t happen.

A good deal of leadership is a daily struggle for survival. Many of us have significant stressors or have our overwhelming moments – but we rarely admit it.

It’s not easy to carry the weight of the company and all our employees on our shoulders. There’s a reason why they say it’s lonely at the top. It takes its toll but, at the end of the day, the battle scars we earn will make us better leaders.

How do leaders make it through? How do they survive on a daily basis? The struggle is as real as it gets, but there are a few safe havens from the chaos.

Organizations like YPO (Young Presidents’ Organization) and Vistage® Worldwide are two great examples of peer-to-peer networks designed to provide refuge for CEOs. Another resource, which has been a lifesaver for me and countless other CEOs — is an executive coach.

An executive coach can be many things to many people. Some of us consider executive coaches as our business consultant, teacher, mentor, big brother or sister, and even marriage counselors! For many resilient, growth-minded CEOs and entrepreneurs, executive coaching is considered a basic need. As basic as water or oxygen.

Jerry Swain, Partner at CEO Coaching International

Jerry Swain – Partner, CEO Coaching International


No one knows this better than Jerry Swain, a highly recognized and accomplished CEO and Entrepreneur – and a partner at CEO Coaching International, a world-class global leadership consultancy for entrepreneurs and C-level executives.

Jerry coaches talented executives of emerging companies and facilitates many of their annual planning meetings. He has also been on the other side of the table, having worked with coaches who transformed how he views leadership earlier in his career.

Jerry says that his clients think of him as more than a coach, even a confidant. For example, many of them call him when something really good happens or when their kids do something funny.

As an executive coach and confidant, “you are part of the short list of people they call to share enthusiasm and excitement with.”

For me, this is one of the spoils of coaching. But coaches aren’t just there to share in times of triumph. More importantly, they are the ones you call in times of defeat, or to avoid defeat!

During our discussion, I asked Jerry for the top 3 challenges he consistently sees from his struggling entrepreneurial clients:

1. Being Self-Aware

As Jerry puts it, there’s wartime and peacetime in any business, and he makes sure to be there on a consistent basis.

“I’ve realized that there is a theme in working with entrepreneurs. There are emotional triggers which can affect many things and it’s especially heightened when the stomach starts churning during times of stress.”

According to Jerry, an executive’s lack of self- awareness is the most challenging thing to address. This is important because the biggest motivators in life are based in either fear or love.

When tackling their role, most executives start with love but fear often sets in. And when their confidence decreases, executives “find themselves in a funk and can become very doubtful of themselves.”

In his role as a coach, the key for him is to know where these feelings are coming from. He’s been in their shoes before, so he understands the emotions and can provide direction toward a logical outcome. Because many aren’t aware of what’s causing their reaction.

Jerry’s approach is to help them uncover the root cause and support them by asking probing questions and instilling confidence.

As an entrepreneur earlier in his career, he found himself in a situation where he asked the person looking back at him in the mirror, “What the hell am I doing?”

Thankfully, Marvin (his executive coach) was there for him and was able to relate, because Marvin had been there himself! Marvin showed Jerry compassion, and the trusted bond between them was key to Marvin serving as Jerry’s confidant.

2. Planning

Thanks to executive coaches and mentors like Marvin, Jerry learned that executives need someone who understands their role and what they’re going through.

It takes someone who has been there before to truly know how and what they’re feeling. Interestingly – this confidant seems to be most helpful to me in situations I didn’t plan for. I would say it’s unfair to call it a lack of planning, but some of you skeptics out there (including my wife) might disagree.

For the most part, I think most executives appreciate the power of planning. However, Jerry believes there’s a prevalence of ‘under planning’ by most leaders – especially entrepreneurs and leaders of lower middle-market companies.

By and large, when you’re struggling or stressed out, it’s easy to lose focus on your long- term goals. We tend to focus on the things we need to do to get through the day.

We’ll worry about tomorrow when it comes. But procrastination is not a strategy and it will only lead us to more struggles. Taking a step back on a regular basis and planning for the future is worth the effort.

Sure, you can’t plan for everything and planning takes time. But you’ll usually come out with some ‘aha’ moments, and the time you spend today should reduce the time you spend fighting fires in the future.

Planning is so important, and advisors and executive coaches like Jerry are vital to helping executives think strategically and view their situation objectively.

3. Talent Management

In today’s talent market especially, entrepreneurs are losing sleep over how to attract, hire and retain a great team. And maybe even how to justify the investment it takes to have a great team.

Building a dream team is a major challenge, from the hiring process, to performance management, to retention – and it’s even more exacerbated in today’s business environment.

We’re big fans of developing a strategic talent plan. When you have a well thought out talent strategy that aligns with your business strategy, you can (and should) build a talent roadmap for the foreseeable future.

And when you have 6 to 12 months to make a hire, you’ll definitely be able to hire better than you can when you hire reactively. Ultimately, you will be well on your way to building the dream teams you aspire to build.

Talent may be just one factor in the CEO stress fest, but it’s a big one and we know how to solve it. If you’re going to take back your sanity, you’ll have to face your challenges head-on. Your talent plan is a great place to start.

Having an executive coach with a relevant background and skills, like Jerry and his partners at CEO Coaching International, is invaluable to the process. They appreciate the circumstances of the executives they coach and can offer unique insights.

A good coach can also share their personal experiences of what worked for them and what didn’t, helping the leader gain clarity on next steps to take.

There’s no doubt that an executive coach is necessary to overcome the top 3 challenges of struggling CEOs. For effective coaching to happen, it’s crucial that the coach helps the CEO get to know themselves better.

Executive coaching’s real value isn’t in solving their problems for them, it’s asking the right questions and enabling them to solve it themselves.



Jerry Swain, Partner at CEO Coaching International

Jerry Swain is a highly recognized, accomplished CEO and Entrepreneur with over 20 years of experience in executive leadership, planning, strategy, and business operations. His leadership is unique with his ability to blend his success in corporate leadership with his success in his entrepreneurial grit and drive. He started coaching for CEO Coaching International in 2018 and, because of his entrepreneurial experience, he has been one of the most sought-after coaches in the organization.


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