CEOs of small businesses often face similar concerns, thorny problems or challenging issues that they need to deal with from day one in their leadership role. Let’s call them CEO Conundrums. A conundrum is defined as a confusing and difficult problem or question. Common CEO Conundrums include: Leading Effectively, Making Difficult Decisions, Accelerating Change and Growth Initiatives, and Getting Unbiased Coaching or Feedback.

Leading Effectively: The higher you go and the more you grow, the more impactful your leadership skills are in your company. CEOs can read a thousand books on leadership and still fail to practice habits that make leaders effective. CEOs who are SMEs (subject matter experts) on their products and services, but haven’t transitioned into being an SME on effective leadership are limiting their organizations.

Making Difficult Decisions: You may have an advisory board, financial partners, or even competitors in an industry group that offer some perspective, but at the end of the day, when you’re the CEO, the tough calls are yours to make. Whether you were founder or came in as a replacement either as an internal or external hire, you’re facing challenging decisions that won’t always be solved by consensus. Some of your decisions will be unpopular, and may even generate a backlash. Yet, you’re responsible for the company’s direction and growth.

Accelerating Change and Growth Initiatives: The wise CEO is fostering a psychologically safe culture, where all team members are included, where it’s safe to learn (and even fail) together, where diverse perspectives are welcomed, and where it’s okay and even desirable to challenge the status quo. Innovation and growth mindsets are part of your ways of doing things at your company. Yet if the CEO hasn’t experienced this kind of safety, chances are they’re sabotaging their organization by not modeling it consistently.

And the last CEO Conundrum I’d like to mention today is this – CEOs are in the unenviable position of having few or no people who can offer feedback or coaching from a neutral, unbiased position. So you’re not hearing what needs to be heard or seeing what needs to be seen.

One resource to help CEOs who are managing these and other CEO Conundrums is the CEO Mastermind Group. Connecting with others who are going through similar situations, in a confidential, safe peer mastermind group can help you unlock the leadership, decision making, change management, and feedback issues you’re facing in your job.

If you’d like to explore a membership in a CEO Mastermind Group, reach out to me at to set up a short call to learn more.