Three Greatest Leadership Challenges a CEO & Second-in-Command Face

You’ve built a successful business, have loads of customers who love your product and have hired some great people. But you’re still stuck in the weeds of the business and facing some of the greatest leadership challenges out there.

A good friend and fellow entrepreneur suggests you hire an “orchestrator” or “second-in-command”. Someone who can focus 100% of their time on the successful execution of your vision. 

Brilliant idea! You hire your orchestrator, feel confident for the first 90 days, then go home one Friday regretting ever having taken your friend’s advice.

How come?

We’ve seen this many times before. It’s not easy bringing in a new, high-level teammate who, rightly so, needs to be a strong and experienced leader. It takes guts, a firm commitment to a long-term relationship and the ability to weather some storms.

We’ve found there are three core challenges which, if you understand them upfront, will help you and your second-in-command form a successful relationship.

The three greatest leadership challenges a CEO and their orchestrator (often a second-in-command, COO, President, or deputy) face when working together are:

1. Role ambiguity
2. Trust and communication gaps
3. Differing strategic priorities

Outlined below are the reasons for these leadership challenges, the impact and the steps to remedy:

Role Ambiguity  

Reason: A CEO/owner and orchestrator often lack clearly defined roles, leading to overlap or confusion about responsibilities. Without crystal-clear expectations, both may step on each other’s toes or leave critical tasks unaddressed. For example, a CEO might focus on vision-setting, but expect the orchestrator to handle execution, while the orchestrator assumes they have authority over strategic decisions. This can cause inefficiency, frustration, or power struggles.  

Impact: Ambiguity erodes confidence and slows decision-making when employees receive conflicting directives or unclear guidance.

Remedy: Map out your expectations BEFORE you start interviewing for an orchestrator. Sell yourself on the value of the role for you and your business. Be intentional about having your expectations documented first as this will help you qualify the right candidate faster.

Trust and Communication Gaps 

Reason: A strong partnership requires trust and transparent communication, but differences in personality, style or uncommunicated expectations create friction. A CEO may hesitate to delegate fully, fearing loss of control, while the orchestrator might feel micromanaged or undervalued. Poor communication can also lead to conflicting priorities or withheld information, especially if either person prefers to avoid tough conversations.

Impact: Lack of trust undermines collaboration, leading to siloed efforts and decisions that erode the organization’s best interests.

Remedy: Establish a monthly “Alignment-at-the-Top” meeting. Just having this meeting on a regular basis will address 95% of issues that may arise. It’s a simple agenda: 

1. Check in
2. Ask each other “what’s most important to you right now?” and “what’s most bothering you right now?”
3. Build a list of answers
4. Address each item with solutions
5. Wrap it up 

Differing Strategic Priorities

Reason: A CEO often focuses on long-term vision, external relationships, and stakeholder management, while the orchestrator typically prioritizes operational efficiency and internal execution. These differing views can lead to conflict on what matters mos t— e.g., the CEO pushing for rapid expansion while the orchestrator emphasizes stabilizing current operations. Without alignment, they pull the organization in conflicting directions.

Impact: Conflicting priorities confuse employees, dilute resources, and hinder the company’s ability to achieve goals.

Remedy: Build your strategic plan together. Book a full-day (4-6 hours) meeting once per quarter in which the two of you celebrate wins, distinguish lessons learned, define core priorities for the next quarter, solve key issues and leave clear, confident and aligned on what matters most for the next 90 days. 

Conclusion

These three greatest leadership challenges are rooted in the dynamics of shared leadership and can be mitigated through clear role definition, regular communication, and aligned goal-setting. Be overly intentional about setting up this relationship for success early and often so you avoid the costly implications of an unhealthy relationship.

You want solutions. Our goal is to help you get aligned and reap positive organizational results, like our client Kevin Odle, Managing Partner for Work Rehabilitation Specialists: 

“Preston has become an indispensable part of our Executive Team. More than anything, he has instilled the discipline of tremendous focus. Through this journey, we shrunk our leadership team and learned to play a bigger game while reducing the number of initiatives we sign up for. The result: organizational alignment, greater harmony, and revenue growth.” - Kevin Odle, Work Rehabilitation Specialists

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Preston True

Preston True is the founder of Get TPA Fit, a rapidly growing business coaching and value-building firm. Based in Detroit, Michigan, TPA has worked with hundreds of entrepreneurs and leadership teams on day-to-day problem solving, business culture and long range vision, so they ultimately learn how to delete chaos, earn more and build value.

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