As a business grows, its leaders face new challenges, often in strategy, organizational development, and values and culture. They may be faced with complicated decisions regarding capital, partnerships or corporate structure. In November, we hosted our Fall Leadership Retreat where Trajectify coaches were joined by CEOs and business owners from a variety of industries. In focused, mastermind-style discussions, each leader took turns sharing business challenges they are facing. The group got a chance to provide feedback and offer outside-in perspectives to their peers.

Here are challenges that some of the CEOs presented. If you are a leader, entrepreneur, or business owner, we know these will hit home for you, too. We share these so that you may know you’re not alone, or to be aware of what might be lurking around the corner.

As a Founder, I seem to be stuck in operations.

The CEO of a Marketing company asked for outside-in perspective to challenge their thinking. They have plans to grow their business over the next few years and is unsure of what challenges to expect to face. Their company has three teams for marketing, design and development, yet their three person leadership team is the biggest limitation in the company’s availability to take on additional work.
One of the leaders is a CEO of a Technology Consulting company whose teams are self-sufficient, yet without any “upper management.” The CEO is feeling very capped and trying to get to the next level, but not sure what that is yet. They are unsure if they want to bring on a business partner, hire multiple managers horizontally, or vertically bring on a marketing or sales team to offload the CEO.
The CEO of an Analytics company shared that the technology and methodology their company uses is unique to the industry. Their company currently does very little marketing and has been growing by word of mouth. They want to be able to better communicate what the business does and to expand the thought leadership role of the company in its market. Specifically, they’d like to take themselves out of the day-to-day so they can focus on selling.

I cannot figure out the right time to scale operations given it requires finding talent, building processes, and financial investment.

The CEO from a Staffing company shared with us that they are ready to scale their business, however they are struggling with several challenges to growth. They are afraid of growing too big too fast and losing control of the process and the quality of candidate that the company employs. They want to hire team to help with the workload, as they are taking on too many different roles. However, they are not sure how to find the perfect hires that will do everything the right way and preserve the quality that the company is known for.
The CEO of a Software company shared that they want to scale their business but the company is limited on how much work the teams are able to do. They sought insights on how to expand given the current limitations of their team.

I am unsure if the current Leadership team will scale with the company.

One of the CEOs wanted to insight in dealing with a business culture that has become segmented due to a lack of unity in the leadership team. The business is a partnership where the co-owners might not share a common company vision given differences in their personal visions.

I don’t know if growth through M&A is a strategy or distraction.

The CEO of a Software Development firm has been approached to buy their company. The opportunity seems too good to pass up. They’ve been in talks for several months and believe this would be a good move for the company. They personally have built and run the company since its inception. As a part of the acquisition, they would continue to work within the company and have control over internal operations, though would no longer be the CEO. They are not sure how to make the decision whether to sell the company.

The good news is that every challenge can be overcome. Stay tuned. Over the coming weeks, we’ll share some of the feedback and insights to these challenges from the retreat.