What Keeps You Up at Night? A Halloween “Treat” from BottomLine

No matter how much experience and knowledge we have as CEOs, making critical strategic decisions is not always easy.

First, there is a lot riding on our choices. Not just the success and sustainability of our companies, but also the livelihoods of the people we employ.

Second, our expertise is usually within our own industry. We can’t possibly be expert in every area required to guide and grow a company.

But the problem is not that CEOs have uncertainty at times. It’s that we tend to think that every other CEO except us has it wired.

In other words, many CEOs tend to think that they’re the only ones who are lying awake at night with a stream of questions pounding through their heads.

So, this Halloween, we thought we’d put together a little “treat” for all the business owners we know. Specifically, we’ve put together a list of 20 of the most common questions that keep CEOs up at night.

How do we know what issues and challenges are costing CEOs a good night’s sleep?

Quite simply, because these are same questions we get asked every day as strategic consultants.

Our hope is that after reading this list, you’ll be certain of at least one additional thing: That you’re not alone.

20 of the Most Common Questions that Keep CEOs up at Night

• Where should I invest capital for the highest ROI?
• Who do I need on my leadership team?
• What’s the most sustainable long-term vision for my company?
• How do I decide between multiple growth options?
• When should I expand into new markets?
• When should I add new services and/or products?
• How do I scale?
• What’s the best to-market strategy?
• How do I quickly build connections in new territories?
• What financials do I need to project?
• What assumptions should I base future decisions on?
• Are my company’s processes efficient?
• When is it time to make new hires?
• What systems do I need in place to avoid costly mistakes?
• How do I position my company for a merger, acquisition, sale, joint venture or succession?
• When, how and where should I seek equity investments?
• What key performance indicators should I benchmark against?
• Is my company protected against embezzlement?
• Where do I need to innovate?
• What gaps in knowledge must be filled in order to achieve my long-term goals?

While the above questions can clearly cause much uncertainty and second-guessing, they’re also an important sign that a company is growing – and that it’s time to take action. Which means, the most important question you can ask is likely this:

Am I going to lie awake wondering, 
or will I take the short cut and tap into existing expertise 
that’s just waiting to be leveraged?