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Raising Capital & Strategy—In the Clouds

I can’t stand it! Every day our CEO gets excited, comes up with three or four new ideas, and wants me to make them an immediate priority. She thinks that each one is vital to our success, but she has no idea how much time or resources it takes to get even one of them done. And what do I do with the things that I’m already working on?!

Have you ever said those words or heard someone else say them? Many CEOs operate much of the time being in the clouds. But as much as a detail-focused CEO can cause the company to crash and burn, she can’t operate in the clouds all the time either.

In the Clouds

I was visiting with a friend who is a senior business executive last weekend. He recounted how he recently resigned from a start-up because the CEO was mostly in the clouds. The management team had grand plans when they started, raised over $100 million dollars in VC funding, and had gotten some large customers. But, they didn’t understand that their key customer base was churning because the CEO wasn’t aware of what was happening at a granular enough level. No matter how much my friend tried to ground him in the details that they were losing customers in their key vertical, the CEO wouldn’t listen. His mantra: “Ah, I don’t need to talk to the customers—that’s your job.”

Just like this scenario, it’s the details that will make your company successful or cause you to fail. How customers are using your product, their level of satisfaction, churn rates, reaction to price changes, and similar issues all must be understood, tracked, and reflected in your strategy. This is getting into the details.

Key Point: If you’re always in the clouds, looking at the scenery, and coming up with new ideas, it’s easy to miss what’s happening on the ground.

So, how do you know if you’re spending too much time in the clouds?

Ask yourself, are you:

  • Creative, constantly generating new ideas, and forgetting about your great ideas from yesterday?

  • Not completing work on ideas that were important when you made your last strategic plan?

  • Averse to numbers, charts, spreadsheets, and anything that may take more than ten minutes of your time?

Having one or more of the above traits isn’t a death sentence. It does mean that you may be a creative type and will need to surround yourself with detail-oriented people and work hard to listen and understand when your team is trying to pull you back to earth.


You need to spend time on the details to develop a successful strategy, raise capital, or run your business effectively. If you’re a creative type who likes to fly above the fray, then being in the details isn’t fulfilling or enjoyable. But as you spend more time in the details, you’ll become more grounded and able to generate more successful ideas and high-value options for the company to pursue.

How will you get out of the clouds to be more focused?


Are you spending too much time in the clouds? Need help getting into the details more regularly? Schedule a one-hour call with us here to find out how we can help.

Until next week!

All the best,


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