Ceilings Abound: How to Break Through



“You started your business with passion, purpose and a commitment to make a difference. Look what you've built. Congratulations!”

That’s a congratulatory comment I got from a friend (many years ago), in recognition of having built from scratch a network of successful companies. But what my friend didn’t see were the scars on my head from hitting more ceilings than I can remember.


Hitting ceilings while building a business is inevitable — and the ability to scale, employ the best people, work with the right clients and be profitable are all dependent on breaking through them.


The Problem with Ceilings


Failing businesses hit rock bottom because they can’t break through ceilings. On the other hand, successful businesses hit ceilings frequently. And they hit them in the following ways:


Across the organization – through growth, market shifts, product viability, cash flow

At the departmental level – because of wrong people, poor management, inconsistent delivery

At the individual level – due to skill set, time management, energy & well-being


Ceilings are born of complexity and we create complexity in many

different flavors:

  • We confuse complexity with value

  • We believe simple is “dumb”

  • We define “smart” as complex thinking or demonstration

  • Our people often make things complex because it’s easier

  • to avoid accountability amidst ambiguity and confusion

Be honest with yourself — you’ve been in endless meetings where people discussed the hell out of issues and didn’t solve a thing. That’s a team reveling in ambiguity and that’s complexity. When it takes hold in an organization, you’ve hit the ceiling.


Let’s start breaking through your ceilings now.



There are five skills leaders must master to break through ceilings. They are the antidote to complexity.


1. Simplify: Less is more.

Your business — and the number of people — have grown. You’ve hired many who are similar to you in their entrepreneurial thinking, but it likely means there are far more ideas than execution. There’s no lack of vision, but there are at least 30 versions of vision in your head.

You must:

  • Simplify your vision so everyone can see it clearly

  • Get agreement and commitment from your team on one unified vision and plan


2. Delegate: Let go of the vine.

Bootstrapping entrepreneurs get really good at too many things in their businesses. You’ve worn many hats; some you love, some not so much. But if you continue to wear all the hats as your business grows, you’ll create an impenetrable ceiling.

You must:

  • Avoid any tasks which you can pay someone less than you’re currently paying yourself to accomplish

  • Demote any tasks that can only be done by you (limit of 2), to one specific time during the week

  • Delete any task you can simply stop doing without the world taking any notice


3. Predict: Your future depends on better forecasts.

Do what you say you’ll do. Get everyone on the same page with:

  • Highest priorities: Invest effort and resources to the vital few, not the trivial many

  • Smartest predictors: Define 5-10 leading indicator metrics to track weekly that give you a pulse on the health of your company

  • Embrace accountability: Coach your team to get really good at delivering what they need to


4. Systemize: Make hamburgers, fries and milkshakes the exact same way, every time.

Imagine how much waste exists when your teammates do the same things differently. There’s no way to measure if it’s the best way or worse, how would you train a new person? You must:

  • Define and document the small number of core processes needed to make your business run (Hint: it’s about five)

  • Train everyone on those documented processes so you experience both consistency and speed of results.


5. Structure: Porous foundations make for a toppled house.

You hired some really good people, but they’re stepping on toes and crowding swim lanes. This happens when we organize our companies based on who we have (people) rather than what we need (function). You must:

  • Design a functional blueprint of what activities (seats) your business must have to succeed over the next year

  • Determine which person is the right fit for which seat

  • Take a “structure first, people second” approach to designing your

  • operational structure


Mastering these five skills is a never-ending journey, but once started, progress is immediate and continuous.