How the best entrepreneurs build momentum

Voracious reader. Curious observer. Determined experimenter. Constant thinker. Driven achiever.

As an entrepreneur, learning is a strength baked into your DNA. It fuels your sense of possibility.

Coming up with reasonable — and often brilliant — business solutions is rarely an issue for founders.

So why does your team struggle despite your problem solving skills and all that learning? Poor hiring decisions, slow progress, low engagement, instability. Things seem to be getting harder as you grow. The good times aren’t rolling as fast as they once did… or as you think they should now.

Here’s the thing. Your strengths come with a shadow — a dark side. Until you see it, that shadow holds you and your team back. It keeps you exhausted. Frustrated. Unable to achieve sustained forward momentum. As your business and team grows, that shadow becomes your nemesis.

Confusion is the dark side

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Your team needs a certain amount of predictability. When they don’t have it, they spin their wheels. Rather than focusing on incremental improvements, they’re busy trying to interpret your latest brilliant plan.

For you, every problem provides a new challenge. It’s an opportunity to test out your latest thinking. Newer is better. For them, every new process, meeting agenda, and set of expectations brings confusion, uncertainty.

The best entrepreneurs understand this. They follow five simple habits that feed their desire for progress and meet their team’s need for predictability.

Ritualize it!

The “it” is anything the team should be doing consistently. A strategy conversation. Providing quotes to clients. Hiring. Celebrating a big sale. Think of “it” as a mini checklist of to-dos — a list of team commitments. Rather than seeking perfection, start with good enough for now. Ritualizing “good enough” always outperforms a confused team searching for perfection.

Here are some examples from inside my clients’ companies:

When a software developer “breaks the build”, he or she needs to buy donuts for everyone on their team.

EVERY Tuesday and Thursday at 11:07 am a company-wide meeting begins with good news stories.

Four times each year, a preset group meets to review sales compensation payments.

At 4:30 pm on the last Thursday of every month the company hosts internal TED-style talks.

As the final step in the company’s onboarding process, each new joiner has a debrief with the CEO.

Steven Handel, author at The Emotion Machine, suggests the following as characteristics of rituals.


…are symbolic and meaningful (created with purpose)

….are internally motivated (and not an attempt to replicate something better suited elsewhere)

….require full engagement (be all in or don’t do it at all)

….are anchored in celebration (celebrate success, learning, growth, failure, innovation)

….tell a story (the whole thing needs to hang together)

….bring a sense of belonging (everyone who is part of the ritual has a voice in its creation and evolution)

….focus on the performance of tasks (something needs to get done)

One owner

Every ritual needs an owner. One owner. That person, sometimes referred to as the host or custodian of the ritual, keeps the ritual alive. There are two ways I’ve seen ownership handled best.

The first is having a single, consistent owner who is passionate about the ritual and sees value in it.

The second is rotating ownership, where ownership responsibilities are clearly documented. Rotational ownership of a recurring meeting or mentorship of new team members are examples.

In either case, ownership does not need to include content. The owner of a quarterly strategy meeting doesn’t need to prepare the meeting content. Their role is in making sure the meeting happens with necessary pre-work circulated.

As a general rule, busy entrepreneurs and CEOs make for poor ritual owners. Its best to outsource this role to the team when possible.

Have a trigger and a target

Every ritual needs a trigger. Without one, time passes and so does the ritual. The best triggers include personal commitments to others. It’s just too easy for us to ignore triggers when no one else knows or cares about them.

Each ritual also needs a declared target. When does it need to be completed? A good example of a failed target is a company strategy meeting that gets pushed out, again and again and again. Rituals fall apart when they are not prioritized as important. When setting up your ritual, agree to when moves or cancellations are okay.

Here are the triggers and targets for the examples I shared above [targets are in square brackets].

Software developers bring donuts when the build breaks… you can’t hide a broken build. [Same day, always]

The company-wide meeting is on everyone’s calendar every week, forever. It’s designed to run independent of any single person’s attendance. [Same day always unless the entire team is unavailable]

Sales compensation payment review meetings get scheduled by the company’s sales analyst. He needs to meet a payroll deadline. [Flexible within first 7 days of each new quarter]

TED-style talks are pre-scheduled, standing meetings owned by one individual. [As scheduled monthly except December]

Preparing to onboard of every new team member follows a preset checklist. [Completed before new hire’s first day]

Put it on (virtual) paper

The goal with rituals is consistency over time. Documenting the steps, the flow and the responsibilities ensures things don’t get forgotten. A simple checklist can do the job. It works for airline pilots and surgeons, and can work here too.

For example, having a simple standing agenda brings consistency to meetings. It ensures the little things don’t get missed like assigning a host for the next meeting.

Improve, continuously

Continuous improvement should be built into the ritual. It’s needs to be a core element rather than something set off to the side. It’s building on the foundation you’ve created rather than repeatedly starting from scratch. Retrospectives using a simple start, stop, continue exercise can take less than 5 minutes.

Perhaps the first meeting of a quarter includes a mini-retrospective. The last step in a process flow can be a quick review and update. It’s here where you can bring all your latest learning, tweaking the “good enough” ritual to be even better.

It’s true that sometimes step changes are needed and incremental change won’t do. The best entrepreneurs limit step changes to a critical few areas. They prefer instead to build a strong, lasting and predicable flow to their business.

I blog to help Founder CEOs on their journey from kitchen table to 200 employees. My latest book, Reinventing Scale-Ups can be found here. Be the first to receive new articles by signing up for my newsletter here.