5 Best Practices for Effective Entrepreneur Updates

At the end of the year, I’ve enjoyed reading different entrepreneur updates and communications. I always find it fascinating to learn what’s going on in a variety of businesses—what’s going well, what’s not going well, and especially where the entrepreneurs need help.

There are a variety of styles. Some entrepreneurs are better storytellers and deliver great anecdotes, while others are more matter-of-fact and like sharing metrics and KPIs. There’s no right or wrong communication style as long as it’s productive and worthwhile. The only style that is destructive is no communication. Surprisingly, many entrepreneurs still don’t share regular updates with their advisors, partners, and investors. That’s a big no-no in my book.

Now, for the entrepreneurs who do communicate regularly, which is most of them, there are a few best practices that I like to see:

1. Connect the Reader with the Mission: Why are we here? Why are we on this mailing list? What are we trying to accomplish with this startup? While it might seem obvious from the entrepreneur’s perspective, it’s important to get in the reader’s shoes and think of it from their perspective.
2. Provide Highs and Lows: Too often, entrepreneurs use their regular communication as a hype session, trying to make it sound like everything is going well across all aspects of the startup. We know from experience that that’s never the case. There are always challenges. It’s important to have the hype, excitement, and energy in the communication while also level-setting that it is hard, there are challenges, and here are some of the current challenges. Again, be real with the challenges—don’t sugarcoat them.
3. Goals and Metrics: Every entrepreneur needs a simple one-page strategic plan at a bare minimum, and the regular communication should incorporate updates on the project goals as well as the quarterly and annual metric goals. Again, they should be succinct, understandable, and focused on the highest priority items. These goals and metrics should not be lower-level or department-specific. The most common ones are big, company-wide rocks that have to get moved, as well as metrics like revenue, profitability, cash in the bank, and burn rate. The metric goals should not be more fine-grained, low-level items unless they somehow tie in at a very strategic level.
4. Consistency of Communication: Whether it’s weekly, monthly, or quarterly, the most important thing is that it’s done on a consistent basis. Too often, I see an entrepreneur get excited about providing updates, do it one or two times, and then fall off the wagon. If it’s something that the entrepreneur is excited about and committed to, great—do it weekly or monthly at a minimum. If it’s something that’s really painful for the entrepreneur to do, try to convince them of the value of regular communication and provide it at a minimum quarterly. Personally, if the entrepreneur really enjoys it, they should do it weekly, as it’s a great way to organize thoughts and priorities and reflect on what was learned the previous week. As a tool for the entrepreneur’s own development, writing and synthesizing everything that’s happened recently is a great exercise.
5. Make It Reflect a Personality: Some entrepreneurs like to focus on the product and the innovation—great, reflect that in the communication. Some entrepreneurs like to focus on energy and momentum—great, reflect that in the communication. Some entrepreneurs love the people side and characters, both in and outside their business—great, reflect that in the communication. Entrepreneur updates and communication are more fun when they reflect the voice and style of the person behind them. Don’t be afraid to make it feel and sound authentic.

Ultimately, regular entrepreneur communication helps everyone. It helps the entrepreneur get their thoughts, metrics, goals, and reflections down in one place. It helps partners, mentors, advisors, and investors stay up-to-date with both the good and the bad, as well as ways they can help and contribute to the mission. And when the journey has come to a close, it provides a diary of sorts, documenting all the craziness and effort required to build something from nothing. Every entrepreneur should write a regular communication, and the best time to start is now.