How We Communicate with Entrepreneurs to Optimize Their Time and Get What We Need

Posted by Catherine Jelinek on June 29, 2016

At Junto, we communicate with entrepreneurs daily: conducting program sessions, sending meeting reminders, publishing a weekly update and calendar, sharing interesting opportunities, and discussing goals and challenges as their companies grow.

With every new cohort, we try to improve our communications so that the participating leaders need to do little more than have the sessions on their calendar, prepare their pre-work, and just show up. After all, they’re investing 8-16 hours a month in personal and professional development on top of the countless hours they’re working to build their companies.

Below are a few things we do to help communicate more effectively with these busy people to optimize their schedules and productivity.

Pithy Communication

In the early days of Junto, Raman Chadha trained me in how to write pithy emails. It sounds easy but a truly clear, detailed, and concise email is tough to craft.

For the amount of time we engage and communicate with the Apprentices in our program, and the number of emails we send out, it’s become vital to:

  • stick to the basics
  • start with the vital information
  • use brief bullet points/numbering to add further detail; and
  • always ask a question when we need a response rather than a passive phrase like “Let me know…”.

By using this formula, we try to maximize the chance that they'll open the email, read it, and respond, if necessary. 


Over-Communicate, Regularly

For entrepreneurs, the amount of people, projects, tasks and emails begging for their attention is innumerable. It can be hard to get a hold of them for a much-needed response.

At Junto, we believe in empathizing with our Apprentices and not making assumptions. Even when I can see they have accepted a calendar invite for a certain meeting, event, or program session, my experience is to not assume anything among all the other things on their mind.

We believe in sending several reminders, confirming via email and calendar invite, and reiterating time, place, date and to-do items with every communication.

Highly Valued Time

No matter how much an entrepreneur is paying him/herself, the most valuable thing is their time. There is never enough, and that rarely changes.

Our wonderful Apprentices spend 8-16 hours a month with us so it is paramount we optimize the time they spend at Junto. We believe they should have the opportunity to be fully present in the learning sessions they’re engaged in.

We ask that their devices be turned over and closed so they can avoid distractions. We take copious notes that are a near-transcription in all sessions. We try to schedule and reschedule meetings in person. And we take on every administrative burden we can for them: setting and distributing agendas, scheduling Mentor sessions, distributing follow-up materials to Mentors, etc. All of this is so they can be - and remain - engaged in the conversations: listening, processing, questioning, and sharing.


Entrepreneurs make this world go round. They create, invent, disrupt and provide livelihoods for those they employ and inspire. Their time, attention and energy are precious. And at Junto, we believe in doing all we can to run a program that empathizes with the in-demand lives they lead and provides an escape for present and engaged learning.

If you know a growth-stage company in Chicago that would find this interesting, please share this blog post with them or recommend them for our next cohort, scheduled to begin this fall.

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