coworkers gathered around a table in a  planning meeting


Growth  |  3 min read

Why your Offsite Planning Must be Offsite

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Clate Mask

About 13 years ago, my two partners and I were running our custom software company called Infusionsoft. Like all five-person businesses, we had our fair share of fires, challenges, deadlines, and stress. We had decided that we were going to do our planning session offsite, away from the business on a Friday and Saturday.

When the day came to leave the business on Friday and entrust our employees to hold down the fort, I felt like we couldn’t possibly leave.  My partners convinced me to leave and we all committed to shut off our phones and email so we could be fully present to the planning process. I remember stressing about different customer issues, cash concerns and other matters. But we stayed focused, for the most part, and did our planning work. We came away from that two-day annual planning with clarity for the future and confidence that we were on the right path.

Fast forward to yesterday. My team and I are leading a $100 million-plus business, dealing with our fair share of fires, challenges, deadlines, and stress. But we are committed to our planning process, and after one day, I am reminded of this powerful tool that all entrepreneurs need, but most overlook. The offsite planning exercise is critically important, especially if you’ve got at least a handful of employees.  (BTW, it’s still very important if you have a couple of employees or even if you’re a stage one solopreneur.)

In one day, we did important team building work (thank you, Patrick Lencioni and your books, “The 5 Dysfunctions of a Team” and “The Advantage”), we dug deep into a couple of key current issues for the business and we broke bread together, building our friendships and deepening our trust. We came away from the first day with more clarity and an excitement to get together today for day two of our offsite planning.

So, why is it such a big deal to get “offsite?” Because it’s only by changing the scenery and getting away from the distractions that you can immerse yourself in the issues, be present with your team, and look at issues through a different lens. When you take this approach, you come together to solve tricky problems and you build the trust you’ll need to work through problems together as a team.

SBS Idea of the Day: If you’re not already doing it, commit to an offsite at least once per quarter and avail yourself of this powerful, creative, problem-solving tool that will help you overcome obstacles and achieve success in your business.

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Infusionsoft is now Keap. That’s weird to write, but it’s also exciting.

In 2001, trying to get Infusionsoft off the ground, there were many times when I wanted to quit. I’ll never forget my wife, after two years of struggling to survive, hugging me and saying, “Keep going.”

Over the last two years, we’ve talked with thousands of small business owners to get a deeper understanding of their unique challenges in today’s market. We learned that it’s harder than ever to succeed in small business. Customers expect more. On-demand is the rule. There’s no shortage of platforms on which to complain. A failed job or two can be damaging to your business.

Keap is our signal to the world—and to ourselves—that it’s time to make it easier to succeed. We’re on a mission to simplify growth for millions of small businesses. Our new name is a nod to the tenacity of the small business owner and encompasses everything we know to be true when it comes to success: keep going, keep serving, keep growing.

Along with a new name, we’ve expanded to two products. Keap, our newest product, is smart client management software that helps service businesses progress leads to satisfied clients. Infusionsoft by Keap is powerful CRM and sales and marketing automation software for advanced business needs.

Both are designed to make it easier than ever for more small businesses to get organized so they can deliver great service and close more business.

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To your success,
Clate Mask
CEO + Co-Founder