The 2 Most Important Lessons That Helped Us Overcome Challenges in 2018

Scaling / January 21, 2019 / Kristie

As a small business with a mission to empower other small businesses, we hope that by sharing our challenges and lessons learned, it will help inspire others struggling on the road to achieving your dreams.

2 lessons for overcoming challenges

Every business faces challenges. What you learn from your challenges defines you. Use those lessons to propel you forward.

Learning is a big part of our vocabulary here. It’s woven into our core values, part of our individual goals, and how we start any planning.

We’re a group of talented people who are passionate about small businesses, but we’re human and sometimes we make mistakes. While success isn’t optional, sometimes you need to fail at a few small goals so you can succeed in your overall vision.

Lesson #1:  Focus, Focus, Focus

Focus sounds simple. You just put a lot of work into something, right? The truth is that focus means saying NO, even when it’s really, really hard.

One of the difficult challenges we faced this year was the decision to delay Daylite Mail for iPhone & iPad. You’ve asked for linking emails on the go for a long time, but Apple doesn’t allow plugins for Mail on iOS. So, we decided to build that functionality right into Daylite on the iPhone & iPad. That way you can link emails to people and projects on the go as well as create follow-up tasks and schedule meetings right from your inbox. This is a major feature that requires us saying NO to a number of other potential features and projects. 

It’s always exciting to build something you have been needing for years. We had it working and to keep the feedback loop tight, there was a gradual beta roll out that increased in size slowly as we got more feedback.

The initial feedback was promising. Then, it wasn’t. We kept hearing that people loved how it worked, but it was too slow. Most stopped using Daylite Mail for iPhone & iPad after a few weeks.

We thought… just make it faster, right? Can’t be too hard.

So, we went to work making all sorts of tweaks and changes to improve the speed and performance. Still, the feedback was that it was too slow. It was clear it was a foundational problem. We’d have to go back to the drawing board. This meant severely delaying getting it out to customers. It also meant we had to continue to say NO to other features in order to get this right.

We focused on what success looked like. Success is you using it every day to help you move through your inbox and action items quicklywhile on the go. With this focus, it was clear that the right decision was to say NO to moving forward. It was a gut wrenching decision to say NO to getting it out to customers and take a big step back to go back to the drawing board. But it needed to be made.

After a lot of hard work, we’re now in the final stage of smoothing out the main issues that were hindering speed. We’re getting ready to get the ball rolling again to gradually roll out the beta to more and more people in small batches.

Lesson 2: Communicate, Share, Repeat

Getting everyone aligned requires communicating through repetition. When you’re a small team, alignment happens organically. As your head count grows, communication can break down and people end up going in different directions – not because they intentionally want to go in different ways, but because they aren’t constantly reminded of what’s most important.

To get everyone on your team moving in the same direction, you must repeat your priorities over and over again so they are top of mind.

Our biggest challenge in 2018 was making the transition to a fully Software as a Service business. Many businesses don’t survive the transition. During this transition, your up front deal size drops to a fraction of what it used to be while expenses stay the same. Making this transition was an incredible risk and required us to be very prudent and diligent about managing our cashflow.

A key part of making this transition was helping to move our customers on Daylite Self-Serve to Daylite Cloud. This posed a whole bunch of hurdles to overcome.

The sizes of databases we were seeing from customers wanting to move kept increasing.

The process of moving customers to Cloud was time consuming and difficult when dealing with customers in different time zones.

On top of that, we had all sorts of questions and misconceptions from customers that we needed to address at scale such as customers thinking Daylite Cloud was a web app or not understanding the benefits of moving to Cloud.

To keep everyone focused on helping us move our Self-Serve customers to Cloud, everyone had to be aligned on our mission. From engineering and design, to customer service and marketing.

This was achieved by repetition. Over and over again. At every monthly company-wide All Hands we repeated our top priority for the year and why it was so important. Explaining the “WHY” is critical here to getting alignment.

We repeated our priority in weekly meetings and daily huddles. We said NO to things as they came up that could have diverted our focus. If someone was tempted to start up a new initiative, someone else would ask “does this help our priority?

We created a theme to visually convey the priority and our progress each quarter. We held company-wide training sessions to make sure everyone understood what challenges we needed to overcome and what questions we needed to answer for customers to make sure people were prepared and educated.

By constantly repeating the top issues that stood in our way of helping move customers to Daylite Cloud, it helped us gradually make more and more progress each week towards our goal.

We started off only being able to move databases of 1-2 GB, then gradually larger and larger to databases over 100 GB. At first, you had to book a time and moving could take a whole day. 

Each day, little by little we kept improving the moving process so it now only takes about an hour and can be done by yourself on your own schedule.

Focus and repetition helped us reach our goal and they can help you reach yours, too. We have successfully completed our transition to 100% Software as a Service and have heard from multiple customers how impressed they were with the smooth process of moving to Cloud.


By staying focused and saying NO to things that don’t relate to our key priorities, and communicating our priorities through constant repetition, it has helped us achieve our goals in 2018. We’ll continue taking these lessons of focus and repetition with us into 2019 and are excited for the year ahead of us!

Will there be more challenges? Absolutely.

But by taking the lessons we’ve learned over the past year with us into 2019, we’re even more prepared for the year ahead of us.

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