6 Things I Learned From My First Year In a Startup

by Heather Hansson - Director of Product, Docket

Five months into my startup journey, I shared 5 Practical Skills to Bring To Your First Startup. I learned so much in such a short amount of time and wanted to share my experience with those looking to break out of the corporate world, as I did, to explore a world of new beginnings with startups. Another seven months have gone by and as I celebrate my one year anniversary at my first startup, Docket, I have grown even more in my career and behaviors. I find myself in awe of what working in this environment has given me. Here are just a few examples of how working in a lean, agile, aggressive, and exciting startup has made me see the world a little differently.

The Docket team

Look for the Wins

Every startup has a different product, service, and mission. It may seem easy to make generalizations about startup life, but it can also be easy to get caught up in the weight of wanting to do more every day. While product releases and customer contracts are significant milestones, every day has a win that can and should be celebrated. 

Track key performance indicators, follow unique internal projects, and have every team member’s anniversary on the calendar. While a small company may not have an assigned office coordinator, it’s important to create a cheerleading section within your team that makes celebrations happen every step of the way. These pockets of joy can make even the toughest days brighter.

Docket celebrates their official launch with mimosas

Be Flexible to Change Direction at Any Time

Dedicated team members often throw themselves into the heart of every project to make it right and get it done. It can be constant and even overwhelming. However, change happens daily — and sometimes even more frequently — so remaining in the same spot in our work or decisions does not necessarily benefit the company or team.

To keep the wind in our sails, sometimes we have to make the tough decision to drop what we are doing and work towards something else. In the beginning, this felt like a waste of time, energy, and effort. But in a startup, I quickly learned that every moment is an opportunity to learn, and that every effort we make is a step in the right direction — even if that step is telling us to go in another direction. Requirements, code, and messaging can be used or tweaked at any time. Nothing is wasted and everything is a learning experience.

Be Okay with Okay

The perfectionist in me is now an “okayist.” In a startup, every release, message, price, and sales pitch is a test. We release features, monitor feedback, and then we edit and release again. Emails and in-app messages are trials in what is or isn’t read and who does or does not sign up. Pricing is a methodical guess. The number of contracts dictate what changes we make. And a sales pitch to a prospect or potential investor is a test to see how well we know our product and how well we can share it with others. 

Releases may be imperfect, pricing may be too high or low, and messaging may not be eloquent but the key is to try, listen, learn, and try again. If perfection is deemed present at the moment, it too will change so we should be okay with being okay and continue to grow as a product, team, and company.

Docket's first year startup included a trip to Zoomtopia
Darin Brown, Docket CEO, and Heather Hansson at Zoomtopia

Lead with Others

It is easy in corporate culture to see the organizational charts and aspire to climb the ladders. In very large organizations, leaders can be mascots or celebrities seen at big events that we can only hope to shake hands with, receive recognition from, or snap a selfie with. 

In startup, leadership takes a different form. It is found in each contributor during day-to-day decisions in their work, through collaborative meetings, and stand ups in the hallway. While titles exist and individuals seek to grow and excel, decisions tend to be made as a team. Everyone is a part product manager, part messaging expert, part customer service rep, and part investor relationship manager. I experience leadership every day as I interact with each Docket team member, and while I may have more experience on my resume by years, I learn from even the greenest peer at every level. Being a leader in a startup requires maturity to know we need to work as a unit and inspire each other to be and give our very best.

Have Patience

This is the hardest lesson for me, in every aspect of my life. Being a hard worker with a solid work ethic, I’ve been known to anticipate rewards — from fast product releases to customer signatures to promotions. 

It’s important to know that the right rewards at the wrong time aren’t always a positive thing.  Pushing for a funding round to close may not result in the right investors, enough funds, or the best possible audience. Being anxious for a promotion, even well earned, may not be the best timing when it comes to the impact on the business or perception of reason. And hiring to fill a critical position should never be rushed for the sake of filling the seat as the right person significantly impacts the business and culture. The time will come for all things to fall into place. 

Focus on Your Path

It’s easy to watch social networks light up and get caught up in the announcements and successes others around you are having. Watching similar products or other young companies seemingly rocket to the moon is a startup fairytale that we all dream of. I’m a strong believer that we’re placed where we are for a reason. 

While observing others’ success and failure is a great learning tool for all of us, it’s important to to keep envy or jealousy at bay, using the information garnered through watching other companies launch only as a data point to help aid decisions and direction. All in all, I’ve learned to celebrate with others while also focusing on our path and enjoying our hard-earned success.


Heather Hansson is the Director of Product at Docket, a meeting-focused workspace for collaborative agenda creation, decision documentation, and action item tracking. If you want to host more productive meetings, get started with Docket today at dockethq.com/get-started.

Casted Raises $2.35M to Build the First Platform for Branded PodcastsRead More
+