10 Simple Lessons in Automation from a Technologist

Shawn Clybor, Ph.D.
6 min readMay 22, 2024


Image generated using Stable Diffusion 1.5 on May 22, 2024.

Hey there!

In my role as a CTO/CIO, I led pivotal initiatives that spanned strategic planning, IT, and operations. One of my significant achievements includes boosting operational efficiency at an artist residency program in Miami by automating workflows, developing protocols, and integrating new software platforms. These efforts helped streamline operations and optimize the technology stack for scalability as the organization begins a multimillion-dollar campus expansion and redevelopment project.

Today, I want to share the top 10 lessons I’ve learned from my experiences with automation while at Bakehouse. These lessons will highlight how small businesses and nonprofits can leverage automation to maximize their financial and human resources, ultimately streamlining workflows and enhancing productivity.

Lesson 1: Embrace Small Wins to Build Momentum

A common challenge faced by small nonprofits is the overwhelming nature of large-scale projects. The solution lies in taking incremental steps to achieve these goals.

For example, automating the lease application and renewal process for artist residencies at Bakehouse was initially daunting. However, by focusing on automating small tasks first, like automating calendar updates and generating draft emails from templates, we were able to build momentum. This approach ensured a smooth transition and immediate improvements in efficiency.

When I was leading the technology overhaul at Bakehouse, our goal was seamless expansion. By automating minor workflows first, the administrative team build the necessary confidence to tackle more significant projects. Embrace small wins to build momentum towards larger goals.

Lesson 2: Prioritize Process Documentation for Smooth Transitions

You might think that automation alone can solve all operational problems. And it’s true that you might see short-lived improvements. But the truth is that detailed process documentation is crucial for sustainable success. Remember:

  1. Automation without documentation can lead to confusion.
  2. Documentation ensures consistency, clarity, and scalability.
  3. Documentation also streamlines onboarding and succession planning.

At Bakehouse, we integrated our Trello project management solution with Confluence to build out a fully indexed and searchable organizational Wiki that documented standard operating procedures (SOPs) and workflows. Prioritizing documentation like this ensures that automated processes remain effective over time.

As alluring as immediate results may be, especially when faced with limited resources and a vast amount of needs, remember that the future success of any organization depends on organizational memory.

Lesson 3: Customize Automations to Fit Unique Needs

A frequent mistake is designing automations “from above” that require the creation of new workflows, processes, and employee training. This will create a lot of work and have a negative impact on productivity. Instead, take a user design approach by focusing on the unique needs of your administrative team.

For instance, at Bakehouse, we developed an automation plan based upon careful observation of the administrative team’s workflows. One shortfall we surfaced was the work of posting and reposting information about events across many diffrent social media channels and organizational platforms. To resolve this, we used Zapier to pull information about events from Google Calendar and then sent automatic updates to Discord and WhatsApp, creating a fully automated multi-platform system of real-time communication. Customizing automations allowed us to address specific needs effectively and maximize their impact on operational efficiency.

Focusing on what works best for your organization is key. Tailor your automation efforts to fit your unique needs for maximum impact.

Lesson 4: Leverage Free and Low-Cost Tools

Many small nonprofits believe that effective automation requires expensive tools. This misconception can prevent them from exploring available options.

  1. Numerous free and low-cost automation tools are highly effective.
  2. These tools often integrate seamlessly with existing systems.
  3. Starting with affordable options can yield significant improvements.

At Bakehouse, we implemented productivity tools to modernize operations without breaking the bank. Google Workspace in particular offers many powerful tools. For example, with a bit of coding, you can write and run custom scripts that will do things automatically, such as organizing your entire email inbox into an organized and searchable system of labels. Say goodbye to the 10,000 unsorted emails in your inbox!

Leveraging cost-effective tools like this enable us to enhance our workflows without significant financial investment.

Lesson 5: Focus on User-Driven Automation

Automations that do not consider the end-user can lead to resistance and poor adoption rates. Engaging the users in the automation process is essential for success.

At Bakehouse, we involved our administrative team in developing automation workflows. This user-driven approach ensured that the automations met their needs and fit seamlessly into their daily routines. For instance, automating data updates from spreadsheets to populate operational reports saved time and reduced errors.

Engaging users in the automation process leads to higher adoption rates and more effective outcomes.

Lesson 6: Plan for Continuous Improvement

A common misconception is that once an automation is implemented, the work is done. However, continuous improvement is vital for long-term success. This is not a “once and done” operation. You will need to:

  1. Regularly review and update automations.
  2. Solicit feedback from users to identify areas for enhancement.
  3. Stay informed about new tools and technologies.

At Bakehouse, we continually updated our automated systems based on user feedback and technological advancements. This practice ensured that our automations remained relevant and effective.

Remember, committing to continuous improvement helps maintain the effectiveness of your automations.

Lesson 7: Train Your Team Thoroughly

Automations are only as effective as the people using them. Inadequate training can undermine the benefits of automation.

At Bakehouse, we provided comprehensive training sessions and onboarding materials for all new automated processes. This ensured that our staff could utilize the automations effectively, leading to smoother operations and fewer errors. Automations made this task easier. At Bakehouse, I was able to use a free piece of AI software to track my workflows in real time, and then generate how-to guides and SOPs with step-by-step text instructions and images.

Thorough training and training resources like this will empower your team to make the most of automation.

Lesson 8: Balance Automation with Personal Touch

While automation can streamline many tasks, some aspects still require a personal touch to maintain human connections and engagement.

  1. Automate routine tasks to free up time for meaningful interactions.
  2. Ensure that customer-facing processes retain a personal element.
  3. Use automation to enhance, not replace, personal engagement.

At Bakehouse, we automated administrative tasks, allowing staff to focus more on building relationships with artists and the community. Letters to donors, on the other hand, were written by the administrative team (sometimes by hand). This helped us maintain a personal touch that is crucial in the nonprofit sector.

Balancing automation with personal engagement can significantly enhance your organization’s impact, but no solution is “one size fits all.”

Lesson 9: Evaluate Impact Regularly

Failing to evaluate the impact of automation can lead to missed opportunities for improvement. Regular assessments are essential.

  1. Measure the effectiveness of automated processes.
  2. Identify areas for improvement.
  3. Adjust automations based on evaluation results.

At Bakehouse, we regularly assessed the impact of our automated workflows, making necessary adjustments to ensure they remained effective and aligned with our goals.

Regular evaluations help you optimize your automation efforts.

Lesson 10: Foster a Culture of Innovation

Encouraging a culture of innovation is critical for embracing automation and driving continuous improvement.

At Bakehouse, we fostered a culture that valued innovation and experimentation. This approach led to creative solutions and more effective automation strategies, ultimately supporting our mission and enhancing our operations.

Creating an environment that encourages innovation can drive your automation success, but this journey of automation cannot begin if that culture of innovation is missing.

These 10 lessons provide a comprehensive overview of how process automation can transform small businesses and nonprofits with limited budgets and small teams. By embracing these principles, your organization can leverage financial and human resources more effectively, streamline workflows, and ultimately achieve greater impact.

Shawn Clybor

Founder & Manager, Clybor Consulting, L.L.C



Shawn Clybor, Ph.D.

Educator, Game Designer, and Instructional Designer who specializes in learning theory, game-based learning, and world history.