Make 10 Men Feel Like 100: Or, Building a High Output Information Technology Team in Startup Environments

Cassian Andor is the ultimate tech startup leader. Let me be clear, he may sometimes use unethical means, like his encounter with Tivik on the Ring of Kafrene, but that is a blog post for another day. When we look at what Cassian is able to achieve with his meager resources, we see an incredibly talented individual that is pushing the boundaries of his team. He is able to achieve incredible results by utilizing a small core team, inspiring them to take big risks, and using creative means to solve problems. But most importantly, Cassian leads by example. He embodies the first in, last out mentality, always willing to do the work alongside his team. In small startup IT teams, we often have to do the same thing for an entire business that is growing rapidly. You may have a core group of folks, three-to-five, or sometimes just yourself; attempting to spin multiple plates. As the business grows, the plates themselves grow in size, reproducing and multiplying rapidly. Once you find you have one plate under control, three more suddenly pop up and your small core-team can quickly become overwhelmed. Your core team may be able to keep up with basic configurations and BAU (business as usual) tasks, but may be unable to advance on things like automating repetitive tasks or inter-app configurations.

Where do I start?

Often this is the biggest question. “I’m overwhelmed with things and I don’t have time to focus on these items. So how do I start making change?” It’s a great question and also one of the hardest to answer as each business has different needs, objectives, strengths, and budgets. After building IT organizations at multiple rapidly scaling start ups I’ve found that the four principles below greatly help me to get a handle on things quickly after I assess the needs of the business.

But before you get into the principles, it is best to adopt a 90-day ramp strategy. I’ve found it incredibly helpful to break it up into three sectors spanning thirty days. You may find you need to extend or compress that timeline:

Understand, Identify, Execute

Day 1-30: Understand

• Setup 1-on-1s with other department heads to find their pain-points.

• Schedule a weekly “Office Hours” session that is open to the entire company to hear their feedback on how things are going.

  • An executive’s problem will never be the same as an engineer’s, and it’s wise to hear both so you can build trust at all levels.

Day 31-60: Identify

• Collect the findings from your “Understand” phase

• Include small Quick Wins (see below) to show your team’s value.

• Align with the executive team on Larger Project Plans

Day 61-90: Execute

• Start your executing on your plan and building towards longer term and recurring changes that add value to the business.

• Ensure you have a clear, concise, way of reporting your Quick Wins and larger project progression to stakeholders on a weekly basis.

  • A Slack channel that automatically posts updates from Jira is a great way to keep people informed asynchronously. (more on this in a following post)

Four Principles of New IT Orgs

• Utilize a ticketing system to start planning and tracking your team’s work (both Customer requests and your operational improvement tasks)

  • Jira Service Management is a complete ITSM offering (and my personal favorite!) and has incredibly powerful automation capabilities to supercharge your team’s productivity.

  • It may be easier to start with a basic Kanban Board (David Anderson’s book is a great read if you are unfamiliar) before you evolve into a larger change management process with approvals, implementation plans, etc.

    • Change management will be something to adopt (in the way you deem fit) if you are helping a company get to an IPO-ready stage.

• Start with a Quick Wins Strategy for each department

  • If you are new to the organization, or building out an IT function for the first time, using a Quick Wins strategy will build trust with fellow leaders, helping you align on larger projects in the future.

  • The Quick Wins strategy will also help you find easy ways to reduce other team’s Operational tasks.

• Adopt a Ruthless Prioritization strategy

  • Focus on what will 10x your team’s productivity or increase business efficiencies across other departments.

• Automate your Business Sector

  • Either build your own automations in Web2.0 tools like Coda, Jira Cloud, Slack Bots, or with the help of Zapier.

  • Lean into marketplace applications to extend functionality for platforms like GSuite, Jira, Zoom, and Slack.

Setting Priorities

Part of starting also includes setting a standard of priorities that you can share with the company at large. If the company decides to adopt your Prioritization Matrix, even better! If not, you can still make it clear that any requests should also be accompanied by a priority label that defines how urgent the request is. I like to utilize the following prioritization structure and broadcast it to the company so that there is a set of guidelines that allows your team to focus on what really needs to be done:

Your priority matrix might change or have different timelines and that’s OK! It’s important to set expectations and outcomes using a matrix to share with your fellow employees.

How do I start with Automation?

In my next blog post I’ll discuss some practical automations using tools like Jira Service Management and Coda to automate IT processes and make your small core-team have the impact of a full scale rebellion!