Lessons from the Tech Frontline

1,740 Days

That’s the number of days I devoted to architecting, implementing, and then improving best-in-class enterprise technology at a top global law firm.

3,500 Days

Across all industries, it's closer to 3,500 days as I write this. Here are five key lessons I’ve learned:

Lesson 1: Prepare to fail often

Despite your best intentions, you’ll build things that people don’t like or worse never use. The least successful projects I’ve led were over-planned and rigid. That said, failure often leads to the most valuable insights. You must strive to cultivate a culture of continuous improvement. Organizations that can shift to a more fluid mindset around technology typically succeed. Persistent iteration turns initial stumbles into effective solutions. Build fast, ship fast, take feedback and please celebrate the small wins!

Lesson 2: There’s no such thing as over-communicating

In busy environments like AMLaw 100 firms, people are pulled in many directions. Firms prioritize direct revenue generation over most else. Users are at best skimming technology-related emails and likely multitasking during training. Communicate essential information as many times and in as many ways as possible (email, live training, office hours, on-demand training, user guides and tutorials, collaboration channels, and in-app guidance). Remind people that things are not set in stone and progress will continue.

Lesson 3: People + Process >> Technology

We tend to focus on the shiny new thing. Invert that tendency because technology just amplifies culture. Unaligned and siloed firms get low-value solutions. Tech-enabled bad processes are just bad processes. Engage stakeholders, establish personas, map processes, define success metrics, evaluate business cases and requirements, draft training and communication plans, encourage feedback, and identify champions. If you’ve started down the tech-first trap, remember, nothing is set in stone. Take a step back and refocus on the soft stuff.

Lesson 4: Better can mean harder

People resist change, even for “better” solutions, and better isn’t always faster. Advocate for long-term growth and innovation, even if it means moving away from comfortable legacy methods and tools. Let users know their expertise and guidance are crucial. Remind them you won’t get it all right the first time, but nothing is set in stone. Meet resistance with empathy and understanding.

Lesson 5: Demonstrate value early and often

If you build it, they won’t necessarily come. Perpetually ask, “What’s in it for the user?” Can you get some quick wins to drive adoption? Assume users need convincing, and design tools to fit into their current workflows. Assure folks that improvements will continue to roll out and nothing is set in stone. Involve users in the development process to build trust as well as foster a sense of ownership and buy-in.