The 5 Hardest Challenges of Implementing Scrum

April 16, 2014

Whether you’re new to Scrum or an old pro here are five challenges you need to address for your next daily standup.

Having practiced Scrum for seven years at OpenView, I consider myself very familiar with the methodology. And yet, throughout that time I’ve found that it can often be difficult to define for others exactly what the process is really all about. It’s funny — immerse yourself in Scrum long enough and practicing it eventually becomes muscle memory. But try to step back and explain it to others and the results can be anything but fluid.
What is Scrum? In many ways, it just is!
It can be easy to forget how different and difficult the adoption and practice of Scrum can be. That’s certainly true for my own experience 7 years ago. Our path to adoption of the practice at OpenView was not simple, especially since we are not software engineers working on building awesome products. In our work there aren’t natural analogues of the feature backlog, a user story, or acceptance tests. A lot of time and work went into determining how to interpret some of Scrum’s best practices and guidelines in order to adapt them to our consulting or recruiting work. Over time, the terminology and rituals of Scrum have become deeply ingrained here. Of course, it has helped that every new team member at OpenView Labs typically undergoes Scrum Master training, still hosted by the inestimable Jeff Sutherland, as an essential part of their onboarding process.

We eventually overcame the initial challenges of our implementation, but over the years, as we’ve grown the firm, split into multiple scrum teams, and evolved our organization to adapt to what our portfolio companies need most, we have continued to go through growing pains and learn a lot in the process.

The 5 Hardest Challenges of Implementing Scrum

As a ScrumMaster and later as a Product Owner, I have found my team has had to work the hardest to address five particular challenges:

  1. Developing a truly empowered, self-organizing, and self-examining team
  2. Embracing rapid iteration
  3. Adopting prioritization by impact
  4. Applying realistic but practical estimation
  5. Managing Effective Scrum meetings

I also think that these happen to be the most essential aspects of the practice — I guess that’s what they are difficult to achieve. In my next series of blog posts, I will explore what addressing each of these challenges means in practice, why each is so important, and why each is so hard to get. I will also share some of our own experiences in working on these challenges at OpenView. Stay tuned!
How has implementing Scrum been a struggle for your company? Share your stories below.

Chief Business Officer at UserTesting

Tien Anh joined UserTesting in 2015 after extensive financial and strategic experiences at OpenView, where he was an investor and advisor to a global portfolio of fast-growing enterprise SaaS companies. Until 2021, he led the Finance, IT, and Business Intelligence team as CFO of UserTesting. He currently leads initiatives for long term growth investments as Chief Business Officer at UserTesting.