How Sketch Empowered a Fortune 100


At Sketch, our favorite thing is to see an organization perform to their fullest potential and have a great time doing it. Most companies already have dynamite people who are both skilled and talented, but they’re lacking the right set of tools to put the whole picture together. With embedded agile coaching from Steph, this corporation was able to start alleviating communication problems, close their empathy gap, and model an example of a better way to work for their whole company.

“Most companies already have dynamite people who are both skilled and talented, but they’re lacking the right set of tools to put the whole picture together.”

The “Before”

Though this department within a Fortune 100 company was achieving a lot of success, they felt like they could be communicating better. An inkling started to creep in that the “old school” way of working didn’t suit them anymore. With upwards of ten internal software development teams overseen by a software leadership team, it’s understandable that they would have some trouble navigating communication challenges—being open can be tough to start with, but it’s especially tough amongst a huge team.

When Sketch met with them, the development team worked using an agile methodology, which was working great for them. However, the software leadership team hadn’t yet been trained in that method. This led to a gap of understanding between what was asked for by leadership and what the developers were trying to execute. Since the leadership team served as a mid-point between the company’s upper leadership and the developers, they also weren’t empowered to properly advocate for their developers or explain this different way of working. This, coupled with communication trouble and a lack of transparency, led to some friction.

Another challenge that emerged was an empathy gap between the leadership team and their developers. Leadership couldn’t fully understand the challenges their team faced since they didn’t fully understand the complexities of their work. This made removing impediments for the team hard, and the developers were starting to feel unheard and unacknowledged. These issues were starting to point the team down the path of disengagement, which nobody wanted.

With a feeling that they could incorporate agile practices into their own workflow to improve the overall work environment, the leadership team reached out to Sketch to see how they could get started.

The Plan

Sketch first suggested an intensive training workshop to illustrate what modern leadership is all about and get everyone familiar with agile roles, methodology, and terminology. After the training, Steph served as their full-time, in-house coach, available for the team as a resource every day in addition to helping facilitate plannings, retros, and demos. She helped the team keep the question “Would we expect our teams to do this?” top of mind with every decision.

The Execution

To start, the leadership team created a Team Charter, which included a mission, vision, and values for the team, as well as defining their own agile roles. This got everyone speaking the same language and rallied them around a common goal.Then the leadership team incorporated working in iterations, including sprint planning, retros, and demos. They also rotated scrum master and product owner roles so everyone could get a feel for what those positions involve. They iterated on the length of time they stay in one of the roles based on how people are feeling, which really helped spread empathy and understanding around the whole team.

The results were quick to start rolling in. Something as seemingly small as agile management software became an eye opener for the leadership team. Before, they assigned developers to enter their work in JIRA, without using the software themselves. Having the leadership team track their own work in JIRA not only led to greater transparency, it also gave  the leadership insight into challenges using the JIRA software. They experienced the same learning curve their team did and began to feel more empathy as a result.

In particular, demos were a huge success. The leadership team scheduled demos in a conference room that anyone could attend and streamed them for remote team members. In these demos, they’d recap what they’d accomplished in their previous iteration and allow for feedback and questions. Immediately the attendance at these demos was high and feedback was really positive. One team member’s reaction summed up the result: “This is a very transparent way to lead.”

These demos also fostered a sense of pride and accomplishment within the leadership team. Being able to look back at all they’d accomplished in an iteration felt good, and it alleviated the negative perception some had that the leadership didn’t do anything. That feeling was bolstered even more when other leadership teams became interested in working as an agile team. The leadership team felt like organizational pioneers in pushing for better ways to work.

The Challenges

Originally, the leadership team broke into two smaller teams. However, they felt this led to too much duplication of work and decided to become one large team of 14, bending the Agile 6 +/- 3 team members rule. Breaking this rule had a few consequences—decision making slowed down and consensus became harder to come by. This piggybacked on other typical challenges of a large team—difficulty in building trust, expressing vulnerability, and maintaining consistent energy, mood, and buy-in with 14 unique personalities. Going forward, the leadership team will continue to iterate on how their team functions and shake things up it isn’t working out.

The “After”

Overall, the change to the leadership team’s way of working has been a success and they plan to continue on their current track. The developers appreciate that their leadership has “walked a mile in their shoes,” and can better understand the challenges they face as well as advocate for them throughout the whole organization. Being able to see what their leadership team is doing in JIRA and through demos has also helped everyone feel like they’re working towards the same goal. The overall environment has improved, and things can continue to look onwards and upwards through continued feedback and adjustment loops. The increased transparency and better communication has also encouraged other teams at the company to adopt some agile practices, indicating that the good feelings generated by agile are contagious.


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