Why Agile Leadership Requires Doing the ‘Hard Stuff’

As a leader, from the moment you engage in your first work exchange to when you close your computer, every day can feel like a trade-off between technical project delivery items made to the humans you empower behind those decisions. Factor in the demands of an evolving technological landscape, a shifting global economic climate, and the growing cost of poor software quality at an estimated 2.41 trillion in the U.S. alone? For some leaders, it feels like a challenge to even get out of bed.

Fortunately, we sat down with Elisabeth Hendrickson, an experienced leader in software quality and development, to gain new tips for agile leaders to succeed, deliver quality software to their organizations and customers, and well, do the ‘hard stuff.’ If you are in software development, agile software testing, and/or any adjacent industry, you know that Hendrickson is a celebrity and she has a demonstrated background in leadership to explain why.

In our conversation, Elisabeth shares agile leadership tips, including the sacred ingredients to delivering effective feedback, strategies for managing in challenging work environments, and  balancing the technical vs. human-centered approach to leadership.

In addition, we will cover what AgileTD USA attendees can expect in her much-anticipated return to the international conference scene. Let’s dive in. 

Why is learning how to do the hard stuff essential for agile leaders today?

Honestly, I think doing the hard stuff well is essential for anyone in a leadership role. The thing about agile is that teams are more self-directed. In a high-functioning self-organizing team nearly everyone steps up and demonstrates leadership skills on a daily basis. It’s not up to a boss to fix things; it’s up to the people on the team.

Whether that means facilitating difficult discussions, addressing a growing conflict, calling on all team members to uphold team values, or pushing back on something that’s not right, everyone ends up doing the “hard stuff.”

What do you believe is an essential ingredient for delivering hard and/or constructive feedback?

I think two things must be true simultaneously. [First], the feedback must be clear, specific, and actionable. Be direct rather than using vague language in an attempt to soften the blow. Use examples to illustrate the behavior or work that was not acceptable, and explain what you wanted instead.

[Second]...that feedback must be delivered with kindness and empathy. It might seem like these two things conflict. Being direct about critical feedback might not seem “nice.” But nice and kind are two different things, and it is possible to deliver even quite critical feedback with kindness. The key is that you have to care, genuinely, about helping the person to whom you’re giving feedback. It’s also important that you have the time and energy necessary to talk through the feedback without feeling rushed or cranky.

Feedback is an incredible gift, and well-delivered, thoughtful feedback delivered at the right time can change the trajectory of someone’s entire career.

As a technical and human-centered expert, what is the #1 constant that you have seen in toxic work environments that managers should first address when building teams? 

There are many different flavors of toxicity. Some toxic work environments have a blaming culture that makes people feel anxious and unsafe. But others can have a culture of “nice” that it’s not OK to give any form of critical feedback or challenge the status quo. A blaming culture and a “nice” culture might look nothing alike and yet they can be equally toxic. 

The common thread is that the culture tolerates or even promotes unhealthy patterns of interpersonal relationships that makes it feel unsafe for people to engage fully and bring their best to work. For a work environment to be healthy, it’s important that everyone be able to own responsibility for their own actions and words, be accountable to their team, treat each other with dignity and respect, be a good partner, and create space for their colleagues to do the same.

As a renowned international software developer, test, leader, and executive, what inspired your upcoming AgileTDUSA tutorial, “Doing the Hard Stuff”?

Someone I worked with in the past recently commented to me that they thought I’m particularly good at what they called, “the hard parts of managing.” They were referring to holding people accountable and driving difficult changes in organizations, while simultaneously treating people well. The idea grew from there. This tutorial draws on my experiences leading, including leading a 170-person organization with a complex set of enterprise-grade products.

Is there any pre-work that attendees should prepare before your tutorial and/or recommended resources of your’s to review?

[While] there is no specific reading or preparation needed…it will be valuable for participants to spend a little time in advance thinking about what the “hard stuff” is for them or for their organization. Are there recurring pain points? Are there trade offs that are particularly difficult to make or to reason about? Are there changes that everyone knows need to happen, and yet they don’t? How does the culture within the organization make the “hard stuff” easier or harder?

Elisabeth, we greatly enjoyed our conversation and can speak for all when we say how excited our AgileTDUSA attendees are to attend your tutorial live, finally meet you in-person, and dive into learning how to do the “hard stuff” with you. On a personal note, from meeting so many leaders that I admire to learning new agile tools, technology, and techniques, AgileTD USA has been the best in-person software testing experience that this author has ever had.

We understand that for many experiencing financial hardships and/or limited professional development dollars, attending live may feel daunting. This is why the AgileTD community created multiple discount tiers for those experiencing recent unemployment to discounted opportunities to bring your whole team!

Learn more about our upcoming in-person event in Chicago starting May 22nd, including Elisabeth’s tutorial here. We can’t wait to see you all in-person.


Elisabeth Hendrickson is an experienced software developer, tester, leader, and executive. She has a track record of creating high functioning organizations and growing strong leadership teams. As a member of the executive team for Pivotal (acquired by VMware), she headed up the R&D group responsible for Pivotal’s Big Data Suite. Prior to joining Pivotal, Elisabeth ran her own small consulting company, Quality Tree Software, Inc. where she helped organizations build better software sustainably by adopting agile practices and values. Elisabeth is the author of Explore It! from Pragmatic Books.