Resilient Leadership During Challenging Times

Brad Wills
Former CEO at ProductPlan


A crisis can bring out the best (and worst) in people. Throughout my career, I’ve seen a spectrum of responses from leaders that have shaped my views on which strategies work and which ones don’t.

I had no idea that a crisis would unfold so quickly into the start of my tenure as CEO of ProductPlan.

I transitioned to CEO of ProductPlan in early February, which for those of you keeping track was a month before a global health and economic crisis unfolded.

Resilient Leadership During Challenging Times

As a leader, I believe in radical candor, and I have always strived to create an environment where my team feels safe to share their feedback and opinions. If you operate from a place of authenticity and transparency, then you can facilitate an environment of trust. Teams that feel safe also tend to trust each other and are, in turn, well-positioned to step up in times of crisis.

Download From Product Manager to Product Leader ➜

Demonstrate flexibility

Our team has done a tremendous job building a fantastic product and a durable business model. Anytime a company goes through change management, I believe it’s essential to honor and sustain the elements of what makes the company great—while infusing your own philosophy to move the business forward. For ProductPlan, I recognized we needed to develop a more comprehensive mindset toward growth. We had been gearing up our offensive for several quarters investing in engineering and building out our go-to-market team to better capitalize on opportunities within the business. The results were really starting to show.

However, business growth and global economic uncertainty don’t necessarily mix well. As the crisis unfolded, we had to immediately ask hard questions of ourselves and our business to assess what the correct strategy was for us moving forward. During times like these, sometimes you’ve got to play defense.

First, we took a magnifying glass to the entirety of our business. We recalibrated our revenue and expense plans based upon different scenarios. We made adjustments to hiring plans and created a more rigorous and gated approach to releasing investments. On the product side, we are building a system of record to help product teams and executives better align and standardize their priorities and ultimately drive better outcomes. We have been ‘pedal to the metal’ on this strategy for the better part of 9 months. We also recognized that we have customers significantly affected by this crisis. We reviewed our product roadmap with an eye toward “what do our customers need now?” This exercise spun up some short-term wins we were able to deliver quickly.

Trust in your team

In a world where there’s no face to face interaction, one can fall into the trap of feeling less in control of the business. If you and your leadership team have hired right, then, hopefully, you have a deep bench of intrinsically motivated people. These are the people that will step up and do the right thing if you have done your part to convey the mission and the situation at hand. This is the absolute wrong time to turn into a micromanager.

To me, the concept of a workday feels a bit antiquated for knowledge workers anyway. Our lives are such that we have them, and that means, at times, things in our life are going to intertwine with our workday. Sometimes a workout in the middle of the day is exactly the best use of your time.

Ultimately, if we empower the right people to manage their time, then I’m going to bet on them doing the right thing.

The decision to switch to remote work to protect the health and safety of our team happened over the course of an afternoon. About half of the company has already been remote for years, so we already had somewhat of an established blueprint. This certainly helped. For the other half, however, remote work was an entirely new practice.

The transition to remote work

Interestingly, I’ve noticed that since we have transitioned to 100% remote in response to the crisis, we’ve actually improved our communication. For my part, I wanted to make sure the entire team had a better picture of how the crisis was impacting our customers and our business. This has translated to a cadence of team updates where we openly share our business performance, our views of the potential impact of the crisis and how that impacts decisions we are making. I’ve observed cultures where information is kept tucked away to only be parsed out on a need to know basis to employees. That kind of culture breeds mistrust.

Our leadership team also increased the frequency of our communication to stay aligned. Initially, we experimented with meeting every day before determining an every-other-day cadence was sufficient. We have also had to improve our asynchronous communication to help fight off Zoom fatigue.

As we can no longer walk down the hall to ask a question or solicit feedback, Slack has become our go-to channel for establishing a shared understanding of doing what matters. We have opened up new Slack channels such as #research to serve as a central repository for relevant information. Going 100% remote has forced us to be more intentional about how, when, and why we’re communicating.

Consequently, our alignment about what to do is better. We no longer need a daisy chain to keep people in the loop. Instead, we have the information we need to make qualified decisions. As such, I’ve noticed the timeframe for decision-making is faster than when we were in office. I don’t think these results would be possible without a foundation of trust.
Download the Product Manager's Toolkit ➜

Embrace vulnerability

As the CEO, strategy and culture are two of my key focus areas. During moments of great challenge, we owe it to one another to tune in to the signals and EQ indicators of how the team is doing. There’s so much scary information out there about the pandemic and the economic fallout that can really affect our morale. You can usually tell when someone on your team is having a tough day. People give a lot away. In a world where you aren’t able to comfort face to face – follow up, lean-in, and ask questions.

As a team, we are forthright and honest with each other. I will often share with my leadership team when I’m struggling with an important decision. In a way, I’m hoping to elicit more information from them to help make a better decision. It’s a misguided assumption that CEOs have to have the answers. You need to be open and approachable with your team. It’s okay to say, “I don’t have all the answers.” If you want a culture where people feel safe, then embrace your own vulnerabilities.
[Free report] 2021 State of Product Management ➜


Even in the worst of situations, I still believe a company can flourish and achieve awesome things. Trust in one another, be flexible, and, most importantly, stay real.