After I shared “Five Principles for Leading Through Uncertainty,” several leaders I work with asked me to expand on each idea. That led to this five-part series. These are not hard rules. They are simply principles that I believe helped me become a stronger leader over time. I hope they help you too.
The first article focused on establishing communication channels. This second piece is about what happens once those channels are in place. It explores one of the bedrocks of strong leadership: effective communication.
Communicate Clearly, Consistently, and Personally
Your team wants to hear directly from you. Not filtered through layers. Not heavily polished. Just directly from the person leading the effort. And once you start speaking, you need to keep showing up. People will notice if you go quiet. Whether the message is positive, challenging, or still taking shape, your presence matters. This cultivates trust.
Not every message needs to feel heavy. Humor can break tension. Stories make ideas easier to grasp. Simple visuals and clear communication help people see the bigger picture. These are not performance tactics. They’re practical tools to make communication more effective and human.
When I was leading Coupa in our early years, we focused on usability (circa 2010s) as our initial point of differentiation. At the time, most companies emphasized feature depth and breadth. We believed that unless the platform was easy to use, it would not drive adoption, which meant spend would not be fully captured and value would not be realized.
We used repetition, storytelling, and a personal tone to help align our teams. I communicated directly and often, focusing on clarity and humor, as in this clip from our 2015 user conference. This approach helped us reframe the conversation and win buy-in. I believe the consistency of message not only helped us internally, but also helped alter the market conversation and put us in a stronger competitive position.
Provide Frameworks and Direction
Strong leadership is not just developing a winning strategy. It is about helping others understand the landscape and make sense of what comes next.
At Coupa, I often turned to familiar tools to guide strategic discussions. Frameworks like Porter’s Five Forces, SWOT analysis, and BCG’s Growth Share Matrix helped ensure that board members, leadership, and functional teams shared a common understanding of the challenges and opportunities we faced. I believe that shared context made decisions more grounded and more collaborative. You don’t need a Harvard MBA or experience at strategic consulting firms to leverage these frameworks. Their power is in their approachability.
I also brought forth commonly known benchmarks like the SaaS Magic Number and the Rule of 40. These helped us balance the pressure we were placing on the gas pedal of our business with the distance we were clocking toward aspiring to lead the developing market.
It also proved valuable to continuously reinforce our overarching strategy as a three-act play. Act One focused on winning through usability. Act Two expanded our breadth of offerings both organically and through key acquisitions. Act Three unlocked the power of data. This narrative helped our team know where we were, where we were heading, and why each step mattered. I believe that it also gave us the space to be collectively contemplative along our journey, as we leveraged tailwinds and overcame headwinds day in and day out. By consistently speaking to this simple strategy, I believe we helped align our internal teams and made it easier for customers, partners, and analysts to understand our direction and believe in our vision.
Lead with Empathy, Not Just Optimism
Optimism has a place, but empathy is a prerequisite. Especially when challenges arise.
Earlier in my leadership journey, I often jumped straight into problem-solving. I thought that was the most impactful thing to do. Having begun my career as a computer programmer, I was flexing my analytical muscles instead of developing leadership acumen. But I ultimately realized that people are not always ready to move forward until they feel understood and acknowledged. I liken it to being a taxi driver who gets to a destination in record time, only to realize the passenger never got into the vehicle. Moving too fast can leave people behind.
Empathy begins with presence. It means listening (which we’ll explore in the next article). It also means naming what others might be feeling. The onset of the Covid epidemic in 2020 was a huge test of leadership for myself and my team. I believe that above all, empathy is what allowed us to survive and maintain pace through the many hurdles that presented themselves during those years.
None of this is about being soft. It is about being real. And when you show up that way, I’ve found that people respond. They rightfully trust you more. They bring their full energy to what’s next.
In Conclusion
Strong leadership is not about always having the answers. It is about being present, consistent, thoughtful, empathetic, and honest. It is about knowing when to step forward with clarity and when to pause and listen. It’s about bringing everyone along the journey.
Speak consistently. Speak clearly. Speak thoughtfully. Speak with empathy. Speak with integrity. Speak in a way that helps people feel aligned, respected, and ready to move forward with you.
Published:
September 9, 2025
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