The duality in leading others: Trust optimism in trying times

Spend Matters welcomes this guest post from Daryl Hammett, Amazon Web Services’ Global Head of LM and Operations, about optimism in the workplace. 

Duality continues to teach us that every aspect of life is created from a balanced interaction of competing forces. Yet these forces are not just antithetical; they are interdependent of one another. One such concept that we can identify with is also one of the most consequential in all of our lives: Happy and Sad.

What has become crystal clear to me during the Covid pandemic is that we should embrace and understand the challenges ahead of us but also acknowledge the fundamental role that obstacles have in helping us grow.

As I look back on this past year, I have to take a moment and reflect on the duality of what 2020 presented and how it has affected my leadership experience. When I talk about duality, I mean the yin and yang, light and dark, failure and success, mind and body, rhythm and blues (smile).

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Over the course of the last several months, I have met with hundreds of leaders across all industries. Common hyperbole throughout the many conversations I had with leaders and teammates about their journey throughout 2020 is that they would often focus on what they lost rather than the valuable lessons they gained. However, what they missed is that being out of your comfort zone, acting in an unstable and ever-changing environment is one of the most valuable playing fields for a leader because there is always room for growth.

A common thread I found among most successful leaders that have bounced back this year is that they possess an incredible level of optimism.

Becoming an optimist through adversity itself 

To provide a more tangible notion of optimism, I would like to share what shaped me in the tough year of 2020.

In February 2020, I was COO of ConnXus, and we received an offer to sell the supplier diversity and SRM firm. We were incredibly excited as a team. After 10 years of work, ups and downs, starts and stops, highs and lows, wins and losses … and of course, the duality of it, we had finally reached where we wanted.

Then contrast this joy with what happened next: 30 days later, our world changed. Once the pandemic hit, we had to immediately pivot to a home-office model, which entails several changes in workplace dynamics. In the meantime, my team and I were also taking care of our current clients, closing the sale of our business, taking care of our employees, paying bills, and lastly but not less importantly, taking care of ourselves.

This was, and still is, one of the most difficult and rewarding times of my career. I had not taken a vacation in over a year to make sure I was available to support our organization and my team during this process. It doesn’t matter what you are doing, as a leader you always have to show up and be there for the ones around you.

In hindsight, it is clear that optimism brought us through these dark times. Through reframing the situation, we saw the duality of it all. Get it? Optimism played a pivotal role in making sure that our customers, investors and future acquirers did not lose faith in us as we managed the entire process. It showed them the adaptability of our team in handling the difficulties in the most transparent and efficient manner. The Brits once called this “pluck.”

People ask me today how did we pull off selling our startup during Covid? Stock markets were down, people were being laid off, thousands of startups closed their doors …

Of course, we had our struggles, and they were apparent every day, but our optimism was more important and weighed more heavily on us than the difficult times. Plus, this attitude reverberated in a way that the strength that we summoned last year became the “Rallying Call” for our team. This is what I mean when I talk about duality — there is always a way to see the cup as half full.

Ultimately, there are great learnings and innovations that happened as a consequence of Covid, and as leaders, I believe we cannot focus all our energies on the negative things that have impacted our journey. Again, observe the duality of the situation, shift your perspective and then pivot when the opportunities are presented.

Becoming an optimist — even when the glass really is half full  

I know that optimism might not be something innate for everyone, but there are ways that I have found that have helped me to develop into an optimistic leader.

First things first, whenever you are facing challenging times, you have to interrogate your beliefs.

As a leader, it is critical to have emotional intelligence so you can understand the duality of situations while keeping your team focused and taking care of your stakeholders. To do so, you have to interrogate your own beliefs about the situation. Some questions you might want to ask yourself are:

• Do you feel overwhelmed?
• Are you bringing your whole self to the situation to see the other side?
• Are you thinking objectively, or are you allowing the situation itself to dictate your decisions?
• Are you seeking counsel from other leaders and your team as you make decisions?

Once you have reflected on your own core values, you have to ask yourself whether you are asking the right questions.

During times of uncertainty, this is pivotal, and needs are constantly changing.

• Am I asking my key leaders and customers about the things they need?
• Are we having enough meetings to support your objective?
• Are your goals achievable?
• What type of resources are we bringing to the table?
• Does the client feel supported by your team?

Now, once you have meditated over these first two steps, it becomes clear the role that communication has in building relationships of trust and managing unsettling circumstances, especially in times of instability. Therefore, the third and probably one of the most important things is to communicate clearly.

Over communication, when people are going through change and in times of fear, is one of the best ways to show stability and be a safety net for your clients, customers, investors, etc. Turning a blind eye on any stakeholder will never do you good. So, make sure to take these points into consideration:

• Do you have a plan, and are you communicating it with your team?
• Does your team know about your decision-making processes?
• How are you aligning with the team?
• How are you supporting them?

Always remember, being a good listener is probably one of the most important acts of communication.

The fourth and last point about exercising optimism is to watch for the health and welfare of your team. Some of the ways that you can prioritize their well-being include:

• Rally call your team to check in on everyone and see how they are coping.
• Encourage them to look at things differently.
• Incentivize specific activities and goals.

As leaders, we are constantly faced with challenges. The challenges of 2020 were so abundant that we are still coming out of them today, but are we able to suspend disbelief — even under the worst trying times — and flip the narrative? There is always another side. Ask yourself: What is the duality I am dealing with and what’s my plan to overcome it?

I’ve learned through the worst times that we need to leverage duality and think divergently. We need to train our brains and our leadership style to see duality and divergent thinking as assets to our team and life. It allows us to be courageous, to have empathy, to understand a situation from a multitude of perspectives. And to adapt and react, and ultimately, to be better leaders.

Daryl Hammett is a highly regarded and influential mind in supplier relationship management software and procurement technologies. He has been recognized as a Top COO by Cincinnati Business Courier for his significant achievements — leading cutting-edge advancements in software development at ConnXus, a Top 50 “Company to Know” by Spend Matters and a firm that was acquired by Coupa in 2020. Hammett also has partnered with top procurement organizations to drive supplier risk education and supplier relationship management and is certified in supply chain management, third-party risk management and intelligent software automation. Daryl is a member of the YPO global leadership community and holds four certifications via the Sourcing Industry Group (SIG), where he is a member of the Advisory Board.