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Art of Leading

Ryan Williams

Anything Worthwhile Is Going To Be Incredibly Tough and Challenging

June 27, 2023

Ryan Williams, founder and CEO of Cadre, shares key leadership insights in this “Art of Leading” interview with Adam Bryant.

Q. What’s your approach to leadership? 

A. The first pillar is leading compassionately. That really comes down to understanding and listening, and having a level of care for each individual and their circumstances, both professional and personal. That’s the best way to engender trust. And my background — feeling like an outsider for a large part of my life — has allowed me to relate to people from all walks of life.

The second one is embracing change. That is an attribute I’ve always had but I’ve become really intentional about leaning into it. There’s just so much change happening today on all levels and across all dimensions. Whether it’s the pandemic or artificial intelligence or people trying to manage their physical and mental health, the role of a leader has become much more multidimensional.

Embracing change is about being honest with people about the fact that building a business is about always dealing with ambiguity and change. I like to pride myself on my ability to absorb that ambiguity and help others see that anything great is going to involve a ton of change.

Servant leadership is the third. That’s about leading by example, which really goes hand-in-hand with the first point about leading compassionately. I am someone who will never ask someone to do something I wouldn’t do myself. Given my background, I don’t look down on anything or anybody.

And I always have been focused on creating an environment where diversity is celebrated and leveraged for its unique perspectives, and where humility and being able and willing to speak with anyone are important. That approach to leading, where you’re a player/coach, has allowed us to be agile and to really prosper in the face of a lot of change and adversity.

Q. Compassion is a balancing act, because you also have to hold people accountable and sometimes make tough decisions about them. How do you think about that?

A. I’ve learned that often the most compassionate thing you can do for an employee is to show tough love, to be very open and honest when they’re not succeeding or thriving. Now that I’m a dad and have a kid, I’ve also tried to think about how I would treat a colleague if they were my son or a close family member. How would I deal with that fact that in certain cases the organization has outgrown them or they’re not succeeding or thriving?

The most compassionate thing you can do is help them to find a new context or a new environment where they can succeed. You first help guide them and provide transparent feedback on what has to change. And if things don’t change, you don’t just toss them by the wayside. You figure out how to offboard them respectfully and help them land on their feet. You play the long game, because your team sees how you treat everybody, including those who are not meeting certain goals or thresholds.

You play the long game, because your team sees how you treat everybody.

So over time, I’ve become a lot more comfortable with being very candid and direct in holding people accountable, despite how awkward or anxious it may make me to have those discussions. It still does today, but I always go back to, again, if this person were a close family member or my son, what would be the right thing to do here?

Q. What was the learning curve behind this insight? 

A. Early on, I was afraid of having tough conversations with people, because I was hiring a lot of folks who were twice my age and who had way more experience. You doubt yourself or you say, “Maybe with enough time this person will step up. Maybe I’m just not doing a good enough job as a manager and leader.”

But we got to a point where we made a couple of important senior hires who did not pan out. I recognized that I let those people stay in their position far too long and it did become corrosive culturally. It signaled to other people that it was okay to just get by. So when you’re spending that much money on people and your board is asking, “What are you doing differently this time around?” it forces you to do some introspection.

I’ve also learned that environment and context are critical to success. You can hire someone who is an incredible COO of a Fortune 500 company, but if you bring them into an environment where they have to be resourceful, where they’re the ones doing the day-to-day work, where there’s a lot of ambiguity, where they don’t always know what resources they’re going to have years out, you can see a very different outcome than if they had been in a more structured and mature organization.

Q. So how do you hire now?

A. If they have the requisite experience for the role, then I focus more on trust and understanding what motivates them and what drives them. It’s about understanding times they dealt with adversity and conflict, and how they navigated and managed that.

Then it’s just about understanding their influences and the people who have been important to their success and their career. I find that people who say that they’re self-made and that they didn’t receive much help along the way tend to be “me” people. That just doesn’t work in our environment, where you’ve got to check your ego at the door.

And I focus a lot on how they deal with conflict and adversity, because the only constant with a startup that’s trying to transform a big industry is change. With change, there’s always tension, so being able to drive impact while dealing with conflict is definitely something I focus on.

In terms of motivation, we’re a mission-based company, and one of the things I’ve learned through my time at Cadre is that there are days when things seem amazing. There are days when things seem really, really tough. What keeps people going is the mission, something bigger than themselves.

In our case, it’s about democratizing multigenerational wealth creation — letting any individual be able to own assets like real estate that provide long-term wealth creation opportunities and give them better financial stability and financial futures. People who are still with me today are people who embody that mission and who know that to do anything worthwhile is going to be challenging and is going to be incredibly tough to manage and navigate.

If I know that you’re working toward the same goal and the same mission as me, things won’t get personal if we have disagreements. When it comes to making decisions, we know what our north star is. Whenever there’s cross-functional collaboration, there is a thread of alignment and consistency that will help us ultimately make the right decision faster.

Q. What do you think is the hardest part of leadership?

A. It’s loneliness. Being a leader, you have to make countless decisions that sometimes take unimaginable courage. You’ve got to be willing to be humble. You can get to the highest of highs and the lowest of lows, and both places can be pretty lonely. There’s not a lot of people as a leader that you really can talk to about what it means to run a company or an enterprise, and what the implications are for your personal life and your professional life. It’s not like there’s a ton of great playbooks, especially given how fast things are changing now.

I try to remind myself all the time to stay focused and level-headed — never getting too high and never getting too low. It’s just so easy today to have a great day or win a big client or account and over-index on that. Then the same is true when things do not go well. If one of your great employees moves on or you lose a client, you can take it personally because your identity is so inextricably linked with the company you’re building. That’s where some of the loneliness comes in as well.

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