How to Adapt and Lead When Times Get Tough with Jason Shen

How to Adapt and Lead When Times Get Tough with Resilience Expert Jason Shen

On this week’s episode of The Leadership Habit podcast, Jenn DeWall talks to Resilience Expert Jason Shen about how to adapt and lead when times get tough! Setbacks are a natural part of life, but they can throw us off track and make us lose confidence. Join Jenn and Jason for a heartfelt conversation about how great leaders can get through challenging times by learning to adapt and pivot their strategies!

Meet Resilience Expert Jason Shen

Jason Shen is a resilience expert and executive coach who works with unconventional leaders and organizations that want to chart a course through change and swing big at work that matters. As a three-time founder, former NCAA athlete, and product leader at companies like Facebook and Etsy, Jason knows the challenge of leading in competitive and rapidly changing environments. His latest book is called Path to Pivot: How Startup Founders Can Reboot Their Business and Get a Second Chance At Breakout Success.

Grit, Pivot or Quit – What Do You Do When Times Get Tough?

As the episode opens, Jenn introduces Jason to the audience, and they begin by discussing Jason’s latest book, Path to Pivot. Jason explains, “Path to Pivot is a playbook for startup founders who’ve raised venture capital money who have hit maybe a wall or a sort of difficult time in their business, and they’re wondering what they should do. And so one of the big things that come up for entrepreneurs in this situation is whether you grit, pivot, or quit, right? And grit is all about sticking with it, pushing through. 

And it’s, it’s that thing that we sort of hear all the time. You know, winners never quit. Pivoting is what I think a lot of entrepreneurs should do because sometimes, just running your head into a wall isn’t going to work out. And quitting is that four-letter word that we’re all super scared of, but sometimes it can be the right move to get you to that other side of your next endeavor. Because this one just isn’t it.”

What Do People Usually Do in Tough Times? 

Jenn points out that sometimes quitting is the right choice, but it can feel like a failure. She asks Jason about his perspective on how people handle these choices when things aren’t working out. Jason explains that sometimes people get stuck in survival mode and try to just keep trucking even when things are not going to work. He agrees sometimes quitting is the right choice, but also, there is often some middle ground. 

Jason points out that many times we simply need to adapt and make a change in the plan to set things back on track. However, he sees many entrepreneurs wait too long to make a change, and they miss their chance. So, Jason wrote his book to explain an approach that allows you to make changes earlier in the process in order to work through the problems and pivot to a better outcome. 

Lowering the Stakes

Jason’s first tip is to lower the stakes so you can fix the bugs in the system. He explains, “So the key is to lower the stakes. And we lower the stakes by saying, you know what? We’re gonna dedicate a certain amount of time to exploring some new directions. We’re gonna put our current business in what I call maintenance mode. 

I work with a lot of software companies. And this idea of putting software in maintenance mode means you fix the bugs. You know, if any critical issues are coming up, you keep doing what you need to do to keep the system operational. But maybe you turn off any big marketing campaigns, maybe you turn off any new customers. 

If you’re onboarding, it takes a whole bunch of effort, but you keep the ones you have, you don’t fire them, you deal with the support that comes up, and then you just sort of leave it alone, and then you spend the rest of your energy in this expiration period. But you do it for a limited amount of time. 

It’s kind of like if you were thinking about moving to another state or another country, you might book a four-week trip there first, right? You have to see what it’s like to live there. You don’t sell your house immediately and then just, you know, move over. You spend some time in that other place.” 

What Happens When Leaders Don’t Adapt? 

Later, Jenn and Jason discuss the consequences of not adapting to new circumstances as a leader. Jason explains that failing to change course in times of crisis can harm relationships with your team members. When leaders simply keep trying to push through, it can create a lack of trust in teams. When what you are saying and doing is obviously not working, it creates a disconnection. 

He explains that the ability to adapt requires emotional intelligence and courage. It takes courage to admit when something isn’t working and to take a pause to reset and take a new approach. Effective leaders can’t let the fear of being wrong stop them from making difficult decisions. 

Jason then shares an example of a company that had a powerful “wartime” CEO during it’s startup phase. His approach was great for raising capital and launching the business. However, as the business grew,  his blunt and aggressive leadership style began to cause the staff to turn over. So, at a critical point, the co-founders of the company decided to ask the CEO to step down so they could rebuild trust with employees. 

Self Awareness is Key 

Then, Jenn and Jason talk about the leadership skills needed to encourage adaptability in the workplace. Jason points out that self-awareness is a crucial skill for leaders at every level. Knowing your strengths and weaknesses, along with your personal style and passions is crucial to success. 

He says, “I like to say that every person has a shape. You can adjust your shape a little bit, and you can build new skills to kind of change your shape, but you already start out with kind of a shape. And certain shapes work for certain organizations. A pointy place is not gonna work in a round, you know, environment and vice versa. And so you have to go and find that, and you have to know what your shape is. And sometimes, it’s hard to see that phrase. It’s hard to read the label from the inside of the bottle, right?

We can’t always see what our shape is from the inside, which is why it’s helpful to have a coach. But then, to put yourself in that right environment. And the same is true for an organization. You know, an organization, a startup that has a lot of creative people and is really in touch with the cultural zeitgeist, might be not suited for A B2B business where you gotta kinda be a little bit more buttoned up, a little bit more boring. You gotta do this sales process, you gotta hire salespeople and spend a lot of money on paid advertising. They might be not going in the right direction because they were told that that was the right thing to do. But actually, their shape might be more fit for a consumer-facing business and vice versa, right?”

Finding the Courage to Adapt 

As the episode wraps up, Jenn asks Jason what advice he would give to someone that is afraid to pivot despite having new information. Jason explains that though it is difficult to let go of the path you thought would lead to succeed, you have to be honest with yourself. He tells the audience to remember that having the courage to step into a new direction is more likely to find success than staying stuck in the same spot. 

Where to Find More from Jason Shen: 

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