KServicing CEO: Leading Backward: How to Guide an Organization to Its End

Laquisha Milner

Friday, April 29th, 2022

When your company exists for a single purpose -- for example, to help other companies get through the PPP loan forgiveness process -- it means your organization has a shelf life. No more loans, no more forgiveness, no more business. 

But how does a company grow if successful work looks more like shrinking?

Like a startup with the mentality to sell in three years, an organization designed to last only the short-term does not take any less effort to build from the ground up. Leaders must be present in every department. The company lifecycle must be defined. Talent must be acquired. Phone lines. Business licenses. Customer service operations. Finance. HR. Legal. To become successful at shrinking, the organization must first grow.

So how does an organization with an expiration date fill its ranks with the best talent possible in the meantime? 

It’s a question they don’t teach in business school; I can tell you that. And it’s a facet of leadership that executive podcasts aren’t covering. How do you grow to shrink? How do you guide a company to an end?

If you’re tasked with leading an organization with an expiration date, the answer is to lead backward. That is, to start with the end goal of your organization and your employees in mind.

In the years before I became a CEO, I supervised strategic initiatives that massively impacted the organizations I was a part of, like overseeing earthshaking software deployments to deliver shiny new capabilities that redefined what the business can do. I worked on projects that raised the bar in Fintech. I led teams that set our company up for decades of success down the road.

Today, I’m asked to do quite the opposite: the better we do our jobs, the faster the company will conclude.

Now, that’s not to say that leading backward requires a different skill set than traditional leadership. The role is still strategic. The role means constantly organizing key initiatives by identifying cross-functional impacts, risks and dependencies, keeping multiple stakeholders happy and making tough choices. But as we get borrowers through forgiveness and shrink the number of outstanding loans to zero, it’s as if we’re building up an organization only to wind it down. 

Such alternative employment arrangements can be a tough ask in recruiting. The Zoom-powered world of remote employment offers people more options than ever before, and the Great Resignation makes retaining talent harder by the year.

Nonetheless, the right people are out there. Success in my world looks like hiring the right people for the job, knowing that I don't need them forever, which is honestly a funny position to be in from a recruitment standpoint. Or it would be if it weren’t for the shifting tides of culture and work in the U.S. marketplace. 

Historically, people used to take a job expecting to be a part of that company for decades. They'd stay forever, growing into more senior roles at the company, before retiring with a comfy pension and a gold watch parting gift. 

It goes without saying, but that’s not how the 21st-century workplace is constructed. 

Today’s workforce is mainly filled with tech-forward workers who have seen the redefined culture of work in the dot com era, alongside gig working economics, the great resignation and various crisis downturns all chipping away at workplace longevity. It’s more normal today to work somewhere for a few years and move on than it is to stay with one organization forever. 

People are now fundamentally more comfortable forgoing the traditional long-term work experience. And so, success in today’s marketplace has become far more goal-targeted, driven by those in the workforce who bring a specific skill set for a particular period of time. 

The most important thing to do to attract these kinds of workers? Communicate, be open and honest about the short and long-term vision for the brand. Find people who get it. Hire those who want to be part of the process, growing their skillset, being agile, and gaining opportunities to lead and train that they may not have had in other, more formal environments.

While it may not be the best way to run a life insurance agency or a real estate practice, in tech, it works. Ours is an industry where skilled workers apply targeted talents to project-focused, mission-driven teams with singular objectives. We do the job, and then we do something else. 

Backward leading starts with recruiting employees that understand the task at hand. Attracting talent familiar with the “grind now and sell soon” mentality of the startup world.

And so, what can an employee gain from that kind of experience? 

Is it the chance to work on a once-in-a-lifetime program that will be the foundation of many other small business lending programs to come? Or to leverage experience on a transformational government lending operation into the next big government tech contract? Or learn how to apply technology to the partnership between Fintech and the government? 

No matter what you glean from leading backward, learn this: there’s opportunity in the short run. Power to gain in sprints. A story to tell.