I Just Hired Your Best Employee

I Just Hired Your Best Employee 

The war for talent is impacting everyone. How you retain top talent is your game to lose. Are you prepared?   

By Scott Case, CEO Upside Business Travel & Founding CTO Priceline.com


Retaining employees is hard. Retaining great employees is even harder—seemingly impossible in tight job markets. With unemployment rates at the lowest they’ve been in 50 years, you have to assume that everyone on your team is being recruited by someone else.

No matter your company’s size or stage, you’re in a battle for talent. Which means you’ll need to do what it takes to keep top employees feeling great about working on your team. Here’s how to consistently retain your workforce so that you can achieve your objectives.

Advice for startup executives 

Other companies are actively attempting to woo your top employees away from your company. You need to get ahead of the challenge. 

If you’re leading a startup, you need a consistent strategy to retain employees. Resources are tight, and workloads are robust—everyone is already wearing multiple hats, so making a conscious effort to make sure high performing employees are feeling good about their jobs may seem like an unnecessary burden. It’s not. It’s critical that you stay in touch with your team. Without your high performers, you’ll never be able to create momentum, grow, and scale. 

If you want high performers to stick around for more than a cup of coffee, figure out what fuel they need and “feed” them. Overfeed them, in fact. Traditional perks aren’t the answer—free lunch Fridays and video game rooms or competitive health care, 401k, stock ownership plans, and competitive compensation are expected.

The truly most important thing you can do to keep top talent is to trust your people. Trust equals light speed—operate with a lean set of policies, approvals, rules, and procedures because top-down mandates hamper momentum and agility. 

Your highest performing employees—your leaders—will stick around for the long haul if they feel they have the responsibility and authority to make decisions. 

Here’s the short list of what they’re looking for:

  • Transparency—a leader wants visibility into the entire operation. How does the P&L look this month? What positions should we be recruiting for? When employees step out of their lane, in terms of responsibility, remember to see this as a sign of investment in your company—they want to make sure you’re successful. 
  • Ownership—a leader admits mistakes as fast as an average employee takes credit for something they did. Celebrate when employees are honest, open, and constructive in the face of adversity. They will gain confidence and experience. Everyone will benefit. 
  • Challenged—a leader takes on more than they are comfortable with doing. They may not be perfect at it, but it’s better that you have employees trying harder than expected. When they mess up, help them see it as a lesson in growth. The minute you chastise a high performer, is the minute they start to wonder if there’s another job out there that’s better suited for them. 

At Upside Business Travel, we strive to be transparent, treat everyone like owners, and challenge our team every day. But we still struggle to retain top talent from time to time because there are so many opportunities out there. A person having one bad week can see greener grass on the other side of the fence and jump before you know it. 

Recently, I was reflecting on some retention issues from the early days of our company. I realized that I failed to reinforce our vision and our mission consistently. I let it coast. As a founder, I now know that I need to constantly put that fuel in the tank for everyone on the team. I won’t make that mistake again, and hopefully you can learn from me and avoid it for yourself.

Advice for executives at larger companies

All of the challenges facing startups apply to more established companies, and then some. To an outsider, your company may be seen as “getting old.” By that I mean the perception is that, as a larger company, you have more rules and processes in place compared to a start up. 

While this may seem restrictive to some enterprising candidates, it’s important to remind them that you operate from a position of strength—you have more resources at your disposal and a broader range of opportunities within your organization for them to advance. They can literally see the career in front of them because job families are better defined than at a startup. Plus, you have brand equity, customer relationships, and products or services that are profitable.

To keep top talent at a larger, established organization, it’s your job to keep employees motivated and growing. Don’t let the stability that your proven organization provides become your Achilles’ heel. On an individual level, make sure your managers are meeting regularly with their teams, setting quarterly goals, and holding people accountable. Gradually layer on more responsibility to ensure your employees are learning and enhancing their skill-sets.

If people need tools or resources to acquire the skills needed for the next level in their career, do whatever it takes to provide them. It’s far less expensive and less disruptive to have people stay at your company than to leave. 

Advice for every leader

Whether you’re a successful entrepreneur leading a startup or an executive running a company with a predictable pipeline of customers, coaching and development of talent should be viewed as an important part of everybody’s job. 

Start by building a group of people around you that you trust to communicate and demonstrate your company culture—colleagues who will provide mentoring, coaching, and development for your teams. 

Then, listen to your team’s feedback—just like you listen to your customers.  

At Upside, we’ve doubled down on communicating our core values and reinforcing them on a daily basis: 

  • Trust
    • Find people who can handle extreme ownership and authority to make decisions. We hire brilliant people to make decisions for the company. We trust them to run a lean operation and I get out of the way.
  • Development
    • Set aside a budget for each employee to be used for professional development. Let them define how it should be used. Subscriptions, online courses, hosting events and meetups within the active startup network—all are viable options. The goal is to establish constant feedback loops outside of the office.
  • Resiliency
    • Invest in the people who are energized by constant change—not folks who would rather move on when faced with unexpected challenges. No matter your industry or company stage, change is inevitable.
  • Transparency
    • At Upside, we share the status of company-wide OKRs (objectives and key results) to keep us on track, and host an “Ask Me Anything” forum every month to get after the questions on the team’s mind. Further, we share achievements with everyone. I send a bi-weekly internal newsletter to the team to celebrate our wins and focus on our future objectives. When the team sees the forward progress we’re making, they understand what they’re working toward. 

Most of your employees aren’t going to work for you forever. However, you can build and scale a company with the right approach to taking care of your people. It starts with creating a culture that attracts, challenges, and rewards hard workers. Once you establish a critical mass and everyone is consistently living your core values, you can retain more people and easily manage the occasional teammate leaving for their next opportunity. But don’t take that for granted. Keep putting energy into communicating those values day in and day out.

Scott Case regularly shares his leadership experiences on LinkedIn. Connect with him if you’re ready to level up your leadership style, or if you have best practices to share.