Post
April 19, 2020 | 7 min. read

Playing for Keeps: Retaining and Growing High Performers

Article Highlights

  1. The quickest way to lose star employees is to surround them with less than stellar ones. 
  2. People who don’t live up to your organizational values must go.
  3. Setting and sharing individual performance goals like OKRs is a transparent way to motivate people.

This post is by Jessica Klek, RVP of Enterprise Sales at SalesLoft. Our leading sales engagement platform helps sales organizations to deliver a better sales experience for their customers.


I’ve always been intentional with my career. Even though my plan has changed many times, just having a plan gets you where you need to go.

Being an intentional leader is equally important. Have a plan for how you want to treat your team, live by it, and adjust it as you learn to lead better. I promise you’ll get back what you invest.

The first place I truly realized this was at LinkedIn. That’s where I discovered I wanted to be a leader. The culture was all about compassionate management. There were no jerks allowed.

But they actually meant that. In my first week, I saw them fire a top-performing sales rep because, frankly, he was a jerk. 

It was such a relief to be part of a culture that’s stated values aligned with its actions. 

That experience left an impression on me. It illuminated the type of team I wanted to build, the type of leader I wanted to be, and the values I wanted to perpetuate anywhere I went.

And it’s caused me to seek authentic cultures that say what they mean and play by their own rules, which is one of the things I love about SalesLoft.

Building Your A Team

Part of retaining the best talent is attracting it in the first place. Not only because you want great players on your roster — you want to keep the great players already there challenged, fulfilled, and content. The quickest way to lose a star employee is to surround her with less than stellar ones. 

So, when I’m searching for a new team member, the skills I look for depend on the role, but there are certain things I always bear in mind.

First, I take inventory of my team’s existing skill set and look for additional levers that would elevate both the incoming individual and the team — it’s like putting a puzzle together.

My two non-negotiables in hiring are culture and personality. Will this person be successful within both the company culture and the microculture on my team? Will their personality fit? If I have any doubt in answering either of those questions, it’s a no-go.

While tech sales experience is important, what’s more valuable is that the person has tons of passion for what they’ve sold in the past. Two more points: can they articulate why they want to join the organization? And, is their nature collaborative and giving? 

These qualities aside, I wish more leaders recognized that a diverse team is a high-performing team. There’s so much opportunity for people of color and women to bring more to the table in the workplace — especially in sales organizations. 

For many recruiters and managers, it’s tempting to default to candidates who are easiest to find. But seek the ones who may not be as prevalent. They’ll push your team to grow and offer alternate perspectives you need to hear to be an effective, well-rounded leader. 

Protecting Your Team

As I witnessed during that formative experience at LinkedIn, people who don’t live up to your organizational values must go. It’s the only way to protect your culture and the people who’ve put their trust in you as a leader. 

I believe in bringing my whole self to work and encourage my team to do the same. We behave authentically with one another, and they know I care about them beyond the confines of our office. When people realize this, that inspires and motivates them.

Leaders also need to protect their team’s free time. When I see people not using vacation, I demand it. Sometimes I’ll Venmo them money for a massage as a way of saying, “I’m begging you to take some time for yourself.” Emphasizing the importance of breaks gives people the mental freedom to actually unplug and get away.

Even so, work/life balance can be illusory. Instead, look at work and life through the lens of harmony. Choose how to invest time in work or home. And when you’re over-investing in one or the other, recalibrate and ask your team to do the same. 

Motivating Your Team

Having transparency at the executive level goes a long way in retaining top talent. Choose to be overly transparent with people because the more they know, the more comfortable they are with change. And the more agile they become.

Setting and sharing individual performance goals like OKRs is a transparent way to motivate people. At SalesLoft, anyone in the company can see anyone else’s OKRs. We aren’t a secretive culture and that keeps everyone accountable and invested.

Beyond goal setting, motivate individual team members simply by asking what drives them. Devote some one-on-one  time to talk deeply about personal and professional goals. Then provide meaning for people by tying the organizational goals back to their personal ones.

As for team motivation, each year I ask, what do we want to be known for? What’s our stretch goal? Obviously, we’ve got to make quota but beyond that, what’s the one big thing we’ll do to move the company forward?

And that becomes a rally cry we come back to when we need to inject some excitement or passion into our work. To move a bit quicker or bound up a big hill. That rally cry is the touchstone that grounds and motivates us.

Promoting Personal and Professional Growth

But eventually, even those measures may not be enough. Because of the expectations they place on themselves, high performers sometimes feel stuck, or maybe they’ve outgrown their job. To mitigate this, I do quarterly check ins about career pathing and personal and professional goals with everyone on my team.

From there, I’ll give them projects to help them achieve their goals. Let’s say someone wants to be in leadership but they don’t have enough experience or we don’t have an opening just yet. I’ll delegate projects to help them exercise that leadership muscle. I also give them exposure to the duties required of a leader, like having tough conversations.

It shouldn’t be enough for a sales team to hit their number. You want them to also give back to the organization. Be project-driven with your people, and through these projects, they can develop other skills, succeed, and move on, whether it’s with your company or elsewhere. Make sure your team feels supported, challenged, and excited about work every single day. That’s how you’ll help great people grow.

Bonus Tip for High Performers

High achievers are always looking for an edge. Here’s one transformative tactic I wish I had heard about earlier in my career: building your own personal board of directors. 

This is a group of advocates, mentors, and sponsors that can give you great career advice. Ideally, your board is made up of people both inside and outside your organization, with varying degrees of progression (choose people both more senior and more junior than you).

Then when you need to, lean on your board to help you solve challenges. This group of people will provide you with balance and perspective. They’ll guide you through the politics of business. They’ll inspire you. And they’ll help keep you sane.

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