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Guest Post: How to Keep Top Talent

6 min read
Updated Aug. 16, 2021
Published Mar. 7, 2020

Guest post by Scott Leese, CEO & founder of Scott Leese Consulting, and founder of The Surf and Sales Summit.

We are competing every day. Competing for talent. It’s never been harder to retain your best performers, and the data backs it up. 

According to, the average tenure of a VP Sales was just 19 months as of 2018! That was two years ago. Now? It’s widely known to be 15-18 months. 

The average tenure of an SDR and an AE respectively are 14.2 months and 2.4 years. We’re moving in and out of roles at an incredible rate, and velocity is increasing.

So, what can we do (if anything) to retain our best people?

“Relationships – of all kinds – are like sand held in your hand. Held loosely, with an open hand, the sand remains where it is. The minute you close your hand and squeeze tightly to hold on, the sand trickles through your fingers. You may hold onto it, but most will be spilled. A relationship is like that. Held loosely, with respect and freedom for the other person, it is likely to remain intact. But hold too tightly, too possessively, and the relationship slips away and is lost.”

Kaleel Jamison, The Nibble Theory and the Kernel of Power: A Book about Leadership, Self-Empowerment, and Personal Growth

Don’t Hold Your Employees Too Tightly

I often think about the passage above when considering talent retention. So much conventional wisdom about retaining high performers involves gripping too tightly and holding people back.  Eventually, this kind of control leads our best people to give up on us and walk away.

You can find examples of this “gripping” everywhere:

  1. Golden handcuffs
  2. Delayed payments on closed deals, meaning, if you walk, you don’t get commission (yes, this still happens)
  3. Not paying unused sick leave
  4. New options grants that don’t backdate vesting
  5. Failing to promote someone because you’re afraid to lose their production

These are long-standing mistakes in leadership and oppressive forms of retention that might have some short term benefits, but are losing strategies in the end. With the power slowly shifting more and more in favor of employees, employers who continue to behave in this manner are in trouble.

Serve Their Needs, Not Yours

So, what should we do instead? The basic construct is this: treat your people well and care for them. Provide monetary incentive, leadership opportunities, and exposure to new roles and projects. And finally, never stop coaching, mentoring, and training them. 

If we do these things with our colleagues while helping them set professional and personal goals, investing in their future and the path where they want to go, we increase the odds that they’ll choose to stay with us.

Our aim is not to focus on how these folks serve our needs, but to support their natural abilities, orientation, and their definition of success while we serve them.

Let’s take a deeper look into a solid strategy to keep top performers.

  1. Foster a corporate culture that treats people well. Show employees you care by promoting a culture of inclusion, communication, safety, health, fairness, opportunity, flexibility, growth, challenge, support, and success.
  2. Provide monetary incentive. A small raise is not enough to keep top performers around. On the open market, these professionals are often worth much more than they’re currently being paid, and more than they are probably even looking for to feel appreciated. Provide 10-20% lifts in base salary. Do the same with variable compensation. Add deeper benefits and paid perks. Double their equity stake and backdate vesting if you can.
  3. Provide leadership opportunities. You’re going to lose a top rep seeking leadership experience if you don’t provide leadership roles. It won’t matter how much money you throw at them. If you’re selfishly keeping an AE in their role because you can’t hit your next quarter’s goal without them, you’re sending a clear message that you matter more than them. Wrong message, my friends.
  4. Expose people to new roles and projects. Let reps run a sales training. Let them help in the recruiting process so they can learn more about it if they want to. Seek their advice on sales cadences or sequences, or let them help build that new sales script for your new product line. Hell, maybe even let them run point on selling that new product. 
  5. Maintain a growth mindset. Don’t ever stop coaching, mentoring, and training your people, both for the roles they’re in now, and the ones they might want down the road. Allow them to participate in leadership and selling events or summits at no cost to them. Have deep conversations about their lives, goals, and career direction in your one on ones. Reps don’t need to talk about pipeline all the time and neither do you. 

These things don’t seem that complicated when you look at them on paper. So why don’t they happen and how can you fix that? How about starting with honesty, transparency, and clarity?

  1. Create and adopt clear policies around workplace culture and hire accordingly.
  2. Make promotional paths and compensation increases universal and clearly attainable, eliminating back alley handshake raises.
  3. Promote from within. Give people a chance who have potential but aren’t quite “experienced” enough yet. 
  4. Create consistent dialogue and collaboration across departments, always asking “How can I help your team? What can my team do to support yours right now?” And loan your team member out to assist another department in their project.
  5. Have a set coaching cadence that touches all your team members, ignoring nobody, and eliminating favoritism and preference.

You control this more than you think. Will it double the retention rate of your top producers? I won’t promise you that. But if you change your mindset and approach by implementing some of these strategies and becoming action oriented, I do know that the odds of retaining your best people will increase.

Doing nothing ensures that people will walk. So, do everything you can to support and prop up your team. What have you got to lose? That’s right, nothing.