So You’ve Grown Yourself an All-Star Player. Do You Pay ‘em or Let ‘em Walk?

Person swinging a softball or baseball bat

Photo by Geronimo Giqueaux

The other day I was asked whether we had written anything about how organizations should think about paying to retain technology talent. I immediately thought of the Oakland A’s baseball team.

Being an Oakland A’s fan is a rollercoaster of exciting and disappointing. Somehow, despite always having one of the lowest payrolls in baseball, the A’s have frequently been able to stay competitive by finding ways to identify hidden talent (remember Moneyball?)

They consistently seem to assemble a bunch of unknowns, draft picks, and prospects into plucky teams that compete with the big spenders. Countless formerly unknown A’s players eventually become league-wide superstars.

So why is this disappointing?

Well, those superstars never end up playing for the A’s for long, because the A’s aren’t willing to pay them what they’re worth in the market. All long-suffering A’s fans know that as soon as a young star player’s contract runs out, another team will sign that player and pay market value for their talent.

So maybe it shouldn’t be a surprise that it’s been over 30 years since the A’s last won a championship. They’ve been pretty good, but not good enough.


Many organizations do the very same thing with technology talent. We’ve written about the wonderful phenomenon of discovering that you have a technology jedi-in-waiting right under your nose as long as you’re on the lookout for the right qualities (think: communication and strategy rather than coding or technical mastery).

This often works out to the benefit of both the organization and the staffer. The staffer might not have had the formal technology background and therefore may not yet be commanding an extremely high salary. But they are happy to be in the new role, learning new skills, immersing themselves in the technology, being well appreciated, and making tremendous impact for the organization. (We see this often when people catch the Salesforce ‘bug’ specifically.)

So what happens once that staff person has acquired the skills and knowledge to be appropriately recognized as a heavy hitter in the market?

Quite often, organizations will balk at increasing a salary range enough to retain this kind of talent. There are lots of understandable reasons. It will break our salary scale. We don’t want to have to keep paying someone at this rate forever. Such a large increase might not go over well with other staff. What are we going to do when this person leaves?

But at the end of the day, you either pay for talent or you will lose it. And for your organization, the costs of losing it are probably a lot higher than the incremental costs of retaining it.

At least when you’re talking about baseball, if you lose a shortstop to another team, you can plug in another skilled shortstop without too much getting lost. Hit the ball, throw the ball, field the ball, let’s go. We all know how this game is played.

By contrast, skillfully leading technology investments at an organization is much more complex and nuanced, requiring a massive amount of context, understanding, and communication. That’s true in terms of the details, nuances, and history of the technology stack itself, and, even more important, in terms of the organization’s strategy and tactics and what each member of the team is trying to accomplish.

When you lose a star player at that level, it’s a massive setback. It’s going to cost you dearly, probably many times over what you would have had to incrementally pay in salary to retain that person. Every member of your team is going to lose some percentage of their effectiveness. Ideas will get squandered and opportunities will be lost. Your external firm also loses a key partner helping steward the effectiveness of their work.

Eventually things will get dire enough that you’ll realize that you have to hire a new star player, probably at a salary a lot closer to what you could have paid to retain your home-grown talent. Best case scenario, eventually the new person will grow to achieve the same level of context and understanding and relationships that your former player did. But how much time and energy and effort and potential was lost during that transition period?

The game has changed for technology. You need people — great, skilled, talented people — to steer the technology ship. This is a strategic priority for your organization. Covering your eyes and opting out might seem tempting, but it’s only digging you into a deeper hole.

So if you’re lucky enough to find a home-grown prospect right under your nose who fits the bill and becomes the all-star player your organization needs? If that happens, which road will you choose?

Will you take the Oakland A’s route, letting your best talent leave while you spend endless amounts of time and energy scouring the landscape for new bargains as your team struggles to stay competitive?

Or will you recognize the incredible asset you already have by investing appropriately in the internal all-star you already have, and harvesting the bountiful returns on investment that they create, day in and day out?



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