“What have you done for me lately?” It can feel like a harsh sentiment, whether in professional sports or the corporate world. I was reminded of this recently when speaking with someone downsized after 15 years with a company. They felt their long tenure and past successes weren’t appreciated. Around the same time, a similar dynamic was playing out with Toronto Blue Jays star Jose Bautista, whose future with the team was uncertain despite a storied career. These situations highlight a critical reality: organizational needs evolve, and what was invaluable yesterday may not be the optimal fit for tomorrow.

A Sports Analogy: The Star and the Shifting Team Strategy – A Look Back at 2016

For those who recall the Blue Jays’ exciting playoff runs in 2015 and 2016, Jose Bautista was a hero. His record-setting home runs and iconic “bat flip” embodied the team’s peak. Fans clamored for him to be re-signed at any cost.

Fast forward just a year to the end of the 2016 season. After an injury-plagued year and a playoff performance that didn’t meet expectations, fan sentiment had noticeably shifted. The team’s needs appeared to be evolving towards a different style of play; perhaps more focused on “manufacturing runs” than relying solely on power hitting. Bautista, a quintessential power hitter, didn’t seem to fit that emerging strategy as perfectly as before.

How could perceptions change so quickly? It often comes down to those current organizational needs asking, “What have you done for me lately, and more importantly, what can you do for me tomorrow?”

The Parallel in Business and Technology

This isn’t just a sports phenomenon. I’ve seen it (and experienced it) in the business world. You can deliver high performance for years, be a recognized leader, and deeply believe in an organization. But when that organization undergoes transformational change, new leadership, a shift in strategic focus (perhaps from front-end innovation to back-end execution efficiency, or a pivot in technology platforms), the skills and approaches that once made you invaluable might no longer be the primary ones needed.

The key difference in my own experience, compared to my acquaintance who felt “hard done by,” was recognizing why the shift happened. It wasn’t a personal failing, but a change in organizational direction where my specific strengths were no longer the priority. And that’s okay.

Reframing Change: From “Wronged” to “Realigned”. A Fractional CIO’s Perspective

For the SMB leader, this “What have you done for me lately?” reality has several implications:

1. For Your Team: As your business evolves, the skills and roles needed will also change. It’s crucial to continuously assess if you have the right people in the right seats for your future direction, not just your past. This sometimes means making tough decisions about reassigning or even parting ways with long-standing team members whose skills no longer align, while helping them find new opportunities where their strengths are needed.
2. For Your Technology & IT Strategy: The IT systems and strategies that served you well five years ago might be hindering you today. A “reality check” (as discussed in “Reality Check Your IT“) is essential. Are your tech investments aligned with your current and future needs? Are you holding onto legacy systems due to past successes, even if they no longer serve the business effectively? As a fractional CIO, I help SMBs make these objective assessments and ensure their technology evolves with their strategy.
3. For Yourself as a Leader: Are your skills and focus evolving to meet the changing needs of your business?

Parting ways, whether it’s a player from a team, an employee from a company, or a company from an outdated technology, doesn’t have to be a “win-lose” where someone is “wrong.” It can be a “win-win” if reframed as a realignment. The organization gets to pursue its new direction with better-suited resources, and the individual or technology can find a new context where their specific strengths are once again the perfect fit.

What’s Next

Just because skills, experience, or even past contributions are no longer the primary need for one organization doesn’t mean they aren’t immensely valuable elsewhere. The key is honest assessment and a willingness to embrace change, ensuring continuous alignment between capabilities and strategic needs. This proactive realignment is far healthier than waiting for a crisis or feeling “wronged” by inevitable evolution.

Is your SMB proactively aligning its talent, technology, and strategic focus with its future needs, or is it primarily looking in the rearview mirror? If you’re seeking a strategic partner to help you navigate these crucial realignments and ensure your IT capabilities are primed for what’s next, let’s connect with Succeed Sooner Consulting.