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A crucial mistake leaders make: ignoring cultural shifts

  • Writer: Jessica Crooker
    Jessica Crooker
  • May 11, 2024
  • 2 min read

Updated: May 21, 2024

I started working at a founder-led company in its 10th year. The entrepreneurial spirit upon which it was founded was palpable. Cultural values included:

-being scrappy; figuring it out as you go

-doing things you’ve never done before

-not feeling ‘above’ any task (ex: I brewed coffee for events and created the learning strategy!)

-an ‘earned, not given’ mentality


Working in that environment was exhilarating! Discretionary effort was off the charts. Collectively, employees built strong bonds and shared immense pride in their work.


As the organization matured, there was a shift. Leaders told employees to ‘stay in their lanes’ instead of jumping in wherever needed. They intended to create role clarity and efficiency.

New hires, often executive-level leaders from much larger companies, were tasked with elevating the simplistic and homegrown operations to match the complexity and scale of the growing organization.


Veteran team members became resentful, sensing their voices no longer had the same value.

Likewise, new talent encountered internal roadblocks making it hard to effect change and build strong working relationships. They felt bamboozled.


Was this the company leaders' desired outcome? Of course not.


But the impact was jarring and sadly, because this challenge went unaddressed, cracks formed in the cultural foundation.


So, who dropped the ball? Who should have taken responsibility for this?

We could argue that anyone could have had the courage to speak up, but...


Leaders, when it comes to culture, WE have to be vigilant. We have to cultivate trusting relationships with team members who will feel safe telling us when we’re missing something.

We’re human.

We’ll make decisions that create unintended outcomes.

We’re responsible for filling the cracks.


Do these things to stay vigilant about your team's culture:

  • Ask for feedback: in-person, anonymously, from your peers, leaders, and employees; ask what they need more and less of from you

  • Ask what keeps them up at night: By doing so, you're uncovering pain points that may be going unacknowledged and creating an opportunity to provide empathy, support, or solutions

  • Observe how your team solves problems: Are they coming to you when they could go to each other? If so, get curious. "What's holding you back from talking to (teammate's name) about this?" Listen to the response. Is there a need to repair trust? Build communication skills?

  • Tap into their purpose: "What is the most meaningful work you do here?" Or "on a scale of 1-5, how much of your work is rewarding?" Then get curious about what constitutes rewarding work, so you can give them as much of it as possible.

  • Ask what you're missing: humbly assume you don't know or see everything; ask your employees what you should be aware of that you may not be seeing



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