Overcoming Challenges: Evolving Company Culture

The hardest challenge wasn’t getting employees to engage. It was getting leadership to let go.

When I led Culture Club at Microsoft, in Azure, the whole design was employee-led: teams ran their own cultural experiments, chose what to try, and were judged on what they learned, not whether leadership approved. That sounds simple. In practice, it ran straight into the deepest reflex leaders have—the urge to steer. The moment an experiment went in a direction leadership wouldn’t have chosen, the instinct was to step in, correct it, guide it back. And every time that happened, it quietly killed what made the initiative work. People can feel the difference between “you own this” and “you own this as long as you do what we’d have done.” The second one isn’t ownership. It’s permission with a leash, and people disengage from it fast.

So the challenge was really about the leaders, including me. We had to learn to tolerate experiments we didn’t control and outcomes we wouldn’t have picked, and to resist the reflex to rescue or redirect. What let us overcome it was reframing leadership’s job entirely: not to direct the experiments, but to protect the conditions and remove barriers, and then genuinely get behind whatever employees built, even when it wasn’t what we’d have built. Concretely, that meant leaders sponsoring without steering, and holding our own discomfort when something went sideways rather than reaching in to fix it.

What I learned has shaped everything I’ve done since. You cannot delegate ownership while keeping control; they’re opposites. The real work of changing culture isn’t designing the right program. It’s the leader’s willingness to let people do things differently than you would, and to survive the discomfort of not controlling the outcome. The moment we did that, something shifted: people stopped waiting for permission and started genuinely owning the culture. And a surprising thing happened: they stopped complaining. Complaining is what people do when they see a problem but don’t believe they’re allowed to fix it. Once they had real permission, that energy went into experiments instead of grievance.

The lesson in one line: culture doesn’t change when you give people a program. It changes when leaders can tolerate not being in control of how it changes.

One of the hardest parts of evolving culture in an 80-year-old family business was helping people understand that change did not mean everything that came before was wrong.

We were not trying to replace an 80-year culture. We were deciding deliberately what deserved to come with us into the next 80 years.

That distinction mattered. Many of our employees have deep institutional knowledge, long-standing relationships and tremendous pride in what they helped build. I learned that what leaders sometimes interpret as resistance to change can actually be a much more human question: “Does what I helped build still matter?”

So rather than framing culture evolution as a break from the past, we focused on three things: what we wanted to preserve, what needed to evolve, and what we had to let go.

We preserved the strengths that had made the company successful for decades: expertise, customer commitment, resilience and pride in the work. We evolved the behaviors we needed to operate differently as the business grew, including greater accountability, stronger cross-functional collaboration and more transparent communication. And we became more willing to challenge practices that existed primarily because “that is how we have always done it.”

One of our values, “Win as One Team,” became a useful example. We translated it into specific expectations: share information earlier, own outcomes beyond your function, and solve problems across departments rather than simply handing them off. We also reinforced those behaviors through recognition and leadership expectations, so the values became more than language on a wall.

The timing was especially meaningful because we were celebrating our 80th anniversary while also introducing refreshed values and expectations for the future. I realized those messages could not compete with one another. They had to connect.

What I learned is that culture change fails when people believe the future requires them to disown the past. People are far more willing to move forward when they understand what is being protected as clearly as they understand what is changing.

The work of culture evolution is knowing what to honor, what to evolve and what to leave behind.

One challenge in developing our team culture was helping people understand what “care” should look like in everyday work.

At Zeva, we bring together advances in scalp science, trichology expertise, and genuine care. The science and technical knowledge give us clear things to teach our trichologists: what to look for during an assessment, how to evaluate a treatment, and when a concern needs further investigation. Care takes more explaining. Everyone can agree that clients deserve it, but that does not necessarily mean we all picture the same thing.

I came into this business after losing hair following cancer treatment and struggling to find effective help. That experience shapes how I think about the person sitting in front of us. But I cannot expect everyone on the team to have been through what I have. I need to explain how that experience influences the choices I make.

Product selection is one example. I often remind my staff that safety comes first, and I ask myself whether I would feel comfortable with my own children using a product every day. That does not replace checking the evidence or assessing a client’s needs. It makes the responsibility feel personal: someone is trusting our advice and may take that product home and use it long after their appointment.

The same thinking applies to a conversation with a client. Have we explained something in a way they understand? Have we given them room to ask what is worrying them? If they seem unsure, do we pause and find out why? These are small decisions, but they are where care becomes something a client can actually feel.

What I learned is that “be caring” is too vague to be useful on its own. I have to connect it to the ordinary choices we make throughout the day, so the team understands what I am asking of them.

The hardest one was that I was the problem. I wanted a team that pushed back and made decisions without me, and I had built the opposite by being the fastest person in every conversation. When you answer first, consistently, people stop forming their own view. They wait. Then you get frustrated that nobody takes ownership, which is a complaint about a situation you created yourself.

What fixed it was going last, deliberately, in every meeting for a few months. It was uncomfortable and the silences were long. Some early decisions were worse than mine would have been, and I had to let a few of those run instead of stepping in, because rescuing a decision teaches everyone the old lesson all over again.

What I learned is that culture is downstream of what the founder rewards in the moment, not what the founder says in a meeting about values. If the fastest route to approval in your company is agreeing with the boss, that is the culture, whatever is written on the wall.

The hardest culture move for me was getting my team to stop treating each sales channel like its own territory. When we were running marketplace listings, direct-to-consumer, social commerce, and clinic and boutique accounts at once, each channel had someone who guarded their numbers and their inventory. People quietly hoarded units rather than let another channel’s promotion use them.

I broke it by changing what we reviewed together. Each channel used to report its own wins. We started every week looking at total customer count and total sell-through across all channels, then talked about where a unit belonged that week. If a marketplace push would move stock faster than a boutique order, we moved it, and the person who gave up the units was the one credited in the meeting.

That took a few months of me repeating it before anyone trusted the credit structure. Once people saw that giving away inventory kept their standing intact, the fighting dropped off and we started planning launches on one shared calendar. When we expanded into the UK and Germany, my team already knew how to hand off volume across regions, so a new market became another line on the same board.

Since we’re bootstrapped, every dollar we spend has to earn its place, and that mindset shaped our culture more than I expected. The hardest part was getting the team comfortable saying no to fast growth if it meant compromising something else.

One early debate was around discounting to close deals faster. I pushed back hard, and instead we built the free case backfill for annual contracts, which let firms switch without eating a huge upfront cost. No discount needed, and usage climbed immediately because pricing stayed usage-based.

That decision became a pattern for how we operate. We’ve kept nearly every customer we’ve signed, over 150 firms now, and I credit that to choosing sustainable growth over quick wins. The lesson stuck with me: slower, disciplined growth beats chasing numbers that don’t hold up later.

As CEO of AITAKON, a B2B pet hardware manufacturer supplying over 50 global brands, our biggest cultural hurdle was transitioning our team from a traditional “cost-and-speed” factory mindset to an “empathy-first engineering” culture.

The Challenge:

In traditional manufacturing, success is historically measured by volume, output speed, and shaving cents off unit costs. When we set out to build higher-grade smart pet hardware, our production and engineering teams initially treated products simply as molded plastic and circuit boards. There was resistance to adopting rigorous pre-production testing or upgrading to costlier materials like 304 food-grade stainless steel because it slowed down standard production lines.

How We Overcame It:

We changed how we define and reward performance. We stopped evaluating R&D and QA teams solely on delivery deadlines and began tying performance incentives directly to product failure reduction and safety benchmarks. More importantly, we instituted hands-on testing where engineers took 3D-printed prototypes home to evaluate them with their own pets. Once the engineers physically watched a dog struggle with an overly hard toy or saw a cat hesitate at a vibrating water pump, the mission stopped being an abstract corporate policy and became personal.

The Lesson:

You cannot mandate empathy through a handbook. To evolve a company culture, you must align your actual operational KPIs with the quality standards you preach—and create opportunities for your team to see the real-world impact of their work on the end user.

The hardest culture change we’ve run had nothing to do with values on a wall. We asked our own team to do all of their hiring inside our own product, and for a couple of months people quietly kept a LinkedIn Recruiter tab open on the side. Nobody was being difficult. They didn’t trust the thing yet, and telling them to trust it more did about as much as you’d expect.

What broke the stalemate was making the workaround visible instead of banned. Every Monday we walked through any hire that came from outside the product and asked what the product failed to do. Half of those turned into bug fixes, the rest into people finding out they’d been avoiding a step we’d already fixed. Took about five months. All a mandate did was move the workarounds somewhere I couldn’t see them.

The hardest culture challenge we faced was fear, not skill. When AI started landing in our workflows, the reaction across the company was that it would replace people. That is a culture problem before it is a technology problem, because a team that is afraid of a tool will quietly refuse to use it no matter what leadership announces from the top.

We did not overcome it by mandate. What changed things was watching a handful of early adopters actually use it and realize the opposite was true. They cleared the mechanical parts of their work in a fraction of the time, which freed them for the higher-judgment work, and their quality went up, because the hours that used to go into pulling data together by hand now went into checking and improving it. Once the rest of the team saw that firsthand, the fear turned into curiosity.

The lesson is that culture does not change because you declare it changed. It changes when people see the benefit with their own eyes. Show them proof, not a policy. And the mistakes AI makes turned out to be the point, not the problem. Correcting the tool is exactly where a person’s judgment matters more now, not less.

One major challenge I faced while changing company culture was resistance from long-tenured colleagues when I led change at a two-hundred-year-old organization as the youngest person on the team. I overcame it by taking time to listen, ask questions, and understand objections, and by clearly explaining what was changing and how it would affect people. I also gave skeptics concrete roles to execute or provide feedback on during implementation so they were engaged rather than sidelined. The changes themselves did not alter, but addressing those conversations exposed communication gaps and helped people feel heard. I learned that securing buy-in is more important than seeking full consensus and that channeling dissent into responsibility produces better outcomes.

One of the hardest culture changes I led came during the rebuilding of an early childhood education organization after a period of significant instability. The real challenge was not introducing new ideas. It was rebuilding trust in an environment where people had already experienced inconsistency and disruption.

I learned quickly that culture does not change because leadership announces new values. It changes when people repeatedly experience a different way of working.

Instead of beginning with broad culture statements, we rebuilt the operating structure: clearer responsibilities, stronger protocols, more consistent communication, and defined expectations for how decisions were made and how families and staff were treated. Leadership also had to demonstrate those standards consistently rather than asking others to adopt them first.

Over time, the organization became more stable, enrollment recovered significantly, and the internal culture became far more consistent.

The biggest lesson for me was this: culture is not what an organization says it believes. Culture is what its systems repeatedly allow, reward, and reinforce. If you want to change culture, change the daily experience people have inside the organization.

The challenge we faced was bringing on people who had come from larger, more structured organisations and helping them adapt to the pace and ambiguity of a startup. The behaviours that serve you well in a big company, waiting for sign-off, being careful not to step on other teams, managing upward, can actively slow things down in an early-stage environment where everyone needs to just make calls and move.

The way we overcame it was being much more explicit about what we actually expected rather than assuming people would figure it out. We started naming the behaviours we valued rather than leaving them implicit. Things like making a decision with imperfect information and flagging it afterwards rather than waiting for certainty. Once people understood that moving fast and being wrong occasionally was genuinely okay, the culture started to shift. The lesson was that culture change requires you to name what you want clearly and then model it consistently yourself.

One of the biggest challenges I faced was realizing that the culture I created naturally when my company was small wasn’t going to scale automatically as we grew. In the beginning, I knew everyone personally. I was involved in everything, and our values were communicated largely through how I showed up every day. As the company grew, I had to accept that culture couldn’t just live in my head or depend on my personality.

We overcame that by getting much more intentional about defining what we valued, how we communicated, and what those values actually looked like in practice. More importantly, I had to empower other leaders on my team to carry the culture instead of feeling like I had to personally protect it.

The biggest thing I learned is that culture isn’t something you establish once and then preserve forever. It has to evolve as the company evolves. Growth will expose the places where you’ve been relying on relationships, intuition, or “the way we’ve always done it” instead of actual systems. The goal isn’t to keep your culture exactly the same as you scale. It’s to make sure the things that made it special in the first place don’t get lost along the way.

The thing I’ve found most challenging regarding company culture is the sometimes tension or distrust from the original or longer-term employees with new hires. My company is growing rapidly, and I’ve had struggles with early employees feeling like they aren’t as “key” as they used to be as I’ve added more high-level people to my team. I have found managing egos to be an extremely important part of what I, as a founder, have to do.

I think what’s helped me the most is overcommunication and continual reassurance with the long-term team members that we are in a growth stage and I’m bringing on more people to help them, not replace them. I do my best to make everyone feel like the new hires are going to make their jobs easier and they shouldn’t look at it as a threat, but a blessing and an exciting sign of where we’re going as a company. This isn’t easy, but I’ve been very much in the thick of this problem the past 6 months.

If you announce a culture change to 60 remote people, roughly nothing happens. Maybe 4 of them read it twice.

Our headcount is around 60, and everyone works from home, so what I wanted to change was the expectation that a message gets answered within 10 minutes. People sat in chat all day to look present. I wrote the policy, and it did not survive the first genuinely busy week. What worked was smaller. We put an agenda requirement on every internal meeting and let anybody decline one without an agenda. Response times drifted out on their own once fewer meetings were breaking up the day. 2 of our leads still sit in chat all day and have not moved an inch.

One of our biggest cultural challenges was preserving the speed and ownership of a startup while introducing the accountability and operational discipline required of a larger healthcare company.

As MEDvidi grew, informal communication and individual heroics were no longer enough. At the same time, adding too many processes risked slowing innovation. We addressed this by creating a culture that is intentionally “tight” around patient safety, compliance, clinical quality, and measurable outcomes, but “loose” around how teams experiment and solve problems.

We also made it safer to discuss failures openly. Instead of hiding missed targets, we examine what happened, what the data tells us, and what needs to change. The biggest lesson was that culture cannot remain static as a company scales. Leaders must continuously clarify where consistency is essential and where employees should have the freedom to challenge assumptions and move quickly.

I’ve organized sourcing trips across multiple countries for over 300 entrepreneurs, and the biggest culture problem I kept running into was process. My early trips had unclear decision-making structures, so people defaulted to whatever felt comfortable, which usually meant siloed work and no accountability between groups.

I started changing how work got done. Before each trip, I now run a data-driven assessment of the group. I look at prior sourcing experience, risk tolerance, and collaboration style.

That assessment tells me where the friction points will be before anyone gets on a plane. Then I restructure the working groups around cross-functional tasks with shared deliverables, so collaboration becomes a structural requirement.

My own behavior had to change too. If I wanted people to flag problems early and share supplier contacts openly, I had to do it first, visibly, in real time, in the daily decisions about which factories to visit and how to split negotiations. I started sharing my own supplier contacts in front of the group, walking through my reasoning on factory selection out loud, and pulling people into joint negotiations instead of assigning them separately.

A meaningful culture challenge was reducing the romance of certainty. Wellness businesses are often rewarded for sounding definitive, even when the underlying science is early, mixed, or context-dependent. That pressure can shape internal culture, making teams feel that confidence is more valuable than precision. In a category touching sleep, recovery, and grounding, that is a risky norm. I wanted a culture where nuanced communication was treated as a strength rather than a conversion obstacle.

The practical answer was to make language discipline part of operations. Terms like supports, suggests, and remains unclear were not legal hedges; they became markers of intellectual honesty. I also treated customer education as a human-factors problem because people need clear explanations without false certainty. The lesson was that trust compounds when a company resists overstating what it can prove. Short-term persuasion is easy, but durable credibility comes from leaving room for uncertainty without sounding evasive.

When we expanded our remote team, I wanted to begin building relationships between team members, even though they might only see each other in person once a year. I instituted a process where each new team member had a 20–30 minute call with each other team member, where the desired outcome was simply to get to know each other. New team members were responsible for scheduling these Zoom meetings within their first 2–3 weeks on the job, and compliance was tracked.

The goals for these meetings are:

– build initial connection between team members

– help new team members feel more comfortable and a part of the team

– foster cross-team communication

– remind and reinforce the importance of relationships on our team—to both the new and existing team members

This practice continues to meet all of those goals and is one of the most important parts of our onboarding process. I recommend this foundational practice to others frequently.

The biggest challenge that I faced was actually just trying to figure out the specific steps to take to achieve what I was hoping for. I knew what our culture was like at the time and what I wanted it to evolve into, but I wasn’t sure what exactly should be done to get from point A to point B. I was basically all idea but no plan! It made me realize that, being in my position as a leader, I couldn’t exactly see things from the same perspectives as my employees, and that was creating that mental block. Once I realized that, I knew the only way to figure out what to do was to get input from my employees, so that’s what I did. That experience only reinforced the importance of making sure your employees have a voice and are included in decision-making, so that was the biggest thing I learned.

One major challenge was that remote work exposed long-standing communication gaps, and my first instinct to add more meetings only increased fatigue without fixing the problem. I addressed this by establishing clear ownership for projects so everyone knew who was ultimately accountable for decisions. That change improved day-to-day communication and reduced the time wasted chasing answers across teams. I learned that culture shifts come from setting clear expectations and building habits of open communication, not from more meetings or one-off events.

One of the biggest challenges I faced was realizing that the culture I had built around my company no longer matched the company I wanted to have.

Early on, I was very focused on being responsive, accommodating, and saying yes. That approach helped me build strong client relationships and grow the business, but over time it also created a culture in which everything felt urgent and too much of the business revolved around other people’s priorities.

As the company evolved, I had to change that. I became much more deliberate about the kind of work I accepted, the standards I expected, how I communicated with clients, and how I protected time for strategic and creative work. That meant saying no more often, establishing clearer boundaries and, importantly, modeling those boundaries myself.

The biggest lesson was that culture isn’t something you create with a mission statement. People learn what a company values by watching what its leader actually does. If I wanted a company built around thoughtful, high-quality work rather than constant urgency, I had to demonstrate that in the way I ran the business.

That experience taught me that evolving a company culture often starts with the leader being willing to change first. Once the behavior changes, the culture has a much better chance of following.

One challenge was changing the internal view of negotiation. Many people assume leverage comes from the demand package itself, but in practice it often comes from what the other side believes will happen if the case does not settle. When a team treats negotiation as separate from litigation, offers may reflect that gap. Insurers read preparation levels with surprising accuracy.

I worked to align negotiation strategy with actual courtroom readiness, including damages organization, witness consistency, and motion posture. That changed the tone of settlement discussions because the case no longer depended on persuasion alone. The lesson was that culture shifts when people understand that preparation is not overhead. It is the source of credibility, and credibility is what changes negotiating power.

One of my biggest challenges has been trying to create a strong culture in a fully remote company. We’ve realized that in-person relationship building is invaluable for a strong team and have been investing in opportunities where our team members get to meet and spend time together. In order to bring additional value to these opportunities, we have decided to sponsor events where our ideal customers tend to gather, bringing several team members to work together, as well as have social time opportunities. And this year, for the first time, we are all gathering off-site together!

Aligning on clear shared goals for growth, strategy and profitability, and having regular check-ins with our entire team. Consistent communication across the entire group kept everyone aligned. When your leaders are focused on the same aims, your culture stays strong, even while scaling distributed teams.