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I wanted to be friends with all my employees. Now I have 100

Ben Crudo writes about the excitement of helming a growing startup—and the challenge of ensuring that your company’s culture adapts at the same rate.

I wanted to be friends with all my employees. Now I have 100
[Photo: monkeybusinessimages/iStock]

I recently paced the length of my company’s new office, amazed at how long it was taking me just to walk from one end to the other. We’ve doubled in size over the past year, reaching a major milestone when we hired our hundredth employee not long ago. But as I walked down the hallway, I was hit with another realization: I didn’t recognize many of the faces looking back at me.

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From the beginning, we have tried to create a strong workplace culture at Diff, building the kind of company I had always wanted to work at. Over the years, this turned out to be a great way to keep employees. (We have a 90% retention rate in an industry notorious for high turnover.) A huge part of that culture has been making sure I build personal relationships with each new hire. Up until recently, it was easy to find time to connect, whether it was grabbing a beer after work or chatting before a meeting.

But suddenly, that’s no longer possible. I’m now faced with the challenge of having 100 people that I want to be friendly with, during a time when my responsibilities as CEO are evolving and there are more demands on my time than ever.

Talking with other founders and senior leaders, it turns out my challenge isn’t that unique. Some warned me not to expect the intimacy of the early days to last. Others emphasized that trying too hard to sustain an existing “culture” can end up stifling the creativity and independence of new hires. Everyone echoed the importance of treating people as individuals, even if that gets challenging at scale.

I’m under no illusion that I’ll be able to cultivate close friendships with everyone. But I really believe having a culture of personal relationships—where people feel connected to me, to the company, and to each other—matters. Here are a couple ways, some more effective than others, I’ve been working to make this happen:

No one gets a culture pass

I once heard that you can either have the company culture you want, or take the culture you have. For me, “just settling” was never a viable option, especially considering that culture alone can account for up to 30% of the differential in corporate performance.

With that in mind, we recently laid out five core values that were always part of our work but never really made explicit: creativity, collaboration, respect, accountability, and excellence. Nothing revolutionary here. But these aren’t meant to be just words on an inspirational poster. Instead, the hope is that having this common language and framework can help people preempt disagreement and find alignment.

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As we grow, I can’t monitor every single interaction to be sure our values are lived. But I can encourage everyone to see their role through the lens—and the language—of these five values. A concrete example: If someone is asked to stay late or work the weekend without being given prior notice, they’re encouraged to have a conversation with their manager. This can seem like a hard thing to do in practice (and is), but what can help is framing it not as an interpersonal conflict but a matter of misalignment with a core value, in this case, collaboration. With concrete signposts, conflicts don’t need to become personal—at least, that’s the goal.

That kind of values alignment is especially important for hiring. Research has shown that not hiring a toxic worker can save more than $12,000 in future turnover costs. For me, this means extra vigilance during the recruiting stage—hiring slower and more carefully even as we get bigger and grow faster. Referrals from existing employees (backed by a $1,000 referral bonus) have proven a great hack for keeping values aligned and chemistry intact.

The expectation of values alignment also extends to senior leadership. There are so many examples out there of executives and “rock-star” employees preaching one set of rules and living by another. But the reality is that leaders and managers play a far too pivotal role in spreading culture to give them a free pass. The longer someone works for me, the higher my expectations are that they live and breathe our values. No exceptions.

Engineer one-on-one interactions

These days, there’s rarely time for a spontaneous connection with a coworker at the end of the day or before leaving the office. The irony is that this kind of connection is probably more important than ever. Studies have shown that having one-on-one meetings with CEOs, managers, and team leaders makes employees more likely to feel engaged in their company and thrive in their jobs. So I hacked together a work-around: engineering that one-on-one time that used to happen all by itself.

I started using our HR department as a touchpoint to see who might benefit most from meeting (new employees, recently promoted folks, etc.) and then scheduling a 15-minute meeting with people a few times a week. Rather than talk about performance, I use the meetings as an opportunity just to be personable . . . and mainly to listen. And guess what? It’s been working. In the time it takes to drink a coffee, I’m able to form the foundation of a friendship with each person and have received positive feedback as a result.

I’m also encouraging senior leaders to find the time to have these one-on-one meetings. After all, the idea that work occurs in a kind of professional vacuum is, frankly, ridiculous. Without checking in to learn a bit about people’s personal lives, how can we truly support them? I want a culture where employees feel comfortable telling me (or their manager) that they’ve been coming in late because their dog is sick and one where managers also feel connected enough to ask, “What’s up?”

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Bring in outside help

I’ve spent a lot of time talking about how important it is for culture to permeate every aspect of a company and how it grows and spreads from person to person. But the truth is at a certain point, this growth stops being organic, and it needs some outside help to continue thriving. Enter: values coaches.

Yes, this is a thing, and no I couldn’t live without them. Values coaches, at least the way we’ve used them, are a lot different from performance coaches or executive coaches. Instead of productivity hacks, what they offer is more or less a kind of “workplace therapy.” Staff set up meetings to speak with them about basically anything, whether it be job stress and expectations or just taking time to chat about the intersection of their personal and professional lives.

I brought in a coach for the first time a few years ago to speak with our senior leadership team. We now have three coaches who meet with all staff in leadership positions, with the goal of making coaching accessible to every employee. We’ve already enlisted these coaches to help develop new interview questions for job candidates, ensuring we’re looking beyond just surface-level professional qualifications.

My day-to-day life as CEO looks much different today compared to last year. There are many evenings I find myself quietly slipping out of the office, knowing full well that if I stop to chat, I may not make it home for several hours. I’m trying to make peace with the fact that casually grabbing a beer with my employees may no longer be in the cards. Now I have to schedule time to connect with people, and that’s okay. For me, it’s still a genuine chance to connect on a personal level and keep the culture we’ve worked so hard to build alive for the next 100 employees.


Ben Crudo (@BENGMN) is the founder and CEO of Diff, a full-service e-commerce agency based in Montreal.

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