28 November 2022

Building a Culture of Honesty and Learning – Remotely

“Your team is so nice”: Remote Work, Culture, Honesty and Learning



One of the greatest compliments I get for my company is:

  • “Your team is SOOO Nice.”
  • “Everyone here is so nice.”
  • “Those are some special humans you have there.”

We get this. A LOT. And it’s genuine. Our team of 8 shows up with a level of authenticity, thoughtfulness and care that sadly is rare in many businesses. Our people are engaged. They want to help others. They trust that everyone is doing their best. It’s not lost on me that if our people are our secret sauce, our culture is the recipe.

Here are the steps we took to shape our culture that made us pleasant people to work with:


We were intentional

We had someone on our team build a culture plan (thanks Eric Phung). It included things like daily Huddles on Slack, company All Hands Meetings, monthly Happy Hours, Lunch and Learns, special ways to acknowledge team members, and more. We haven’t done everything on this plan, but it kicked off many key connection points for the team. Super important in a remote working environment.


Constant learning is a company value

We instil a growth mindset. Everyone on this planet starts anything from a place of unknowing. I readily say that I ‘do not know everything’. We strive to create psychological safety around learning, trying, innovating – and fearlessness. (I recommend reading the Fearless Organization by Amy Edmondson – it is life changing for leaders.) Case in point … we don’t do a rating scale of 1-4 on performance plans. We’ve replaced them with Beginning, Developing, Practicing, Extending (similar to what you’d see on a modern report card). This creates an honest view of where someone is, without the negativity in receiving a 1 or 2.

Which brings me to…


Normalize stumbles

Mistakes are part of learning – and innovation. We have normalized this in our culture. In fact, during our weekly meeting, when we round table, we talk about a “stumble” from the previous week. As a leader, you might worry that this creates complacency or gets in the way of excellence. Here’s the benefit … because our people can identify and vocalize mistakes without fear of reprisal, as a team we are better able to analyze, learn and react. Our people can take risks confidently and bravely, creating a flywheel effect of improving and innovating – and coming up with better solutions.


Coaching approach

In the spirit of constant learning, all of our people – even those early in their career journey – have been trained on the coaching leadership style, aka the GROW methodology. Again, this serves to build the understanding that everyone can contribute; everyone has ideas that matter; everyone has an answer within them. If you are unfamiliar with this, I recommend reading either Quiet Leadership by David Rock or The Coaching Habit by Michael Bungay Stanier.


We celebrate

We have a channel on Slack where all team members are asked to celebrate other team members. I avoided calling this “big wins”, or something similar, because I wanted to see a lot of activity in this channel. (Why wait for something “big” to celebrate?) We’ve even provided a framework for providing effective positive feedback (thanks Tanja Halsall from Potentia). Our team regularly gives thanks and shows gratitude for people showing up and contributing. It makes people feel seen in the workplace.

If you worry about creating a culture where everyone gets a medal, consider my next point:


Thoughtful candor as a value

We want all of our team’s opinions brought to the table. We expect everyone to speak truthfully and plainly. And when we do, we generally understand that the feedback isn’t coming from a weird place or ego-driven, it’s given with the shared intention of helping everyone improve. This doesn’t mean that we don’t mess this up sometimes – feelings do get hurt, and messages sometimes get misconstrued – but we don’t hide or avoid sharing feedback. We’ve created a trusting, honest culture as a result.


Convene your team

We do not have a physical office so I don’t have that overhead – instead I invest it in travel. We have folks in various locations. We hosted an in-person summit twice this year. Sure, remote work is magical, but nothing can replace having the team meet each other IRL, breaking bread, working side-by-side.


Invest in tech

Do. Not. Skimp. On. Tech.

Tech – whether Zoom, Slack, Miro, Monday.com, whatever – is the primary way that your team shares knowledge and communicates with each other. My business is largely run on Slack, and Slack Huddles, in particular, are a core part of our communication. Yes, this can add up. But if you are running a knowledge business like ours, it’s important to facilitate knowledge sharing and remove as much friction as possible. (Incidentally, Crisp is an approved Digital Advisor as part of the Canadian Digital Adoption Program. We can help you with your tech!)

Finally, if you haven’t read it already, read the classic business book The Five Dysfunctions of a Team by Patrick Lencioni. It’s required reading for any business leader. Getting past these five dysfunctions is the backbone of any healthy, trusting team culture.

Happy leading!