You Can't Put Culture on Autopilot

I am not a culture expert. However, as CEO of Reachdesk, a fast-growing software company, I think a lot about culture these days.

There is no shortage of research and thought leadership on the topic. Many organizations “talk” about culture. Some “talk” a lot about it— They pour the culture Kool Aid out. They indoctrinate new hires from the get-go and constantly impose their ideas around culture on their teams. Their teams find themselves drowning in ideas around culture.

From the top down the culture starts to feel inauthentic, disconnected and scripted. Countless times, I have listened to executives talk about positive culture. But a quick walk out of the Ivory Towers, conversations with different team members reveal misperceptions and misalignments between management and their teams.

And you may think this only happens in big companies in suburban office parks, but it doesn’t— it happens at companies at all shapes and sizes, including startups. How do so many leaders become distant and disconnected from the reality of the culture in their own organizations? It’s because too often they treat culture like a one size fits all sweater. They apply corporate culture policies through a cookie cutter approach. Let me explain.

You walk into the hottest new tech startup and what do you see? Quotes plastered across the walls from famous people throughout the years. At their regular town hall meeting, what do you see? Scripted executives, answering the same questions on repeat. And afterwards, they pat themselves on their backs for transparency. As you peer around the office, what do you see? An open concept office, that’s silent, uncollaborative, and political, enabled by leadership’s distance. It's static. It's uninspiring.

How did culture become a coffee table book with a nice pretty picture on the front, published once, and left in reception for everyone to ignore?

Again, I am no expert, but I think there are a lot of leaders that just go through the culture motions and expect that it is going to work.  Or like me in the past, letting myself get caught up in all the work, the crazy schedule, and the never ending projects. I would forget to pay attention, or use being busy as an excuse not to do so.  Culture can’t be put on auto-pilot. Culture is a conversation.

One day in a previous organization, I heard a few negative undertones surrounding a team. I was surprised. We just performed a culture survey, and for the most part the feedback was incredibly positive.  Concerned and curious about the disconnect, I had a conversation with one of the team members. I told her I was surprised to hear some grievances surface. I didn’t hear anything up until that point— No one brought it to my attention. No one asked for help.

She told me that the leadership team, including myself, was not asking enough questions. We were waiting for people to ask us, and we weren’t proactive in asking the hard questions. We were not asking the people on the ground everyday for what the sentiment across the organization actually was.

And it’s not that we weren't getting feedback, but the feedback often came from the same people— people who were empowered and secure within the company. Those less empowered, less confident, less recognized didn’t speak up in our surveys.

Our culture surveys were formulated to answer top down questions, not to solicit bottoms up ideas.  We didn’t provide anonymity to make it safe for folks to ask leaders difficult questions. We didn’t look proactively for the new ideas and  insights we needed to understand and prepare us for tomorrow.

This was an epiphany moment for me.

Unintentionally, we created pathways that excluded so much valuable and important feedback.  Unintentionally, we were reinforcing the culture of a few at the expense of the many.  

What a huge problem, but what an incredible opportunity to learn to be more proactive in finding ways to gather more valuable information from more team members.  It was an opportunity to make it safe to provide feedback. We had to break the old processes and pathways.  We had to have a conversation.

What is a Cultural Conversation?  

If you want to have a strong culture,  you need to cultivate cultural conversations. What does this mean? Here are 7 concepts to think about.  

First, there is no start or end to the conversation.  

If this is about culture, then we need to commit to our culture being alive. It’s a living breathing part of our organization. The conversation is ongoing and needs to be tended to continuously.  Commit to proactively asking way more questions to way more people than you normally would. Find ways to tap into this conversation weekly to keep it relevant and alive. And since your organization is ever-evolving and growing, your cultural conversations not only are about culture today, but also what we want it to become in the future.

Conversations are not presentations.  

No one wants to hear you talk. Trust me— I spent years in sales. Don’t present to your team about culture.  Don’t train them on company culture.  Instead, engage your team members to talk about your culture and to contribute to the culture through their own words and actions. Leadership’s job is to prompt the conversation. Facilitate workshops, leverage slack channels, use surveys, but never present. If you do your job as a leader, the concepts will come from your team and be led by your team.  

Conversations are not waiting to answer questions.  

If you are waiting to get asked about an idea or problem, chances are it is already a missed opportunity.  How do you ask more questions?  The first leadership trick here is to turn questions back to the team.  Again culture has very little to do with the leader.  If you are one of a team of 100, you individually contribute 1% to the true culture of the organization. As the leader then, it is your responsibility to resist the temptation to answer questions and bias the company’s ideas— Your responsibility is to turn the questions around and pose them back to your team.  Common themes and patterns will emerge from these conversations.

Conversations are not restrictive.  

My favorite thing at town hall meetings is when that one question comes up that the leadership team doesn’t want to answer. I love that. This is either the moment when leadership brushes it aside or they step up to answer the question.  Don’t brush anything aside.  If you can’t talk openly about something at that moment, what else is being hidden from the team?  Maybe nothing, but the perception becomes the reality.

Conversations are open and safe.  

You will never really know what concerns folks if you don’t provide a truly anonymous way for your team to contribute to the conversation. Not every feedback opportunity has to be or should be anonymous. Anonymity has a time and a place. You should educate your team members on the value of providing different levels of anonymity and disclosure to address certain types of issues.  For example, knowing that X is a problem is helpful but it is often more helpful and actionable to know that X is an issue in this particular department and this particular team. Educate your team on the different levels of disclosure and how best to apply and leverage them to instigate change.

Conversations are inclusive.

If you are hearing something from one group, that’s a great opportunity to ask another group about the topic. Proactively seeking opinions from different teams and from people with different backgrounds will give you well-rounded feedback. Broad engagement from different stakeholders will help fill in your blind spots.

Conversations are hard.

Nothing listed above is easy.  None of these topics are easy to do consistently. It is hard to keep this conversation active, consistent and inclusive. This conversation is the hardest thing to build into the DNA of your organization. But building and nourishing your culture isn’t and shouldn’t be easy.

Team Culture Workshop Exercise:

How to start a Cultural Conversation?

A great exercise you can use to start a cultural conversation is a future vision workshop. I have used this approach many times. It helps tee up a great cultural conversation by having the team come to agreement on core cultural elements and changes required to sustain that culture. It also empowers the team to feel ownership of the culture in their daily routines and opens a conversation around change.

I have used this workshop in moments when I introduced myself to a new organization. I used it successfully when taking over an under-performing team.  I used it in both small and large team settings.  It's not hard to do, and I have found it to be a great way to start a really important cultural conversation.

1) Ask the team to write on the board the positive & negative words that describe their teams’ culture today. Write them all down on a white board.

2) Ask the team to come up with words that describe the team from the perspective of another group.  What are the perspectives of a different team, different job function, leadership, board member, investor, customer, competitors of this team?

3) Ask the team to describe words that describe the perspective they want these different groups to have of them 2 years from now.

4) Ask the team to describe the words that describe the perspective they want within the team 2 years from now.

5) If we want to get there in 2 years, what do we need to get done in 1 year to get us on that path? What then must we do this year to get to the 1 year goals?  How do we make and own those changes together?

Again, I am no expert on culture. It’s a fluid and complex topic that many leaders, including myself, are trying to navigate. But I am committed to the journey, I am committed to the conversation.

Alex Olley
Co-Founder, Chief Commercial Officer

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