Building, maintaining “deep wells” in a growing organization

At some point in your startup’s growth, you’re going to find more distance between you and your employees, particularly individual contributors. It’s an inevitable and appropriate part of scaling a business, with more of your time going into strategy, partnerships, recruiting, investors, etc. Hopefully, you will have a strong management team that you can lean on to synthesize and share important team-level feedback. But in order to truly stay on the pulse of your company and culture, you also need to build and maintain “deep wells” within the organization — relationships and open lines of communication with employees at all levels.

I first received this advice about eight years ago, when our headcount went from three to 30 in about 18 months. Since then, from 30 to more than 100 employees, I thought I was doing a pretty good job with my deep wells. I’d periodically take random employees out to lunch. We had lots of happy hours and company events where I’d mingle with as many people as possible. I’d try my best to have casual conversations in the community kitchen. I repeatedly invited employees to put time on my calendar if there was anything they wanted to discuss, and I sat in the middle of our open office and encouraged people to swing by my desk to chat at any time.

But during my annual performance review for the past two years, by far the biggest theme was that employees wanted more CEO interaction, but were intimidated by me. Intimidated? I couldn’t believe it. The advice from my management team was to be more chatty, curious about what everyone was working on, eat lunch in the break room instead of at my desk, etc. “Just make it more organic,” they said. I tried all these things, but had mixed results.

So I brought the issue to my CEO coach, who asked me if I had regular one-on-one meetings with people other than my direct reports. I told him about my lunches, which I thought worked OK. When he forced me to objectively assess how well the lunches were working, I had to acknowledge that they didn’t always foster conversations that uncovered useful insights or help develop stronger deep well relationships. The lunches could be a little awkward and disorganized, and the random nature of the lunch invitations would sometimes create unintended anxiety. Furthermore, it’s really quite challenging to have a good two-way conversation when you’re stuffing your face with a cheeseburger and the server is constantly interrupting.

After some more discussion, my coach and I decided to experiment with a series of “rapid fire one-on-one” conversations. I would block out a couple of hours at a time and fill it with 20-minute conversations with a mix of employees who would be given three intentionally ambiguous prompts to consider in advance.

  1. What’s one thing that’s going well?
  2. What’s one thing that could be going better?
  3. What’s one idea that you have?

I had my first rapid fire one-on-one with one of our QA engineers, Syed, who was eager and thankful for our conversation. He had some great ideas about documentation, QA tools and even content marketing, which I encouraged him to pursue in various ways. I figured this first conversation was an exception; there was no way other people would be so prepared, grateful and passionate. Amazingly, they were. I have now done 23 such conversations with more scheduled, and the ROI is through the roof. Here are some of the benefits so far.

  • Certain important themes emerged right away. For example, people were craving more “forced” interaction with other teams. It’s great to have happy hours, they told me, but it’s a hard format to get to know folks on other teams. So we immediately brought back our Lunch Roulette program in which we randomly choose five to six people for a company sponsored lunch outing once a week. We launched Whiteboard Wednesdays using a topic to spark a fun conversation starter among employees each week. We even created a Culture Committee led by an employee who was particularly passionate about the topic. All of these initiatives have been low-cost, warmly received and useful so far. Many of the ideas, concerns and areas of interest were things that were relatively easy to address. And in most cases, the employees already had some solutions in mind. The rapid fire format also allowed me to help connect people with similar interests, which has facilitated some nice cross-functional collaboration.
  • These 20-minute conversations were tremendously helpful for my rapport with employees. The intimidation perception seems much improved, and it’s made it easy to have more causal interactions with employees. Following up with people about their ideas and agreed upon next steps has created a great connection point.
  • The brief coaching and encouragement I am able to provide in these meetings has, I’ve heard, been empowering to employees and deepened their engagement at Wyzant. “Why don’t you do some research and write your findings in a one page document that you can share with your manager,” or “Joe is the person who’s closest to that part of the product, so why don’t you run your idea by him.” You may think that your employees all know about your “open door” policy and are comfortable sharing ideas and feedback without being given a platform. But it’s amazing how much more you get by providing a simple, time-bound, comfortable platform for feedback.

The bottom line is that our company, like all companies, is merely a sum of its people. It’s crucial that everyone feels like we are in this together, we can all solve problems, and great ideas can come from anywhere. Rapid fire one-on-ones have been a great tool to engage employees and very valuable to me as well.

Andrew Geant is CEO and Co- Founder of Wyzant