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Leadership and Listening

Jason Wishard
4 min readApr 9, 2017

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I can remember several years ago, Dan Brown (former co-manager at EightShapes) approached me because I had a bad day. A really bad day. So bad in fact, I tweeted about it. It went something to the tune of “It’s days like this, I really hate my job.” It’s the only tweet I’ve ever deleted in full regret. Sure, I’ve deleted other tweets due to bad spelling and grammar, only to repost, but that one I truly felt bad about only minutes after posting.

We all worked remotely, so Dan sent me a message over AIM (AOL Instant Messenger; this was before Slack) and said (paraphrasing), “Hey man, everything OK? I saw your tweet. Can we chat?” I of course said, “Sure.”

As I picked up the Skype call, my stomach turned, figuring I was in big trouble. Dan, as he always does, said calmly, “Wanna share what has you frustrated?” I then spent about 10 minutes telling him what was bothering me, the situation of conflict I could not get past, along with some other grumbles. He didn’t ask me any questions, he just listened. When I was finished, he said (again, paraphrasing), “I feel ya man. I’ve been in your shoes, we’ve all dealt with [difficult individuals name redacted], and it just so happens you’re turn has come to pass. Can I ask one thing? In the future, instead of tweeting about your bad day, send me a DM, chat, email, whatever you want, and I’m happy to listen. That’s what I’m here for.

That’s what you’re there for (in part)

That day, I learned something that only truly stuck and became a part of my daily mantra once I had a team. Listening is one of the hardest skills to be good at and one of the most beneficial to any leader and their team. This is my three-stepped approach to listening that I’ve learned and apply with anyone who wants me to listen:

  1. Take notes (preferably) and repeat back what you heard
  2. Ask to take action
  3. Follow through on the conversation

Repeat back what you heard

You won’t always get the opportunity to take notes. Many conversations I have, happen off the cuff, either in the hallway or while at someones desk. Don’t stop the conversation to get a pen and paper, let the conversation happen naturally. Actively listen and tease out (in your head)the problems that you can help with. This can be a team member conflict, a meaty discipline problem, or even time management. It can be anything. Pull those things out and confirm that what you are hearing, is what they are saying. Only do this once they have finished speaking.

Ask to take action

Again, avoid asking questions until they have finished. I look at listening like ideating through designs on paper. If you stop to ask tons of questions, you’ll miss the best ideas. The same is true when listening to individuals. Let them talk. The best nuggets come out when they are allowed to speak free-form. Once they have finished, and you have clarified what you heard, ask, “Where can help? What action can I take for you?” Let them define the action. If they want none, then take none. Sometimes, people just want to vent and that’s OK. If they want action, work together on a solution and repeat back what you heard for taking action. Then, follow through.

Follow through on the conversation

Last, but certainly not least, is the follow through. This comes in two parts:

  1. If they asked for action, follow-up with appropriate communication channels (Email, Slack, etc.) with the action you promised to take. It could be removing a road block or freeing up their time to get more focus.
  2. If they didn’t ask for action, still follow-up. It could be as simple as a hallway conversation a week later asking how everything is going on the project or if they are still having issues.

In either case, the process is continual, and you will basically rinse and repeat on the above three steps.

Continual Listening

Listening has no end game; it will always happen. Sometimes it will be good, and sometimes it will be bad, but it will always happen. The more you do it and the more I’ve followed the steps above, the more people have trusted me to not only help, but to listen.

This post is in response to Thomas Meimarides more recent post and Laura McGuigan’s post from some time ago. Both of which are fantastic posts on war stories of leadership.

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