Have The Hard Conversations!

Jake Johnson
UpLaunch
Published in
4 min readOct 10, 2017
The UpLaunch team in Las Vegas and Matt and I celebrating the official launch. (Some conversations happen with beer)

Last week, Matt Verlaque and I had a long conversation. We solved a ton of issues, did some strategic planning, talked about life, and reflected on our journey (check out some cliff notes from it — The No-BS Story Of How Our Startup Started Up). One of the issues that we explored was a decrease in productivity because we weren’t utilizing our strengths (and each other’s strengths) the way that we have done previously. The takeaways from our conversations are incredible (except for this blog — the blog is average).

Naturally, a portion of our conversations are centered around solving problems or answering questions related specifically to UpLaunch. However, on a personal level, we end our conversations with more respect for each other and motivation to accomplish what sometimes seems insurmountable.

Over the last few days, I have reflected on the growth that has resulted from our phone calls and realized that our conversations are so good because we are committed to bettering ourselves. It comes down to raw, unedited truths that are spoken in support of similar goals: creating the best lives possible for our families, our team, our partners, and for anyone involved with UpLaunch!

No one enjoys having hard conversations.

But here is the deal: When you commit to working with a team, you commit to having hard conversations. By avoiding uncomfortable dialogue, you’re guaranteeing that your team will begin to build resentment and decrease productivity — which will impact every person on the team and ultimately begin a slow and steady breakdown of your organization.

With every new phase of a business, there are new challenges. New challenges create discomfort, and discomfort creates anxiety. You get the point! Being an entrepreneur is a roller coaster of emotions. Over the years, UpLaunch has had a ton of hard conversations, and through them, we have learned a lot. It would be pretty lame if we didn’t drop some of that knowledge.

Here are five rules for enhancing team communication.

Rule #1: You must reflect on your own individual performance

It comes down to emotional maturity and recognizing other people’s thoughts, opinions, and beliefs. You have to be comfortable with who you are and what you are capable of doing.

Notice I did not say “comfortable with what you are doing.”

If you’re comfortable with your work, you’re complacent. Routinely as an entrepreneur, we are doing things we are uncomfortable doing. That is the beauty of it. You will not fail, you will figure it out (all about that mindset). A team depends on each player, so push yourself harder and challenge yourself! If you’re complacent or if you refuse to be your own harshest critic, you’re NOT a true member of the team — you’re an anchor who is slowing your team’s progress.

Rule #2: Embrace the difficult face-to-face conversations

Emails, texts, Slack messages, Notion comments, etc are all great, and they each have specific applications for team communication. However, there is NO replacement for face to face human interaction.

If you are working remotely — no problem! Use Zoom, FaceTime, or any of the hundreds of applications where you can see someone’s face and have a real conversation. Remember that it’s okay to have a little silence during these conversations as well!

Some of the best ideas or solutions we have ever had have come out conversations with awkward, mid-conversation silence. Just let it happen.

Rule #3: Be open and honest

If you are playing a shell game, you should probably just save everyone the time. Jump back to Rule #1 and look in the mirror for a little while. It almost seems childish to even bring this up. We are adults, working in the real world to accomplish amazing things. Right? Open and honest conversation solve a lot of problems before they even start. Be real, and say what’s on your mind — even when it makes you uncomfortable!

Rule #4: Don’t cry

I don’t mean in the “tears flowing” kind of way. It’s okay — grown men can cry. I’m talking about acting like a kid, throwing a tantrum, “how dare you to accuse me”, “it’s my way or no way”, the “blame game”, etc….

We are all playing together in the sandbox with the same toys trying to build a MASSIVE castle!

Do not let personal insecurities turn into an emotional outburst. When in doubt, go back to Rule #1. Never forget that we are all building the same castle — so don’t cry, just BUILD!

Rule #5: Keep the conversation focused on solutions

Nothing good ever comes out of conversations that start with accusations and negativity. If you are starting with that type of emotion, take a second and think about the fact that you are on a team. Put yourself in the other person’s shoes for a minute.

Your role as a team member is to help your teammates overcome weaknesses, not to just point them out without offering a solution. Ask if you can help them with anything! If everyone on the team takes a helping stance, each person’s strengths will be magnified, and their weaknesses will be minimized. The tide rises together!

Now round up your team and go have a conversation. Get in the sandbox and build that massive castle!

Have any thoughts or tips on communication? Drop us a line!

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Jake Johnson
UpLaunch
Editor for

Partner Director @UpLaunch, Owner/CEO @CFGettysburg, husband, and father. Life is Short. Be Nice. Be Humble. Be Purposeful.