I screwed up last week—don't make this communication mistake

I screwed up last week.

And it had potential to be really bad.

Every week I sit down to write this newsletter, sharing leadership lessons I’ve accrued. Usually these admonitions have steeped in years of reflection and application. With time, I have not only thought about what happened and what I learned, but I’ve lived through several iterations of similar situations.

Last week I made a mistake, recognized it, and made an immediate effort to fix it. I think it’s fitting to share here, while it’s fresh.

Theodore Roosevelt said nine-tenths of wisdom is being wise in time. This is a bit of a double entendre. Roosevelt meant wisdom is knowing when to act on knowledge, but I see another meaning.

Wisdom is more than decisive action and awareness. Wisdom is the application of knowledge, which often comes with time.

I’m reminded of a sign I saw while visiting someone in prison once, which puts this another way:

“Knowledge is knowing the street is one way. Wisdom is looking both directions anyways.”

Let’s look both ways.

The mistake

As most startups in the United States right now, our team is under a lot of pressure. While some businesses may be happy with 20% growth in revenue, venture-backed startups need 100%, if not far more. In addition to this pressure, we’ve launched a new product that is betting big on our tech and team. It’s created a demanding environment right now, and many people on my team are navigating changing roles. For the record, we love this kind of pressure—it’s why we all signed up for a startup. But still, it’s a lot at times.

Our team gets hourly revenue updates to Slack. At any given moment, we know how much money we’ve not only made today, but within the last hour. A recent partnership with a brand had stirred some conversation around revenue, and I chimed in. A team member defended a different position, and I double downed in disagreement.

The employee took it to a direct Slack with me, and I leaned in again. I bit back, and hit hard. I am absolutely slammed right now, and in my attempts to end a conversation quickly, I hit with too much force and with too little explanation.

I’ve seen this play out with many leaders in the past. I’ve been victim to this myself, via emails long before we had instantaneous chat communications. Written communication is often misread. Think of how many times you’ve labored over someone’s short text or email, reading into something that turned out to be nothing.

This happens with leaders all the time.

They are busy, and they “resolve” or answer a question briefly, but give little thought to how something might be interpreted. Or worse, they don’t think about the emotional consequences.

Many leaders despise emotions, and it’s weird. I want people who care about their work, and the challenge that comes along with that is you’re going to have employees who are not going to back down and will go toe-to-toe with you.

I felt the situation unraveling, and realized I was doing exactly what I used to hate as an employee.

Pick up the phone

In 2020 when COVID hit, I wrote a blog predicting some of the challenges ahead. One of which was the challenge of written communication. Most notably from this piece:

“Remember, communication via Slack, email or whatever non-human system you are using always comes off stronger than you intended. I am most guilty of this. I am a blunt and bold communicator and this one bites me sometimes. Over-communicate with gratitude, and lose the attitude (seriously, I needed this advice as recently as yesterday).”

I’m apparently still guilty of this. I always have been—every year at my last ad agency, my review was some version of “Brad, we love you, but your communication is just too blunt. Can you please soften the blows?”

I’ve worked really hard to do this. Up until this past week, I thought I was past it. I saw my old self rearing his ugly bald head, and immediately knew what to do.

I picked up the phone.

I did not change my position. My position was not wrong, it’s just that I was operating with context my teammate did not have, and I had made no effort to share it. I was being a stereotypical leader, throwing hard hitting jabs, establishing my power, and looking for a knockout.

While my position wasn’t wrong, how I delivered it was poor. I also had not shared the critical context that was informing my decision. I took the time to do that during the call. I apologized, and I made a public apology to the team who saw the argument commencing.

I also told the team member I cared about them, and know they’re going through a lot with our shifts in the business. I said I needed to do a better job of communicating how that was going to impact them, but was honest in that I haven’t yet figured it all out.

And there was the power in calling. Admitting that while I’m in charge, but am still figuring out the right way forward with all of this. This kind of honesty has risk—too much of it, and you look weak and without any sense of direction. But I’ve chosen to lead with transparency over the years because I find it builds loyalty, and creates teammates who bring problems forward so they can help inform you to make the right decisions. I want that candor. The alternative is being excessively confident, causing teammates to hold in concerns for fear of being reprimanded for disagreeing.

Which is exactly the situation I had put myself in by throwing down a hammer.

At the end of this call, I told the team member I wanted them to never lose that fight. It’s what love about them, and why they’re going to be a great fit for us as we build a totally new category of business—Social Commerce as a Service.

The call was critical

We were coming into the weekend. Had I let this go, and let the employee simmer, it could have done irreparable harm. Negative thoughts are just like lactic acid building in a marathon runner—a small amount is fine, but when a surge hits the system beyond what you’re used to and isn’t given a chance to be filtered out, it can take you out of the race.

It can actually kill you.

With the call, we were able to talk until we both felt it was resolved. And by publicly apologizing, I was able to put it behind me and kill any behind-the-scenes chatter before it started (this is not something I worry about with our team, but that’s because I stay hyper aware of negative and toxic moments and do my best to counter).

Leaders do have the final say, but it doesn’t mean you shouldn’t share context. And sometimes, you have to go above and beyond to make sure that context is properly resonating. I failed at this last week, but I am so glad I took the time to make it right. The teammate is an absolutely critical part of our team, and I would have never forgiven myself had this grown into something more, simply because I was being short, stubborn and not forthcoming with the “why” of my decision.

Fellow leaders, don’t think for a minute that the finality of your decisions is enough. If you want to build autonomous teams, ensure you’re giving them information to guide them.

And for Pete’s sake, don’t do it on Slack.

3 lessons in communicating better

1) Expand on the why, not just the what

I was sharing the what—the decision. I was not sharing the “why.” The why is so important, and I forgot about it in this moment of selfishness. I wanted to get back to the 100 tasks I felt I needed to be focused on, but keeping the team privy to the “why” of what we’re doing is always at the core of leading.

2) Don’t fight in public

Alphas often end up in leadership positions, and being in a public debate can often fire up the need to win or be right so others can see how great or wise you are. This is a false dichotomy—it feels you’re going to prove how right you are, but usually it does more harm than good. Sure, maybe you’re right, but you’ve belittled or at the very least, battled, a person on the team in public, shaming them in front of everyone. Quite frankly it’s just dumb. Always go 1:1 for these types of discussions.

3) Stop operating in chats or emails

Written communication is horrible for these debates. No matter how thorough you think you’re being, you’ll appear brash. In fact if you over communicate, you’ll come across even more heavy handed. Pick up the phone or go for in person, and hash it out. Be open when you’re talking, and lean into the “why” to share the real reasons behind your decision, not just what the decision is.

Who I’m listening to: Low Water Bridge Band

What I’m reading: “Blood Meridian” by Cormac McCarthy

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