How to Bring Up Issues With Your Business Partner or Leadership Team

I help run two different businesses: GAN and GAN Ventures. At GAN, Dani runs the day-to-day operations as the company’s COO. And, at GAN Ventures, Reilly and I run the company as equal partners, which—of course—makes Reilly my business partner.

This means I have two allies, Dani and Reilly, who I’m constantly working with to build and grow these organizations. We have incredible relationships and I couldn’t have chosen more fantastic people to work alongside. But, as with any business, conflict and issues emerge along the way.

I’m writing about this now because, after looking again at the latest CB Insights startup postmortem analysis, I was reminded that 23% of companies fail because they don’t have “the right team.” Specifically, the article describes the issue as “disharmony among the team,” including discord between co-founders.

With that in mind, I wanted to share how my closest business partners, leadership team members, and I tend to work through conflict when it arises. I hope there’s something here that can be useful to you and your coworkers.

Working Through Conflict

When you sense conflict, treat it as a misunderstanding, at least initially.
My go-to reaction when something comes up is to assume the worst. But my business coach, Evan Roth, always says that conflict only comes from one of two things: 1) True disagreements or 2) Basic misunderstandings. Most of us tend to think that any discomfort or frustration is from an actual disagreement, when—in actuality—we’ve simply misunderstood each other. You say or do something that I interpret one way but, in reality, you intended something very different. Or, you make a decision I assume was made for the wrong reasons, but you’ve actually taken an action that was founded on better, correct information and for absolutely the right reasons.

Because I know this is our human tendency—for our brains to assume the worst-case scenario—I’m working hard to enter conflict with my partners and leadership team with the assumption that something has come up because of a misunderstanding, likely based on miscommunication. There may truly be a disagreement, but by starting with the less dramatic explanation first, it makes the conflict seem like much less of a big deal.

Rhythms are vital.
Another way that conflict can seem like a much bigger deal than it actually is? Not having a mechanism set up where everyone involved can share their frustrations. So, as you try to figure out the best time to bring up an issue, you might feel like you have to schedule a meeting to discuss it. Even scheduling this meeting can feel like a lot of work and sparks unnecessary nerves and emotions as you have to both voice the need to talk and to wait until that awkward meeting to voice what’s going on. And, the other person now knows you’re frustrated and is waiting patiently to hear about the problem. So, both of you come to the table with needless built-up emotion. The desire to avoid this scenario alone is enough to keep you from even wanting to bring up your issue in the first place.

For this reason, our team set up regular outlets to discuss various issues. Right now, those rhythms look like:

  1. Daily: I talk with Dani nearly every day and Reilly and I speak every other day. These daily check-ins allow us to bring up minor issues as they emerge. They also keep us from feeling like it’s a big deal when we need to jump on a call to ask for clarification or to bring up an issue that happened in the last 24 hours.
  2. Weekly: We have a weekly meeting with a specific agenda that includes a “things to discuss with the other person” section. This gives us a mechanism to discuss any bigger issues that might have emerged in the previous week.
  3. Monthly: Every month, we have an “Accolades and Annoyances Meeting.” The purpose of this 30-minute meeting is to do exactly that: Share what we are thankful for and like about the other person and also where we’ve been frustrated over the past month. The realizations that come out of this meeting are normally so good.

What I love about these rhythms is that they get all of us in a practice of hearing constructive feedback consistently. The more we strengthen our muscles to hear feedback, the better we are at receiving it. Plus, the more we hear it, the less that feedback feels like a big deal. This kind of de-escalation of emotions tied to hearing critique (even constructive critique) helps make everything feel less personal and like a much smaller deal, which it usually is.

Bring things up in a productive way.
The major reason people dislike conflict is that it doesn’t often end well. But conflict—when done right—can be incredibly useful. Not only does it build transparency and honesty among your colleagues, but it creates a sense of trust. You know you’re able to be vulnerable with your colleagues and that your relationship is strong enough to withstand honesty and transparency. This creates an essential foundation for when things get really hard—which they inevitably will.

Here’s what helps me bring things up in a productive way:

  1. Having empathy. In all of my meetings, we start off by asking one another how we’re doing professionally and personally. We actually give a green, yellow, or red for both aspects of our lives. We can get a true snapshot of the other person and better understand what may be causing the other person to act in a certain way.
  2. Making honesty “normal.” When conflict emerges, we aren’t afraid to come out and say what we’re feeling because we do it so often that we know it’s not weird to say hard things. It makes hearing “I’m frustrated” a common occurrence. And, by sharing these things, we’re being true to ourselves and actually doing a good job bringing those issues to the surface.
  3. Backing things up with facts. A few weeks ago, Reilly brought up the fact that I wasn’t having conversations quickly enough with startups he connected me to. Instead of just saying that, he came to our discussion with charts showing how quickly startups move through his process versus how quickly they move through mine. The facts spoke for themselves.
  4. Bringing it all back to the company. This one sounds simple, but can be difficult until you get used to the practice. It’s important to try to not make conflict personal. In other words, try not to blame the other person. The easiest way I’ve found to do this is focusing on how a certain behavior is hurting the business in a particular way.

Never stop being open to hearing one another.
There is this amazing marriage psychologist, John Gottman. If you’re married and haven’t read his books, go read them—now.

What he’s been able to do is determine, with something like 85% accuracy, whether a couple will get divorced. And one of the biggest determining factors for that divorce? Whether the couple is still open to hearing one another. If couples stop hearing one another, there’s very little left to rescue the relationship.

I think about that fact a lot in my relationships with Dani and Reilly. The second I feel like I’m not hearing them or like they’re not hearing me, we stop being productive. So, I make it a point to make sure that I’m personally, emotionally, and physically in a place to hear my allies in this business—while also ensuring that we never reach a place where anyone is so frustrated with someone that we can’t effectively communicate.