Manage your Relationship Debt

Relationship debt, just like technical debt, is the accumulation of emotional baggage in a founding team that’s created by making choices that feel expedient in the moment but which has a lasting and wildly deleterious impact if not attended to. Choosing to avoid or ignore difficult, potentially emotion-filled conversations is often the default because founders don’t know how to message their thoughts productively, or are afraid of what their cofounders’ response might be.

Founding teams can get by with some relationship debt for a short time. However, when founders choose to deprioritize a tough conversation, they contribute to a relational plaque that builds into resentment and frustration that won’t go away without thoughtful attention and direct action. Enough relationship debt will rust out the very foundation of your company – the founding team – and this psychological erosion (and the misalignment and intense feelings that come with it) kills founding teams in the long-term. Too much relationship debt in a founding team who has no tools to resolve conflict is the reason why almost all startups die of suicide rather than homicide.

Founders: You need to engage in tough conversations before your relationship debt kills your founding team and your company.

These “tough conversations” are what I call “level 3 conversations.” Here’s what I mean:

In the above distinctions, I’ve taken all possible forms of human communication and boiled them down into three categories that perfectly illustrate my point. ;)

Imagine that there are ‘levels’ of intimacy when it comes to conversation:

The first level is the ground floor - the surface level, chit-chat. A level one conversation builds connection without substance. It’s casual and light. Most people stay on this level because it’s comfortable. It doesn’t require vulnerability and doesn’t build much intimacy.

The second level of conversation is a step deeper, below the surface level. It’s a bit more vulnerable. Level 2 conversations are substantive but not explicitly emotionally meaningful. A level 2 conversation could be about direction, strategy, or a roadmap. This is the level most of you probably stay at most of the time. It’s a discussion, and so different opinions are coming up. And that might feel risky to some people depending on their comfort level with difference in general - but there is no mention of phrases like, “I feel” or “I need” or “I’m afraid that..”. Level 2 conversations are about ideas and thoughts - not about vulnerable emotion or emotional need.

A level 3 conversation is a deep conversation - way underneath the surface level. Level 3 conversations are the riskiest and most vulnerable we can be with another person. In them, you’re naming and discussing your emotions, your needs, or your thoughts about crucial things. You’re using very clear, very simple sentences like, “I’m afraid that..” or “I need [this] from you to be different.” or “I’m finding that I don’t trust you.”

A common failure mode is when a founder **thinks** they’re having a level 3 conversation when they are in fact having a level 2 conversation. For example, let’s say you’re feeling like you and your cofounder no longer share a vision for what you’re building. You sending an email in which you describe your vision, and ask your cofounder to do the same - is a level 2 communication. The level 3 version is you literally saying: I feel like we’re working toward different things. If we keep going, I’m afraid we’ll run out of money in 6 months and our investors will be upset. Can we talk about this?”

Do you see the difference?

Level 2 conversations communicate thoughts.

Level 3 conversations communicate feelings. They are explicit, emotional transmissions.

So, level 3 conversations are the only type of conversation that can resolve relationship debt.

Level 3 Conversations resolve relationship debt

Remember - emotions are the data that tells us about the strength and safety we feel in relationship. So of course we need to talk about emotions if our goal is to build the strongest relationship possible. Emotion is the only data set that can support that goal.

Founders scale their relationships when they have regular level 3 conversations to clear away relationship debt and keep their relationship strong - there’s simply no other way to do it.

The purpose of the level 3 conversation is to bring your thoughts and feelings out into the open where they can be discussed and resolved. Because level 3 conversations contain vulnerable emotional revelations, they are easily avoided and easily botched. I implore you to dive in and risk it. Level 3 conversations are what will save your startup and your relationship with your cofounder when things get hard, and what will strengthen both when things are “easy.”

How to have a Level 3 Conversation

I’ve found that the main thing that blocks founders from level 3 conversation is that they don’t know *how* to say what they want to say.

So here are phrases you can use to start a level 3 conversation. I call these “sentence stems” - they’re good fill-in-the-blank prompts for you to get a handle on any relationship debt you’re carrying. I recommend using this list to brainstorm before a level 3 conversation. Sentence stems can help you organize your experience and put it into words.

Here are some examples of the sentence stems in action:

I feel… some tension between us.
I think… there’s a problem with our communication.
I notice… you were late to ship our last 3 releases, and now the team is blocked. I feel helpless - what’s been going on for you?
I wonder…if you’re starting to burn out or lose interest.
I imagine… if this keeps up, you’re eventually going to leave - and that terrifies me.
I want… to have an open discussion so we can start to rebuild trust.

Another framework you can use is shown below:

You can’t solve a problem you don’t understand and never talk about, and the script above allows for both. The general outline of a level three conversation is that you share the impact that your cofounder’s specific and observable behavior had on you, ask your cofounder to share their experience of the same, and then you move into joint problem solving to address the issue in a way that suits you both. The sentence stems can help you brainstorm how to fill in the blanks.

For example:

“When you pulled out your phone when I was addressing the team at our All Hands (x), I felt embarrassed (y) because it made me feel like what I was saying wasn’t important, and I don’t want us to signal that to our team (z). What was going on for you then?”

Both of you need to practice active listening skills during a level 3 conversation. Literally repeating back word for word what you heard the other person say is an effective and simple way to do this. (i.e. “Let me make sure I’m hearing you properly. When you kept checking your phone, it was because you were expecting a response back from [BIG NAME VC] and you were feeling so nervous about it you couldn’t concentrate on what I was saying. Do I have that right?”

Conspicuously absent from this framework are your own assumptions, judgements, or ideas about the other person’s behavior. In order for a level 3 conversation to be productive, you must “stay on your side of the net,” i.e. you must only share the impact of your cofounder’s behavior on you along with any observable, fact-based behavior that is indisputably true and which could never be disagreed with.

Stay on your side of the net

When you’re engaging in a level 3 conversation, your task is simply to relay your experience of your cofounder’s fact-based, observable behavior – its impact on you – while leaving space for your cofounder to share what was going on for them.

Imagine the playing field of the level 3 conversation as a tennis or volleyball court. Your “side of the net” (i.e. your script) must only contain your experience of their behavior (your emotions, assumptions, and/or response to their behavior) OR the specific, fact-based, and observable behavior of your cofounder which is inarguable and inoffensive. You should endeavor mightily not to reach over the net to grab any assumptions about your cofounder’s motives, needs, context, or backstory for your script – leave space for them to share all of that with you later in the conversation. Again, your job is to describe the impact of their behavior on you and/or the observable facts of what happened and nothing else.

FYI, it’s okay if your side of the net contains an emotional story about your cofounder which is wildly wrong (e.g. that they pulled out their phone while you were talking in a meeting because they don’t value what you have to say). It’s a really good thing if you’re self aware enough to know why you’re reacting the way you are and you’re brave enough to say it, as these stories often reveal deeply skewed beliefs we hold about ourselves and how others see us. Being honest with your cofounder about why you feel the way you do, while holding that emotional story loosely and communicating it without blaming your cofounder for it, provides them with an opportunity to correct your internal storyline. And it provides you with an opportunity to heal a place deep inside of you that has been wounded, often without your realizing it. This is how the level 3 conversation is a tool that makes cofounder relationships stronger.

When you stay on your side of the net, you’ll be working with the benefit of your cofounder’s full attention and dedication, as this thoughtful framework should rarely result in defensiveness or high emotion that would disabuse your cofounder of being a thought partner and helping you find resolution. We defend only when we feel attacked, but there’s nothing to attack in a conversation in which you’re talking only about yourself and how you feel.

“What was going on for you?”

Asking your cofounder to share what was going on for them – what’s on their side of the net – is the magical phrase that makes level 3 conversations productive and reparative. Both of you sharing what was true for you, and how you perceived the other without judgment, assumptions, or shaming, builds trust and allows deep understanding to develop. It strengthens the founding team and builds the rock-solid foundation a startup needs to weather the storm and survive in the long-term. It also pulls out half of the information needed (the other person’s experience) to develop a solution that works for both parties.

Moving into joint problem-solving transforms rupture into repair

At the end of this exchange, you’ll have the full range of information available – your experience as well as your cofounder’s – and can solve the whole problem in a way that suits everyone’s needs. Having a level 3 conversation to share fully, listen completely, and THEN problem-solve TOGETHER transforms relationship debt from a professional and personal hazard into an opportunity to strengthen your relationship and grow closer together.

You might notice that the discussion that happens in a level 3 conversation is much more direct than most of us have been socialized to be. That’s why they can feel intimidating. But if you’re not direct about how you’re feeling, then you’re obscuring the data needed for a better relationship. Honest sharing, back and forth, strengthens relationships and builds trust. It allows you both to connect with what’s really true for each of you on a fundamental level. And then make choices, together, from that shared reality.

It’s a failure mode not to have level 3 conversations. If you aren’t talking openly with your cofounder about how you’re feeling - about them, about your relationship, and about your startup - relationship debt will accrue. Then it will explode into an unhealthy argument. That will cause more relationship debt. And the cycle will continue until your relationship has failed. And probably your startup.

Leave that flow to your competitors.

Founders scale their relationships, when they use tolerate their discomfort and initiate a level 3 conversation. Founders scale when they clear relationship debt, build trust, and get back to building with a stronger relationship.

Relationship Debt & the Level 3 Conversation