5 Key Questions Elite Cofounder Coaches Must Answer To Help Startup Founders Improve Teamwork

Cofounder coaching is a service designed to end cofounder fallout.

As Noam Wasserman highlighted, about 65 percent of high-potential teams fail due to issues within the founding team. These challenges are fixable. Coaches, therapists, and psychologists are available to help teams improve their communication and performance.

Unfortunately, the lack of research on cofounding teams and the deficit of credentialing within coaching means most providers working with entrepreneurs are shooting from the hip—not knowing how to best support teams. Many therapists entering the space fail to understand what questions to ask to be most effective.

As a licensed psychologist and cofounder communication coach for startups, I have unique insight into the domains most helpful to assess the health of a founding team.

Leveraging existing knowledge from the Gottman Institute, I compiled a list of five key questions each coach should assess early in the coaching process to diagnose the potential challenges teams are facing.

1. What is the quality of their relationship?

This question has several sub-components.

You want to understand how the team shows (or fail to display) respect and admiration. Take note of whether they finish each other’s thoughts and understand informal references. Ask yourself if they validate and empathize with one another or if they demonstrate signs of emotional disengagement.

Do they have a discrepancy in the emotions they display?

From an individual perspective, this hints at whether someone prefers a thinking, analytical approach or a feeling and intuitive way of processing information. Identifying which emotions are most uncomfortable for the team to express may guide you towards stuck, unexpressed affect.

In general, you want to get an impression on whether they like each other as people, as this may inform their degree of closeness.

Learn more about whether they spend time together outside of work and the similarities and differences in their connection personally compared to their professional environment.

2. How would I describe their sentiment?

Digging deeper into the emotional climate, get a read on whether they have chips on their shoulders or demonstrate comfort with mutual vulnerability.

Try to notice defensiveness or preemptive reactivity as if they anticipate criticism or blame. These patterns can help you better understand the severity of negative sentiment override—a state in which teams are more likely to interpret neutral or positive statements as negative.

Focus on their communication process.

Do they attempt to re-direct conversations that get off track? Are those efforts successful?

It can be helpful to assess the ways in which they connect, as well.

Do they rely on humor to connect and repair? How upset and heated do they get? Take note on how they respond to the different emotions that arise during the session.

3. What are their communication challenges during conflict?

Many teams struggle to navigate disagreements well.

In your coaching sessions, it is important to identify their individual contributions to dysfunction and help them understand the systemic, relational patterns preventing optimal communication.

Here are a few questions to help guide your inquiry in the domain of conflict:

• Do they both avoid naming issues directly?

• Do they escalate in blaming or criticizing?

• Does one push and the other pull?

• Do they cross the net?

• Do they use I-messages?

• Do they label emotions?

• Do they state emotional needs?

• Do they compromise?

• Do they take breaks and reset?

• Do they access the deeper layers of conflict?

• Do they feel a sense of resolution to these issues?

Aim to answer these questions with description of how each process takes place rather than a simple yes or no.

4. How do they co-create meaning?

Another factor contributing to the quality of their partnership is how they co-create meaning.

You want to understand how they tell the story of founding the company. Sometimes you’ll notice patterns of inequity right from the start.

It’s also helpful to consider how they discuss their shared values and mission (or do not), and how they describe their different personality and operational preferences.

Get curious about how they talk about these different factors, as it illuminates deeper struggles coaching must address.

5. What business issues impact the team and vice-versa?

The business is the single most overlooked aspect by therapists entering the coaching space.

Personal issues are reflected in the company and issues in the company exacerbate personal issues in founding teams.

You want to understand relevant context from their stage, size, funding structure, industry, equity split, and any personal financial investment to the company. It is helpful to understand their individual levels of commitment and whether they perceive commitment to be symmetrical.

Assess what unspoken expectations for one another need to be made explicit and conscious.

Some teams struggle with unsaid expectations for closeness, in which one founder wants distance and the other wants emotional support. Others fail to articulate their vision for how their roles can and should change as they scale. Countless variety exists, but the underlying process is the same: Cofounders need to be far more explicit than they anticipate.

Here are other helpful questions to consider:

• How do they make decisions?

• How do they communicate face to face and organize async communication?

• Are they transitioning roles? Do they like their roles?

• Are they aligned with their long-term vision and strategy?

• How do they manage the board?

Ongoing Assessment

These five questions are important starting points to assess the health of a cofounding partnership. Cofounder coaches would be wise to implement these questions and subcomponents into their assessment process.

In time, coaches and therapists will develop core competencies to support cofounding teams, and startups will be healthier for it.