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Becoming a Series A company raises the stakes for Founders. The velocity of change, the rapid increase in relational dynamics, the need for a new level of clarity, and the sheer emotional weight of scaling a Series A company frequently surprise even the most prepared Founders. 

That’s because the Series A brings new terrain to navigate. While a Series A Founder may bring competence, confidence, and a strong mental map, they soon discover that the map is not the terrain. They’re suddenly facing new and challenging dynamics of team management and leadership, and are often caught off guard by how mentally and emotionally demanding this work can be. They find themselves facing an entirely new landscape and soon come to realize that these lessons have to be lived in order to be learned.

This is a critical phase of both company and individual growth, where partnering with an experienced and knowledgeable Coach can make a difference. Engaging a Coach ensures the Founder doesn’t have to go at it alone. A Coach provides a reliable reference point and the perspective of someone who has traversed similar terrain before. By engaging a Coach, the Series A Founder can access:

• Support: A Coach offers the Founder a space to speak freely and unpack everything they are carrying around, without judgment or impact on their business reputation or operations. In this space a Founder can gain clarity and have room for better and more proactive decision making. 

• Guidance: A Coach provides a neutral third-party perspective, as an informed professional with valuable insight, without any links to the Founder’s company, board, or investors. A Coach can advise the Founder in areas where logical or emotional clarity may be out of balance, and help the Founder to hone both critical elements of their leadership approach.

• Teaching: A Coach assists the Founder in learning the lessons of leadership and internalizing these learnings in order to truly come to understand who they are as a leader and where they may need to focus on growing into their true leadership potential. 

This series will explore the unique demands placed upon the Series A Founder and how that Founder can best navigate this new terrain. Today, we’re considering five common waypoints we see all Series A Founders encounter, and exploring ways Coaching can help them successfully navigate these challenges. 

1. They realize the need to take action more quickly and decisively: "I wish I had done it sooner" or “I regret that I didn’t move faster”

All Founders face difficult decisions and crucial inflection points, and one of the most difficult shifts for a Series A Founder is increasing their speed and agility in decision-making. 

We often hear from Series A Founders that they’re surprised by the compounding nature of moving too slowly—a decision invariably influenced by, or rooted in, fear. A Founder may have a perception of themselves as a quick decision maker, or a logical decider; yet when the stakes are high, even the most logical decisions can become imbued with emotional weight that makes the path forward less clear. If a hesitancy to act results in even a small slowdown, when compounded across the many decisions a Series A Founder is called to make in the course of their work, the end result is a loss of one of their most valuable resources: time. Thus, a Series A Founder’s ability to remove barriers to decision-making will have a direct impact on the efficacy of their work.

Founders new to the Series A have often not yet internalized the fact that speed is a skill. And, only upon reflection can a founder begin to identify what is hindering their ability to move at speed.  

How Coaching Can Help: 

• Support: As a truly neutral party, a Coach can help shine a light on what is impacting the speed of decision-making and help Founders put in place mechanisms allowing them to decide, implement, or course-correct more quickly. Founders often feel isolated by the responsibility of being the decision-maker: while many voices may weigh in, ultimately the decision is on their shoulders. A Coach can help them grapple with the emotional impact of carrying this weight while also reflecting the logical implications of why these decisions matter so much. 

• Guidance: Coaches can point out common places where Founders sacrifice speed and help Founders to close this pacing gap. We often see Founders resisting quick action when it comes to firing, giving feedback, and providing clarity on direction, and in our experience, they nearly always share their regret that they didn't move sooner or more quickly.

• Teaching: A Coach can help a Founder observe and identify internal patterns and realize where the decision-making process may be distorted or inefficient. Coming to terms with the decisions they’ve made in the past and building a system that supports them in prompt decision-making in the future is a common focus of our coaching work with Series A Founders. And, realizing where fear comes into play—such as fear of conflict—allows a Founder to move swiftly into crucial conversations that would otherwise linger, hindering forward progress.

Supporting Founders in pattern recognition, self-awareness, and implementation of changes that enable them to operate at the pace their business demands is a core part of our work. Every Series A Founder we’ve worked with eventually identifies a place in their leadership where they’ve moved too slowly. It’s a lesson that comes for everyone, and a conversation we have with every Series A Founder.

2. They need to fire someone: “How will this impact the team?”

Every founder we work with knows that firing someone will, eventually, be a part of their job. 

Startups cannot scale without navigating personnel transitions. And while a Series A Founder may have the vision of crossing the finish line with an intact team, the shifting demands of a startup often mean that the team experience is less a marathon, and more a relay race.

The responsibility of managing these difficult personnel transitions falls to the Founder. Sometimes this looks like hiring the right person for the job, but often it means letting someone go.

A Series A Founder may not have faced this task in the past. In our work with Series A Founders, we often find ourselves working with compassionate leaders who have a sincere concern about how firing the team member will impact both the individual and the team. Yet they may underestimate the emotional impact that firing a team member will have on themselves. Firing people is hard, and is a decision ripe with fear.

Yet our work with Series A Founders overwhelmingly shows us that while their concern is well-placed from a human perspective, as leaders they tend to over index on how the team will react. This often leads to a lack of clarity regarding who will be impacted and what that impact will be. Founders are reluctant to fire someone because of how it will impact the individual, what it means about how they’ve supported—or feel they’ve failed to support—the person in question, and how the firing will impact the team as a whole. However, they may fail to see the extent to which keeping an underperforming team member on is also negatively impacting the team. 

When Founders face the first firing on their team, we find it is a powerful intersection of several key elements. Firing a team member is emotionally demanding, requires thoughtful execution, and demands our clarity and conviction as a leader. The high emotional amplitude of this event can make this a tricky crossroads to navigate. This event always presents a powerful opportunity for growth that requires thoughtful support, awareness, and clear-mindedness as the Founder grows into this specific leadership skill. Many of the Founders we work with are deeply stressed by the personal and emotional weight of this action, to the extent that it can distort their read of the situation more broadly in ways that are ultimately more detrimental to the company and the team. 

How Coaching Can Help: 

• Support: A Coach provides the Founder with critical emotional support as they navigate the difficulty of firing someone with whom they may have a deep, personal relationship. Founders who must fire those they’ve started a company with are often seeking emotional validation for making a difficult decision and reassurance that the decision is the right one to make in spite of the reactions it may provoke.

• Guidance: Once the decision has been made, a Coach can guide the Founder by highlighting important things to pay attention to in the process. A Coach also offers insight on how to communicate with key stakeholders and the team throughout this process.

• Teaching: Unfortunately, firing a team member isn’t a one-time action. Once the action has been taken, a Coach can work with the Founder to review what they learned that can be applied to similar scenarios in the future.

A Series A Founder facing their first firing needs clarity in both the emotional and practical aspects of this task. Seeing the situation as clearly as possible requires both emotional and logical clarity; attaining this clarity will support the Founder as they step through this difficult process and make it more straightforward—although perhaps not easier—when they must do it again in the future. When a Founder realizes that they need to fire someone, they’ll benefit from support that makes this process as painless as it can be. It’s a conversation we have with every Series A Founder.

3. They want to quit for the first time: “I realized that there’s no finish line.”

Founders pour their heart, sweat, and tears into their Series A startup. Yet, after achieving milestone after milestone, they will often realize that there is no end in sight: the path ahead may feel like it goes on forever. The work of being a Series A Startup Founder is the work of making difficult decision after difficult decision, with no relief or moment to catch their breath.

With so much complexity and the fast-paced nature of the Series A, Founders may feel like they are drowning and without hope for resolving whatever barriers they face. Giving up can feel like the clearest way forward, and the desire to quit rises to the surface. 

For many Founders, this is a surprising feeling. It conflicts with the effort they’ve invested to date, and conflicts with their image of being “all in” and committed to their project. Yet acknowledging the desire to quit and actually deciding to quit are two very different decisions, and we’ve found that Founders draw rich learnings from exploring their desire to quit from a place of both emotional and logical clarity. This process also often yields discoveries about how they build the company going forward and what changes are both necessary and practical.

How Coaching Can Help: 

• Support: A Coach can help a Founder to identify what about the current circumstances is making them want to quit, while also helping them to realize that this is very normal. A Coach also creates space for the Founder to explore what changes may be necessary to make their work more sustainable.

• Guidance: Once a Founder reaches this point, they are often ready to commit in a new way. In some cases, a Founder decides that quitting is their path forward. Regardless of their choice, a Coach can help them navigate this crossroads, determine what an offramp or detour would require, and help provide clarity on what it means to move forward after crossing this emotional rubicon.

• Teaching: As with every challenge in the Founder’s journey, grappling with the idea of quitting can teach the Founder much about what it takes to sustain themselves in the long-run as a Founder, and how they can evolve as a leader. By working with a Coach, a Founder can identify what tasks they may need to stop doing, delegate, or shift in order to avoid burnout and the desire to quit.

When a Founder realizes they are at this crossroads, it turns into a conversation we have with every Series A Founder.

4. They realize they are lonely or resentful: “I feel like I’m carrying all of this weight by myself.” 

The role of a Series A Founder comes with intensity, excitement, and opportunity. Invariably, it also brings loneliness or isolation. A Founder may suddenly find themself faced with unprecedented challenges and for the first time, feel the full weight of their solo responsibility. This may be their first recognition that leadership can be lonely, and the first time they truly grapple with the burden of leadership.  

This realization can be especially difficult for Founders who have always felt like part of the team, or have previously been surrounded by co-leaders. Realizing that despite the best intentions and true commitment of their team members, as a Founder everything rests on their shoulders. They lack someone to share the burden, confide in, or rely on when things take an unexpected turn. This unexpected loneliness often sneaks up on a Founder and can be a sobering experience. A Founder may realize they need to diversify their support network, without knowing what exactly they need or where to find those they’ll need to rely on.

This can become even more complex in the event that they share the experience with a Co-Founder. Unsaid expectations of what it means to be “in it together” can lead to resentment and feelings of isolation, even when the burden is ostensibly shared with a partner. In this scenario, a Coach can help each Co-Founder gain a clearer understanding of each person’s role, clarify the relationship dynamic, and understand to what degree each individual can or should serve as a buoying element or thought partner in the lonely work of leadership.

A certain amount of loneliness is inherently part of the role of the Founder. But that doesn’t mean that the Founder must do it alone. Coming to terms with loneliness and developing a strategy for managing it is a requirement for being an effective leader.

How Coaching Can Help:

• Support: A Coach provides a space for the Founder to share their emotional struggles. This includes the work to identify the circumstances that exacerbate their loneliness, come to terms with the fact that being a Founder will always have some inherent loneliness due to the nature of the work, and discover what they truly need to feel less isolated. How are they getting their own needs met, and what needs to change for them to do this effectively? 

• Guidance: When coaching Founders in this scenario, we often explore how to build a network and connections that will reinforce them in times of loneliness or solitude, and identify who they can rely on in various circumstances to receive various types of support. A Coach also helps a Founder dig into questions like, who did they think they could rely on who has let them down? What other types of support roles would make a difference in their experience?

• Teaching: A Coach and Founder can explore ways that their belief of being in it with others has directed their leadership and decision making. This may yield recognition of unexplored opportunities, or other possibilities for powerful adjustments. A Coach will also help a Founder come to terms with how loneliness helps them evolve as a leader.

Establishing a healthy emotional foundation and coming to terms with the inherent loneliness of the role: it’s a conversation we have with every Series A Founder. 

5. They realize it is ALL mental: “It’s one thing to articulate it, and another thing entirely to put it into practice.”

Founders often focus on what actions to take. They believe the biggest challenges will be first knowing what to do and then executing towards that goal.  But at some point they realize that the largest barrier is ALL mental.