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As a startup, you generally aren't large enough to build or need a formal leadership development program. Work with the leadership team to ensure you are all aligned in expectations of leadership and management, and that each person on the leadership team is managing his or her own department effectively. Your role in a startup is still important and you need to drive conversations and learning and development around leadership skills so the leadership team is modeling strong leadership behavior to others in the organization.

You might have to coach the CEO and each leadership team member when you see or hear about behavior that doesn't align to values, and good leadership team members will appreciate that feedback in an honest and direct manner. We all have blind spots and identifying, giving feedback on, and helping leaders manage these blind spots early on will give you a good foundation on which to build. This can be difficult for you when it's the CEO or a co‐founder who has a blind spot that impacts other people or when they act in ways that don't align with company values. These can be tough conversations, but if you have strong relationships and explicit permission to give feedback, your impact on the leadership team and the company can be significant.

As you grow beyond the ability of the leadership team to manage all direct reports, you'll need to hire managers and you'll need to develop and deliver management training for first‐time managers. This is a prime opportunity for you to put in place the culture, values, operating system, and DE&I principles that will be the foundation with which you can scale quickly. Your management training needs to include necessary tasks such as approving expenses and PTO, managing compensation, and building an effective operating system, but it should be more than a list of do's and don'ts. You should also build leadership skills, such as emotional intelligence, listening, coaching, and having difficult conversations. You don't have to carry this weight alone. Ask leadership team members to develop and deliver training in their areas of expertise. This helps them deepen their skill and it gives them an opportunity to connect to the development of their team members and really embed the leadership behaviors that you want to reinforce.

As you scale, ensure you have enough People Business Partners (PBPs) to coach all managers across the organization. The PBP will help support managers' growth and development and continue to help you build your leadership bench. It takes a long time for a person to become a strong leader but you can shorten the path with intentional training, practice, and coaching. As you grow, many of the scaling practices in this section such as leadership development programs and leveraging volunteers across the organization can reduce your PBP:employee ratio.

In addition to training for managers, develop and deliver training on core leadership skills that you expect from every employee. Things like communication skills, interrupting unconscious biases, emotional intelligence, and receiving and giving feedback. When you help individuals develop these skills, the organization is better able to handle conflict and change. Collaboration, conflict, and decisions can be managed by the people closest to the problem, rather than needing to be escalated to formal leaders.

As you grow and start to hire second‐level managers, you'll need to develop and deliver leadership training in the skills required to lead multiple teams. Emotional intelligence is even more critical here; the leader is even more in a “fishbowl” than first‐level managers, as they are leading bigger teams or departments, and people have higher expectations of their standards of behavior.

When you get to this point, consider engaging an outside consultant or leadership development firm to support development and delivery. Ensure that the consultant is highly aligned with your values. Build and facilitate content together whenever possible; the consultant will have a big impact on your organization, since they will be impacting the people who role‐model behaviors for others. At Return Path, we co‐created one of our senior leader programs with the Refinery Group. Angela Baldonero, our Head of People at the time, worked very closely with them to ensure that they fully understood our culture, values, and leadership expectations. In addition to building high quality programs, the investment paid off in other ways: one of their consultants, Mark Frein, later became our Head of People, and another of their consultants, Russ Hamilton, later partnered with us to build communication and leadership skills throughout the company. The last program that we built with Russ, “Leading Teams”, was one of the most impactful leadership programs I've ever experienced. The participants were from across the company, and the cohorts still regularly get together to connect and support each other, even though most no longer work together. See www.Startuprev.com for a table showing the components of our leadership development at Return Path.