Startup CXO. Matt Blumberg

at the leadership team level, and then on team “building” for other teams. All teams benefit from having support and intention around how they operate and interact. Skills built around team development for the core team also help each individual be a better team member when they work cross‐functionally.

At startup level the most important team is the leadership team, as they impact the entire company. It's absolutely critical that the leadership team build a high level of trust and the ability to have productive conflict. There's always going to be conflict; it's unavoidable. But it doesn't have to be debilitating or result in damaged relationships. If there are high levels of trust, conflict can be extremely helpful to the team. There are many tools and assessments you can use to help with team diagnostics, and the most impactful, and simple, tool I've used is Patrick Lencioni's book, The Five Dysfunctions of a Team. (Lencioni's book, The Advantage, combines his thinking in both the prior books I mentioned (Death by Meeting and The Five Dysfunctions of a Team), as well as introducing an annual planning framework that we adopted and modified at Return Path with great success). Do yourself and your company a favor and take the 5‐minute assessment every quarter, evaluate the results as a team, and agree to the development you need to make the team successful. The type of development the team requires depends on the results of the survey: if you score low on trust, work to deepen relationships. If you score low on conflict, understand the underlying reasons, and then offer coaching or development on conflict. Having a highly functioning leadership team sets the stage for having a highly functioning organization. Without that, it's very difficult to keep teams aligned and working together effectively.

      In addition to building an effective leadership team, you may also facilitate strategy development and planning discussions or offsites. Some of the most impactful work you do will be to help your leadership team have deep conversations on business strategy. Strategy development discussions are not just straightforward conversations and it's crucial to build an agenda that helps drive toward your goals. It's often helpful to partner with someone outside the team to help build agendas and facilitate offsites, so that you can participate fully. At Return Path, we worked with executive coach Marc Maltz for almost the entire lifespan of the company. Marc helped us to build and adapt the leadership team over time, coached our CEO, individual team members, and the team as a whole.

      Once you have a high functioning leadership team, it's much easier to build high functioning teams who report to them. Teams at the startup stage are often very cross‐functional and the more you can help all individuals build the skills and practices to work effectively as team members, the faster they can make an impact on the teams that they join.

      Picture a scaleup of 50 people. All employees report to a leadership team member. Some teams are small and each individual wears multiple hats. Even larger teams don't always have a standard role. Everyone knows each other. If these cross‐functional teams don't have the skills to communicate with each other effectively, and they let their egos get in the way, even small conflict becomes painful and takes an emotional and productivity toll. If the teams all have the tools to set up effective operating systems and are able to communicate effectively, small conflicts can easily be handled between teams or people, making the team quickly productive.

For teams that work together regularly, treat them as an intact team, and follow the same steps from the “Five Dysfunctions” process that you did for the leadership team. Because all team members have a common language and skills, often the focus is on team dynamics and calling those to the surface. These skills also help teams be more inclusive. Working with people who come from different backgrounds and cultures requires more effective communication and inclusive practices such as ensuring that everyone has a chance to speak up at meetings, and that quieter people aren't ignored.

      When team membership changes with a new hire or a change in role, take the opportunity to talk about your team operating system and dynamics and build new relationships and dynamics where appropriate. As Matt says, “Every time you add or lose a team member, you have a new team.” At Return Path, we had every new employee take a Strengthsfinder assessment, and they used that to introduce themselves to the team. That helped to build trust quickly.

Chapter 29 Leadership Development

      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,