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Creating Confidence and Competence in Young Startup Teams

Scaling a startup is an exciting milestone, but it often brings cultural challenges that can be painful for the team. As the millions in ARR start to roll in, the team tends to “jump” in size and reset. This often brings growing pains for the founder, who is prioritizing growth goals while also ensuring:

•The team feels connected to the vision.

Team members who now have a manager when they used to report to the CEO can feel “left out” or “downgraded.”

•The startup stays on track with business goals and doesn’t get caught up in unnecessary replatforming, like switching between HubSpot and Salesforce based on the last marketing leader hired.

•The CEO is also making sure s/he is raising their own bar on new competence that comes from scaling (i.e., you are your own glass ceiling, how are you feeding yourself?).

What I suggest, and see working in the startups that get it right, is the CEO, working with the leadership team as a sounding board, developing 2-3 light, iterative processes that address these issues head-on. There are no easy fixes.

CEOs need to know this one thing about startup cultures

What I think is most important to embrace is, while you can read everything ever written on startups, when it comes to scaling your own, building the culture is actively up to the founder. It’s your culture. No two cultures are the same. If you know anything about SpaceX, Uber, Theranos, WeWork, ExactTarget, Salesforce, Google, Apple—they all have strong, founder-driven cultures. (Not all good of course.) Know in advance you’ll be the fulcrum of your culture, and let that inspire you. It’s okay to have a culture that reflects your unique values. It is, in fact, part of the value add you are building. Embrace that.

Team Connected to Vision

Quarterly Team “In Service” Days: Bring in outsiders to work with the team on “working competency improvement” issues the leadership team prioritizes. Examples are–speaking, having difficult conversations, doing pro/con analysis, becoming better prompt engineers, etc. This should also include fun activities like painting and playing together to build trust and vulnerability.

Leadership Circles: Team members who exceed their quarterly goals participate in the next quarter’s “leadership experience”—typically a conference (like SaaStr, or OpenAI Dev Day) where they go as a team, stay as a team, and present their experience as a team to the rest of the group during an in-service day.

Best Idea Lottery Lunches: On the last Friday of the month, the CEO hosts lunch for team members prepared to present and defend an idea that will make or save the company $100K in the next year. Ideas must be submitted in writing, and then you get the invite.

Staying the Course

Project Change Process: Implement a process requiring individuals to propose 2 alternatives to their suggestion, with rough cost/benefit for both. Before something is approved, the range of options must be on the table. This becomes part of the “startup’s way.”

Regular Milestone Reviews: According to Fred Wilson, regular milestone reviews can help keep the team aligned with the company’s vision and goals. These reviews ensure that everyone is on the same page and any deviations are addressed promptly.

Standardized Tools and Processes: Jason Lemkin emphasizes the importance of standardized tools and processes to avoid the inefficiencies of constant replatforming. Choose tools that fit the long-term needs of the company and stick with them unless there’s a compelling reason to switch.

The CEO is Raising His/Her Own Bar

This is probably the toughest one for the most dedicated founders because it can feel selfish to take time to work on yourself when there are so many other squeaky wheels in a growing startup. Let me be super blunt: your startup will stall if you don’t prioritize your own leadership growth, so make it a priority. This sets a great example for the team too, that just doing the job is good, but if they want to grow, they have to actively train themselves up–like you are. Here are some examples of ways CEOs can help themselves scale:

Join a Founder-Only Peer Feedback Group: I got lifetime value from my decade or so in Entrepreneurs Organization and recommend it highly. The peer-led structure and gestalt are incredibly useful.

Get an Executive Coach: For areas you struggle with—or a therapist! I’ve done both at different times. One of my favorite founder coaches is Elise Mitchell, a three time Southern founder who sold her last company to a large Japanese conglomerate. In her earn-out, she acquired other companies. She’s been there, done that–on both sides of the table–and has the motorcycle. Contact her here.

Pursue a Passion Outside of Work: Some of my favorite founders have golf addictions. Others love martial arts. I’m a fantastic advocate for horseback riding and dressage. Find something that frees your body and mind to move together and integrate. The more regularly you integrate your emotions with your body, the more whole you can be for your team.

Creating the best startup culture you can–it’s a journey.

Scaling a startup isn’t just about hitting revenue milestones; it’s about nurturing a culture that can grow and thrive. By implementing processes that keep the team connected to the vision, ensuring the company stays on course, and continually raising your own bar as a CEO, you can create an environment where your young startup team not only survives but excels. Embrace your role as the cultural fulcrum, and let your unique values shine through. Your dedication to building a strong, cohesive culture is a crucial part of the value you’re creating, setting the stage for sustainable success. Here’s to your courage in fostering confidence and competence in your team and leading your startup to new heights!