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Scaling a Startup = Scaling Empowerment

Real EIR Andrew Sider shares his key insights on growing a strong team

Photo by rawpixel on Unsplash

Framing the challenge

As an early-stage company CEO, you’ll likely spend the first few years using a very small team to figure out product-market fit, validate your core value proposition with every customer and put out all the fires that inevitably come up. When you’re in that mode, the team works cohesively — you’re small and lean and everyone is working toward the same goals. But success and growth bring new challenges that you need to be prepared for — you’ll need to shift your mindset and priorities as a founder and leader.

  • How will you structure your organization to optimize results and flow of information across the company?
  • How do you select the right people to manage your teams now that you have too many direct reports to lead on your own?
  • How do you maintain the cohesion that’s helped your team achieve the success it’s already had?
  • And what are the best ways to make sure that communication remains strong both within and across teams?

Design, define and refine the org chart

Before jumping into hiring, you’ll need to revisit or design your org chart if you haven’t already done so. This will force you to understand how responsibilities, competencies, delegation, processes and information flow across the organization. The more lines that connect the dots on the org chart directly to you, the more painful scaling the organization will become.

Identifying what your management team should look like

It’s clear that you will need to hire or promote team members to leadership positions, but how do you select these leaders? While a common approach is to simply promote top performers, this doesn’t always work out. Despite what many people think, becoming a manager isn’t simply the next step on a career path: it takes a completely different skill set from being a stellar individual contributor.

Building cohesion among the management team

Once you’ve hired (or promoted) your leaders, it’s crucial that you onboard them to succeed and act like a leadership team. You need to share the same values and communicate effectively as a group before you can send managers off and expect them to succeed with their direct reports.

Communication is the key to alignment

Once you have grown above 30 people, the CEO can no longer be the sole voice of truth in the organization. Your managers will spend as much time with their team members as you used to spend with your team of 10, so they need to be your key communicators and live and breathe your mission, vision and values. Alignment, clarity and connectivity with that group of managers become key to amplifying your vision of the company and its culture as the CEO.

  • An all-teams-stand-up where each team reviews their objectives for the week every Monday
  • An all-team or per-team 15-minute stand up every morning to review progress and blockers
  • A demo on Fridays where people who completed products show them off and disseminate learnings and information to the whole organization and where you also celebrate shipping
  • A Friday afternoon management meeting with your core group so you know what was accomplished during the week, what wasn’t done, and where you can recalibrate objectives and plan for the next week (which are then presented to the team on Monday morning)

Closing thoughts

Being proactive and thinking about the changes coming to your growing company will save you and your team a lot of headaches. By clearly defining your org structure, hiring or promoting the right people to manage your teams, and building alignment through tight communication, you can ensure that your employees have the information they need to be successful and know what other arms of the organization are doing. This will not only help avoid any “us vs. them” scenarios between your teams, but by focusing on building cohesion among your managers, you’ll also create a culture where everyone is in it together, working toward the same goals.



Actionable insights from entrepreneurs and VC partners to help early-stage founders build globally-impactful companies.

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