My Startup Has Doubled in Size. Now What?

From hiring to firing, two executive coaches share advice on how to manage the stress of scaling.

September 17, 2021


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When we started our monthly coaching sessions for M13 portfolio company founders this summer, we wanted to provide a safe space for candid, off-the-record conversations. Given that many of our founders have raised common challenges, we also wanted to introduce them to a variety of coaching styles and see how a coaching mindset might help them solve those issues.

One question has consistently popped up: “My team has doubled in size. Now what?”

To help more early-stage founders navigate the logistics—and stress—of rapidly scaling a team, we tapped two experts in our coaching series to share their best advice:

  • Dina Smith is the owner of Cognitas, a boutique coaching and consulting firm in the San Francisco Bay Area.
  • Matt Blumberg is the founder and CEO of Bolster, a marketplace for on-demand executive and board talent.

    From how to hire to when to fire, here are their thoughts on how to tackle common problems around scaling:

It’s hard keeping up with all this change, and I’m struggling with letting go. What can I do?

Dina: This is, of course, common and normal, especially given our minds’ bias toward loss aversion (we over-index on what we might lose versus what we might gain). To offset this cognitive bias, refocus your thinking. Ask yourself:


What might I gain by letting go?


What is it costing me to hold on?


What is it costing others?

Matt: The biggest thing I see here is calendar overload. Recurring meetings almost never get removed—they only get added. Be intentional every few months about doing almost a zero-base calendar process. Forget what’s on your calendar. What do you need to be on your calendar now?

How do I keep everyone informed? How do I stay in the loop myself?

Dina: Communication structures will necessarily evolve as you grow. Consider what it is that you need to communicate, who needs to know what, and only then think about the how (i.e., what is the most effective channel, format, and frequency for the various comms).

Matt: Bigger companies require different information loops. And the further employees get from you as you add more layers and teams, the more times they’re likely going to need to hear the same message to get it to sink in.

Design your Company Operating System so that key messages are disseminated multiple times and followed up in multiple ways—for example, publish your quarterly board book, then follow it up with an all-hands meeting to highlight key topics, then follow those up with a series of team roundtables to do Q&A.

In terms of your own level of information, you’ll have to develop some routines like skip-level meetings and team roundtables so that you make sure you’re in touch with the organization as it grows and as you see individuals less directly.

Just be careful in those meetings to do more listening than talking, and to always keep the manager of the people you meet with informed about those conversations so people aren’t taking your casual remarks as a directive.

I’m worried that our company culture is heading (or will head) in the wrong direction. What steps can I take?

Matt: “Break glass in case of emergency.” This is a serious, serious issue that you need to nip in the bud. Scaling a culture is one of your most important jobs as a CEO … Begin documenting values (which shouldn't change) as a way of shaping culture (which will evolve over time). Personally work with recruiting (each new employee, 1:1 or in groups) to make sure there is a high degree of consistency and adherence to them.

Where possible, rely on other leaders and early employees to transmit culture and values. Begin to weave values into critical people-oriented business processes (hiring, reviewing, etc…) to reinforce the values more systematically and start expecting others to reinforce values and shape culture as well. Counsel those who violate early, and terminate on repeat behaviors.

What should I do if some of my early employees are no longer who we need in order to keep growing?

Matt: Do your best to coach them and guide them into new (and likely more specialized) roles. Their institutional knowledge and loyalty are worth a lot. If their career paths look more like jungle gyms than ladders, that may be good for both them and for the company.

Ultimately if a super-early employee doesn’t work out for whatever reason, treat them exceptionally well in terms of notice periods (and working notice), finding a new job, exercising options or extending their exercise period, and severance. And celebrate the heck out of them on the last day.

Any advice for managing my own stress level during this growth?

Matt: Work less. Seriously. Work fewer hours. Force yourself to be more efficient at work, and make time for sleep, exercise, family, friends, and hobbies. As Stephen Covey says, “Sharpen the saw.” You’ll never regret this.

Dina: You can’t sprint a marathon. Restorative practices, which mean different things to different people, are essential for sustainable effectiveness.

Get more tips from Dina in her Fast Company article, “Your Company Is Scaling Fast. This Is How You Can Grow at the Same Rapid Pace.

How else can I successfully double the size of my team?

Matt: Hire slowly and carefully, even if it hurts because everyone is “too busy.” Doubling the size of the company without maintaining the same level of quality, cultural fit, and performance means you’ll double your cost base without doubling your output.

About the coaches

Dina Smith is an executive coach and the owner of Cognitas, a boutique coaching and consulting firm in the San Francisco Bay Area. Clients include premier brands such as Adobe and Netflix, high-growth tech companies like Dropbox and Stripe, and private equity-backed startups shaping the world. She writes regularly for both Fast Company and HBR.

Matt Blumberg is the founder and CEO of Bolster, a marketplace for on-demand executive and board talent. He was previously chairman and CEO of Return Path (No. 2 on Fortune’s “Best Companies to Work for” list) and the founder of the Internet division of MovieFone (777-FILM). He is the author of “Startup CEO,” “Startup CXO,” and the forthcoming “Startup Boards” (Wiley & Sons).