Three Things I’m Trying Differently — Start-up Boards

Photo by Headway on Unsplash

Venture capital investing is really the only job I’ve had (outside of a brief stint at Jamba Juice in smoothie construction). After several years in the industry, I’m grateful to have progressed and begun earning the privilege of serving founders as a board member.

Thus far, I’ve observed and participated on a number of boards at technology companies at varying points in their journey, from seed-stage to pre-IPO on a few different continents. Being a perpetual student, I have asked for plenty of advice from veterans on how to serve founders as best as I can. My hope is to do the should-haves as best I can, while thinking about could-haves — as to be the most helpful I can be to founders. I always try and push myself to operate from first principles and think creatively which I’ll touch on below.

There are plenty of great write-ups on startup board management and the core responsibilities (i.e. managing compensation, operating plan agreement, executive hiring, firing, etc.) — Mark Suster’s introductory post comes to mind — but from my perspective, board governance lies on a continuum and I believe the important principles are:

  • Humility. Asking in service what is needed, rather than presuming you know.
  • Being data-driven. Making observations and suggestions supported by data on an ongoing basis, not judgments from low-effort pattern recognition.
  • Continuity. Understanding that the real work happens post meeting, and that the conclusions reached inside the boardroom should have continuity outside.

Below are some newer ideas that encapsulate these principles which try to bolster a healthy and productive board dynamic. These may not suit all boards, but the early results are promising, and I wanted to share them in order to start a dialogue:

1. OKRs for founders / companies, as well as for board members

I have found it useful to ask for quarterly Objectives and Key Results (OKRs) for founders as well as the company as a whole. When this exists visually as a slide in board decks, upon review I have observed some board members communicate in a hierarchical tone particularly when the company or individual misses its targets. If board members do act this way, founders may offer a rose-tinted explanatory response to shortcomings which doesn’t address core issues and therefore isn’t the most productive for change. One helpful way I’ve avoided this is to level the hierarchy and instead create goodwill by asking founders to submit OKRs to me, which I’m held accountable for.

As a board member you really don’t want to be there for the 1000+ decisions a CEO makes in a given year. Rather you want to be a sounding board and thought partner for the 5–7 strategic questions that matter most. Early on in the founder — investor relationship, board member OKRs can unearth these while at the same time highlight founder expectations, biases they may have, and / or war stories they’d like to avoid in the future. Some examples of my seed-stage and Series A companies OKRs include (but are not limited to):

  • Providing feedback via email to the board deck at least three days prior to the board meeting. This ensures that the CEO will start working on the deck one week before the meeting, which is great :-)
  • Introducing two qualified Product Manager candidates per quarter
  • Conducting an annual review of the customer data / marketing stack with management, ensuring data-driven culture exists for product and user experience from the top-down

In general, I’ve found asking “how can I help” is one of the most important questions to posit before or after I invest. It is simplistic but being open and more egalitarian just invites transparency.

2. Request gender-based HR data in the board deck

I’ve long been interested in diversity and its impact on organizations in the technology industry. Research shows that homogenous teams are not optimal, but in order to change this in companies effectively it must be measured first. In board decks I request the CEO to provide data on gender split by function, as well as capture employee turnover by quarter. Most CEOs I speak to in Silicon Valley and elsewhere don’t have any idea of where they stand on these vectors. If diversity and related metrics aren’t central for the board, it likely won’t be something the company focuses on. It’s important that GPs and LPs know that high performance and employee retention may be the result of many things, in addition to an inclusive workforce and healthy culture. This is a no brainer and reasonably simple to do.

3. Set time for post-meeting feedback

I’ve started doing 5–10 minute calls with founders the day after the board meeting to get feedback, that often exists but gets lost in meeting fatigue. At most meetings I find there isn’t a structured space to capture the following:

  • What was the least productive part of the meeting?
  • Was there an area we over-spent or under-spent time?
  • Was there an area you didn’t think the board would want to discuss as much as it did? Why do you think it was discussed so much?
  • What is an area you thought was worth covering more that wasn’t? Why do you think it was overlooked?

Founders take on a massive task in building an early stage company. As board members we have an obligation to continue pushing our own boundaries in being helpful. To keep building on this base, I would love to hear about other discrete, new ideas (from founders too) that have been productive in these settings.


If you like what you read be sure to share on social or give the author a round of applause!

www.costanoavc.com