The 10 Point Plan for Getting Your First Board with Sukhinder Singh Cassidy

Board opportunities remain incredibly fragmented and hard to discover, so you need to figure out a game plan to be considered for the right board opportunities for you. Here are the 10 things I tell every leader I talk to who is interested in joining a board.

My Path to Board Service

I was thirty or so years old when I interviewed for my first board seat. One of my VC board members at Yodlee suggested to another founder at a portfolio company that I would be a great addition to the board (thanks Bud Colligan!).

Quite frankly I was surprised and flattered. While I interviewed and didn’t get the job, I was grateful that I had even been referred. It was the first time I’d ever considered that I may have something to offer a boardroom. 

A couple of years later, it was Bud who again recommended me for another board opportunity at Jobtrain, a Bay area nonprofit board that he was chairing. This time I joined, and almost 20 years later I’m still proud to be involved in different ways with this incredible organization.

Several years later, in 2008, I felt it was time to re-examine joining my first corporate board; I was an executive at Google, and felt I had skills to contribute as a “digital director” and much to learn about how to add value as a public board member. 

The very first thing I did? I started telling everyone I knew about my desire. This included tech colleagues and friends as well as every executive recruiter I knew, or who called me. I also let my boss know I was looking. 

After a year plus of looking, and several different board interviews, I ended up on the J. Crew board. I had a deep interest in fashion and ecommerce, and the CEO at the time was on a board with two Google C-suite members, and close to a 3rd valley VC who was also a friend. He disclosed he was looking, they shared my name, and I was lucky enough to get the role. 

I’ve since gone on to serve on multiple boards in the past 15 years - both public and private. As is often the case, with the first experiences under my belt, board opportunities have come more often. Board service has become a consistent part of my professional journey and an area of continued learning and contribution. But I know first-hand how opaque the board process continues to be, whether it’s your first board, or you’re looking to expand your board portfolio.

Tackling the Problem

Through my work at theBoardlist since 2015 (a talent marketplace for diverse board members that I founded), and now at BoardProspects (the broader board recruitment platform with whom we merged in 2023), I’m continually asked by accomplished leaders how to land their first board. 

My answer usually starts with being visible on platforms like BoardProspects where many companies and talent partners come to search, and where we also drive passive discovery of great board talent. The idea of aggregating great supply (great board talent!) in order to aggregate demand (great board opportunities!) is not new when it comes to building premium online marketplaces, and we continue to scale. But the truth is - given the entrenched ways of working in board recruitment over many decades - there is so much more you need to do. 

Board opportunities remain incredibly fragmented across the tens of thousands of companies and nonprofits who may be looking at any given time Thus board opportunities are hard to discover, let alone access for potential candidates. To give you some sense of this fragmentation, platforms of scale, like ours or a large search firm, may have access to  hundreds of these searches a year. But with more than three hundred thousand companies with 50+ employees in the US (of which only 3.7k are publicly traded), and 1.5m nonprofits, there remains no single site or platform where all the opportunities are listed. Platforms like ours at BoardProspects hope to change that, as we keep driving discovery and distribution of board member profiles at large scale, and offer coaching services to get you ready.

So what do you need to do as a board candidate? Devise and execute a simple gameplan to get yourself “ discovered AND considered” for multiple board opportunities, in order to land the opportunity that is right for you. 

To that end, I’m sharing the 10 things I recommend to every leader I talk to who is interested in joining a board. 

1. Clearly define your domains of deep expertise and thought leadership.

Simply put, you need to understand in what fields (functions, industries, markets) you are deeply experienced and considered a thought leader, that can be valuable to a CEO of another company. Most boards are composed of specialists (outside of investors or one potential seat for another ‘sitting” CEO/general manager)l Understanding your own 2-3 areas of specialty is critical.‍

2. Do your research.

Clearly research and define the types of companies or nonprofits (including size, industry) where your domain expertise would be highly desirable or critical to have in the boardroom. Take some time to think about where your domains of expertise are most applicable, as it relates to companies that would potentially want you on their board. In my first board search I was clear that if my specialization was “digital advertising /consumer tech”, the industries most in need of a digital director were likely to be traditional or multi-channel consumer /retail companies.‍

3. Polish your personal brand online.

Get a great headshot, create a great LinkedIn profile, and then draft your board bio. 

I know it’s tempting to obsess over a board bio - and you need a good one - but please first and foremost get your LinkedIn in order, and get a great headshot. You may think LI is not relevant to you as an executive, but you’re wrong. The very first thing that will happen when your name is passed around for a board opportunity over email? You’ll be googled, well before someone reads your carefully crafted board bio attachment. 

Your public content is an expression of who you are professionally. What does it say about you? Beyond a good, modern headshot (meaning not one that shows you looking 10 years younger, or 10 years older than who you really are:), what pieces of content have you written that help express who you are and what you know? Make sure they are easily findable/accessible if you have them. Then do the work to draft a great board bio.

Free Resource: Developing Your Board Bio

4. Write yourself up in a TL:DR format :)

We live in a short attention span world. Write a 2-3 paragraph email write up of who you are, what your areas of expertise are, and what kinds of boards you’d be open to joining where your experience is valuable and why. This is what you’ll be using when asking your network to help you with your board search. . Make it EASY for folks who are on the receiving end of a referral to you,  to understand who you are as a leader, the types of boards you’re open to, and why your experience and specializations are great for those boards.

Be succinct and make sure that this write up is easy for someone in your network to simply “forward” as is. Make sure the email write up includes your LinkedIin link and attached board bio…. but presume no one opens the attachment unless they are seriously interested in you:)

5. Evaluate your network.

Make a list of everyone you know WELL, who are board members at companies today.  Send them a kind note, with the write up included , and ask them to share with others when they hear of board opportunities (including with executive recruiters).

The people you ask for help would ideally have worked with you in some capacity that allows them to recommend you easily for board service.  Sending a general “I’m looking to join a board, can you help” email to people who don’t know you well has limited usefulness. But if you are going to send a broader email to all your professional acquaintances who are on boards, know that the likeliest people to actually recommend you to a recruiter, or a board opportunity specifically, are those who can speak to you deeply as a leader/peer/colleague (current or former).

6. Actively network with executive recruiters.

Many executives I know turn down recruiting calls if they are not actively looking for their next full-time role. This is a mistake . If you want to be considered for public board opportunities, take every executive recruiting call you get, and use it as an opportunity to tell headhunters that what you want is a board. 

The person who is calling you about a job has clearly researched you or been referred to you by someone else.Take that warm lead and turn it into an opportunity to meet the partners who lead board search at the bigger firms, or partners who do boat board and executive search both, at boutique firms.

Search firms want to cultivate a relationship with great leaders over time, and bigger public board or late stage private/private equity backed board searches are most likely to have a search firm or in-house talent partner involved.‍

7. Say yes to every interview.

Don’t be too picky - take every board interview you are offered as you start.

One of my first ever board interviews took place in a setting where the interviewer had flamingos roaming behind them as we spoke, for a board I wasn’t sure was a fit with my interests. But it helped me to start learning what board interviews were all about, and I cultivated a new professional relationship with a highly respected CEO, who was a leader in their field and someone I admire.In at least 2 other cases where I’ve been offered a board seat, I didn't go into the interview thinking of them as my “dream” board. But when I learned about the company’s opportunities and challenges more intimately, and met the impressive people I could learn from and work with in the boardroom, I became way more interested in the opportunity.

In all cases, board interviews can be thought of as a 2-way street. Use every opportunity to learn about different boardroom cultures and recruitment questions on the path to getting the right board for you. ‍

8. Value the “who” as much as the “what” in your board opportunities.

To double click on the importance of the point above, let me go deeper here. Boardroom contribution, and learning is not just about a company’s opportunities and challenges, and how passionate you are about them, but about the team you’ll be working with to tackle them. 

Joy and impact come from the who as much as the what in our professional journeys. While you initially will look at the board opportunity through one lens - “the what” of the company and the role, step back and add 2 even more important lenses regarding “the who”. Will you be in a boardroom full of leaders who have a diversity of skills, styles and experiences that you can learn from? Secondly, will you be with a “tribe” of people, and indeed part of a broader culture that shares a good portion of your values. This is “who” you want to be in the boat with, in the boardroom. 

Pro Tip

Place particular emphasis on the CEO and the lead independent/board chair in these evaluations. These are the two people who most of all set the culture of the company and the boardroom, and who will influence in large part the quality of your board experience.  ‍

9. Prepare for the interview.

You absolutely must practice for board interviews. Start generically when you’re still looking for your first board opportunity, and then deeply prepare for your first actual board interviews, even if you’re unsure whether you want that actual opportunity.

Board interviews require prep, because they are not about you and your resume.  They are about how you can contribute uniquely to, and how you relate to the company’s opportunities and challenges and the other perspectives already in the boardroom. This is similar to a full time executive interview, but quite importantly, NOT the same. You are being tested for your knowledge PLUS your ability to influence outcomes, not dictate them. You are being judged as a “non-operating” operator and how well you can handle not being the decision maker (as you likely are in your day job), but yet able to add value. ‍

10. Clearly articulate your distinct board superpowers.

Learn how to articulate your board superpowers, distinct from your areas of specialization and thought leadership. What are the top 2-3 leadership skills you have that can help you drive a company’s strategy and outcomes, as an influencer.

Think traits, not domains of expertise. For example - your domain of expertise may be consumer technology and the board superpowers you have might be your ability to lead strategic visioning, your ability to communicate, and your collaborative style. 

Need help honing your exact board value proposition, including your areas of specialization and board superpowers? Take advantage of 1:1 coaching services like those offered through BoardProspects' Premium Plus membership that are specifically designed to work on your board superpowers, board bio, and board interview prep. Often premium services like this may be paid for by your company as part of their professional development investment in you as an executive.

Otherwise, find a friend with board experience and ask them to spend an hour with you reviewing your bio and helping you hone your pitch. 

The Don'ts

Similarly, there are a few things I’d advise everyone who comes to me seeking board search advice not to do.

• Don’t presume that the boards that want you come from your specific domain of expertise.
  Board candidates tend to assume that the boards that will want them are in their very specific industry, or already strong in their very specific area of expertise. Think twice about that presumption. 
  
  Most boards don’t add specialization where they are already very strong; they add it where they need very relevant capabilities to their current or future strategic remit. They seek help where they need help.
  
  I’ve heard traditional media executives say - well I think I’m equipped to serve on X, the largest traditional media company in the world. But that company already knows traditional media. Perhaps your traditional media vantage point is best suited to a new media company, who wants to understand how traditional media thinks! Or to an ecommerce company looking for how to drive a content strategy. 

• Don’t presume non-profit board or smaller private company work doesn’t matter.
  It’s easy to be dismissive of small private or non-profit board experience. After all, many of these boards don’t have brand name recognition nor offer cash compensation. And in the case of nonprofits, an expected part of the board role is to fundraise and/or donate also.
  
  What these companies do offer is the boardroom experience you seek, the opportunity to contribute your expertise, and to spend time in areas you’re passionate about. They are also a lot more open about their searches, easier to network into, and welcoming of great talent. If you really want to experience board service, smaller companies and non-profits offer it. They also give you direct understanding of boardroom service and culture and credibility when you talk about such topics in bigger for-profit interviews. 
  
  The value of these experiences in bigger company board recruitment searches is mixed; some companies will value it less and some will value it more. The main takeaway is to take these smaller or non-profit opportunities seriously if you are serious about getting some governance experience now, vs a “go big or go home” mentality to board service. More importantly, if you are building a “portfolio of board experiences”, these boardrooms offer a diversity of board culture, impact, compensation and industry you can experience if you stay open to the possibilities.

• Be careful to pursue board opportunities that may conflict with your day job.
  As you seek out board opportunities, be very aware and critical of time you’re spending pursuing roles in a similar industry to where you currently work fulltime, or are hoping to work in as a sitting executive. 
  
  On a related note, make your current company aware early that you are seeking out board opportunities, so they can support your journey, and you can also understand or clear any conflicts they may anticipate in your board service.
  
  Board recruitment takes months, sometimes even longer, and the last thing a board wants is to recruit you, and then be surprised at the very end that there is a conflict situation that you didn’t flag or anticipate, that prevents you from serving. 

• Don’t presume you are bound for life, but do presume you need to be committed for 3 to 5 years at least.
  Board service can be anywhere from 3 to 10+ years long, depending on the type and size of company involved, and their own board terms or “strategic cycles."
  
  Boards are recruiting you in line with their current strategy and hoping you have impact. It’s very hard to do that if you are on a board for only a year or two. But, it is completely reasonable to talk board terms upfront and potentially negotiae the length of your first term, so that you don’t feel like you are bound forever to something you may not enjoy.
  
  I have negotiated starting board terms of 3 years (on both a private and a public board) when I'm unsure of what the future situation looks like (their’s or mine). But in the majority of cases, a board commitment is likely to be 3-5 years on a private or non-profit board, and 5-7 years on a public company (one longer term or 2 shorter terms consecutively).
  
  Ask what the board term is in your interviews, and if a company doesn't have one defined, you can suggest one.

• Don’t presume board service is equated to high compensation, unless it’s your full-time job.
  Boards are not built to make board members rich. They are designed to find people who can contribute knowledge in a part-time but important capacity, who are taking some time and risk in doing so, and need to be compensated for that time and risk.
  
  Join a board because you’re excited to contribute, feel good about what you’re learning, and feel you’re getting paid fairly for it. If you’re building a full-time board portfolio as your post-retirement gig, then you’re looking for a good mix of forms of compensation, either fixed or variable depending on your personal circumstances and financial risk appetite.
  
  Last point - and it's an important one:
  ‍
• The people you know and who regard you well want to be helpful in your board search AND they are also exceptionally busy.
  Before you call them up and ask them to spend 30 minutes with you talking about boards generally - make life easy for them by doing the things on this list first. It shows them you have done everything you can to prepare for board service on your own, while leveraging their time very specifically for intros or to answer a company board specific question when you’re in process. 

Any questions? Any advice you’d add, based on your own experience? Leave a comment on LinkedIn and I’ll do my best to address these publicly for everyone’s benefit.

About Sukhinder Singh Cassidy

Sukhinder Singh Cassidy is the CEO of Xero, a $10bn global fintech platform for SMBs and their advisors.  She is an experienced executive, entrepreneur, and board member with more than 25 years’ experience building and scaling global companies including Google, Amazon, Yodlee, Joyus and StubHub.

From 2018-2020, Sukhinder served as the President of StubHub Inc (a subsidiary of eBay) - a leading global ticketing marketplace for live entertainment. Sukhinder was responsible for running the company and also served as a member of eBay’s global executive leadership team. In 2020, she led the company’s sale for $4bn+ to international ticketing leader Viagogo, and successful response to the COVID crisis.

Prior to StubHub, Sukhinder was Founder, CEO, and Chair of Joyus, a video commerce startup from 2011-2017. From 2003-2009, Sukhinder was President, Asia Pacific & Latin America at Google, where she successfully built its operations from less than US$100 million in revenue into a multi-billion dollar business, spanning 103 countries. Prior to Google, Sukhinder co-founded fintech pioneer Yodlee from 1999 to 2003, where she served as SVP of Sales and Business Development.

Sukhinder currently serves as Lead Independent director of Upstart.and has previously served on the boards of Ericsson, Trip Advisor, Urban Outfitters, Stitchfix, J.Crew, Jobtrain and more. She is also a pioneer in advancing diversity and inclusion in the boardroom. In 2015 Sukhinder founded theBoardList, an online talent marketplace connecting CEOs with qualified diverse board candidates. In 2023 theBoardlist merged with BoardProspects, a leading platform for board recruitment, where she remains a large shareholder and director. 

Sukhinder is the author of the Wall Street Journal best-seller, “Choose Possibility” which offers advice on how to manage and optimise risk-taking for professional growth. She currently lives in the Bay area with her husband and three kids and is a graduate of the University of Western Ontario with a BA from the Richard Ivey School of Business.