Advisers can either sink your time or be your secret sauce, bringing valuable solutions, experience, and relationships to get you to the next level. Throughout the peaks and troughs of building my company, I have retained a core set of advisers - and these relationships have been enriching personally and brought maturity, perspective, and solutions to me professionally at every twist and turn of company building. The best advisers can oscillate between mentor, champion, coach, and confidante.

As the CEO, you must create the environment to deepen your adviser relationships so that they function at peak performance, across the cadence of your company's lifecycle. Here are a few ideas that can help you design, execute and operate a winning advisory board.


At the outset, you will have to manage the interplay between hard skills and advisory capacity. Do you wish to skew more towards domain experts in your field to address gaps on your team or operational weaknesses, or towards generalists and seasoned entrepreneurs who can serve as sympathetic counsel to broader challenges like fundraising or building company culture?

This may change over time, and that's fine - but it's helpful to map out the spectrum of hard and soft skills that you value now, and anticipate needing, to hit your next major milestones (e.g. to raise your next round of funding or your next product launch).

I have a one adviser who knows little about my specific industry but is a serial entrepreneur with multiple exits and IPOs under his belt, and another who was a venture capitalist and operator of marketplace businesses (we operate within B2B, SaaS & marketplace). Both bring tremendous, and complementary value to our advisory board meetings and allow us to collectively and iteratively go wide and narrow on the various topics and challenges in our discussions.


You can certainly interview advisers like you do co-founders, but I have found the best way to learn and engage is to have a "honeymoon" period during which you can evaluate just how vested they are in you and your business. A few months of working together on a tactical project or a problem will help you learn their style (too blunt, too soft?), applicable skills, and breadth of network. Anybody that asks for equity upfront comes with a red flag - they should be willing to spend time with you, assimilate and assess whether the partnership is a strong fit both in the near and long-term. Moreover, advisers should be vested in your success as a CEO and a leader, as well as in the success of the company.

Once the momentum to move forward is clear, structure a formal, legal adviser agreement detailing equity compensation (two year cliff, monthly vesting provisions are considered quite standard, but there is a ton of literature out there to support various incentive models), as well as a schedule of their role and responsibilities. These can be as granular as outlining the frequency of advisory board meeting, down to ways they can leverage their network for you through customer introductions, investor meetings, etc.


As with most things, preparation is key and you should treat adviser meetings like board or investor meetings. For them to be helpful, they need to know the data and have a clear understanding of your exact needs. Do you need their input on an operational decision (such as hiring, firing), do you want to debate pro's and con's of a particular strategy or opportunity, or are you craving some emotional coaching within a more informal context. You should also regularly audit and benchmark your advisers. How frequently are you connecting with them and are they vested enough to reach out to you ad-hoc to check-in? I set calendar reminders and keep a Trello board to ensure that we are maximizing the value of our advisers who are all shareholders in the company.

As you move along, it will be critical to continue to evaluate your progress against shared goals and give advisers feedback on how their advice and recommendations are working out. This is often the hardest part in the early stages of your relationship, but you have to be explicit and clear where things did not work and be able to learn why. You also shouldn't be afraid to cease the relationship if it's not working out and make space for fresh mindshare. On the other hand, there is nothing more gratifying for your adviser than knowing when a professional introduction leads to a new hire, a customer lead turns into a new sales contract, or a strategy pivot that is showing early signs of promise after a brainstorming session.

While advisory roles and relationships are likely to change as your company evolves, taking time to think about and be deliberate in the way you design, execute and operate your board will help ensure your long-term success.

Jag Gill is the Founder and CEO of Sundar, which is building the world's largest global sourcing platform connecting the apparel supply chain. She founded Sundar after a decade-long banking career where, as a senior executive working as trusted advisor to some of India's leading apparel industrialists, she uncovered a paradox: the complexities and inefficiencies of the fashion supply chain were at odds with the fast pace of consumer demand for on-trend fashion. This became the white space from which Sundar was borne. Jag is a graduate of the Massachusetts Institute of Technology and was a 2016 New York City Economic Development Corporation Venture Fellow.