AI, boardroom unknowns and preparation, with Mark Williams, Chief Revenue Officer, Datasite Group

In this episode:

“The amount of unknowns that I had on the table, I joked with my CEO at the time that we needed a bigger table.” 

This week's guest on the Boardroom Confidential podcast is Mark Williams, Chief Revenue Officer at Datasite Group, a company providing secure software solutions for managing the full spectrum of financial transactions. 

Mark has years of experience as a senior sales leader and, unlike our previous guests, Mark doesn't sit on a board, but his experiences in the boardroom have often come at the most crucial times for a business. 

He shares with us the boardroom stories that have shaped his career, including being thrust into a high-stakes board meeting at just 28 years old when a single deal could materially impact quarterly results for a public company. 

He talks about overcoming imposter syndrome through meticulous preparation, using preparation as a tool to overcome boardroom unknowns, the "one build rule" that transformed how he approaches board communications, and why understanding the people in the room is just as important as knowing your numbers.  

He also shares his views on how AI is enhancing rather than replacing human connection in business, and why he is “bullish” about the positive impact the technology can have on business dealings in the near future. 

Boardroom Confidential is brought to you by Sherpany, a leading meeting management solution, designed to meet the unique needs of the board, board committee, and executive meetings. 

Chapters:

(00:00) Introduction 

(01:31) Evolution of Data Rooms 

(04:39) Preparation and Support 

(06:15) Overcoming Imposter Syndrome 

(09:03) The One Build Rule: Effective Communication in the Boardroom 

(16:53) The Future of AI in Board Meeting

Key Takeaways 

The two levels of board meeting preparation

(04:44) 

Mark Williams: The preparation was extensive. You don't always know what question you're going to get, so you may get four or five questions — but you need to be prepared to answer over a hundred. The second level of preparation is understanding the intent behind the question, so that you can interpret how your answer will be received. I was taught by some very senior people that less is more: answer the question you are asked, while understanding the intent — but don't provide more than what has been asked for. 

The one-build rule: why boardroom answers need a hard limit 

(09:07) 

Mark Williams: My CEO at the time explained the one-build rule to me. You have a designated point person for the question. When they answer it, if there is more detail or an additional point of view that somebody feels the board will benefit from, that person can call an audible — and add to the answer. But only one person gets to do that. That is the one build. It forces a degree of discipline. You have to be very confident that what you are going to build on the answer with is actually going to add value. And if you're not sure, you shouldn't say anything. Because if somebody builds a second or a third time, you take the board further and further away from the original question — and ultimately that leads to confusion. In a board meeting, you want a hypersense of clarity. 

The small language habit that undermines boardroom clarity 

(10:48) 

Mark Williams: When you talk about your company on a daily basis, you can quite often use jargon or acronyms that you're comfortable with — but board members may not be, because they are not in the business on a daily basis. Preparation can really help with providing clarity for a board member you're answering a question for: make sure you are not using jargon or acronyms that won't be fully understood by somebody who isn't in the business every day. 

Know who's in the room — and why their questions come from where they do 

(12:00) 

Mark Williams: Understanding the people on the board is very important. It gives you an opportunity to assess and interpret where their questions may be coming from. Is somebody on the audit committee? Does somebody have a finance background? Has an independent director been a CEO before — are they taking a holistic view of the business? Understanding where somebody's questions may be coming from helps you prepare, but also helps you prepare any clarifying questions you may ask before actually answering. 

Why agentic AI will be shaped by people outside the industry — and what boards should expect 

(17:30) 

Mark Williams: I think some of the capabilities that will be imagined over the next couple of years are going to come from some unfamiliar sources — people using the technology in ways that folks who are currently in the industry, in the market, haven't considered yet. Ultimately, that capability is all underpinned by the data you have access to. And as much as the technology is advancing, we're going to see policy advance equally as fast — so that people understand the constraints they have, the responsibilities they have. Those AI privacy and data policies will be forced to acknowledge capabilities that are as yet unimagined. And I think that is going to unlock a lot of value for people.