Having Hard Conversations (Live Panel Discussion from 2022 MIT Sloan Search Fund Summit)

In this week’s episode, we discuss the importance of having difficult conversations, something that CEOs find themselves doing on a near-daily basis. We discuss three primary types of difficult conversations, including:

  1. Hard conversations around internal company dynamics (eg: terminations);
  2. Hard conversations about dynamics external to the company (eg: politics and global affairs);
  3. Difficult conversations that CEOs must sometimes have with themselves (eg: how and when to ask for help).

This is a particularly special episode of In The Trenches for a number of reasons, including:

  • This is our first ever video podcast! The video can be viewed below, or within Spotify (video unfortunately not available within other podcast apps, however)
  • This is our first ever episode featuring a panel discussion, including myself and a panel of four SMB CEOs, investors and Board members
  • This episode is a recording of a session that I moderated during the 2022 MIT Sloan Search Fund Summit, hosted by the ETA@MIT club

My Guests

Rafael Alfonzo is an entrepreneur and attorney with more than 20 years’ experience operating, investing in, and representing startup and growth businesses. Rafael is currently a Managing Partner of Radien Legacy Partners, an investment group focused on acquiring small, growth businesses.

Jenna Whigham is the President of Abound Health, which provides a comprehensive array of supports and services to children and adults with all types of intellectual and developmental disabilities (I/DD). Abound Health also offers OnTarget, an EHR platform for I/DD and mental health providers.

John O’Connell is an experienced entrepreneur, investor, and board member. He was Co-Founder and CEO of Wind River Environmental, the nation’s largest provider of non-hazardous liquid waste services presently servicing customers nationwide via 27 locations.

Pete Seligman is an investor, entrepreneur, board member and business coach who focuses on finding and inspiring the next generation of business owners. His investing activities focus largely on small and medium sized private businesses.

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Having Hard Conversations (Live Panel Discussion from 2022 MIT Sloan Search Fund Summit) In The Trenches

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Specific Questions and When They’re Asked

Internal Dynamics

  • (3:50) When terminating somebody, how do you have that conversation with the individual being terminated, and how do you communicate it to the rest of the company?
  • (11:35) How do you handle situations in which the company is facing some sort of meaningful challenge or problem? Do you shield your employees from concern and anxiety, or do you simply just tell them the unvarnished truth?
  • (16:40) For entrepreneurs purchasing other businesses: What types of difficult conversations did you have with the previous owners? What, if anything, would you do differently if given the opportunity to have the same conversations over again?

External Dynamics

  • (19:45) With respect to discussing political issues in the office: What role, if any, do you think a small business CEO should play in either fostering or discouraging these types of discussions among their employees?
  • (26:35) Increasingly, employees are expecting employers to take a stance on issues that are external to their company. A few recent examples include the murders of George Floyd and Breanna Taylor, and the current war in Ukraine. What role if any, do you think a CEO has in taking a public stance on these issues?
  • (30:25) What has the COIVD-19 pandemic taught you about how to best manage a company through a crisis (in this case, a crisis that was entirely outside of the company’s control)?

Personal Dynamics

  • (35:40) How vulnerable should a CEO be? Should they share whatever may be weighing on them personally at any given time? If so, with whom should they share it?
  • (42:50) CEO is a very lonely position. What outlets should CEOs create for themselves? What advice would you give to current CEOs who feel like they don’t really have an audience for the difficult conversations that they may need to have?
  • (45:55) How vulnerable should CEOs be with their Boards? How do they balance the need for support with the risk of appearing “weak” or unable to handle the challenges of the job?

Questions from the Audience

  • (50:10) As a CEO, how much financial information do you share with your employee base, and why?
  • (52:25) How did you approach difficult conversations with your customers (for example, when passing through price increases to them)?

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