How to Mentally Prepare for a Difficult Conversation

Terminating an employee, especially someone who has been with your startup for a long time, is one of the most difficult and unpleasant tasks a founder has to face. Imagine that, in five minutes you have to fire your co-founder. How do you mentally prepare for that difficult conversation? We sat down with Matthew Bellows, a serial entrepreneur who has spent decades cultivating successful businesses and mindfulness. In a conversation with Shikhar Ghosh, Bellows shares how meditation can help you mentally prepare for the dreaded conversation of firing a colleague. And he guides us through a three-minute meditation you can do before any stressful situation.

Steps to Help You Prepare for a Difficult Conversation

1. Prepare the Environment and Make Sure You Won’t Get Interrupted
2. Take Time to Do a Short Guided Meditation Immediately Before the Conversation
3. Stay Mindful During the Conversation—Listen and Pause before Reacting

During the process of starting and scaling three ventures, Bellows—like most founders—has had to fire colleagues when the venture’s growth outpaced an individual’s skill set. But, uniquely, Bellows made the decision to replace himself as CEO in his second venture. After selling his first startup, WGR (Wireless Gaming Review) Media, Inc., to CNET, he built his second startup, Yesware, into a leading email productivity platform. Eight years after founding and growing Yesware, Bellows advocated hiring a professional CEO to replace himself and he became Chairperson of the Board. He realized that a professional CEO could scale the business to heights it might not reach under a leader with his skills. That decision, plus his experience being terminated earlier in his career, convinced him that mentally preparing for the firing conversation by meditating benefits both parties.

Before the Conversation to Fire a Colleague

Most founders focus on the process and actions required to terminate an employee. You spend weeks, or perhaps months, thinking about the situation and talking to the board. After gathering data to support the decision, you review the compensation package with HR and gather the forms the person needs to sign. Those steps can feel draining and time-consuming. By the time the actual conversation occurs, often, a founder—or anyone forced to fire an employee— feels, “I just want to get through with the uncomfortable conversation,” Bellows observes. 

As a result, most entrepreneurs don’t prepare mentally and emotionally for the conversation itself. Instead, they mechanically convey the news. Bellows sympathizes with founders who “want to cross this off my list as fast as possible.” But taking as little as three minutes to mentally prepare can help you “have a genuine human interaction with the person, as a sign of respect for them and for your relationship.”

Prepare the Environment and Make Sure You Won’t Get Interrupted

First, make sure that you have blocked enough time to have the conversation so you won’t be interrupted. Arrange to meet in a space that affords some privacy and is relatively free from distractions. Bellows recommends arriving at the room you plan to hold the discussion early. “I try to set up the room and make sure the whiteboards are clean and make sure I feel comfortable there.”

Then he takes time to do a short meditation to ground himself immediately before the meeting. Taking as little as two to five minutes to clear your mind can make a huge difference. In the video below, Bellows leads a three-minute guided meditation to prepare for a stressful situation. A summary appears below the video.

Meditation Helps You Stay Mindful During the Conversation

Many people prepare for stressful situations by rehearsing what they will say. “First I’m going to say X. Then, if he or she says Y, I will do Z.” But trying to predict how the conversation will unfold and planing your responses rarely ends in the results you wanted. Instead of planning your responses in advance, meditation prepares you to listen to your colleague’s perspective. Because they will feel emotionally jolted, even if they suspected the decision. And

Begin the Conversation by Being Direct

Bellows advises anyone having to fire an employee to start the conversation directly. “Just say, ‘It’s not working out. You’re fired.’ Or, ‘I’m sorry to say this is your last day at the company.’ Be very clear about it and direct about it.” Then, give the person a chance to process the information and allow them to respond.

Meditating before a challenging conversation has helped Bellows communicate better by providing space to truly listen to the other person instead of instantly reacting. He explains, “after the person speaks, I give them a moment—I let them finish speaking, and then reply.” Over time, he learned, “I give better answers if I let the person finish speaking than if I try to jump ahead with what I think they’re saying.”

After the person speaks, I give them a moment—I let them finish speaking, and then reply.

Matthew Bellows

Providing a space for the person to react and simply listening to them can help “the person ground a difficult emotional experience with reality.” Regardless of your preparation, the conversation will likely feel unpleasant. Bellows acknowledges, “Be prepared for the person to provide explanations and even resist.” But taking time to mentally prepare by meditating beforehand will help you feel more grounded as well. 

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Helpful Tools and Resources

Interested in learning more about guided meditation and how it helps entrepreneurs? We recommend the following resources as a good place to start.

Meditation Apps

Headspace is an app that offers hundreds of guided meditations, animations, articles and videos that teach meditation and mindfulness techniques. Inspired and co-founded by Andy Puddicombe, Headspace allows users to try the app and learn the essentials of meditation and mindfulness with a free “Basics” course. After subscribing, you have access to an extensive catalog of meditations related to health, including stress, anxiety, and sleep, as well as business-oriented topics, including creativity, productivity, and improving focus. You can choose from 1-minute meditations if you’re time-constrained or add time as you progress.

Ten Percent Happier is a platform that provides guided meditations and practical teachings that help users improve their quality of life. The blog and app allow you to learn the basics for free; to access unlimited content, including guided meditations, talks, daily features, you can become a member. Topics include stress release, enhanced sleep, and ways to increase your capacity for joy, gratitude, and love.

Insight Timer publishes the world’s largest collection of free guided meditations. Its free library offers a broad selection of 30,000 short guided meditations on managing stress and anxiety and improving sleep.

Balance app is a unique personalized meditation audio program. Each time you use the app, you answer questions about your meditation experience, goals, and challenges. Based on your answers, the app suggests which meditations would be most useful that day.

Resources and Studies about Mindfulness and Entrepreneurship

In Mindfulness: Can It Help Entrepreneurs Spot Opportunity? Dinah Wisenberg Brin reviews recent research that explores the link between mindfulness—” non-judgmental present-moment awareness brought about by meditation, a focus on breathing, or other approaches”—and “entrepreneurial opportunity recognition.” 

In “Doing Well and Good: An Exploration of the Role of Mindfulness in the Entrepreneurial Opportunity Recognition and Evaluation Process,” authors Louise Kelly and Marina Dorian explore the impact that mindfulness has on the opportunity recognition process of entrepreneurs—the act of recognizing shifts in technology, markets, or government policy and the ability to integrate those insights into meaningful connections and build new products. Their research also underscores the role that metacognition and emotional self-regulation play in entrepreneurship: “improved attention, focus, and increased creativity, as well as awareness of both opportunities and one’s own biases, result from increased mindfulness.”

In “Mindful Entrepreneurship: The New Age of Business,” Danielle Sabrina (CEO of Tribe Builder Media) shares how practicing mindfulness helped her business. She reflects on how slowing down to practice mindfulness may seem counterintuitive but can actually save you time in the long run. Mindfulness, she stresses, “allows us to become more aware of our thoughts, choices, decisions, and reactions. It encourages introspection and lets us step back from the turmoil of a situation, giving us a clear vision”—all of which lead to better business decisions.

The study “Mindfulness, Indigenous Knowledge, Indigenous Innovations and Entrepreneurship,” concludes that mindfulness facilitates innovations and entrepreneurship.

• Category: (Co)Founder Knowledge, Founder-CEO Roles & Challenges
• Tag: difficult conversations, firing, leadership, meditation