The Key to Difficult Conversations as a Founder

Strategies for tough conversations from Laura Crabtree, CEO and Co-Founder at Epsilon3.

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Sep 11, 2024

Hi, friend!

Difficult conversations are part of every founder’s growth path. The high-pressure environment demands clear and effective communication. Without it, team cohesion and culture can unravel quickly.

On this topic, I’m excited to share a guest post from client Laura Crabtree, the CEO and Co-Founder at Epsilon3. Laura offers practical strategies for the toughest of conversations. These insights come directly from her experience as a CEO and have helped her face challenging conversations with confidence.

Thank you for contributing, Laura!

Let’s dive in.

~ Amanda

Some of the hardest leadership moments come when you need to have difficult conversations, which can range from giving critical feedback to making tough calls about your team or negotiating with investors or customers.

Handling these conversations poorly, or avoiding them altogether, can have serious consequences. When tough issues are mishandled or unaddressed, team culture suffers, trust in leadership erodes, and the cohesion you’ve worked so hard to build starts to degrade.

It’s not just about one conversation—it’s about the ripple effect on your entire organization.

I learned this lesson firsthand.

As an engineer, I hadn’t yet learned how to handle a team member who was struggling. While I recognized the need to address specific issues that had arisen, I hesitated. I feared the fallout—how a single conversation could change my relationship with this person, or impact team morale. I delayed the conversation, hoping the issue would resolve itself.

What I learned was that, by not addressing it, I was also directly impacting team morale and dynamics.

By the time I took action, the issue had intensified. The team had noticed the problem and had also noticed my delay in addressing it. I realized then that avoiding the difficult conversation only had the potential to make things worse.

Once you finally make the decision to address a problem, the initial issues may have grown into bigger issues. In addition, your team might also have sensed something going awry, or see the problems firsthand. At some point you may even get direct feedback if you've waited long enough.

Two key takeaways emerged from this experience.

First, it’s crucial to address tough conversations right away. Delays only lead to bigger problems and can undermine trust within your team.

Second, as a founder, you set the tone for communication in your company. By handling these conversations effectively, you model the behavior you want to see in your team.

Since then, I’ve become more decisive in giving feedback. When I have constructive conversations, I’m clear about what I need and the timeline for improvement. By tackling issues head-on and communicating clearly, I’ve been able to maintain a healthier, more aligned team dynamic.

My tips for difficult conversations

After learning the hard way, I’ve focused a lot on my communication. If I could offer you the guidance that made the biggest difference for me, it would be these four tips.

1. Define the goal

Before you start any difficult conversation, clearly define what you want to achieve. Outline multiple potential outcomes—sometimes one of two or three different results might be acceptable. Knowing these desired outcomes helps keep the conversation focused and ensures you’re steering the discussion toward a productive end. Without a clear goal, it’s easy to get sidetracked or miss the point entirely.

2. Outline the key points

Preparation is everything. Write down the main points you need to communicate. This simple step can make a huge difference. It keeps you on track and helps maintain clarity throughout the conversation. Sometimes, I repeat these key points multiple times during the conversation because people don’t always hear everything the first time. When emotions run high, having your key points in front of you ensures nothing important gets lost.

3. Balance directness with empathy

Being direct is important, but so is empathy. It’s a fine line, but striking the right balance makes all the difference. You want to be clear and straightforward without coming across as harsh. Approach every conversation with respect, treating others as you would want to be treated. Show that you care about the person you’re speaking to, even when delivering tough feedback. This balance helps preserve relationships and foster trust.

4. Tailor the message to the individual

Every person is different, and your approach should reflect that. Tailor your message to fit the recipient’s personality and communication style. Some people respond well to directness, while others may need a gentler touch. Understanding the other person’s perspective can make your conversation more effective and increase the likelihood of a positive outcome.

These four tips have transformed how I handle difficult conversations. By applying them, you can tackle these challenging moments with more confidence and ease.

Keep learning and growing

Difficult conversations are opportunities for growth. Shifting your mindset to view these moments as learning experiences can improve how you lead.

My wish for you is that these conversations, while challenging, become ways you strengthen your team, refine your communication skills, and embody the leader you’re meant to be.

— Laura