Approaching Tough Conversations as a Founder

Name Celia Fox Platform Associate at Pillar VC

No one looks forward to tough conversations; it never feels good to head into a difficult discussion. The good news is that you always feel better once you’re on the other side. While it can be tempting to kick the can down the road, you’re better off tackling tough topics head-on. While these conversations are unavoidable, there are also steps you can take to make them easier for everyone involved — including yourself. 

We talked to several Boston-based leaders about how they have navigated tough conversations with team members, employees, and even co-founders.

Here are the top pieces of advice we learned.

Don’t Wait — Dive Into Tough Topics Early

Gabriela McManus, SVP of People Operations at Drizly, notes, “By the time it’s a hard conversation and you don’t want to have it, you probably should have had it sooner.” As a manager, start to build a habit around open conversation. Initiate tough conversations and sharing feedback early and often — ideally before they become tough conversations in the first place. 

Reflect and Prepare For the Conversation

Before you head into a difficult discussion, McManus recommends taking time to reflect on what actions and choices led to this conversation. Ask yourself why this is tough and emotional for you in the first place. Oftentimes, it goes back to mismatched expectations; you may realize you weren’t clear enough about articulating your expectations for the individual or the situation.

Focus on behaviors and actions as opposed to the judgements and assumptions behind them.

Additionally, distill your frustration down to the behaviors involved and consider that your reality is not the same reality as the other person involved. What judgements and assumptions may you be bringing to the equation? When it’s time to sit down and have the tough conversation, it is especially important to take your emotions out of the equation. Focus on the behaviors and actions as opposed to the judgements and assumptions behind them.

Create the Right Environment for Feedback

Brian Halligan, Co-Founder and CEO of HubSpot, shares that in his experience, most feedback is best given in a private setting. Halligan notes, “It took me a long time to realize that as CEO, people really do care a lot about what you think. My words can both really elevate a group or really take someone down.” 

Bhavika Shah, Product Manager at recommends starting by asking the person you’re meeting with whether they are open to receiving feedback. Give them time to get into a prepared mindset, letting down their defenses. Plan ahead to avoid catching someone when they’re having a bad day and are not in the headspace for a constructive conversation. Share your feedback in a confidential environment, where you can each feel comfortable having an open conversation. Some people may even prefer to read the feedback and digest it prior to having a conversation. People don’t like to be caught off guard — certainly not in a public setting. 

Share Concrete Examples and Suggestions

Tackle your message head on, delivering tough feedback early in the conversation, in a clear manner. While some follow the “good news sandwich” approach — good feedback, followed by tough feedback, followed by more good feedback — studies have shown that you should lead with difficult feedback first, as opposed to easing in. This ensures that your feedback will get across and be digested by the other person. 

When giving feedback, Shah also recommends that you focus on providing concrete examples of the behavior you’ve observed and takeaways of what could specifically be changed or improved. This enables you to ensure that the feedback is both objective and productive for both parties.

Ultimately, tough conversations are unavoidable and preparation is essential. Be proactive by opening the lines of communication with your team early on. Reflect and prepare in advance, creating an environment where sharing feedback free from emotional judgment that focuses on concrete examples of challenging behaviors is the norm. Your entire team will be better when you lead with transparency, clarity and honesty.