6 Min Read

10 Ways to Master Difficult Conversations

Every leader will inevitably face a difficult conversation. The ones who master it will not only win the admiration of the people they lead but will achieve results beyond what anyone expects.

I still remember my first difficult conversation. I was selling software at the time, and there was an implementation that was not going well. I was risking my integrity and knew I had to offer to cancel the deal and refund the money. (I had already received my commission which meant I would have had to pay that back. That would have hurt.)

I called the client and reviewed the situation.

I gave her two options:

  • She could cancel the contract, and we would refund her money.

  • She could accept my detailed plan to get things back on track.

I’m grateful she trusted me enough to let me get the project back on track. It was a gut-wrenching experience, but it saved a client relationship, the reputation of the company in the eyes of the client, and my integrity. Avoiding the conversation just would have made things worse.

Difficult conversations define leaders.

That wasn’t the last difficult conversation. In fact, the higher I rise in positions of leadership, the more frequent they seem to come.

Here are some lessons I’ve learned along the way:

  • Do have the conversation as soon as reasonably possible. People generally appreciate candidness. And if something isn’t going well, most people intuitively know but may not be sure how to approach you about what to do next.

  • Don’t have a difficult conversation via email. Just don’t.

  • Do make note of everyone involved or affected by the situation. That doesn’t mean you need to speak to everyone in a group. It does mean that you need to know how and who whatever your difficult conversation leads to will impact.

  • Revisit expectations previously stated and agreed upon. This builds common ground.

  • Identify the contrast between expectations and reality in specific ways. Document your observations in advance.

  • Pre-determine corrective action. Keep the pace of the conversation logical, pragmatic, and rational. If you go into it with just a “hope and a prayer” you could prolong disappointing results and frustrate yourself and others.

  • Allow for feedback and interaction. This shows respect. (Note: Only is extreme circumstances should this be avoided.)

  • Document the conversation and the details. What’s fresh in your mind today, may not be so fresh in a week or so. It’s also important that all parties involved have a chance to reflect and agree on the substance of the conversation.

  • Make the change. Don’t delay. Look for a win-win when possible, but deal with it directly and swiftly.

You can’t delegate difficult conversations.

I choose to have difficult conversations because I want the “win” more than I want to avoid discomfort. Leadership comes with its perks and its responsibilities. You have to accept both.

How do you handle difficult conversations? What have you learned along the way?



Ben Stroup is Chief Growth Architect and President at Velocity Strategy Solutions where he helps leaders design, develop, and deploy smarter business growth strategies. Ben is a futurist, disruptor, and data champion. He leads a team that takes a structured learning approach to business challenges, which allows them to assist leaders in bridging the gap between ideas, innovation, and revenue—taking ideas from mind to market.

Velocity Strategy Solutions is an on-demand, next-generation business strategy and management consulting firm which provides clients with a relentless focus on data, execution, and results that positively impact the bottom line. Velocity delivers integrated people and revenue strategies combined with a disciplined approach to growth architecture that elevates the capacity of leaders, teams, and organizations to succeed and win more.

Topics:   Leadership