Even as a seasoned executive, I still feel that knot in my stomach before a #tough_conversation. With a team member whose performance is slipping. A peer creating friction. Or a partner across the table when I have to deliver bad news. I’ve learned that avoiding it only erodes trust. A while back, I had to tell a long-time partner that a key project milestone would be missed due to an interconnection delay beyond our control. I knew it would land hard - it meant financial strain for both sides. I could’ve sent an email. Instead, I picked up the phone. I acknowledged their frustration, laid out the facts, and - most importantly - offered options for moving forward. It wasn’t an easy conversation, but it preserved the relationship because it became a negotiation, not just bad news. Here’s what works, whether you’re talking to a subordinate, a peer, or a counterparty: - Lead with context, not blame. Show why the conversation matters and connect it to the bigger picture. - Be specific—and bring options. Don’t just drop the problem. Share what’s at stake and what’s possible. - Invite dialogue, not just agreement. Pause. Ask, “How does this feel to you?” or “What’s the best way forward from your perspective?” Even after decades in leadership, I still feel a flicker of discomfort before these talks. But that discomfort is a signal - you’re about to build trust, not lose it. How do you handle the tough talks?
Thanks for sharing, Vitaly
Candid, open and sincere conversations are key while dealing with these challenges and scenarios. Emails are certainly not my favorite form of communications since there is so much lost in translation.
Picking up the phone (or meeting in person) can be really tough. But having a conversation gives so much more life than a soulless email. So much is lost when you send text only. Appreciate you talking about this and providing some guidance from your experience, Vitaly!
Wow, so true and such wise words Vitaly!
Executive Strategist (Coach) | Clarity Creator & Execution Ninja | Facilitator | Webinar Host, Panel Speaker & Podcast Guest | Author of "Keeping It Real" Expected Publication: Dec. 2026
2moVitaly L., as an executive coach who helps folks navigate exactly these kinds of situations, I couldn’t have said it better myself. Well handled. And thank you for sharing this as an executive… It helps others feel less alone.