Business Conversations That Make Me Lose Sleep

Which workplace exchanges do you find to be most difficult? For most people, they’re centered on two things: Personnel and performance. Both of these things straddle the worlds of internal communications and HR, and both are also general managerial challenges.

I recently read an interesting column in Business Insider about the toughest conversations you can have at work. They were:

1. The Emotional Dismissal Conversation
2. The Awkward Personality Conversation
3. The Underperformance Conversation

All these are tough, but they are typically part of the same progression, and the progression usually starts with number three above, and ends with number one. Here are the toughest workplace conversations, from my perspective, and how I proceed.

Personnel
These kinds of issues run the gamut—from people who are squabbling, to turf wars, to folks who simply don’t work well together. Sometimes goals don’t sync up. Other times, actual performance doesn’t fit the needs of the job, and that’s typically when the three-conversation pattern that Business Insider described kicks in. To my mind, all of these things are a huge challenge and all of them divert from the common business goal.

I’ve learned over the years that a sustained, tight focus on performance is the way to go. There should be no politics, no gossiping, just set a tone for the group that all you care about is results. Results require collaboration. Keeping everyone focused on that creates a sense of confidence that relaxes a group and empowers them to experiment and achieve.

Business Relationships
This is another difficult area, but for communicators, it’s critical. Everyone from entry-level account managers to CEOs deals with either external clients, or with the public. Think of how frequent it is that a lower-level employee embarrasses a brand on social media, either when representing the company, or through some personal post that goes viral.

Of course, we’re talking about conversations—whether with a subordinate or a colleague, or with an external customer. I’ve learned you can’t wing it when it comes to customer conversations. Too much is at stake. Policies that everyone knows about and understands are critical, and these have to come from the top. I’ve had many conversations with customers in my career, and when business is on the line, they can be really tense. For me, the way to ensure that you preserve the business—if that’s the goal, sometimes it isn’t—the relationship has to come first. (This is a bit counter-intuitive, because I just stressed the importance of policies.) If your customers trust that you have their interests at heart, and you have thought through their challenges and understand their objectives—you’ll keep the business. If they feel like you’re officious, and policy-bound, you won’t. Never use the word “unfortunately.” That conveys a focus on your internal policy, not on customer-service. It is also condescending. Never use the phrase, "We're not set up to do that" for the same reasons. Always be ready with a solution or two.

Business Performance
For a lot of professionals, in PR and elsewhere, this is always a stress-inducing conversation, especially if you’ve fallen short of your goals. But it doesn’t have to be. Putting aside the possibility of the fundamental lack of skills to do a job, most business-performance shortfalls relate to external factors in the market, not to your execution. So it really is an opportunity to shape a conversation about missing goals into the cool ways you’re going to pivot to adjust to changes in the market.

What are the business conversations you struggle with the most, and what advice can you offer?

—Tony Silber
@tonysilber