Whenever I train People Leaders (supervisors), I ask the crowd: How many of you have been in the situation of being promoted into a supervisory role above your current peers/team members?Always more than two thirds of the room raise their hands.

We’ve all been there. The team meeting is chugging along. Moving from agenda item to agenda item. And then, something shifts. Maybe you can feel the tension, sense a weird energy, or notice resistance lurking below the surface.

Let’s face it. It can be anxiety-producing to wade into hard conversations. You might need to have a conversation about performance with a direct report. Or you need to bring up a touchy subject with your co-worker. We’ve all been there.

When I ask supervisors for their burning leadership questions and the hardest parts of being a supervisor, one theme that comes up is communication.

I often ask leaders in my trainings questions like: "What are your burning questions about being a people leader?" and "What is the hardest part of being a supervisor?" I thought I'd share some of what I'm hearing.

What does it look like to lead in a complexity? That's one of the big questions Margaret Wheatley's book, "Who Do We Choose to Be? Facing Reality, Claiming Leadership, Restoring Sanity," is helping me explore.

I have found the past few months especially stressful. There has also been a lot of uncertainty. Factors that are just plain out of my control.

Think of a leader who you really admire.I would be willing to bet you a cup of coffee that person was emotionally smart. 

One day as I was working in my role as chief financial officer of a national nonprofit, my deputy director blurted out, “Well… we know you don’t like to receive feedback.”   I was shocked. I thought I was just fine with feedback.   I gave her an uncomfortable laugh and asked, “Really? I come across that way?”

Are you managing a team where only a few dominate and others seem to be just watching the clock?  Or is your team just a collection of individuals who report to the same manager?

In emergent landscapes we can’t rely on usual ways of planning. Uncertainty, change, and unpredictability all abound. Making it hard, and ineffective, to focus on planning. But we do have other tools at our disposal.

Emergent landscapes are, to say the least, tricky.It can be hard to even see you are in one!It can be so uncomfortable to stay in the uncertainty and just pay attention.

There are some clues that tell us we are in an emergent landscape. For example, the tools we are used to using just aren’t working. Things feel uncertain. Even uncomfortable. We can’t quite see what we need to do next.

Emergent landscapes are spaces where we can sense the old pattern needs changing. Something new is emerging but we don’t quite know what it is yet. Emergent landscapes often require new ways of thinking and adapting.

We now know that coaching can have a profound impact on organizational culture. We also know that coaching is different from when we act as a boss, mentor, or teacher.

Think of a time you really learned something … Was someone coaching you?

What do you think of when you hear the term "coach"? Maybe you think of coaching an employee with a problem. Maybe you think of a life coach or an executive coach. Maybe you think of Ted Lasso.

A Performance Improvement Plan (PIP) is a document and process to help an employee clearly understand the expectations they need to meet to perform their job satisfactorily.

I think it’s time to get real about where one-on-one conversations can go wrong. We’re going to explore two scenarios that are all too common. Ready to play along?

We’ve covered what can go right and wrong with a one-on-one conversation. And we’ve taken care of the nuts of bolts of what a one-on-one conversation is and why it’s important.
Now we’re going to talk about how to prepare for your conversation.