Defining Moments of Leadership

A common question among managers and agile coaches learning the skills of coaching others is, “How do I coach up”? In other words, “how do I coach my boss to be a better boss and tell them that I think they are the problem?” 

There are two common reasons this question arises: the first is that there has been a specific interaction that has left someone feeling deflated or demoralized. Perhaps they were not heard and understood, or they didn’t like the way they were spoken to. The second reason is that they feel unsupported in their work, or maybe feel like they are being told to lead change while their boss’s behavior keeps rewarding old patterns instead. 

This second scenario is part of a bigger issue—and one where it seems like the boss is the “problem.” Instead of creating change, it feels like you’re just slogging through the mud and getting your foot stuck with each step. 

But chances are, what’s going on is not something that can be solved as simply as the concept of “coaching up.” In fact, there’s no such thing as “coaching up.” If what you’re actually looking for is the opportunity to give feedback about a specific incident, this is a feedback conversation. But when you’re addressing a bigger, systemic issue, it’s time for something more. Instead of trying to “coach up” or give feedback, try inviting your boss to a Thinking Together Conversation. 

Speaking Truth to Power: How to Talk to Your Boss in a Way That Works

The Dark Side of Feedback

What’s missing most from feedback conversations in organizations today is the notion of inquiry. So many of us come into a conversation locked and loaded with our own perspective and the desire to just put our idea out on the table and have it heard. We expect the other person to make sense of what we’ve said and then take the action we desire. 

While direct and candid feedback has a place and purpose, the common one-way delivery of one person’s experience can be unbalanced. It assumes that one person has the complete picture, that one person’s ideas are more “right” than the other’s, and that spending time asking someone else for their perspective or input is a waste of time. 

This quick, get-in-and-get-out feedback style is what I call “driveby feedback.” It’s not really a conversation at all—it’s a one-way “download.”

No one wants to be told that they’re “doing it wrong,” and if you start from a place of assuming you know what the problem is—and only focus on telling your boss what they are doing wrong and what they need to do more of—it’s a monologic approach that makes you right and them wrong. You’ve invited them into a debate and set them up to either defend the actions they’ve taken or worse yet, just check out within the first few seconds of your conversation. 

A Thinking Together Conversation: Speaking Truth!

So, what’s a Thinking Together Conversation and why does it matter? You’re thinking together with your boss in a way that can create real change.

Thinking Together Conversations require 

• all parties to come to the conversation with genuine curiosity 
• the assumption that solving the current problem or dilemma cannot be done by just one person 
• a broader, shared understanding of what’s happening

In a Thinking Together Conversation we

• bring questions instead of solutions
• invite others into a dialogue instead of a monologue 
• support the purpose of learning together to craft a better solution
• engage in inquiry
• engage in a real, meaningful conversation that can shift something important to the dynamic 

3 Steps to a Thinking Together Conversation with your Leader: Speaking Truth

Here are some action steps you can take to invite a Thinking Together Conversation: 

Step 1: Be clear about your intention.

Why do you want to have this conversation? How do you want to show up in it? 

If your answer to either of these questions comes from a place of wanting to reprimand, punish, or blame your boss, then do some work on your own thinking before asking to have a conversation. Coming from that place will not serve anyone, and it definitely does not promote curiosity.

If, however, you’re coming from a place of genuine curiosity and seeking to understand—with a belief that there is more than one side to what’s going on—you’ll be in a much better position to start a real conversation. If you are willing to engage in a way that’s open to hearing different perspectives, both you and your boss will likely learn new information. From there, you will be far more likely to be able to create a new solution together. 

Step 2: Create an invitation.

Invite your boss into a conversation for learning and exploration. 

Behind every dilemma are multiple truths and perspectives about what’s creating the current situation. So make it inviting for you and your boss to want to come to the table. 

Imagine that you’d received the results of a 12-month engagement survey suggesting that your boss’ lack of engagement was impeding progress. You could give driveby feedback that would get you nowhere, or you could create an invitation:  

• “We just got the survey results back. I would love to have a conversation with you about it and get your thoughts.” 
• “I notice that the engagement survey shows a ‘lack of engagement by senior management’ as the greatest barrier to our performance. I’m curious what you make of that?”

Understand that when managers are invited to a conversation, they are often expected to solve a problem or have some solution immediately. Instead of replicating that dynamic, try inviting them to a conversation for learning and understanding. Together, you might co-create a solution. 

Step 3: Be prepared to offer your observations. 

This can be one of the most challenging aspects of a Thinking Together Conversation. It requires you to both be curious about your boss’s experience and perspective and candid about your own observations. David Kantor calls this the speech act of Bystand—a morally neutral observation about what’s happening.  To pull it off, you need to be prepared to share what you notice. Pulling from the scenario described above, here’s an example of how you might offer a morally neutral observation about what you see happening while remaining curious about what’s happening for your boss:

• “Would it be helpful if I shared what I’ve observed? You asked that we schedule more collaborative planning meetings and include you. We now have these meetings booked every two weeks. However,  you have attended 2 of 12 meetings in the past 6 months, and it’s left the team feeling confused and unmotivated. What’s happening on your end that’s pulling you away from these meetings? 

Thinking Together Conversations move us away from looking for someone to blame and hold us accountable to the kind of inquiry that supports meaningful dialogue. When we seek to understand multiple perspectives and learn more about what’s happening in the current situation, it’s much easier to discover a new solution that might not exist yet. It’s an effective way of speaking truth to power while creating space for real results.

Speaking Truth: How to Talk to Your Boss in a Way That Works  

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If this topic resonated with you, we encourage you to listen to this podcast with Aaron Smith!