Courageous Requests

Most leaders share a desire to become more skillful at initiating conversations that require courage. Situations arise every week that invite us to speak up with vulnerability and bravery. We see how relationships, our work, team interactions, perhaps whole organizations could be improved, if only….

Yet, we find all kinds of reasons to side-step these conversations: There isn’t time. The time isn’t right. This issue isn’t a priority. Things will improve. Fear keeps us in avoidance, in stasis.

It takes willingness and  practice to purposefully step into conversations that are hard. In this post, we revisit how to do so, zooming in on the specific skill of making courageous requests — asking a person for something specific, something you’ve reflected on carefully, and doing so in a way that builds trust.  

Not every courageous conversation requires a request. Sometimes, what makes a conversation “courageous” is sharing an emotion, need, or more private aspect of ourselves, and our only need is to be heard and held.

Yet often, a request does exist, lurking in our subconscious. A twinge in the belly or a tightening fist might signal that you have an unmet need. In our coaching, we find that the process of reflecting on what you’re noticing, uncovering the stories you’re telling yourself, and naming your feelings will point you to the request. And sussing out the most important request builds your “agent of positive change” muscle — a core skill of  leadership.

Let's look at an example.

A leader in a small organization — let’s call him “Charles” — expressed increasing frustration in his interactions with a colleague he doesn’t supervise and collaborates with regularly.

Charles and his colleague “Sarah” used to work together in the office; due to the pandemic, they now work virtually. However, the leadership team never discussed or established clear agreements about what virtual collaboration would look like. Working from home, having family members around, and juggling illness exacerbated some existing tension; all the “normal” expectations related to work hours, availability, and desk-to-desk communication went out the window.

Charles described text streams where his colleague went suddenly silent, meetings when she didn’t show or send notice, and last-minute “questions” that spiraled into hours of work. He felt stuck, unsure about how to get untangled and move forward. Specifically, he didn’t feel clear about what to ask of Sarah. He was sure  something had to change — to keep the organization’s work on track and to repair their relationship — but what, exactly?

Enter the practice of preparing for courageous conversations and making clear requests.

In a coaching session, Charles named what he was noticing. He made a list of observations — with no “judgy” words. For example:

  • 3 emails he sent Sarah last week received no response

  • For 2 meetings they’d scheduled last week; Sarah didn’t show up or communicate beforehand

  • Sarah sent Charles an outward-facing communication 2 hours before it was due to go out, seeking his quick sign-off, yet it contained 3 errors and wasn’t in final format.

The list went on.

The length of the list, impact on the organization, and his care for Sarah made it obvious that this was a conversation that was worth the effort.

Let’s linger on “worth the effort” for a moment. A common misconception is that relationships should be free of friction; we disagree. One way humans demonstrate that a relationship matters is by skillfully stepping into courageous conversations as an act of tending. We tend relationships that we value. Charles affirmed that this relationship with a fellow member of his lead team mattered a lot.

Next, he explored the stories he was telling himself. Via email with me, he connected his emotions to his internal narratives. As he practiced, his language shifted from “I’m frustrated with her” to: “I feel frustrated because I don’t experience a sense of trust in our work together. I’m telling myself some stories: that you don’t feel comfortable asking for my help, and that you assume I’ll just jump in and fix things at the last minute, because I’ve done that in the past.”

Through the act of identifying the stories we are telling ourselves, we discover that our emotions arise not from another person’s behavior, but from the sense we make of what we’re noticing. Under the frustration, Charles identified feeling embarrassment.

Finally, Charles identified his requests. Because so many layers of issues had piled up, he initially had a hard time sorting through what the most important request was. In our next session, we talked through his needs, and Charles identified “trust” as most important.

After considering many options, he honed in on three key requests:

  • If you’re going to arrive late to or miss a meeting, would you please send a text as soon as you know?

  • When you need help on a task or project, are you willing to ask me directly, and give us at least 24 hours to really collaborate?

  • When either of us feel that a back-and-forth text exchange should become a discussion, can we name it and shift to phone?

    _____________________________________________________________________________________

    This is a real-time example, so we can’t yet share the outcome for Charles. However, we know this practice works because of our clients’ many successes.

    Although leaders often fear that making a courageous request will cause pain or make things worse, it’s not true — at least the “making things worse” part. Often, it is uncomfortable to make a courageous request. Yet so far, every leader we know has benefited from this practice.

    These types of conversations yield powerful agreements, made stronger through negotiation. Courageous requests live at the heart of strong relationships, teams, and organizations.

This practice synthesizes our learning from multiple sources noted in the Deeper Dive, below.

Making Courageous Requests

Prepare

  • Consider the scratchiest relationships within your professional life now. Who is the most important person for you to “untangle” something with? How could tending to this relationship improve the ease of doing important work together?

(If you realize you have been “letting things slide” and are unwilling to tend the relationship, you have other work to do.)

  • To become clearer about the situation, think through the “Once in the Conversation” steps, below. Most leaders find it helpful to jot notes about their observations, inner story, feelings, and requests.

  • Request a conversation.

“Is now a good time to have a conversation with you?” or “Could we talk tomorrow  at 3:15? If not then, when is a good time for you?”

  • When the time comes, use your familiar practices (e.g. taking 3 breaths; grounding your feet; aligning your hips, shoulders, and ears) to ensure that you enter the conversation feeling calm, open, focused, flexible.

Once in the Conversation

  • Value the relationship. You’re choosing to invest in this relationship, so let the person know why.

“I’m invested in our relationship because…” “We share the goal of…”

  • State observable facts about the situation without evaluation, blame, or moralistic judgment. Identify specific behaviors and give data/evidence.

“I noticed…” “I heard you say…”

  • Illuminate your inner story. As humans, we naturally try to make sense of things by making up narratives. When we  share the “looping thoughts” running through our heads, we help others understand us better and see our perspective. It also helps to remember that our stories are thoughts that can shift.

“A story that I’m telling myself is...”

  • Identify the feelings the situation brings up. We often skip our feelings, yet this step is what humanizes us and builds trust. We also take ownership of our feelings. It’s not “You made me feel…” but rather

“Because of the story I’m telling myself, I feel…”

  • Make a specific request (not a demand or an entitlement), and then negotiate it with the other  person so it feels like a win for all.

“My request is…” “Would that work for you, or do you have a different idea?”

  • Value the intended impact of the conversation, which also reinforces that you value the relationship.

“I’m grateful that we…” “I’m hopeful this conversation will allow…”


This time offers us an energetic fresh slate. Step into the challenge of initiating a conversation you know has the potential to create positive change. Invest in deepening a relationship you care about by naming what you notice, owning your story, and making a request you think will make a difference.

Deeper Dive

Quotes

“Courage is a heart word. The root of the word courage is cor - the Latin word for heart. In one of its earliest forms, the word courage meant "To speak one's mind by telling all one's heart." Over time, this definition has changed, and today, we typically associate courage with heroic and brave deeds. But in my opinion, this definition fails to recognize the inner strength and level of commitment required for us to actually speak honestly and openly about who we are and about our experiences -- good and bad. Speaking from our hearts is what I think of as "ordinary courage.”

– Brené Brown, I Thought It Was Just Me: Women Reclaiming Power and Courage in a Culture of Shame

“People fail to get along because they fear each other; they fear each other because they don’t know each other; they don’t know each other because they have not communicated with each other.”

— Martin Luther King Junior, from a speech he gave in October, 1962

Cyndi GueswelCourageous Conversations, Requests, Nonviolent Communication, Brene Brown, Glenn Singleton, Difficult Conversations, Courage, Leadership, FeedbackComment