Daring Conversations: How to Communicate with Candor, Clarity, Compassion, and Ease

There is no shortage of theories about why there are not more women leading companies, boards, and local, state, and national governments.

Explanations range from the persistence of the glass ceiling, inflexible work-life policies, maledominated networks, and unconscious gender bias. As a result, solutions for correcting the lack of gender parity typically include remedying workplace policies and practices that privilege men and penalize women—or sponsoring women to attend women’s leadership conferences, professional development training, and mentorship programs. And while all of these solutions have merit, what remains lacking is a complementary intervention that addresses a behavior most women struggle with—a behavior that leaders irrespective of gender need to possess.

For the last decade, I’ve supported women to step into their moxie—what I define as possessing the mindset and skillset to be able to walk into any room, or onto any stage, and speak up for yourself and the ideas and issues that matter most to you (and to your company). I have led a range of women’s leadership development programs—independently and on-site at organizations.

And while my work has supported women to develop comfort and competency in a range of areas, including interpersonal communication, public speaking, persuasion, sales, facilitation, and coaching, the top area where I’ve seen junior women, emerging female leaders, and even senior women struggle has consistently been in navigating difficult conversations.

A difficult conversation is any communication situation where someone is worried about how the other party(ies) will respond to what she says. As a result of feeling like the stakes are high, and the possibility for conflict and negative judgment even higher, once a person contemplates such a conversation, she usually experiences negative self-talk and uncomfortable feelings and anxiety in both the build-up and during the exchange itself (if the conversation ever happens— for often, it does not). While most leaders, heck, most people, irrespective of gender, don’t enjoy relaying critical feedback to a junior employee or telling a colleague to step back from a boundary she has trespassed, for rising female leaders, initiating and then following through and having such a conversation is particularly problematic—inter and intra-personally.

A woman in a former cohort of my nine-month women’s leadership development program summarized the discomfort best.

I know that my supervisor is waiting for me to be more rigorous with the feedback I give my team members before promoting me into a senior vice presidential role. Of course, that feels uncomfortable. I’ve received so little feedback in my own career, and I don’t know how to do that effectively for others. But worse than that is my awareness that when I do give feedback, my team members, male and female, react more harshly than they would if a male leader were delivering it. Knowing this just adds to my anxiety and makes me feel stuck.

In any potential difficult situation, we have four choices available to us. We can avoid the conversation. (And we know, statistically, most women do. According to research conducted by Linda Babcock and Sara Laschever published in their book, Women Don’t Ask, approximately 20 percent of women, for example, will never negotiate for anything—from a raise to the price of a car—because of this fear.) 

A second choice is to wing the conversation—just initiate it and hope for the best. While most women don’t choose this option, if and when they do, they inevitably they don’t have the impact or achieve the results they seek.

A third option, which, unfortunately, too many women do choose, is to ruminate on the situation. They mentally rehearse everything that they could say, and that someone else could say, as well as what could go wrong for all parties involved. This option, of course, exposes their psyche to the harshest elements of the conversation without the salve of actually getting it over with, which makes someone feel as wretched as they would after they laid outdoors in one-hundreddegree heat for an afternoon without sunblock!

Finally, the fourth option, the one that we will focus on, is planning out what you intend to say, visualizing your ideal outcome, and then role-playing your words to set yourself up (and set those you are speaking with up) to have a mutually-beneficial outcome.

One of the missing and very necessary ingredients for women to ascend into the highest levels of leadership is the support to develop the moxie to shift difficult conversations into daring ones. The good news is that developing this ability need not be complicated or expensive for organizations. The bad news is that catalyzing women both to make this shift and to develop the habits to consistently step into their moxie in potentially difficult moments, speak their truth, and call people to take action on their ideas is not something that can happen in a one-off, online, or face-to-face training.

For anyone, particularly women, to slay self-doubt, release the fear of judgment that often comes from speaking up in a high-stakes situation, develop their interpersonal communication and persuasive speaking skills, and respond to the feedback they receive when they do assert themselves, they need opportunities to practice initiating and facilitating daring conversations in real-time—over-and-over again. To further clarify, women need opportunities to get up on their feet, practice their verbal and non-verbal communication, and receive real-time, behaviorbased coaching and feedback from neutral coaches/facilitators on what they are saying so that they can transfer their learning not only into higher leadership aspirations but, just as importantly, into sustained, more effective communication and leadership performance.

Here are five tips for organizations who are ready to support their rising and seasoned female leaders to habitually shift difficult conversations into daring ones.

1. Provide women the tools to be present with the sensation they experience during uncomfortable moments.

Our self-talk plays a pivotal role in how we feel and, as a result, in the choices we make—or fail to. In her book, My Stroke of Insight: A Brain Scientist’s Personal Journey, neuroanatomist Dr. Jill Bolte Taylor writes provocatively about the direct relationship between our thoughts and our feelings. As Dr. Bolte Taylor, who survived her own stroke, explains, the moment we have a thought, a chemical is released in the brain. It travels through the body, and we have a corresponding physiological experience (or feeling). That sensation you experience as a result of your thought is not permanent. Dr. Bolte Taylor writes that what you feel will last only about ninety seconds. After these ninety seconds, we’ll have a new thought, and a corresponding new feeling.

Because the moment someone thinks about a potentially difficult situation she likely has a thought like, “Oh, darn it, this is going to stink,” (or something considerably more colorful), it’s critical for her to have tools to survive the ninety-seconds of discomfort that thought triggers. And, also possess the tools not to think such a negative thought again and jumpstart another ninety-second wave of discomfort. In addition to integrating the neuroscience of how thoughts impact feelings into coaching and training on difficult conversations, companies can teach and support participants to practice tools such as breath work, meditation, guided visualization, and affirmations to support employees with thinking possibility-centered thoughts and developing the presence and calm to have more vitality to navigate the conversations they want to have.

2. Support women to reverse-engineer what they plan to say from their desired outcome.

Most of us plan what we intend to say, be it in a pedestrian conversation, an important speech, or a difficult conversation from the beginning to the end. Unfortunately, this is the wrong way. Rather, if we want our communication to move people to take action on our ideas, we want to instead focus on what we want to have happen as a result of our communication. Then, we can reverse engineer each thing we say or ask of those listening to us to ensure that all of what we communicate is leading to that ideal outcome. The process of reverse engineering communication inherently shifts it from feeling difficult to feeling daring—for we see that we actually are the protagonist in what we are about to say. We know where we want to go, and we feel emboldened as we map out how to get there.

When supporting women to sculpt and rehearse for daring conversations, encourage them to ask open-ended questions, questions that make it easy for those listening to them to take action on their ideas. Questions can be about how that other person or people see a situation, what they want more of, less of, and what they are thinking and feeling. Also, support women to distinguish what they are entitled to say from what they want to say. For, in many cases, we are entitled to communicate a laundry list of complaints. Yet, doing so often prohibits us from achieving the ideal outcome we are using our daring conversation to work toward.

3. Choose words and phrases that project confidence, connection, and create safety and trust.

The words we use, moment to moment, in a conversation where conflict could transpire (or has transpired) often determine whether things go difficult or daring. I recommend using the following words as often as possible:

Yes. My favorite agreement word. Ever. It makes someone instantly feel seen and heard. You can say “yes” after someone shares an idea, an opinion, or a feeling, but do refrain from saying “yes and” and then redirecting the conversation back to you. “Yes and” works great in comedy, but “yes” as a complete sentence usually works better in daring conversations.

Thank you. You can say “thank you” to someone for sharing where she is coming from, for being vulnerable, for telling you the truth, for helping you understand her perspective, or for acknowledging wrongdoing or committing to better behavior in the future.

What I want for us is… These words work great for communicating what you want from the conversation. Try not to use them to linguistically wrestle for power over someone but rather to propose something that the other person, no matter his or her perspective, likely wants too.

Tell me more. Whenever people are dropping into vulnerability and you want them to know you really want to hear what’s going on, even if it’s uncomfortable—or on the flip side, when you want to nudge people beyond surface talk so they can go to the source of what’s truly going on—this short phrase is an effective way to do it.

I’m sorry. This is a very appropriate response when you have truly done something wrong, you want to take responsibility for it, and even more important, you want to communicate what you will do differently moving forward. Sometimes you may be sorry for the way someone is feeling, or the way you unintentionally made her or him feel—even if you haven’t done anything super sorry-worthy. Be clear on what you are sorry for, and state that. (To be clear, this is not a hall pass for women to give their power away. The kind of “I’m sorry” I’m recommending here is different from the “I’m sorry” you use when you feel insecure or actually want someone else to apologize to you. “I’m sorry” must not be a quid pro quo.)

What do you need (from me) in order to move forward? When you brainstorm creative ways to play nicely together in the future, the ultimate expression of compassionate (and super vulnerable) power is to ask what someone else would like to see from you now and in the future. This question alone can resurrect a relationship from collapse, if and when safety has been created in a conversation and everyone is fully committed to a mutually beneficial outcome.

4. Practice what you plan to say aloud.

One of my favorite self-improvement expressions is that practice doesn’t make perfect; practice makes permanent. Women are often quite adept at role-playing what they want to say in their heads, which, as addressed earlier, usually increases fear and self-doubt and makes us feel as comfortable as we would if sleeping in a bed of nails. Role playing aloud, on the other hand, supports women to gain confidence by hearing their voices, finding the precise language they want to use, asking questions, holding space for the answers, and using body language to amplify their projection of leadership (confidence, trust, decisiveness, flexibility, and so forth).

Early in my professional career, I was an adjunct professor of women’s studies and public speaking. And, each year, I used to get pushback from my public speaking students when they read in their textbook the recommendation to practice aloud a minimum of one hour for each moment they intended to speak. Yet, not surprisingly, those students who followed the textbook suggestion outperformed their peers who did not practice aloud—and they outperformed both in their projection of confidence and in the impact of their public speaking.

Give rising leaders opportunities, over and over again, to practice aloud the exact kinds of daring conversations (negotiating, giving and receiving feedback, challenging an existing policy, facilitating buy-in for a strategic plan) they will need to have in order to rise and succeed in senior leadership positions. Again, how to have a daring conversation is not a skill to teach; it’s a behavior to practice and a habit to form.

5. Unhook from the desired outcome.

A central tenet of self-improvement is the only thing we can control is our own reaction in a situation. Therefore, while role-play supports us to prepare for the outcome we hope to have when we speak our truth and, by doing so, shift a difficult conversation into a daring one, we want to let go of our expectations or assumptions about the end result. Equally as important, we don’t want to initiate a conversation until we have let go of any anger we may be feeling toward the person or people we are going to speak to. It’s difficult, if not impossible, to have a truly daring conversation with someone when you are still throwing mental switchblades at the person. When you see yourself as a victim or martyr—and someone else as somebody who “did something to you.”

One of my favorite Oprah quotes is “Forgiveness is giving up the hope that the past could have been any different. It’s accepting the past for what it was, and using this moment and this time to help yourself move forward.” You don’t need to let anybody off the hook for his or her actions, but you need to be fully in the role of protagonist and ready to move forward if you are going to have a productive conversation with that person.

Now, if we want more women to step into their moxie by proactively having daring conversations, in addition to strengthening women’s confidence and acumen in this critical area, the equally important task for organizations is to ensure they are cultivating a workplace culture that supports both women and men to be bold communicators. Unfortunately, in too many companies, men who speak up and out are seen as asserting their leadership, and women who do so are viewed as angry and domineering.

For example, according to a 2016 joint Lean In/McKinsey & Company survey of 132 companies and 34,000 employees, women who negotiated for promotions were 30 percent more likely than men to be dubbed intimidating, bossy, or aggressive. What my female women’s leadership participant communicated about where her discomfort around giving feedback comes from makes perfect sense. As a female leader, she (like most women) recognized that while she was expected to perform as a leader based on a masculine model of what leadership looks like, the same leadership qualities that society deems masculine (in her case, giving in-depth performancebased feedback) are judged more harshly when performed by a woman.

Compounding the problem, whether they were afraid of hurting her feelings or of being the target of gossip (or even condemnation) for showing professional interest in a female subordinate, my program participant’s predominantly male bosses had done her a disservice through the years by not giving her the steady performance feedback her male colleagues had received. Particularly in the aftermath of the viral #MeToo and #TimesUp hashtags and corresponding movements to address the prevalence of sexual harassment, abuse, and assault, many men have communicated their belief that it’s risky now to be alone at work in a room with a female employee, take too much interest in her career, or volunteer to be her mentor. This is a travesty. As long as the lion’s share of power is held in our organizations by men, high potential women can only benefit from senior male leaders providing appropriate career and leadership advice, performance feedback, and championing their work.

Irrespective of gender identity, everyone in the workplace benefits from women becoming confident and competent daring conversationalists. Our organizations have a responsibility to create a culture and craft and uphold policies and practices that protect employees from abuse and discrimination on the basis of their gender, race, sexual orientation, or any other marker of identity. And, when done in tandem with empowering female employees to possess the mindset and skillset to turn difficult conversations into daring ones—especially on the very sensitive subject of how to restore safety, trust, connection, and belonging in the workplace— companies will accelerate the conditions for female leadership to thrive.