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Kimberly Penharlow: “Discover what matters most to your audience”

Discover what matters most to your audience: We know that people are wary of the impact of virtual events and retreats. In order to build momentum and alignment, a needs assessment of the attendees must be conducted. The №1 success factor to designing engaging virtual events is to ask and know what your audience/staff will […]

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Discover what matters most to your audience: We know that people are wary of the impact of virtual events and retreats. In order to build momentum and alignment, a needs assessment of the attendees must be conducted. The №1 success factor to designing engaging virtual events is to ask and know what your audience/staff will find valuable talking about — What questions do they have? How do they want to spend the time together? Share the research and themes with senior leaders and design your event around this insight.


As a part of our series about “5 Things You Need To Know To Successfully Run a Live Virtual Event”, I had the pleasure of interviewing Kimberly Penharlow, MSOD, CPCC, an independent organizational psychologist and certified leadership and performance coach with more than 20 years of experience. She’s supported C-suite executives at nonprofits, startups and Fortune 500 companies, including the UN Refugee Agency, World Food Programme, Madewell, The Washington Ballet, MasterCard and more. She works with individuals and cross-functional teams on needs analysis, talent development, building remote inclusive cultures, and managing through organizational change. Some of her recent work in this area includes leading trainings for Accenture’s Accent on Women in Technology group focused on being a virtual culture maker and building resilience.

Prior to launching her own consultancy business, she led global corporate learning and development programs for J.Crew and created high-impact executive and manager training on team development, change management, and constructive conversations. In addition, her director and VP-level leadership training and manager performance management training for Medidata Solutions contributed to the company being named Fortune’s 2016 Great Place to Work. She lives in New York City and is a two-time NYC marathoner with a PR of 3:33:26


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a bit about your “childhood backstory”?

I come from an extremely pioneering family. In the 70s my parents, both educators on Long Island, decided to move to rural Vermont, where they purchased a local hardware store. The transition from education to entrepreneurship wasn’t easy. They were considered “flatlanders” for some time, a term locals give residents who relocate to Vermont from out of state. If anything, being thought of as outsiders propelled my parents to succeed and become integral members of the community. My mother faced added challenges as a woman business owner. Forty years ago, it was rare to see a woman as a leader in a predominantly male business, such as hardware. She, along with my sister and I, experienced gendered comments from customers about their preference to wait for my father to return to the shop. We always replied confidently with a polite and knowledgeable offer to help them immediately rather than waiting. Working at my parents’ store instilled in me the importance of hard work, integrity, community, love and leadership.

Another influential aspect of my childhood was my diagnosis of Juvenile Rheumatoid arthritis. It meant restricted physical activity, daily medications, frequent visits to doctors, and a constant (sometimes uncomfortable) reminder that I must make different choices to protect my health and well-being. Instead of gym class antics, I was focused on practicing joint protection to avoid flare-ups and long-term joint damage. In many ways, I still carry this thoughtfulness in my leadership coaching and virtual retreat design and facilitation work. If you don’t organize an event to support healthy, safe interactivity around what your staff needs to become better equipped to tackle problems, you could cause serious organizational damage.

Can you tell us the story of what led you to this particular career path?

My path has been defined by courageous, radical decisions. I’ve always immersed myself in different and unexpected places, educational experiences and career opportunities. When I graduated I moved to Nashville for a job, not knowing anyone. My career pursuits included being a Coro Fellow in St. Louis, traveling across the country working for the 1996 Olympic Torch Relay and more. My next move, relocating to New York from DC the day before Sept. 11th to work for UNICEF, might have been seen as radical. Every organization and worker in the city were experiencing tremendous uncertainty about the future, but I decided to stay and seize every opportunity leading the Trick-or-Treat for UNICEF campaign at USA for UNICEF and eventually spearheading a mission trip to Afghanistan to increase awareness of our national fundraising campaign to address polio. From the outside, every decision might have been perceived as an ill-fated career trajectory, but it afforded me the opportunity to be present and engaged in finding the aspects of my jobs that most inspired me and where I made the greatest impact. It also allowed me to experience different cultures. For me my purpose came alive through developing leaders within organizations and designing in-person and virtual experiences that build inclusive cultures. Flash forward to today and I’ve launched my own consultancy at age 45, where I’ve led hundreds of in-person and virtual company retreats from 5 to 400+ people and coached C-suite executives from a wide variety of industries.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I didn’t define my market; I defined my skill set. What I quickly learned, however, was that I was trying to do every aspect of my business by myself. It wasn’t until my second year in business that I really started to see that this isn’t a healthy approach or effective strategy to grow. I became so focused on items on my to-do list like building a social media presence or designing a beautiful website that I resisted practicing my actual expertise: leadership coaching and virtual retreat design and facilitation. My “can-do” attitude actually distracted me from honing in on my strengths and value as a professional. Often this mindset is experienced by many women entrepreneurs and leaders. We don’t ask for or avoid help and ultimately get stuck with making endless lists of what we need to do but simply can’t. Instead of re-writing the list, make a budget and allocate resources to find the right people to help you run your business. Changing this behavior not only shifts energy to be able to produce and deliver for clients, it’s a critical ingredient to cultivating business or your professional reputation within an organization.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

Deena Kastor’s book, Let Your Mind Run, has been incredibly inspiring and influential in both my business and passion for running. Deena’s an Olympic marathoner and world-renowned runner. In the book she explains how her own thinking was blocking her potential. Excelling as a marathoner is not only a physical challenge that pushes our bodies to higher levels of performance, it is an equally formidable mental and emotional test. Deena shares that her laser focus on a good attitude and positive thinking required were critical components to success. Each negative thought was met with the discipline of gratitude and enjoyment. As she writes in the book, “A good attitude is part of a discipline that focuses on turning every experience into fuel.” Her approach is centered on being mindful of accomplishments and setting bold goals. And it’s what motivated me to set my own personal running goals.

Despite my health issues as a child, three years ago I made another radical decision to run my first NYC Marathon (3:57:11), the same year I started my business and was getting divorced. Since then, I’ve run my second NYC marathon with a personal record of 3:33:26 at 47 years young! Deena’s books taught me a deep appreciation and practical way to incorporate mindfulness into my own training, relentlessly seeing challenges through a positive emotional lens. If someone said, “Don’t you think the goal of 3:30:00 for your second marathon is a huge stretch?” I simply said, “No, it is attainable, and I plan on enjoying every workout along the way.” This attitude also informs my approach to working with executives to enhance their business skills and build teams that succeed. What is possible is energizing for leaders to think and dream about.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“No is a full sentence.” As a leadership coach for women, I am constantly hearing women justify their “no”. It’s a waste of time and energy. The answer doesn’t need to be justified. The work culture is shifting, but regardless of what women are asked to do, they often perceive advancement and recognition to be tied to always having to say “yes.” This is sometimes self-imposed or culturally recognized as a norm based on the actions they witness of senior women leaders. This mentality can detract them from doing what they’re great at or pigeon-hole them into roles that aren’t as strategic or high-profile. I encourage the women I coach to reframe their thought patterns and any triggers of “needing to do everything.” Instead, practice saying “no” and listening deeply to yourself. This is the single best thing you can do to change your relationship to your work and between your peers and colleagues. And it can be fun to start doing. For instance, start building the “no” muscle with a simple statement like, “No, I don’t have time to organize that party.” Or “No, I can’t take on this assignment, I’m at capacity to be successful.”

For me personally, it’s been freeing to let go of the expectation that I need to justify or explain why I’m saying “no.” Doing this isn’t always easy. Setting boundaries can bring out fears around whether you will be excluded or held back from being promoted. But if you agree to something that you don’t have expertise or interest in or time for, you are going to underperform. Misjudging the outcome of saying “no” is a grave error we can make.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. For the benefit of our readers, can you tell us a bit about your experience organizing events in general?

For the past 20 years, I’ve designed and led national conferences, virtual retreats, trainings, and events for a range of nonprofits and companies, including the World Food Programme USA (WFP), Madewell, The Washington Ballet, USA for UNHCR, and the Department of Education. My sessions often focus on finding strategic alignment in a virtual world, developing high performing remote teams, creating an inclusive remote culture, improving virtual employee engagement and motivation, leadership development assessments, and creating a vision for the new way of work. My approach is research-based and highly interactive. As an example, I can share how I structured a virtual retreat for the WFP to help the organization build trust among the staff as a new CEO and senior leadership team stepped in, months before the entire organization went remote. I organized three events:

The first was focused on vision alignment and team building and incorporated interactive elements to help enhance relationships and increase engagement. For instance, participants were asked to creatively explain why they aligned their careers with the mission of the organization. Their report-out could take the shape of anything — a haiku, video, collage, etc. Where you can incorporate activities that allow participants to creatively express themselves and also engage in real conversations, the more impactful your programming will be. The second session centered on strategic planning, highlighting where there was alignment, overlap and gaps across teams. And the third session, which was held six months after the first event, focused on professional development, education on how to handle volatile, uncertain, complex and ambiguous circumstances in business, and demoing new evaluation processes.

My interest in this work is grounded in the value community provides us, particularly in workplaces. Remember not to lose sight of why we’re designing these types of events in the first place: to build better cultures.

Can you tell us a bit about your experience organizing live virtual events? Can you share any interesting stories about them?

As the event designer and facilitator, a lot of my focus is on balancing leaders’ desire to get something done and the actual experience and feeling we want to create for participants. I always follow Bruce Tuckman’s approach and design the first session of any company retreat or virtual event around understanding the purpose and people on the team. For instance, with the World Food Program USA and USA for UNHCR, we created an activity for everyone to prepare and present on Day 1 of the company retreat that helped staff better understand their individual and shared purpose. The focus of this type of activity is never centered around a business plan, but rather a reflective moment, such as “What am I most proud of with regard to working for this team?” It’s important to start from the relational aspect and from there build into the business objectives. Creating intimacy and connections and learning about each other help to build a comfort level around working virtually together and engaging in tough conversations about the business. This methodology always proves to be successful in inspiring more genuine, effective collaboration.

And it can also be implemented when working with groups and participants from different organizations. Last December I led a virtual training on building resilience for more than 250 women from Accenture and New York Life. When you’re working with larger audiences and multiple companies it’s important to take this approach even further and make it unambiguously action oriented. The best virtual experiences provide information and opportunities for deeper discussion and idea generation, so people leave knowing how to do something different in their work, their homes or their lives as a result. This is an important metric of success for any training or retreat I organize. I design and evaluate the experience based on how participants will respond to Gary Rolfe’s ‘What? So what? Now what?’ criteria. That is, What did I learn from investing this time virtually with my senior leaders and peers? So, what does it mean to my direct work or life and what was significant to me? And, now what am I going to do differently?

In your opinion, what is an example of a company that has done a fantastic job creating live virtual events? What specifically impresses you? What can one do to replicate that?

In addition to my consulting work, I serve on the Board of Directors for SheSays, a creative network for women that advocates for gender equality and leadership. For the past year the organization has been facilitating all sessions remotely and has managed to design global events that are incredibly interactive and educational. Oftentimes these events reach hundreds of women in the creative industries across multiple regions, but they are structured in a way that creates intimacy and relevance. The key to their success is in their ability to present experts who represent a diverse point of view and provide a safe space for women to converse and gain practical knowledge to apply directly to their work. Creating a safe space virtually can be achieved through not recording all or some of the sessions. We live in a world where there is pressure to continually produce new content, but sometimes it is better to prioritize personal connection over social promotion. Safety can also be created by utilizing smaller break-out rooms into the program. We used both of these approaches in a session I led last fall. The program centered on offering tools to help women process the emotional impacts of Covid-19 on our working lives.

What are the common mistakes you have seen people make when they try to run a live virtual event? What can be done to avoid those errors?

Oftentimes, leaders try to do too much in too little time, or they think the agenda is fixed. Having unrealistic expectations of what can be accomplished in a specific timeframe is one of the biggest mistakes I run into in designing virtual programs. It is essential to have the attunement to notice when a change in engagement occurs or a cultural insight is revealed that requires the session to take a different path beyond the line items on the agenda. Those are the ideal moments to give attendees a break so you can make adjustments with the leaders based on the discussions.

A related mistake is designing an unbalanced agenda that makes it impossible for the majority of participants to feel a sense of accomplishment by the end. It is important to be mindful of how introverts, extroverts and ambiverts engage virtually. Activities must provide time for interaction both verbally and creatively and time for individual reflection and contribution.

And finally, the third biggest mistake is not weaving enough creative expression or allowing time focused on celebration. Creative activities are some of the best tools to stimulate new ideas, thinking and innovations. You can incorporate a range of exercises that asks participants to design something that represents why they aligned their careers with the mission of the organization. Their report-out can take any creative shape — a drawing, song, collage, etc. Create the space for people to imagine and share. This leads to new thinking and can also strengthen relationships. Focus on creativity and relationships, and the work will follow.

Which virtual platform have you found to be most effective to be able to bring everyone together virtually?

If a company has a preferred platform, it is always best to use that technology as it’s one less barrier to engage participants; they will already be comfortable using it. If not, I typically use Zoom.

Are there any essential tools or software that you think an event organizer needs to know about?

Even more important than the tools and software is having a technical team ready to address any issues that will inevitably occur for participants. Virtual does not mean less work and less staff. For all of my events, I collaborate with a technical lead who manages all the interactive components of the session. My job is to facilitate the engagement and experience, not to set up the break-out rooms. And before showtime, it’s critical to test the platform multiple times and to be aligned with your tech team.

Ok. Thank you for all that. Here is the main question of our discussion. An in-person event can have a certain electric energy. How do you create an engaging and memorable event when everyone is separated and in their own homes? What are the “Five Things You Need To Know To Successfully Run a Live Virtual Event” and why? (Please share a story or example for each.)

When I begin planning an event for an organization, I use my ‘Head, Heart, Hands’ framework to outline the questions I’ll need to answer. Head is focused on the critical activities that need to occur to stimulate innovation, conversation and reflection. Heart centers on what needs to happen for people to leave inspired, reconnected to the company vision and values, and most importantly to each other. And Hands is dedicated to understanding what can be provided to everyone before the session that will be used during the activities, as well as what materials are necessary to continue personal development post event.

From there I follow five specific steps to make a virtual event engaging and memorable:

1. Discover what matters most to your audience: We know that people are wary of the impact of virtual events and retreats. In order to build momentum and alignment, a needs assessment of the attendees must be conducted. The №1 success factor to designing engaging virtual events is to ask and know what your audience/staff will find valuable talking about — What questions do they have? How do they want to spend the time together? Share the research and themes with senior leaders and design your event around this insight.

2. Create radical value-aligned agendas: Virtual retreat agenda are best when aligned with the organization’s values, with two to three goals and conducted in short spurts of time. I wouldn’t ever design a full day retreat. They should be episodic and organized into two to four hour-long sessions with lengthy 20 minute off camera breaks. This helps staff remain engaged by breaking the programming into shorter focused sessions that afford them time to re-energize off screen. The content of the program should be based in radical curiosity. Design each section to incorporate questions that will foster an environment where ideas, innovation and exploration can occur. Questions like, “What else is possible?” and “What more could be the reason?” help open the discussion for judgement-free exploration. And remember, not all the work has to transpire during the virtual retreat. Design pre-work and post-work for individuals, teams or dyads that weave into the virtual experience.

3. Set the tone by building excitement: When I design virtual events, I work with organizations to create a pre- and post-event communication and marketing plan to socialize the event and offer actionable next steps after its conclusion. The pre-event plan includes regular emails, short videos and the use of all internal communication channels, such as Slack, intranets and more. A virtual retreat is not a normal monthly staff meeting. It is designed for elevated and creative reflection, inspiration, and discussion. And this can be done through a range of activities. For instance, one organization asked everyone to share a song that motivates them and used the submissions to create a Spotify list. The music was played during breaks and turned into a relationship-builder among staff as they eagerly tried to guess who submitted each song and why. These activities serve to create excitement before and during the event and connection when we may be physically separated from one another. This work continues after an event is over. The best programming is focused on the evolution of the experience — how will participants turn the experience into action?

4. Coach speakers to incorporate vulnerability in their presentations to inspire audiences: If this is a semi-annual or quarterly virtual retreat, this is a time for leaders to inspire and be vulnerable. How we work, where we work, and even when we work will never go back to normal. This is essential to recognize and embrace in 2021. I’ve been coaching leaders to acknowledge that they may not have all the answers. But they do need to be transparent about how to move forward. I coach senior leaders to present a ‘State of the Business’ address that re-shares the vision, accomplishments and plans for the future. Program time for an open Q&A or small break-out discussions and report-out to the entire organization. You can guide confidently and vulnerably at the same time. This will set a cultural tone about the value you place on expressing vulnerability.

5. Use the event to celebrate individuals and have fun: If done right, virtual retreats can be a moment for celebration and elevated conversation that will allow employees to be inspired, innovate and feel less isolated and siloed. It’s also a time to let your staff see another side of you. Celebrating staff can also mean bringing in a special guest, like a top chef to teach a cooking class to everyone. If you have an employee celebration committee, ask them to lead and plan this part of the retreat. Your staff often have the best ideas — you just need to slow down and ask them.

Let’s imagine that someone reading this interview has an idea for a live virtual event that they would like to develop. What are the first few steps that you would recommend that they take?

First, create your budget. Virtual retreats require financial investments to be successful. Budget for speakers and consultants, materials used during the session, materials for professional development following the event, and more. Just because you’re going remote doesn’t mean you should automatically cut budgets typically assigned for in-persons events. Instead, re-allocate the funds to cover services or expenses that will enhance the virtual experience, such as video production, interactivity integrations and diverse speakers.

Next, align company values to the program. Make it an imperative to honor and align company values throughout the retreat or conference. The best way to do this is to ask senior leaders and staff to identify these values and use it as a checklist for how you design each section of the retreat. If you are coaching presenters, talk to them about how they show up for their portion of the program. Are they presenting in a way that creates inclusivity? Are their behaviors reinforcing the company values? This can be difficult to achieve during virtual events.

And finally, focus on personal experiences slightly more than business objectives. Start conversations with senior leaders by asking them what they hope audiences walk away feeling versus what business outcomes they hope to achieve. Allow yourself to dream and embrace the creative process of brainstorming. Get into the mindset of the participant. How do you want them to describe the experience to their family and friends and coworkers?

Super. We are nearly done. Here are our final questions. You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

We must stop assuming that titles mean talent. For instance, I am a serious runner, but I don’t have the talent needed to become a world-class runner without my running coach. The same is true for executives and rising leaders transitioning into senior roles. If leaders don’t have the guidance to build a plan focused on skill development, constructive feedback, and strategies to create safe, inclusive and innovative work environments, they will fall short of having the impact they want to achieve on their team.

Leadership needs to be reframed around resource allocation. Organizations need to start aligning more resources to develop leaders. Are you helping your people learn? Are you giving them the grace to build these new skills? Or are you penalizing them for not performing in the way their manager thinks they should despite not giving them the necessary tools and support?

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

Jen O’Malley Dillon, Campaign Director for Biden’s campaign. I’d love to talk to her about how she created a remote team culture, what did she do to motivate a team to win the election, and how she describes her own leadership style and impact. Hartina Flournoy, Chief of Staff for Vice President-elect Kamala Harris is another inspiring woman leader I’d love to connect with. How will she balance the work for the first woman VP and stay grounded in who she is? I want to know the things she will say “no” to in the job, how she will lead her staff meetings, and how she is going to inspire her team and the public. How will she define her success and what would she like to say to women leaders in their 30s who are struggling to be heard or to move ahead? Those are just some of the questions I’d love to ask her.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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