Over the course of my career, I have coached countless women to become bold leaders by breaking through limiting beliefs and behaviors. My 2019 benchmarking study, Challenges Women Leaders Face, focused on what women leaders view as their biggest challenges and what those challenges are costing them and their organizations. I also spoke with male leaders and HR professionals to get a sense of how to help women achieve their goals and the obstacles they saw getting in women’s way.

When I asked the women about their biggest challenge, the number one answer was “myself” which manifested in three primary ways: 

  1.  SELF-DOUBT:  This is by far the #1 biggest challenge. Despite rationally “knowing” they are competent, women still reported the tendency to overthink, overanalyze, over-prepare, second-guess, ruminate, and worry. This tendency is rooted in the feeling of not being enough or at the root, worthy or deserving, and magnifying with increased accomplishments, what I call the “Paradox of Unworthiness.” While women did not refer directly to Imposter Syndrome (doubting accomplishments, fearing exposure as a “fraud”), they identified with it and admitted that knowing about it does not reduce the experience of it.
  2. “STRUGGLE WITH THE JUGGLE”: Many women reported a desire to be all things to all people. They mentioned this dynamic played out in all areas of their lives – with friends, at home and at work – leading to feelings of overwhelm, lack of focus and the sense that they were failing (or at least not succeeding) at everything. Guilt, perfectionism, and being “bad” at saying no were all themes. This played out for women both with and without families.
  3. OVER/UNDER COMMUNICATION: Women often get asked to step up when they  under-communicate – staying quiet, acting timid, literally sitting back from the table, apologizing or refusing to make requests. Or they get feedback when they over-communicate – high telling, low listening, competing, “mowing people over” or driving their agenda without inviting others into the conversation or enrolling stakeholders. Lack of confidence was cited as the root of both, though over-communicators tend to appear confident, and are often described as having “displayed versus real confidence.”

It is not surprising that the largest reported obstacle aside from “myself,” was the bias in organizations. This is mainly evidenced through language (i.e. “she has sharp elbows” while “he is assertive”), actions (e.g. dismissing, “mansplaining”), and processes (hiring, promotion decisions). There is much more to say on this topic, stay tuned for a future article on organizational bias.

Bold Leadership Starts With You

My client Sarah struggled with the juggle for years. The founder of a successful mid-sized company, Sarah was “putting the oxygen mask” on everyone except for herself. Anyone who has ever flown knows this is precisely what you are not supposed to do. While she was putting the metaphorical masks on everyone else, she was overwhelmed, resentful and burned out because she never said no. Her need to be the “go to” fixer who could perfectly handle everything on her own, left her feeling like she was doing none of it well.

Last spring, Sarah confided in me that she wanted to quit the company and was feeling stuck between guilt and resentment. Sarah and I started exploring what gives her energy, what sucks it out of her, and how she could reconfigure her leadership to include herself in her own life.

Sarah has come a long way in a few short months: she has reorganized her team and responsibilities, recontracted her work priorities and how she is delegating and holding her teams accountable. She now brings her child on business trips, has built week-long yoga retreats into her calendar, has lost 30 pounds, and leaves early or works from home when possible. She did this through practicing the principles of BOLD Leadhership .

What is BOLD Leadhership?

The BOLD Leadhership framework is based on the research to meet the needs and address the challenges of leaders like Sarah. It is based on the four key elements below, encapsulated in the BOLD Manifesto.

  • BE YOURSELF: This starts with believing in yourself, knowing you are good enough and learning tools to tame the imposter. This enables you to trust yourself, speak up, say “no,” and set boundaries. You learn to understand and reframe limiting beliefs so you can manage the voices in your head that keep you doubting yourself.
  • OWN YOUR ZONE: Your “zones” are like the rings of a tree. The innermost ring is your “comfort zone” and your brain is wired to keep you there. Most people avoid moving out of the inner ring because they believe danger is lurking just beyond. The next ring is your “learning zone” where you start practicing taking risks. Practice prepares you for the “breakthrough zone,” where you make the powerful, intentional choice to take action despite natural fear, so you can be, do and have what matters most. 
  • LEAD WITH PRESENCE: Informal research tells us that only 7% of your communication are the words you use. So 93% is essentially your “way of being.” Your physical presence communicates everything long before you utter a word. When you choose your way of being, you can define and embody your bold leadership presence. If you want to identify your current way of being, start by asking yourself or others (especially kids, they will always tell you the brutal truth!), “What are 3-5 adjectives to describe me at my best and my worst?” 
  • DARE TO SHARE: According to Adam Grant, 75-90% of giving starts with making the request. Be honest with yourself about what you want (that’s often the hard part for women), and share your desires with others. If you think you’re unclear about what you want – you’re not. You need to be willing to admit what you know in your heart and make the requests to get those needs met. When you do that you are able to drop the guilt, say no, and manage your energy.

The BOLD Leadhership Program develops women leaders to become BOLD leaders through impacting their mindset, skillset, and toolset in a cohort-based program with coaching, 360° feedback and integration with participants’ leadership. When women put BOLD leadership practices into effect, they become influential leaders, inspire others and become powerful drivers of their own destiny. 

Ask Yourself:

  • What is the biggest area where I could be more bold?
  • What would I need to do 10% more or less that would make a difference in my leadership and life? 

If you are not sure how to answer these questions, contact me at ggs@theglenbrookgroup.com to set up a discovery session and gain clarity. 

I’d love to hear what you think about this post. Please drop me an email at ggs@theglenbrookgroup.com and let me know your thoughts, reactions, and questions. 

Yours in practice,


If you are interested in exploring whether we are a good fit to help you and your organization, contact us for a complimentary discovery conversation.

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