Leadership Deep Dive ™

Executive Coaching, Leadership Training, and Personal Development

Ep 149: Dealing with Uncertainty and Making Decisions

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Leadership Deep Dive
Leadership Deep Dive
Ep 149: Dealing with Uncertainty and Making Decisions
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David and Margaret share their strategies for dealing with uncertainty and making decisions.

How DO leaders make decisions, particularly when the stakes are high?

The conversation originated from David’s process when he and his wife had to decide whether or not to evacuate as Hurricane Milton approached. As a resident of the West Coast of Florida, it was headed right towards him.

Intuition in Decision-Making and Travel Plans

David recounted his experiences with hurricanes Irma and Ian, as he tried to extrapolate information for making a decision about the most recent hurricane, Milton. He weighed the importance of heeding warnings to evacuate and the potential consequences of not doing so.

Still he didn’t know what to do … until he did.

David’s process highlights some important elements of the decision-making process:

  • The importance of not forcing decisions
  • The discomfort of being in the “liminal space” of not yet having decided yet (“liminal space” is place between “no longer” and “not yet”)
  • The power of intuition in decision-making

David shared how he ultimately made a decision about how to handle the hurricane.

The “Art” of NOT Making a Decision

Sometimes, people make decisions before they know everything they need to know. Other times, people put off making decisions.

And sometimes, NOT making a decision lives in the land of Avoider, which is a saboteur. And sometimes, not deciding actually becomes a decision.

Where, they challenge listeners, is your sweet spot in between deciding too soon — and avoiding making a decision?

Intuition in Decision-Making

They also discussed the role of intuition in decision-making. How might using our guts and hearts be useful in making decisions?

Margaret shared her experience of transitioning from a cerebral to a more intuitive approach when she was looking for a new place to live post-divorce. She responds to David’s question, “How did you KNOW?”

Many of us are taught to use pro-con lists and use only our brains to weigh out consequences and run scenarios to decide. This was true for both Margaret and David, who come from a history of making rational and analytical decisions.

And cerebral decision making has value, but David and Margaret have both learned to incorporate more intuition into making choices.

Most of us can benefit from listening to one’s gut and heart in addition to relying only on lists and pros and cons.

How Emotions Tangle Decision-Making

David also hunted for a house recently. He recounts how emotions made it a difficult process.

He and his wife struggled to find a new place because they were still emotionally attached to their house. Their process involved a lot of going back and forth between their brains and their hearts.

They encourage listeners to look at the perspective of how things often work out in unexpected ways. What might the perspective of “We’ll see” have to offer you?

And if you’d like to help your team learn how to use intuition to be better leaders, please check out our trainings.

EP 148: Taking on Challenges

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Leadership Deep Dive
Leadership Deep Dive
EP 148: Taking on Challenges
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Taking on challenges: what goes into whether you say yes or no?

David and Margaret discussed their experiences with taking on challenges. They talk about how to evaluate their feasibility and impact.

Taking on Challenges: Jumping into Really Cold Water … and a Big Social Media Goal

David shared his experiences with taking on a personal life challenge: to get his black belt in jujitsu. To stay on track, he’s added cold plunging to his recovery regimen– which is an additional challenge.

Margaret discussed her challenge of posting on LinkedIn daily for 30 days. She has been at her desk at 7 a.m. at every day with her challenge group.

They both agreed that leaders tend to default to saying yes to challenges.

But is that always the best answer? It’s essential to consider the consequences.

Leaders Take on Challenges

David and Margaret agreed that leaders often take on challenges, and those challenges can vary greatly. David cites examples of significant leadership challenges taken on by leaders such as Mahatma Gandhi and Martin Luther King. On a smaller scale, nonprofit leaders face challenges that might include leading a nonprofit to delivering aid in a crisis to fundraising.

David emphasized the importance of leaders being comfortable with challenges.

In executive coaching, conversations about challenge are common — and can be effective. Sometimes saying yes to a challenge is what helps a client go beyond what they think is possible.

Challenges, Perception, and DISC Personality Traits

David shared a recent occasion when he challenged a client who wanted to reach out to someone. David’s challenge: pick up the phone instead of sending a note. It may seem like a big challenge or a little one, but it was an important growth space for the client to consider.

They also discussed the importance of considering the potential outcomes of a challenge before committing to it.

David may have an opportunity to serve on a non-profit board. Because his default is often yes, he is considering what to do. He hasn’t yet committed.

They also touched on the different personality traits associated with the DISC model. David noted that his high D energy often leads him to challenge himself and others. Margaret, a high I, tends to focus on big ideas and completion can be her challenge. They discussed the challenges faced by individuals with different DISC traits, such as the need for action for an S and the need for more data for an C.

Embracing Challenges for Personal and Professional Growth

What might a coach see that inspires them to challenge a client? It’s not just for the sake of stepping out of a comfort zone. The discomfort of a coaching challenge is in service of leadership growth.

Some examples of when David and Margaret (as coaches) might challenge a client:

  • To complete a task that will help stretch this client in their growth as a leader or a person
  • To try something they aren’t yet good at for the sake of building more skill
  • To step up where a client might be holding back

A challenging task is essential for progress — even if it is uncomfortable or even if it doesn’t go well.

When challenging oneself, it’s crucial to not be 100% attached to the results of the challenge.

Embracing Challenges for Personal Growth and Resilience

David recounted his experience of gradually increasing his time during cold plunges. He initially started with 3 minutes and is now up to 4 minutes. He believes that while the cold water is uncomfortable, it will ultimately lead to personal growth and help him with his black belt.

Margaret agreed, sharing her experience of persevering through a challenge of using LinkedIn every day.

They encourage listeners to identify: where are you playing small? Where might you be willing to take some risk?

Please contact David, Margaret or Michelle if you’d like some support around challenging yourself.

Ep 146: The Power of Choice: Yes, No, or Counteroffer

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Leadership Deep Dive
Ep 146: The Power of Choice: Yes, No, or Counteroffer
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Here’s a sometimes shocking concept: when someone makes a request of you, you can say “yes,” “no,” or make a “counteroffer.”

That is the power of choice. And people are sometimes quite surprised by this concept.

David and Margaret dive into the importance of making and accepting requests in personal and professional relationships.  They explore the dynamics of making requests within an organizational context.

Their discussion touches on the balance between saying yes and no to requests in personal and professional relationships. They let listeners know about the power of the counteroffer, which introduces potential for negotiation and compromise through the ‘innovate power‘.

When No Isn’t An Option

What about when you don’t feel you can say “no” to a request at work?

True requests have embedded in them the power of choice.  That is to say, the person receiving the request can say yes to it, no to it, or make a counteroffer.   For a request to really be a request, the person receiving it must have the ability to accept, decline, or counter with alternative suggestions.

If no isn’t a possible answer, well, that’s actually a demand and not a request.

David and Margaret emphasize the need for leaders, including board members, to frame their requests as choices to maintain a healthy power dynamic.

They encourage listeners to experiment with this and offer others these choices when making a request. This approach can improve trust and relationships.

Do I Need To Give a Reason for My No?

Not only is no a fair answer to a request, but you can choose whether or not to provide a reason for your no.

David and Margaret agreed that a person declining a request does not necessarily need to provide a reason, but doing so can be beneficial. Not offering a reason can be a potential trigger for both the requester and the decliner.

Furthermore, they touched on the impact of declining a request without a reason, especially when it involves other people in the organization.

The Power Dynamics of Boards

Board members making demands on executive directors can be complex.

That’s why it’s important to maintain a healthy power dynamic, transparency, and integrity in these interactions. Executive directors and staff struggle with saying no to requests from their boards.

Margaret suggested the usefulness of the counteroffer with boards. It can open up a conversation for brainstorming alternative ways to meet demands, which could increase trust and improve relationships.

Does Your Team Make Requests — Or Just Demands?

They encourage listeners to experiment with this approach in their own relationships. Specifically, leaders should both model and encourage their reports to frame their requests as choices and that they should remind those receiving a request about these choices.

This can create a more positive work environment.

But if your team or organizational culture is a “yes only” situation, the Leadership Deep Dive Team can help leadership teams and boards build more trust, integrity and accountability through their Trust, Candor, and Conflict training program.

Please contact David or Margaret if you have questions.

Ep 144: Unleashing Your Inner Second Grader

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Leadership Deep Dive
Ep 144: Unleashing Your Inner Second Grader
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Ever wondered what unleashing your inner second grader could teach you about leadership? And fundraising?

It turns out quite a bit!

When we become adults, we want to look good and avoid looking bad. We become complex. We move away from who we were as children.

But children offer raw and unfiltered perspectives. They offer authenticity.

And those traits can profoundly shape our approach to leadership. In this episode, Margaret and David explore the invaluable lessons we can learn from unleashing what’s still unfiltered and raw about us . .

Introduction to Authenticity:

  • The conversation starts with a discussion about how our egos and personas protect us. At the same time, they also create barriers.
  • They ponder, how might the qualities of uninhibited and authentic be valuable in professional settings?

Lessons from Second Graders:

  • David shares stories from his wife’s classroom (she’s a second-grade teacher). David took a page out of one of her student’s book. That kiddo described putting his Crocs into “sport mode” for recess. That in turn inspired David to wear his own Crocs in “airplane mode” while travelling.

Challenges of Inauthenticity:

  • Margaret recounts an incident where her son’s innocent question about someone’s weight, though awkward, was entirely genuine.

The Lifeboat Exercise:

  • Margaret and David discuss an exercise called “lifeboat” from their own leadership training. In this exercise, participants must authentically pitch why they should be saved in a hypothetical survival scenario.
  • From this exercise, they learned what happens when adults try to be chosen. They witnessed how the adults masked their true selves to avoid looking bad. That led to inauthentic interactions. And such interactions make us less compelling.
  • The exercise demonstrates how inauthentic behavior can lead to failure. Authenticity, on the other hand, resonates and compels others.

Authenticity in Fundraising:

  • They discuss their program, “Being a Mega Gifts Fundraiser.”  The course teaches fundraisers to be genuine, which exponentially enhances their effectiveness.
  • Sometimes fundraisers tend towards over-calibrating to seem smart or be overly pleasing. These traits often come off as insincere.

Practical Applications:

  • David and Margaret encourage fundraisers to express themselves more genuinely. Some examples of being more genuine might include cracking jokes, being honest about limitations, and showing enthusiasm.
  • Margaret shares a personal story about a donor asking a provocative question. The response from her meeting companion was stiff and not really true. A straight answer would have gone better, and it was a missed fundraising opportunity.

Encouragement:

  • The speakers advocate for training board members and fundraisers to embody authenticity and tap into their “inner second graders.” This is a way for board members to be more confident and willing fundraisers.
  • They emphasize that being playful and genuine can lead to more successful and fulfilling interactions.

Conclusion:

Much like the uninhibited nature of second graders, authenticity is crucial for building trust and compelling others in professional settings.

David and Margaret urge listeners to listen to their own inner urges more often.

You can tap into your natural, child-like enthusiasm to enhance your leadership and fundraising efforts.

 

 

Ep 143: Completion or Decay

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Ep 143: Completion or Decay
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In this season of graduations, Margaret and Michelle “double-click” on the importance of intentional completion.

They look at when a completion is intentional, as it is with a graduation. Such intentional completions offer ritual and celebration. They also have a positive impact on family members.

And when we look beyond graduation, our culture kind of drops the ball on intentional completions.

Intentional Completion vs. Decay

One gift of completion is that it invites intention.

When we acknowledge and observe completion, there is an invitation to say goodbye to what is finished and look at what’s next. Michelle shares the ways she and her husband are looking at their next chapter and asking, “What do we want?”

When we “ghost” or ignore the end of something rather than its completion, it can decay. This can happen when we stay too long in relationships, jobs, phases of life, or places.

How Do We Know We’ve Stayed Too Long?

Graduations and school offer predictable and reliable completion. However, when we move on in life, it can be less clear when an activity is finished.

It’s not always obvious, but if we tune in, we might know more.

Feeling deep resistance or avoidance to work or spending time with people might be one sign.

Michelle shares that clients might be avoiding completion when they start asking, “What have I even accomplished here?” Questions like that suggest that the client no longer feels purpose in their work, which is another sign that it might be time to complete.

On Arcs

Margaret and Michelle explain the concept of an arc, which is the shape of a thing from beginning to end.

One example: most of us notice when a speaker goes past their arc. It starts to get boring or have diminishing returns. Similarly, we know when a movie sequel was ill-advised. We feel they should have left the story alone.

Those are examples of how we know an arc is done.

The challenge is to pay the same attention to our own lives.

The In-Between

Michelle and Margaret note that ending an arc can be complicated. Also, sometimes, starting a new arc is not simple. It can include some serious learning.

As an example, Margaret shares that her grown son has stopped home for a while, and there is a new arc for her as a parent of an adult. Her learning is to relate with this new adult, rather than her habit of parenting the 14-year-old version of him.

When we finish an arc and start a new one, it can feel overwhelming and confusing. Margaret and Michelle challenge listeners to think about how to create from the overwhelm and chaos of transition.

Do you need some help getting through a transition? Does the idea of decay resonate with you? Please reach out for support.

Ep 141: Discover the Secret to Silence the Inner Critic

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Leadership Deep Dive
Ep 141: Discover the Secret to Silence the Inner Critic
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It was an unexpected twist. A seemingly benign LinkedIn training sent Margaret and David into a spiral to silence the inner critic.

Here’s what happened.

Margaret and David attended what promised to be a mundane topic: a training on how to write better posts on LinkedIn.

David left the training beating himself about all he was doing wrong.

His inner critic, nicknamed “The Sledgehammer,” was having its way with him.

When that Inner Critic is railing, there is suffering.

So, how does one even begin to silence the Inner Critic? By which we mean that relentless voice within that can

  • dash hopes,
  • crush spirits, and
  • dismantle even the most inspired of dreams.

In this episode, David, Michelle, and Margaret share their quest to discover the secret to shushing this voice in our minds.

We Don’t Judge ONLY Ourselves

Margaret had a different experience with the training from David’s.

She started by getting locked out of the paid training. She was angry at the host, the trainer, and, by extension, the content of the training.

Acutely aware of falling ‘below the line’ emotionally, Margaret judged others.

Queue: Margaret’s Inner (and Outer) Critic.

Michelle didn’t make it to the training, as she had a conflict.

She talks about “the Blob,” a voice in her mind that made her afraid of missing out on something.

Her critic started telling her she should have made the time to attend live. That’s called judging a circumstance.

The Inner Critic can lurk in unexpected places. (A LinkedIn training? Come on!)

But when it rears its head, it can have a field day. It has us judge — and find wanting — ourselves, others and circumstances.

A Simple but Profound Exercise

Margaret led the trio through a self-compassion practice, which offers a way to reframe the narrative. When we use self-compassion to step out of the shadow of criticism, we can find the light of acceptance.

This simple yet profound exercise counters the inner monologue of harsh self-judgment.

Empathy, self-compassion and quieting that Inner Critic are components of the Leadership Deep Dive Positive Intelligence Coaching. This intensive 7-week program can help foster empathy within your life and organization.

Ready to transform your leadership with the practice of self-compassion?

Contact David, Michelle, or Margaret to learn how the Positive Intelligence Coaching Program helps you quiet that nasty, pestering voice that tears you down.

Your team, your organization, and your future self will thank you.

Ep 138: Master the Art of Coaching

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Ep 138: Master the Art of Coaching
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Master the Art of Coaching: Essential Skills for Leaders

Leadership is no longer defined by barking orders and expecting compliance; in today’s dynamic work environments, the leaders who stand out are the ones who master the art of coaching. Coaching is a subtle yet powerful art of guiding, not directing, and helping individuals and teams to reach their full potential. While it may sound simple, effective coaching requires distinct skills and principles. 

In this episode, Michelle and David unpack the secrets behind great coaching and explore how mastering coaching techniques can transform leaders into catalysts for growth and innovation. 

Whether you’re an aspiring leader, an experienced manager, or an executive, understanding and implementing these coaching essentials will redefine your leadership approach and your teams’ success.

Defining Coaching: What It Is (And Isn’t)

Before we discuss the specifics of coaching, capturing its true essence is vital. Coaching is not consulting or mentoring. Its core is rooted in a process where the coach facilitates the client’s (coachee’s) thinking. It’s about asking the right questions to help clients explore challenges, set goals, and discover or unlock their solutions. Unlike consulting or mentoring, coaching refrains from giving direct advice or steering the problem-solving process.

The Power of Open-Ended Inquiry

At the heart of coaching lies the ability to ask open-ended questions. These questions cannot be answered with a simple ‘yes’ or ‘no.’ Open-ended inquiries encourage expansive thinking and problem resolution. This technique digs deeper into an individual’s thought process, challenges assumptions, and creates innovative strategies.

Active Listening and Empathy

Coaches are active listeners. This means not just hearing words but also understanding emotions and unspoken messages. Active listening is paired with empathy. Coaches build trust and create a safe space for the coachee to express themselves fully.

Championing and Challenging

A great coach balances support with challenge. The support comes from championing the coachee’s ambitions and boosting their confidence. Challenging involves:

  • Pushing them beyond their comfort zones.
  • Inviting them to consider new perspectives.
  • Examining their thought processes.

This balance helps individuals experience growth on their terms and at their own pace.

Leveraging Strengths and Resources

Coaching is future-focused, emphasizing leveraging a coachee’s strengths and available resources. A strengths-based approach empowers individuals by focusing on what they’re naturally good at, while resource utilization ensures that solutions are practical and implementable within existing constraints and opportunities.

The Dynamics of Leadership Coaching

Coaching isn’t a one-size-fits-all activity; the dynamics drastically change when coaching leaders. Leaders who coach need to operate from a place of equality. They’re facilitators who guide other leaders through their professional challenges. This shift in coaching dynamics helps leaders offload their anxieties and rethink their strategies with fresh perspectives.

The Art of Compassionate Inquiry

Leaders who coach use compassionate inquiry to guide their teams. Compassionate inquiry involves inquiring into individuals’ and teams’ experiences with a gentle yet insistent curiosity. It respects the emotional nuances of the work environment and uncovers the deeper reasons behind behaviors and decisions, leading to more effective coaching.

Embedding a Coaching Culture in Your Organization

One-on-one coaching is powerful; an organization committed to a coaching culture is transformational. For leaders who want to take coaching beyond their practice, embedding a coaching culture is the next step. This involves training more people within the organization as coaches and orienting the company towards a coaching mindset, enhancing communication, collaboration, and problem-solving.

The Road to Ongoing Self-Development

Finally, one of the most critical aspects of mastering coaching skills is recognizing that it’s a continuous learning process. Leaders who coach never stop learning; they always seek to improve, learn new techniques, and expand their awareness. Self-development is not just about being a better coach; it’s about being a better leader and, most importantly, a better human being.

Coaching is a multifaceted skill set that takes time and practice to perfect. Leaders can create more engaging, empowering, and productive work environments by incorporating the essentials outlined in this podcast.  

Remember, coaching is not about having all the answers—it’s about asking the right questions and empowering others to discover the answers within themselves. Leaders who understand and apply these principles are poised to inspire innovation, foster autonomous high performance, and support their teams in reaching new heights.

 

Ep 136: Incompletions and Their Impact

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Leadership Deep Dive
Ep 136: Incompletions and Their Impact
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After Margaret shows up for an early morning recording with bed head, she and David launch into a conversation about “big hair” and the 1980’s… (yes: Dune AND Joan Jett!) and, stay with them here: This really does lead to a leadership topic.

It’s a fun (and funny) conversation about a decade that had a lasting impact on the current culture, regardless of your generation or whether you lived through it or not. It was a decade when both David and Margaret were coming of age, and they look back at the era through their lens of “now,” as leaders, grown ups, and people with more skills than they had as teenagers.

The conversation turns to the leadership topic of “incompletions” — and how unfinished business from the past can impact our current lives and relationships.

And they look back on some of the things from their past lives that didn’t feel complete or quite finished.

Margaret, just back from an informal high school reunion, shares about revisiting a relationship over the weekend to share something she hadn’t shared before with a man she dated senior year. And by revisiting, there was a sweeter completion than there had been when they graduated and parted ways.

And David and Margaret wonder, what do leaders do when they feel the urge to walk out? What are the merits of staying versus leaving early? And if we chose walking out in the past, can we still complete unfinished business in the present?

David and Margaret believe that yes, a lot is possible to complete now — even for incomplete past episodes in our lives. David gives several examples of ways he does that regularly, including a recent “thing” with his wife and daughter, when he had to go back later and clean up to feel complete after a hard conversation.

Need some skill and support to clean up something from your past or to feel complete? Please reach out to one of us to schedule a coaching consultation.

 

Ep 134: On Graceful Endings

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Leadership Deep Dive
Ep 134: On Graceful Endings
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Margaret and David recently discussed the topic of (sometimes not so) graceful endings. You know the ones: a project ends, a marriage dissolves, or a loved one passes.  You can read more about that topic in David’s Blogpost here.  If you’re coming to the end of something in your life, feel free to reach out to one of us.  We’d love to help you through that with some coaching.

Ep: 122 What Do You Want Out of Life? with Valerie Tiberius

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Leadership Deep Dive
Leadership Deep Dive
Ep: 122 What Do You Want Out of Life? with Valerie Tiberius
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 Margaret and David talk with Valerie Tiberius about her new book What Do You Want Out of Life? A Philosophical Guide to Figuring Out What Matters.

Valerie, an author and professor of philosophy, shares why she tackled such a lofty topic for a book. We delve deeply into values, and how we need to take a long look at our values to inform us, as they might not be our own.

You can read a full chapter of Valerie’s new book on our blog.

Valerie challenges listeners to reflect on and take inventory of what really matters to them, specifically to track a week to see how much time you spend on what matters. 

Valerie’s new book is out now, and you can order your copy here.

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Our theme music is “Curiosity” by Polysorbate Eighty.  Composed and produced by Patrick Mather and James Celentano.  Performed by Kristen Bussandri. Copyright 2009 Polysorbate Eighty and Kristen Bussandri.