The 6 Challenges of Leadership For CXOs

Also known as “The 6 Biggest Mistakes Founders Make,” however this wisdom is applicable to all leaders.

(This post was written in collaboration with my colleague Ray Foote.)

Leadership can be a conundrum and overwhelming at times. The leaders we work with often look for effective frameworks to level up their effectiveness and the effectiveness of their teams. Breaking down a big amorphous challenge, such as the tech stack, into smaller parts is a tried and true method of solving complex and interconnected problems. The same approach can be used to find insight and get unstuck in your leadership journey.

Thinking about the challenges of leadership through the six concepts presented here rather than one big hairy challenge can be quite clarifying.

Ask yourself: In what area am I stuck? Where is my team stuck? Which of these areas can I lean into? Oftentimes, it can be just one or two of the areas that are truly stuck. The framework below has been tested over the years and has helped many leaders get unstuck.

Here’s another way to hold these concepts:

Just as there are six strings on a guitar, there are six challenges to leadership. When the guitar is in tune, each string plays its role in building chords and solos. When tuning the guitar, one must tune each string so that it works within the framework of the instrument. Consider yourself as a leader: what strings are in need of tuning?

1. Overcoming Delusion

How are you deluding yourself and the team?

Obviously, consciously deceiving your team and your investors are wrong. Delusion is different. Are you willing to face the hard questions and face reality? Pretending that the team is working well, that the product works, or that you know what you’re doing isn’t a good game plan. Does the product work? Are you going to run out of cash? Is this a viable business? Where do you need to tell the truth? Sometimes we delude ourselves because we are not aware of our blind spots, which begs the question: What is your practice to uncover your blind spots?

Below, watch Jerry Colonna’s session — “Disappearing into the Fire: Surviving the Startup Life” — from the Pioneers Festival in Vienna in 2014 for more flavor on how we delude ourselves.

2. Disappearing into the Fire

Are you merging yourself with your business or your product? Are you working in your business or on your business?

The frenzied and frenetic life of startups can destroy you, your family, and your company as you Disappear into the Fire (as you lose yourself in the work, in your company). How can you lead yourself and your startup to success without a meltdown? The magic happens in the crucible that forms a leader.

In the video below, Jerry Colonna talks about the story of the potter in a talk called “Learning to Stand Still” for the MIT Venture Capital + Innovation Conference in 2017.

3. Misunderstanding Your Role

How well do you understand the role of the CEO? If not a CEO, how well do you understand your role?

As CXOs, team leads, and co-founders, clarity around what is our work to do and what isn’t, helps us and our teams function smoothly. When everyone on the team understands their role and others’ roles, the clarity creates boundaries and better cross-collaboration.

As a CEO, it’s uber critical that you understand what your job description is. In working with CEOs, common questions pop up. Among them are what seems like a basic one: What is my job as CEO? Sometimes the question is: What is my job as CEO, now, at this stage of the organization? It’s a role that, when played well, shifts and scales as the company grows and develops.

In this “Operators Manual” conversation of the Reboot Podcast, Jerry talks about What is the Job of the CEO?

4. Being Unclear

Lack of clarity is the single biggest problem in management and among teams. As Brene Brown says: “Clear is kind. Unclear is unkind.”

What are the job descriptions on your team? Do folks know what it means to succeed? Do they know what failing would look like in their role? You don’t want people to learn these things when they are getting fired. Do what it takes to be clear in your communications. Repeat what you heard and ask clarifying questions. As a leader, you have to be able to find new ways to say the same thing, especially as it relates to promulgating the vision and making sure it’s understood. (As one client said, “I feel like my role is Chief Repetition Officer!).

Check out Reboot’s zero-cost 60-day email courses on Practical Skills 101: Putting Non-Violent Leadership Into Practice and Communication 101: Create Safety, Build Trust, Stay Relational–the Work of Non-Violent Workplaces

5. Relating Poorly to Uncertainty

How do you handle the unknown? How does market volatility affect you? How does market volatility affect your leadership? What aspects does it bring out in your personality?

Relating poorly to uncertainty often brings out the sub-optimal parts of us. Our go-to reactions and behaviors when we are afraid can give us a glimpse into the shadowed parts of our personality. Times like these give us opportunities to learn more about ourselves so we can act from a place of groundedness.

“Between stimulus and response there is a space,” wrote Victor Frankl. “In that space is our power to choose our response. In our response lies our growth and our freedom.” The more we can learn to pause and find that space, the greater our capacity to handle the complexity of what’s in front of us.

Find resources in Reboot’s 30-day zero-cost email course: Finding Ground, Managing Fear, and our 80-day course: Managing Your Psychology 101: Resilience in the Rollercoaster of Life, Work, & Entrepreneurship.

6. Being Fierce

Work is a very people-y place. Managers need training. People need performance feedback. Some folks need to be fired. Perhaps your co-founder relationship is tense. And, maybe you have a board member overstepping bounds.

How do you handle conflict? What are you not saying that needs to be said? Do you avoid difficult, fearful, or challenging situations, people, or conversations? How do you resolve what is really going on? How do you deal with trust issues?

Being fierce doesn’t mean being ferocious. But it does mean leaning into the hard conversation, being clear, and sometimes making a hard decision.

Here’s a post from First Round with some good frameworks for giving feedback or leaning into conversations that might be hard(er): Power up Your Team with Non-Violent Communication Principles

For more on this theme of 6 challenges, check out Jerry Colonna’s conversation with Jason Calcanis on This Week In Startups from 2013. Jerry speaks to each one of these points with great articulation and relatability to all founders and leaders: The 6 Biggest Mistakes Founders Make with Coach and Former VC Jerry Colonna

To dive into these topics at greater length, read Reboot: Leadership and the Art of Growing Up, by Jerry Colonna.

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