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Various Leadership Lessons


These last few months have taught a lot. Some lessons are timeless. While these segments are annotated, you can find links to the original posts in the headers.

Face your Worst Fear

"You gain strength, courage and confidence by every experience in which you really stop to look fear in the face." Eleanor Roosevelt

To realize your ideal future, you may need to face your worst fear: Visualize your business totally failing. Everything is gone, including assumptions and legacy restraining your goals.

Now, imagine you have unlimited resources to rebuild. Describe this redesigned company.


What would you value? Who would you bring to help? Take notes freely and quickly.

🛑 Keep reading only after you finished that part.

If your ideal future is far away, and if you want to get there:

  1. List all the steps between now and the future

  2. Slice those steps into smaller, clearly defined pieces

  3. Ask others how to accomplish any piece that is not clear

  4. Identify a few steps to begin and take the first leap

To maintain motivation, track of your progress and be sure to recognize accomplishments


Avoid Perfection

"To improve is to change; to be perfect is to change often." Winston Churchill

It’s tempting to sort out every detail before actually acting. However, startups must be adaptable and nimble.

Focus on the vision. Being caught up in today hold you back. Work backwards from that vision to the broad steps necessary and keep repeating and getting more detailed each pass.

Focus on a handful of projects. Only a few activities will dictate success, so determine which matter. Run trials, measure results, and add resources to high impact outcomes.

Focus on your strengths. Decide where to maximize your energy and delegate the rest. Set clear expectations, regularly measure progress, and evaluate outcomes (not behaviors). Perfection is enticing for many reasons but may actually hinder success.


Recover from Exhaustion

"Whatever thrown at them, leaders emerge from their crucibles stronger and unbroken." Warren Bennis

Being a leader can feel like a battle. When we're exhausted, that causes a loss in focus, delay in making decisions, and less patience and support from the team. You need to re-calibrate.

  • Reset - You may be working from last year's plans and temporary initiatives. Start over and revise your goals. Planning for the new world will have you living it.

  • Reorder – A shift in roles and responsibilities can help to shake up the team in a positive, proactive way.

  • Re-imagine – Find new ways to engage a larger community. A broader purpose brings meaning and enhances our work (e.g. learning new skills).

Feeling fatigue and uselessness is normal. How you respond defines the future.


How to Respectfully say “No”

Know your limits and respect others. While it's tempting to not respond, if someone respectfully and reasonably asks for your help, here are other options:

  • If you genuinely want to help but cannot right now, offer a date when they can reach out again to ask.

  • If you lack the time required, offer to assist that requires fewer hours or less effort on your part. Another option is to offer a substitute.

  • If you simply cannot help now, write a concise response. Be firm and respectful and wish them well.

It's reasonable to say "no" but remember how hard it can be to ask for help and consider taking a minute to respond thoughtfully and firmly.


Enduring Deep Change

“Above all, don't lie to yourself. The one who listens to his own lie comes to a point that he cannot distinguish the truth within him, or around him, and loses all respect for himself and others.” Fyodor Dostoevsky (1880)

Deep, long-term change is grueling whether starting a business or evolving yourself.

  • Be Honest – In a silent room alone, confirm you genuinely want to change. If you find the word “should”, you're likely pursuing someone else’s dream. Reconsider.

  • Be Clear – Write down your vision to stay motivated when exhausted. Decide what you are willing to sacrifice with your relationships and lifestyle.

  • Be Prepared – You will face pain and discomfort. Knowing struggles are necessary, plan how to manage stress and how to reinforce your vision.

  • Be Constant – Keep driving forward. The longest journey still requires one step at a time. Set times to work on your plans and regular deliverables to ensure progress.

  • Be Vulnerable – Seek external input to help you reach further. Ask for feedback, advice, and coaching around your movement and any obstacles.

  • Be Supportive – While commonly used on others, apply this idea to yourself.

Planning and mindset lead to meaningful, enduring change.


Becoming Anti-Racist

“In a racist society it is not enough to be non-racist, we must be anti-racist.” Angela Davis

In my work, I facilitate strong founders to efficiently build and scale infrastructure based on their vision and values. I must my approach to leadership and structure.

There's irrefutable evidence that some leaders and systems are destructive. I’m considered white in a world where that carries privilege, a concept I barely understand.

With racism, “Silence means security, silence means approval” (R.E.M.). I’ve been silent most of my life.

I need to evolve from being non-racist to anti-racist. It's not enough for me to act without discrimination. I must actively seek to identify and destroy examples of racism. Identifying the problem is the first step in moving forward.


Constructive Advice is Critical

“People will do anything, no matter how absurd, to avoid facing their own souls.” Carl Gustav Jung

While we’re flooded with input and news, we need to optimize and internalize feedback.

Here's how:

  • Mentors: Frame their input as collaboration, not as fixing a problem. Bring specific questions (with metrics, if possible) to focus the discussion and value their time.

  • Peers: Resist the temptation to ask only tactical questions or to hear their stories. Gravitate to people who push to discover the deeper cause and your role in issues.

  • Team: Get candid feedback by asking open questions (e.g. “How could I do this better?”). Don’t argue, listen. Remember addressing hard issues now prevents insurmountable problems later.

  • Self: Know that all leaders fail repeatedly and seek improvement, not perfection. Track your challenges and subsequent progress. Revisit people who made an impact.

Recognize the immense value of feedback for your leadership and business.


Tips for Productivity

  1. Kill the to-do list and convert tasks to a calendar. You'll be forced to choose your priorities and needs. Add goals, rest periods, and strategy time to your schedule.

  2. Connect positive habits with normal ones e.g. add a 7-min HIIT before your shower. For big goals, concentrate on next steps. Celebrate each step to reinforce behavior.

  3. Act like someone is watching. It makes us work harder. For me, I record weekly any accomplishments, lessons, and goals by making notes which could be shared.

  4. Determine your energy cycle and complete the most important projects during your highest energy levels. Consider work in shifts of 45 minutes with 15 minute breaks.

Evaluate and keep the tips which work.


Negativity Bias Pounds You

"Courage is not the absence of fear, but rather the assessment that something else is more important than fear." - President Franklin Delano Roosevelt

When measuring two equal pieces of information, the negative far outweighs the positive.


For instance, we linger on a single bad comment in an otherwise fantastic review.

How to best respond?

  • Business growth – Negativity bias can make us risk adverse and slow to act. Derive diverse input from many others and ask how (not if) to move forward.

  • Team growth – It takes five positive encounters to offset a single bad one. If you make a mistake with someone else, you'll need at least five productive interactions before things may improve.

  • Personal growth – Negativity bias adds to our fear of criticism and tempts us to avoid valuable feedback. Keep pushing. Record accomplishments to keep motivated.

Awareness and mindful activity counters negativity bias.


Giving Feedback for Mutual Benefit

“We don’t see things as they are; we see them as we are.” Anaïs Nin

You want your team to perform better but are hesitant to give feedback. Feedback not only helps your business grow but also builds a satisfying career for someone else.

  • Start with trust. Find the path of success for them and for the business, then continue an open discussion. Offer internal or external training or coaching.

  • Give clear expectations. We all benefit from guardrails and a description of expected behaviors, outputs, and outcomes.

  • Create meaning. How does this person contribute directly to your company's growth? We all want meaning in our work.

  • Focus on the future. Don't linger on past mistakes but spend at least 80% of your time looking at ways to improve and grow.

Assume the receiver is trying their best and approach them with one specific adjustment.


Helping others is selfish

When helping others, you gain a lot for yourself.

  • Perspective: Volunteering widens our view, which in turn brings new insights about the world and ourselves.

  • Skills: You may have new responsibilities, enter a different industry, or handle a different role. Interacting with others often uncovers unexpected opportunities.

  • Purpose: Helping others creates meaning which offsets the daily routine.

  • Fun: Offer to help around your interests and increase your exposure to them.

Remember that a full schedule is not necessarily a fulfilling life. Give and grow.

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