Leadership requires operating during high-stress periods. Under stress, most leaders will return to their default leadership approaches, and ways of operating. However, successful leadership requires range, which means both developing awareness of your strengths, as well as practicing and developing one's weaknesses. This slideshow explores two core leadership approaches--head and heart. The talk digs into the benefits and blindspots of each and where a leader can most effectively grow depending on where they fall.

1. Startup Leadership Under
Pressure: Balancing Head
and Heart
Skye, 3/7/23

2. AGENDA
02/ Head and Heart Leadership in Action: A Difficult Conversation Deep Dive
20 minutes
01/ Defining Head & Heart-Based Leadership - 5 minutes
04/ Discussion & Questions - 15 minutes
03/ Role Play - 20 minutes

3. • 7 years as Founder at Looksharp (acq’d by Yello)
• Marketing at Carta during hyper-growth (from 150 -
400 employees)
• Coached 100+ CEOs, founders, and venture partners
(typically Series A-D)
• Coach founders backed by A16Z, Sequoia, YC, and
more.
• Specialize in “Co-Founder Coaching” helping
co-founders expand trust and improve performance.
About Me

4. Sharpend is on a mission to
build the world’s leading
co-founder coaching practice.
We believe strong partnerships are the
foundation to a more dynamic future.
About Sharpend

5. Defining Head & Heart-Based
Leadership

6. How do you lead?
Heart Based
- Core attributes:
- Courage
- Empathy
- Humility
- Leadership style is focused on
on people, vision/inspiration,
and relationships
Individuals have a default / dominant orientation
Head Based
- Core attributes:
- Logical
- Perspective
- Problem-solving
- Leadership style is focused on
strategy, objectives and
getting things done
Gut Based
- Core attributes:
- Willful
- Direct
- Instinctual
- Have a strong internal
compass, which they are
constantly reacting to

7. Every leader has a different default orientation that
informs their strengths, weaknesses, triggers, and
patterns.
Self-awareness helps leaders lean into their zones of
genius, while avoiding blind spots that cause them to
plateau.
Exceptional leaders have range

8. Head and Heart in Action
Real-world startup example

9. Common Difficult Conversations
- Unclear roles and responsibilities
- Decision-making on areas including:
- Vision
- Product roadmap
- Hiring strategy
- Fundraising strategy
- Different expectations on work hours / work intensity
- Giving negative feedback
- Performance dissatisfaction (in particular between co-founders with no
clearly defined hierarchy)
- Equity negotiations

10. Mastering difficult conversations
Heart Based
Default Difficulties
Tips to Improve
Effectiveness
- Emotional flooding that leads
to overwhelm
- Avoids conflict - finds giving
constructive feedback
uncomfortable / intimidating
- Concerned about not hurting
others’ feelings
- Focus on managing your
emotions before and during
the conversation
- Use emotions as data
- Do prep work such as role
playing the conversation.
REMEMBER: 8 months to 1-year as the timeline required to make substantive shifts to your
default orientation

11. Mastering difficult conversations
Head Based
Default Difficulties
Tips to Improve
Effectiveness
- Focus on what they say, not
how they say it (too in the
weeds)
- Comes across as cold or
uncaring
- Disconnected from the
impact of their behavior
- Develop emotional literacy
and acknowledge the other
person’s emotions
- Focus on bottom-lining
express the core of what you
want to say then PAUSE
- Lean into reflective listening
REMEMBER: Change takes repeated exposure to "zones of discomfort"

12. Role Play

13. Cofounder A: I wish you would show up to our meetings on time.
Cofounder B: Yeah, yeah. You wouldn’t believe the traffic on my way in.
Cofounder A: There’s always traffic - Shouldn’t you just need to leave your house earlier?
Cofounder B: Why is it a big deal? We spend the first 5 minutes talking about the weather anyway.
Cofounder A: That’s not the point! We talk about the weather because we’re waiting on you to show up!
Cofounder B: Sure, whatever. No one else seems to mind
Cofounder A: You think anyone would tell you to your face that they care??
Cofounder B: You seriously need to take a chill pill. I’m going to go grab a coffee.
Conversation Gone Wrong
A major issue in difficult conversations is that people focus on the content not the context

14. Role Play
Scene
- Two co-founders had a big investor pitch that didn’t go as planned
- Person A dominated the meeting and is unaware that it went poorly
- After the pitch, Person B was visibly upset and asks Person A to meet
Person A perspective:
- You are the “face” of the company and a better presenter
- Your cofounder asked to do the first few slides, but it became clear that he was nervous and you
didn’t want to blow the meeting
- The investors gave you positive feedback so frankly your cofounder should be glad you stepped in
Person B perspective:
- You rehearsed talking points for the presentation and your cofounder still made it “her show”
- The worst part was when she interrupted you and even cut you off to answer questions
- You left the meeting feeling very frustrated and undermined

15. Best Practices
➢ Do the prep - Plan for the conversation beforehand (when possible)
➢ Ask clarifying questions - Be curious, collect more information
➢ Take a break if needed - Agree on a set time to revisit the conversation
➢ Bottomline your points - Say your most important high-level reflection then PAUSE
➢ Notice emotions - That are present for you AND your conversation partner.
➢ Reflective listening - Confirm you understand where the other person is coming from
➢ Request next steps (if applicable) and/or create a feedback loop to check in and follow up

16. Discussion:
Additional Real-World Examples

17. Additional Real-World Examples
Self-awareness of your strengths and weaknesses is crucial to navigating difficult conversations
Mastering… Heart Based Leadership Head Based Leadership
Decision-making - Noticing internal reactions to different
options. One feels exciting, the other
creates a pit in your stomach. Use
emotions as data and unpack why
they are what they are.
- Brainstorming a wide variety of ideas.
- Able to envision a future where that
idea works. Able to talk through
different components without
committing.
Firing - Able to have high emotional
resonance, be authentic in these
moments.
- Able to make tough choices driven by
logic and business need
Fundraising - Courage and wIllingness to push
through challenging moments.
- Defaults to problem solving and
“ruthless” prioritization

18. Thank You!
nathan@sharpend.co
301-873-8435