Assessment Progress
0 / 150
J. O'Brien Coaching
J. O'BRIEN COACHING
FUELING BOLD LEADERSHIP TRANSFORMATION

BOLD
Leadership Assessment

Lead boldly. It's simple. It's a choice.

How to Use This Assessment

  • Rate yourself honestly on each statement using the 1–5 scale below.
  • Answer the reflection question after each principle.
  • There are no right or wrong answers — only honest ones.
  • This tool is designed to start a coaching conversation, not end one.

Rating Scale

1 Never
2 Rarely
3 Sometimes
4 Often
5 Consistently

Maximum score: 150 (25 per principle × 6 principles)

S
Show Up Consistently
Build trust through reliability. Be predictable in your actions.
0 / 25
1
I follow through on commitments reliably — if I say it, I do it.
2
I respond with steadiness under pressure rather than mood swings or emotional reactivity.
3
I stay visible and accessible when stakes are high — I don't disappear in tough moments.
4
My decisions consistently reflect my stated values — even when it's inconvenient or unpopular.
5
I regularly reflect on how I'm showing up and the impact I'm having on my team.
Reflection
Think of a recent high-stakes moment. How did you show up — and what did your team need from you that you may not have fully delivered?
I
Invest in People
Leadership isn't sustainable without connection. Know your people.
0 / 25
1
I genuinely know what motivates and matters to each person on my team.
2
I listen deeply and give people my full, undivided attention.
3
I actively sponsor and create real growth opportunities for my people — beyond their current role.
4
I acknowledge contributions and effort — not just results.
5
I coach and develop my people rather than doing the work for them.
Reflection
Who on your team is not getting enough of your genuine investment right now? What is getting in the way?
M
Mind the Work
Respect your team's work. Instill ownership.
0 / 25
1
I understand how my team's work actually gets done — not just at a high level.
2
I lead from insight rather than interfering with or overriding my team's work and judgment.
3
I actively remove barriers and simplify where possible so my team can do their best work.
4
I trust my team's expertise and don't second-guess or override their knowledge.
5
I hold my team accountable with clear expectations and instill shared ownership for results.
Reflection
Where are you assuming instead of asking? What would you do differently if you spent a day working alongside your team?
P
Paint the Picture
Give meaning, not just directions. Make the why unmistakable.
0 / 25
1
I make the "why" behind decisions and priorities unmistakably clear to my team.
2
I help my team understand how their work connects to the bigger organizational picture.
3
I articulate a clear, compelling vision that people can understand and act on.
4
I communicate proactively — I don't wait for things to go wrong or for people to ask.
5
I name risks and uncertainties honestly rather than protecting people from hard truths.
Reflection
Where might your team be working without full context right now? What is one thing you could make unmistakably clearer today?
L
Lead with Respect
Lead humans. Model courage, candor, and a learning mindset.
0 / 25
1
I create an environment where people feel genuinely safe to speak honestly without fear.
2
I give direct, truthful feedback with care and empathy — I don't avoid hard conversations.
3
I actively invite challenge and dissent — even when it makes me uncomfortable.
4
I acknowledge effort and recognize the person behind the work — not just the output or the result.
5
I address difficult issues directly rather than avoiding or working around them.
Reflection
What conversation are you currently avoiding? What is the cost of that silence to your team and to you?
E
Enable Bold Moves
Set strategic direction. Clear roadblocks. Share control.
0 / 25
1
I give people real authority and responsibility — not just tasks to execute.
2
I actively clear the path — removing obstacles so my team has what they need to succeed.
3
I protect people who take intelligent, well-reasoned risks — I don't punish responsible failure.
4
I coach forward more than I direct — I ask more than I tell, and develop capability in others.
5
I lead with calm conviction and steadiness — especially when the path forward is uncertain.
Reflection
Where are you holding on when you should be letting go? Who on your team is ready to do more — and what is stopping you from backing them fully?

Your Results

Scores update as you complete each section.
S
Show Up
—
/ 25
I
Invest
—
/ 25
M
Mind Work
—
/ 25
P
Provide
—
/ 25
L
Respect
—
/ 25
E
Enable
—
/ 25
0
Complete all sections to see your level
Your score will update as you rate each section.

Section Breakdown

S · Show Up Consistently
0/25
I · Invest in People
0/25
M · Mind the Work
0/25
P · Paint the Picture
0/25
L · Lead with Respect
0/25
E · Enable Bold Moves
0/25

Ready to Submit?

Your assessment will be sent to your coach at J. O'Brien Coaching. Your responses and scores will be reviewed before your next session.

Thank You

Your BOLD SIMPLE Leadership Self-Assessment has been submitted. Your coach will review your results before your next session. Come prepared to have an honest conversation.