Strengths and Weaknesses

Exercises & Practices

Is This Me?

These questions aren't a test. Just notice your internal response.

• Do I keep trying to succeed at something but keep hitting the same wall, no matter how hard I work?

• Do I feel drained by my work — or parts of my life — even though I'm capable enough to do them?

• Have I taken a personality assessment and used it to explain away something I should actually be working on? ("I'm just not a people person." "I'm not a detail person." "That's just my type.")

• Am I trying to do everything myself instead of asking for help in the areas where I'm genuinely not strong?

• When I think about the trail I leave behind me in relationships, are people feeling encouraged — or feeling bruised, overlooked, or worn out?

• When I think about the trail I leave behind me in results, is work actually getting done — or am I leaving a pattern of unfinished projects, missed deadlines, and good intentions that never became action?

• Do I know what my strengths actually are, or am I still guessing?

• Have I been comparing myself to people with different gifts and feeling inadequate — when really, we're just designed differently?

• Am I in a role or commitment that consistently depletes me, and I keep telling myself I just need to try harder?

Questions Worth Sitting With

These don't have quick answers. Sit with them.

• If I asked three people who know me well — "What's it like to be on the other side of me?" — what would they say? Not what I hope they'd say. What would they actually say about the relational wake I leave? About the results I produce or fail to produce?

• What have I been calling a personality trait that's actually a character issue? Compassion, reliability, listening, perseverance, speaking truth, handling conflict — these aren't gifts some people have and others don't. They're things every person needs to develop. Where have I been hiding behind "that's just how I'm wired" instead of doing the work?

• What do I gravitate toward when nobody's watching? When I have free time, discretionary energy, an open Saturday — where does my attention go? What articles do I read? What conversations do I seek out? What would I do if fear and money weren't factors?

• Where does time fly — and where does it drag? Dr. Cloud noticed that when he sat with people talking about growth and relationships, four hours would pass without him noticing. That wasn't random — it was his design showing up. Where do I lose track of time because I'm so engaged?

• What does my track record actually say? Not what I wish it said. Where have I consistently succeeded, and where have I repeatedly struggled despite real effort? If I've tried something many times and it never works, that's data — not failure.

• If I knew my strengths with confidence, what would I stop doing? What roles, commitments, or expectations am I holding onto that don't fit my design — and what would I be free to pursue if I let them go?

• Who do I need beside me? My weaknesses aren't mistakes — they're invitations to partnership. What kind of person would complement what I lack? And am I humble enough to actually ask for that help?

Growth Practices

Pick one. Try it this week. Notice what happens.

Week 1: Notice Your Energy

This week, track your energy as you move through activities. At the end of each day, jot down: What drained me today? What energized me? When did time fly? When did time drag? Don't judge, don't analyze — just collect data. By the end of the week, look for patterns. You're building a map of your design.

Week 2: Ask Three People

Pick three people who've seen you in different contexts — work, family, friendships. Ask each of them: "What do you think I'm good at? When do you see me adding value or coming alive?" Then ask: "Where do I tend to get in the way or not bring value?" Listen without defending or deflecting. Write down what they say. Look for patterns across all three conversations.

Week 3: Audit Your Wake

Pick one key relationship — a partner, a colleague, a close friend. Ask them: "What's it like to be on the other side of me? How do you feel after we interact? And how are things going on the results side — do I come through, or do I leave loose ends?" This is the hardest conversation because you're asking someone to be honest about the trail you leave behind. Let them talk. Don't explain or justify. Just listen.

Week 4: Quarantine One Weakness

Identify one weakness that's currently infecting an important outcome — a project, a relationship, a role. Then take one concrete step to quarantine it: delegate that piece, ask someone to partner with you, create a system, or simply stop pretending you can handle it alone. Notice how it feels to stop fighting your design.

Week 5: Name the Character Issue

Look at one thing you've been excusing as "just my personality." Maybe it's being harsh when you're focused, or being unreliable with follow-through, or avoiding conflict. This week, stop calling it a personality trait and start calling it what it is — a character gap that needs work. Pick one small behavior to change. Not a revolution — just one degree of turning.

Scenario Cards

Scenario 1: The Talented Artist

Marco is incredibly gifted musically. Everyone who hears him play says he could have a career in music. But after fifteen years, he's still working a day job and playing gigs on weekends. His songs never get finished. His demo never gets produced. He has boxes of half-completed projects. His friends say, "You're so talented — why haven't you made it?"

Is Marco's problem a gift issue or a character issue? What would "quarantine your weaknesses" look like for him? What kind of help or partnership might change his trajectory?

Scenario 2: The "I'm Just Not a People Person"

Diane is brilliant at strategy and analysis. She consistently produces excellent work and solves complex problems. But she's been passed over for promotion twice because "she doesn't work well with others." Diane's response: "I'm just not a people person. I'm an introvert. I'm about results, not relationships."

Is Diane's situation a gift issue or a character issue? What would Dr. Cloud say about her explanation? Where's the line between accepting your design and making excuses?

Scenario 3: The Unaware Wake

Rob manages a team of eight people. His department consistently hits its targets — he's known as someone who gets results. But turnover in his department is twice the company average. In exit interviews, people cite the same things: feeling micromanaged, never feeling good enough, dreading one-on-one meetings with him. Rob is genuinely confused by this feedback. "I care about my people," he says. "I just have high standards."

What does Rob's wake look like on both sides? What is he seeing, and what is he missing? What would it take for Rob to actually hear this feedback?

Journaling & Reflection

Looking Back

• Describe a time when you were fully alive doing something. Where were you? What were you doing? Who was around? What made it so energizing? Write in as much detail as you can remember. What does that memory tell you about your design?

• Write about a repeated failure in your life. Don't judge it — just describe it. Now ask: Was this failure because I was trying to do something I'm not made for? Or was it a character issue I haven't addressed? Or both?

Looking Inward

• What have you been excusing as "just how I'm wired"? Be honest. Write about the times you've used your personality or temperament to justify something that hurt relationships, missed commitments, or held you back.

• If you asked your closest friends and family what you're good at, what would they say? Write their answers as you imagine them. Then consider: Are they right? What do they see that you might not?

Looking Forward

• Make a list of things you need to stop forcing. Where are you trying to teach the pig to sing? What would it look like to let those go and focus on where you actually bring value?

• Describe your ideal partnership. If you could design someone whose strengths perfectly complemented your weaknesses, what would they be good at? What would you bring? How would you work together?

• Write a letter from your future self — the version of you who's figured out your strengths, quarantined your weaknesses, and grown in character. What would they want you to know? What would they be proud of? What would they warn you about?