Head of Design
Design
How Coaching Helped This Executive Rebuild Confidence and Negotiate the Role She Deserved
Deb is a seasoned design leader who had just come through a bruising stretch in a VP role with a round of layoffs and burnout, resulting in an erosion of self-confidence.
Objectively, her track record was strong. Subjectively, she didn’t feel entitled to a top role, or to ask for the resources and boundaries required to succeed in one.
That mindset results in two outcomes: undershooting in the search, and over-committing once hired.
This time, Deb wanted a role where she could thrive, not just survive.
Interviewing & Negotiating to Win
In our first sessions, I challenged a mindset I kept hearing from her: "Don't I have to prove myself before I ask for what I need?"
That's backwards. Leaders define the conditions for impact up front.
We set a more focused goal: target a Head-of-Design role at a values-aligned company, and enter on day one with the clarity, courage, and tools to lead.
Executive Coaching Approach
Our coaching work together broke into three phases, targeting her confidence, the interview/negotiation process, and a dynamic start with her chosen company. I designed specific processes and targets for her for each phase.
Phase 1: Rebuilding Confidence with a System
Sustaining determination and self-assurance requires architecture, a system with support. We identified three beams in her structure:
Story of Value. I helped Deb translate a decade of accomplishments into a tight leadership narrative: business problems solved, meaningful design bets placed, talent grown, and where her judgment is non-negotiable. This replaced a generic “I care about users” with business-credible language an ELT respects.
Standards & Boundaries (pre-negotiated). We defined non-negotiables for role scope, team resourcing, decision rights, and time use. If an offer couldn’t meet the bar, or showed red flags, we would pass. Courage is easier when standards are explicit, and confidence grows from courageous wins.
Rituals (to prevent backslide). With Deb’s input, I crafted weekly reflection prompts, a “no-heroics” time budget, and a reset script for when old patterns (overhelping, overprepping, overexplaining) reappeared.
Tools used: DiSC® insights to anticipate friction with peers; interviewing scorecards; a negotiation prep grid (must-haves, tradeables, walk-aways).
Phase 2: Raise the Ask (Search, Interview, Negotiate)
Targeting: We aimed only at environments where design is a strategic partner, not decoration. Deb practiced saying “no” to good-on-paper roles that would consume her but not grow her.
Interviewing: We reframed “answer their questions” into “lead the conversation.” Deb used a three-part cadence: (1) diagnose the business problem, (2) propose a right-sized approach, (3) set expectations for decision velocity and collaboration.
Negotiation: We rehearsed courageous asks she’d never made before—title clarity, resourcing, onboarding access to key stakeholders, and a first-90-days success definition. She learned to pause, let silence do its work, and trade, not justify.
"Kristi saw my value when I couldn't and pushed me to negotiate for the resources the role needed. She helped me build back my confidence"
Phase 3: Onboarding for Impact, Not Exhaustion
Offer accepted. Now the risk shifts; many leaders overperform on effort and underperform on leverage.
To counteract this, I built a 90-day operating plan for Deb’s quick-start entry to her new role:
30/60/90 Priorities: Three needles to move, not ten. Each with a clear metric, cross-functional partner, and an explicit “good enough” threshold.
Decision Map: Which calls she makes vs. co-decides vs. escalates. Ambiguity is where new leaders lose weeks of time.
Stakeholder Grid: Who matters, what they measure, and what trust looks like to them. Deb set short, punchy 1:1s that opened doors early.
Time & Energy Rules: Maximum meeting hours per day; no after-hours “hero work” except by design; deep-work blocks protected by her EA and her own backbone.
Leadership Habits: Direct scripts for hard conversations, a weekly “wins and tradeoffs” note to her manager, and a delegation checklist to stop taking back work “to be helpful.”
Results
The role: Head of Design at a values-aligned company. Scope and altitude she had previously second-guessed pursuing.
The package: Deb asked for and received terms she’d never have voiced a year earlier, including role clarity, realistic resourcing, and onboarding access that shortened time-to-impact.
The ramp: From week one, she led with calm authority - fewer meetings, cleaner decisions, and one standards-based, compassionate personnel call that stabilized the team.
The leader: Sustained confidence, because it was built on system, not adrenaline.
In Deb's Words
Deb is enthusiastic about Kristi’s impact.
She says, “Kristi saw my value when I couldn’t, and pushed me to ask for what the role needed, not just what I felt comfortable requesting. The 90-day plan helped me lead with clarity instead of proving myself by overworking.”
And ongoing: “Leadership can be lonely. Kristi gave me a sounding board, allowing me to talk things through with someone who didn’t have a stake in the situation.”
Why it Worked
We replaced “deserve” with design. Waiting to earn permission is how strong leaders quietly cap their impact. We defined the conditions for success first, and negotiated for them.
We made confidence measurable. A narrative you can state, standards you will defend, and rituals you will keep. That creates durable confidence.
We optimized for leverage. Onboarding focused on decisions, relationships, and time economics, not “learn everything and be everywhere.”
Does This Sound Like You?
You have done meaningful work, but your self-talk is quieter than your résumé.
You are aiming higher, yet hesitate to ask for the resources and authority required to actually win.
You are tired of sprinting your way into credibility; you’re ready to architect it.
Deb says that Kristi helped her regain her self-assurance. “She saw my value, and supported me even when I felt I didn’t deserve it. She really helped me build back my confidence.”
How I Help
Clarify your leadership value in business terms.
Job search, targeting, interviewing, and negotiation strategies that protect your energy and your impact.
Develop an onboarding system that makes your first 90 days both decisive and sustainable.
Surface blind spots, support you as you build courage and confidence.