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.

SUCCESS STORIES

Lathrop GPM LLP

Visit Tri-Valley

Head of Design

Major Bank

Montgomery & Hansen, LLP

Impax Laboratories, Inc

Blend

Hope Services

Veeva

The Council

Medical Innovation Company

Schusterman Family Foundation

Daly City Partnership