Quadrants of Likes and Dislikes

Director of Operations at a manufacturing company, being groomed for VP role. Has been in current position for three years and repeatedly expresses interest in advancement, but consistently delegates or delays people management responsibilities. Recently declined to lead a cross-functional project that would have been high-visibility.

Frame this as a promotion readiness check, not a self-awareness exercise. 'Before we talk about what VP looks like, let's map what energizes you now versus what drains you.' Expect resistance around putting leadership activities in negative quadrants - many clients think admitting dislike of management tasks disqualifies them from promotion.

Speed of completion in each quadrant tells the story. If 'I love it' fills quickly with technical work and 'I dislike it' takes five minutes of deliberation, the client already knows the answer but hasn't faced it. Watch for euphemisms in the bottom quadrants: 'people challenges' instead of 'managing conflict.'

Start with the 'I hate it' quadrant, not the positive ones. Ask: 'What percentage of a VP role would involve activities from your bottom two quadrants?' Then: 'What would need to change about those activities - or about you - for promotion to make sense?' The gap between aspiration and energy allocation is the conversation.

VP Marketing at a tech startup, considering leaving to start her own consulting practice. Talks enthusiastically about 'being her own boss' and 'creative freedom' but has never worked independently. Company is stable, role is well-compensated, but she feels constrained by corporate processes and team dynamics.

Position this as a reality check for the freelance fantasy. 'Before we plan your exit strategy, let's map what you actually enjoy about work versus what you think you'll enjoy about independence.' Many clients considering freelance transitions focus on what they're leaving behind, not what they're moving toward.

Look for corporate infrastructure activities in the 'I dislike it' quadrant that are actually freelance requirements: business development, financial management, client relationship maintenance. If 'I love it' is dominated by creative work and 'I hate it' includes administrative tasks, the freelance reality may not match the fantasy.

Start with activities that appear in 'I dislike it' or 'I hate it' and ask: 'Which of these would you need to do more of as a freelancer, not less?' Then explore the 'I love it' quadrant: 'How much of your current role involves these activities? How much of a typical freelance day would?' Reality-test the transition assumptions.

Regional Sales Director for a software company, consistently exceeds targets but reports feeling burned out. Spends most of her time in client meetings, demos, and relationship management. Recently promoted two direct reports but still handles major accounts personally. Says she needs better work-life balance but resists delegating client relationships.

Frame this as an energy audit, not a delegation exercise. 'You're successful at what you do, but success and sustainability aren't the same thing. Let's map where your energy actually goes.' Expect the client to fill all quadrants with variations of client work - the insight is in the nuances between types of client interaction.

If all four quadrants contain client-facing activities, pay attention to the distinctions the client makes. 'Prospecting calls' versus 'relationship maintenance' versus 'problem-solving with existing clients' may all land in different quadrants. The specificity of these distinctions reveals what aspects of client work energize versus drain.

Focus on the granular differences within client work. Ask: 'You put prospecting in 'I dislike it' but client strategy sessions in 'I love it' - what makes those different?' Then: 'Looking at your calendar, what percentage of client time is spent in each quadrant?' The delegation conversation starts with energy allocation, not task allocation.

Finance Manager at a mid-size retail company, three years in role. Came from public accounting and thought corporate finance would be more strategic. Spends most time on month-end close, budget variance analysis, and compliance reporting. Expresses interest in 'more analytical' work but unclear what that means specifically.

Present this as a role fit diagnostic, not a career exploration tool. 'You mention wanting more analytical work, but let's first map how you experience the work you're already doing.' Some clients think they dislike their field when they actually dislike their specific role or company context.

The 'I love it' quadrant may be sparse or filled with activities the client rarely gets to do. If 'I dislike it' and 'I hate it' contain 70% of their current job description, note whether the dislike is about the tasks themselves or the context (tight deadlines, unclear requirements, repetitive nature).

Start with the sparse quadrants. If 'I love it' has two items, ask: 'When was the last time you did either of these?' Then move to the loaded negative quadrants: 'What would need to change about budget variance analysis to move it up a quadrant?' This distinguishes between task aversion and context aversion.