Ask AI How Many Jobs Is Your Job

Credit for today’s article goes to the genius idea from Feridoon Malekzadeh and his January 2024 LinkedIn post where he gave ChatGPT a wildly long job description. He asked ChatGPT, “How big of a design team would I need to hire to do all of this work? Suggest team size, structure, number of managers, etc.”

ChatGPT suggested a team of 17–22 people for what was listed as a single open job as “Director, Branding Design — SVP.” ChatGPT suggested:

• One Creative Director/Head of Branding
• Two or Three Senior Brand Strategists
• Three or Four Senior Designers
• Four or Five Mid-Level Designers
• Two or Three Junior Designers
• Two Design Managers to oversee all of these Designers.
• Two Project Managers with an additional Project Management Lead
• Two Copywriters
• One or Two Web/Animation Specialists

I pasted the same job description into Claude.ai, who was more conservative about team size with a team of at least six.

Prompt: “I’m pasting a request for a worker, but I suspect that this company needs more than one person to do these tasks. Please analyze this job description. Tell me how many people you would need to do this job well, and what their titles would be.”

Claude suggested:

• SVP, Design Director
• VP, Creative Director
• Two or three Senior or Mid-Level Visual Designers
• Two or more Junior Designers, scale up as needed

Feridoon’s idea is great!

Companies love to try to hire one person to do the work of two, four, six, or maybe 17. This often comes with being set up to fail, having a moving target of priorities, and all of your teams and projects thinking you’re not good or fast enough. Probably all with an unfortunate stream of gaslighting and eventual burnout.

The next time you see a job description that you think might be multiple full-time jobs glued together, drop it into your favorite AI, and ask how many people should do this work.

You might even want to try it with your current job description.

Then what should I do?

Up to you, but if a recruiter, HR rep, or hiring manager reached out to me with this, you know I will say something. In the future, I might say something and have AI back me up on it. I’m a say something type of person.

You can apply for this job if you want! Just be aware of what they are really asking for. Find out their priorities. The job might list 10 skills, but mostly want your visual design work. Who knows until we ask.

The more roles, skills, or tasks a company expects you to take on, the more likely you are to:

• Have trouble juggling priorities. What should you work on today? Dev is waiting for final designs. You want to do some research to make better-informed decisions. The copy hasn’t been started, and where are the updates to the brand voice? There is only one of you.
• Do some or all of your work poorly. It’s not you. It’s the job. There is only so well you can do any of your tasks when you are one person doing multiple people’s full-time jobs.
• Be set up to fail. Again, it’s not you. But if a job expects you to do the work of multiple different specialists, and they expect that work to be done well (or as well as a specialist would do it), they are probably setting you up to fail. They will want you to think it’s you, so look out for the gaslighting.

Another one… and I did say something.

In November 2023, a recruiting company contacted me with a high-priority “Head of CX” job that they were having trouble filling. I have no idea what it paid, but it appeared to be 27 jobs glued together.

I just asked Claude to review this job description. Once again, it was conservative, suggesting:

• Head of Customer Experience — Owns the overall customer experience vision and strategy. Leads the team. Responsible for aligning efforts to business goals.
• UX Design Lead — Leads information architecture, wireframing, prototyping, interface design, usability testing.
• User Researcher — Conducts user studies, gathers feedback and insights, identifies pain points.
• Front-End Developer — Builds out prototypes and interfaces. Owns technical development.
• Business Analyst — Conducts feasibility analysis, financial modeling, operations analysis.
• Supporting Team: UI/UX Designers, Quality Assurance Testers

I still think Claude went light on this one. Even so, you would be doing the work of eight different jobs. Way way way too much work for one person. You’re less of the “Head of CX” and more the entire CX department doing everything an entire team of full-time specialists should be doing.

Job of 17 people, pay of one.

Let’s do one more.

Here is my prompt to Claude and the original job description.

Prompt: I suspect that this job listing really needs multiple people in multiple roles. Can you please analyze this and tell me which roles and titles you would need to get this job done? And how many people? (I pasted the following job description. It’s long. Feel free to skim it and pick up where Claude responds.)

Key Responsibilities

• Optimising the delivery of business value through business partnering, process improvement, user research and user-centred design.
• Performing user research through qualitative enquiry, quantitative data analysis and user testing within the R&D customer base of this product area.
• Obtaining a solid understanding of the business domain and processes within a product area, capturing user goals, needs and expectations and translating these into personas, journeys and user stories that drive towards improvements.
• Driving process optimisation through process modelling and service design, taking into consideration the product strategy and system and data landscapes.
• Driving experience design activities to improve user interfaces and task flows through wireframing, prototyping and ideation workshops.
• Working closely with the Product Owner and other members of the product team, with a clear focus on delivering value quickly while helping to steer the product area towards business- and user-centred improvements.
• Developing product marketing materials such as videos and newsletters for new feature releases and deliverables announcements.
• Being face of Product Owner and acting as Business Analyst to understand the needs and challenges of the product and business area to provide best practice for requirement analysis and prioritization.
• Engaging with the R&D Tech UX & Design Team to support the maturity of UX and Design across R&D Tech, specifically working with other UX practitioners and sharing experiences.
• Partnering with the business area to understand their challenges and needs, whilst working to manage system and process changes within these user groups, helping ensure smooth deployments and satisfied customers.
• Keeping up with internal and external trends in your product area, including mobile, wearables and social media.

Previous Experience Required

• 5 years’ experience in working in an IT product related industry, with experience in IT software analysis, business analyses, design and delivery, with awareness of the UX space, particularly areas of user research, experience design and service design.
• Practical experience in software design and delivery (both analytical and technical) along with interest in the UX space is the core capability of this role.
• The position involves a large amount of influencing and communication to individual contributors, lower/mid-management and external partners across the Organisation to apply product analysis and design in a business context with deep analytical and meaningful insights.

Basic Qualifications

• Bachelor’s Degree — Business, Information Technology or Sciences.
• Knowledge of IT Software Delivery
• Practical experience in business analysis and software analysis
• Practical experience in software design and delivery (both analytical and technical)
• Strong communication skill — The position involves a large amount of influencing and communication to individual contributors, lower/mid-management and external partners across the Organisation to apply product analysis and design in a business context with deep analytical and meaningful insights.
• Experience in Agile ways of working
• Proficiency in Microsoft Office Suite (Power Point, Excel, OneNote, etc)
• Willingness to work flexible hours including evenings as needed, to accommodate global time zones.

Claude’s response:

Based on the responsibilities and qualifications listed, I would recommend staffing this with the following roles:

1. Product Manager (1 person). This person would own the overall product strategy, roadmap, and business metrics. They need 5+ years experience and expertise in product management.
2. Business Analyst (1–2 people). The business analyst(s) would focus on process optimization, requirements gathering, user research, and analysis. They need 5+ years BA experience. With the scope here, you may need 2.
3. UX Designer (1–2 people). The UX designer(s) would handle user-centered design, prototyping, usability testing and improvement of the user experience. With the breadth, you may need 2.
4. Software Engineers (2+ people). You’ll need a team of developers to build and iterate on the actual product based on the requirements and UX design. I’d recommend starting with 2–3.
5. Marketing Specialist (1 person)
   This person would handle product marketing like releases, videos, newsletters to promote new features.

So in total, I would recommend a team of 6–9 people minimum, with potentially expanding development later. The key roles are product manager, business analyst(s), UX designer(s), developers, and a marketing specialist. Let me know if you need any clarification or have additional questions!

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• Articles on Medium or LinkedIn
• cxcc.to/ckys — “Customers Know You Suck,” my recent book on improving customer adoption, satisfaction, and retention