Career Ideation Workshops

Most professionals treat their career strategy like a lottery ticket. They “put themselves out there.” They apply to 50 roles. They hope something sticks. That isn't a strategy. That’s just anxiety masquerading as action. If you are trying to pivot or accelerate but feel paralyzed by "where do I start?", try this: Start thinking like a Product Manager. Your career is the product. The hiring manager is your customer. Your skills are the feature set. When you view it through this lens, the fog lifts. You stop winging it and start engineering the outcome. In my workshop yesterday, I broke down exactly how to do this using three powerful levers: Product Thinking, Mental Models and AI. Here are the 6 mental models that move you from "stuck" to "strategic": 1. Fog → Frame You can’t solve a problem you haven’t defined. Stop spiraling and write down the actual problem statement. 2. Constraints-Based Thinking What are your non-negotiables? Salary? Location? Culture? Define the walls so you can build the room. 3. Triangulation Don’t trust one data point. Validate your assumptions about a role by checking three distinct sources. 4. One-way vs. Two-way Door (+ Kill it Quickly) Is this decision reversible? If yes, walk through. If it doesn’t work, turn back. Speed matters more than perfection here. 5. Ruthless Prioritization You cannot have it all at once. Pick what matters right now and ignore the rest. 6. Bias Check We are all unreliable narrators of our own lives. Use AI to challenge your assumptions and spot the blind spots you’re ignoring. This isn’t about starting over from zero. It’s about leveraging what you’ve already built but pointing it in a direction that actually fits. I went deep into this in that workshop. Check the slides below. 👇 I’ve mapped out how to use these models (with AI) to build a career roadmap that survives contact with reality. Stop guessing. Start applying.

Most professionals can't access quality career coaching. At $350-600 per session, traditional executive coaching remains out of reach for many who could benefit from personalized guidance. So one of our Supra members, Kavita Anand, taught 25 women at her company to build their own AI career coaches in a 90-minute workshop. In our recent Supra Insider episode, she walked us through the exact playbook she used: 1/ Craft Your System Prompt Start with this prompt to Claude: "Write a system prompt for an LLM-based co-pilot that specializes in career coaching. I want you to focus on scenarios that women in tech and product face. The coach should be inquisitive, use evidence-based research, and be supportive throughout sessions." Then customize based on your needs: ↳ Personality: Direct advice or Socratic questioning? ↳ Expertise areas: Technical leadership? People management? ↳ Communication preferences: One question at a time? ↳ Boundaries: When to use context vs. general advice 2/ Run Your "Kickoff Call" Share your situation: "I'd like you to have an initial coaching call with me. Ask me questions to understand my current situation, challenges, and goals. Here's my context: [Role], [Company type], [Years in role], [One current challenge]." Let it ask follow-up questions naturally. End with: "Summarize everything we discussed into a profile document." Copy that summary into your project knowledge - this becomes your coach's baseline understanding of you. 3/ Test Real Scenarios Pick actual challenges you're facing. Workshop participants used examples like: ↳ "I kept getting interrupted by an exec in my product review" ↳ "My manager asked me to prioritize three urgent projects" ↳ "I'm struggling to influence a stakeholder who outranks me" 4/ Refine Through Iteration Improve your system prompt based on responses: ↳ Add: "Ask follow-up questions about root causes" ↳ Add: "Challenge my assumptions when appropriate" ↳ Add: "Reference my past patterns when giving advice" Then use Claude's "retry" button to regenerate responses with your updated instructions. For advanced users: You can layer in company career documentation, past performance feedback, or notes from 1:1s. One workshop attendee said her AI coach started referencing her work patterns: "I notice you haven't looped in Design yet - that's been a blocker in your past projects." That's not generic AI advice. That's coaching based on your actual history. 🔗 Link to full episode: https://lnkd.in/dv7q5t4z --- Our full episode with Kavita covers: ↳ Why treating AI like a new team member beats quick prompts ↳ The psychology behind why 90-minute workshops drive adoption ↳ Claude vs ChatGPT: when to use each for different tasks ↳ How to avoid AI giving you confirmation bias instead of real coaching ↳ Why "tinkering" might be the most important skill in the AI era

When senior leaders plan their next act, 90% start with a "big idea.” And that's often the problem. Here's why: ㅤ↳ They can tempt you to bet too much, too soon ㅤ↳ They're usually wrong in their first form ㅤ↳ Most leaders aren’t skilled at ideation ㅤ↳ So they’ll go with what they know The cool part? Our favorite innovation frameworks can work for us as individuals too. Instead of betting the farm, try this: 1. Start with your ‘hunches’ ㅤ↳ Capture ALL your ideas about what's next ㅤ↳ Yes, even the “big” and "crazy" ones ㅤ↳ Don't judge too much, just do it 2. Turn those hunches into high-potential bets ㅤ↳ Which versions of which ideas light you up? ㅤ↳ Which are impactful + feasible + viable? ㅤ↳ Which solve real problems? 3. Test by firing ‘bullets’ (small experiments) ㅤ↳ Talk to 15 potential clients ㅤ↳ Run a pilot workshop ㅤ↳ Build a simple version of your offering 4. Scale the winners into ‘cannonballs’ ㅤ↳ Double down on what works ㅤ↳ Cut what doesn't ㅤ↳ Invest your time with greater confidence 5. Productize the true ‘moonshots’ ㅤ↳ Now you can aim bigger ㅤ↳ You have evidence ㅤ↳ You know what works Example: A Fortune 500 CFO in transition might think she should build a full consulting practice out of the gate. Instead, she might: ㅤ↳ Take a step back and evaluate possibilities (hunches) ㅤ↳ Place some bets - e.g. even by testing on LinkedIn! ㅤ↳ Build an offer portfolio ㅤ↳ Start with advisory calls (firing bullets) ㅤ↳ Land some retainer clients (cannonballs) ㅤ↳ Scale to a boutique firm (moonshot) The path will be different for everyone but you get the idea. Zero remortgaging required. Zero reputation risk. Zero regrets. Point is that your corporate innovation skills aren't just for your day job. They can be a secret weapon for what's next. PS. This strategic ideation framework originated in my own corporate innovation practice. It extends Jim Collins’s famous bullets and cannonballs thinking. What innovation frameworks have helped you most? — ♻ Repost so other leaders can use proven innovation frameworks to de-risk their next moves! ➕ Follow Alex Bruton, PhD for more like this

"You’re a generalist who's great at a lot of things. So why does that make career decisions harder?" If you’ve ever struggled to answer “So… what do you do?”—you’re not alone. Some careers have a clear path. You go to law school, become a lawyer, and climb the ranks. But for generalists—people who are great at adapting, problem-solving, and wearing multiple hats—there’s no obvious next step. You can do a lot of things. The hard part is choosing where to use your skills, how you want to keep growing - and of course, how to explain it to everyone else! 😂 Here's a few of my favourite exercises to use when working with generalists on their career strategy: ✅ Diagnostics around what gives you energy (and drains you) ✅ A 'Fit Me, FulFil Me, Fund Me' exercise to get clear on what you're solving for ✅ Entering all of your skills, values, passions, likes and dislikes into ChatGPT to generate over 100 jobs you can do with your skills within 0-3 years ✅ Sketching few different versions of your career vision - continuing on your current path, an ambitious departure, and a dream future ✅ Mapping backwards from a dream future role to the shape of your current skill set (breadth-focussed, T-Shaped, PI-shaped or something else) and identifying the steps between here and there ✅ Identifying whether you want to combine generalism with other career strategies, like skill-stacking, platform-building, wave-surfing and experiments ✅ Creating a specific plan for a manageable period - the next 6 months ✅ Doing a pre-mortem to ask 'if this fails, why will it have failed?' and building corrective mechanisms into your plan to stop it happening Would love to hear from other generalists—how have you navigated career decisions? What have you found helpful? Feel free to share if the comments! ⬇️ And if those exercises sound helpful, you're welcome to check out the new Career Course we are piloting in Fuzzy, which includes them & a lot more!

🎓 Two days into my Stanford MBA, and this has already been my favorite session. It was a career workshop called the “100 Jobs Exercise.” We were each handed a sheet with 100 jobs — everything from surgeon, city planner, psychotherapist, VC, music composer, to vacation resort manager. 👉 Step 1: Circle 12 jobs that excite you in 5 minutes. No overthinking — not about skills, money, or feasibility. Just intuition. 👉 Step 2: Rank those 12 from most to least exciting in 3 minutes. 👉 Step 3: Hand your sheet to two strangers. For 9 minutes, they make observations while you silently take notes in 3 columns: Themes: e.g., “You love working with large groups.” Conflicts: e.g., “Some jobs are highly creative, others very analytical.” Images: (the fun part) — “I see you in a café with your dog… I see you in a blazer on the 50th floor… I see you directing a team with a headset…” The surprising part? With just 12 job titles, complete strangers could spot deep patterns. I thought my choices were random, confused, “all over the place.” But hearing others tie them into themes that were so me was energizing, validating, and eye-opening. Sometimes, others can mirror back our strengths more clearly than we see them ourselves. I’m attaching the 100 jobs sheet — highly recommend trying it if you’re exploring clarity in your career.