CAREER DECISION FRAMEWORK WHY — start with honest self-assessment: is the current role broken, or is the meaning-making missing? Answer truthfully before you move. START WITH WHY honest self-assessment WHAT — evaluate the organization on three dimensions: personal stake (skin in the game), a solid product (no smoke and mirrors), and a great tribe (true culture). EVALUATE WHAT stake · product · tribe HOW — interview the future employer across three lenses to test fit: Vision/Mission/Purpose, Culture/Team/Leadership, and Challenges/Opportunities/Strength. ASK THE RIGHT QUESTIONS HOW · the fit Vision · Mission · Purpose Culture · Team · Leadership Challenges · Opportunity The decision — is this role the meaning-maker and a true value exchange? Personalize your CV, prove your worth, and decide: dream job, or not? Next job = your dream job? Start with WHY — then ask the right questions.
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The Dream Job - This Way Please....

· 6 min read · Originally on LinkedIn
The gist

Picking the next job starts with the WHY — honest self-questioning about whether the current role's problems are the environment or your own ego — before moving to WHAT the company is and HOW it really runs. Part framework, part candid self-reflection, it argues the right move is grounded in meaning and fit, not a stress-driven reaction.

In this article we will attempt to deconstruct how to pick the next ‘dream’ job by building an assessment framework and asking the ‘right’ questions to self and future employer. It is easier said than done, thus sharing some personal and poignant self-reflection on the process more than just a complete guide. Hope you will find it useful, let’s go…!

Always start with the WHY. Asking tough self-questions is hard, answering them candidly even harder, as there is no external impartial validity accept your conscience and morality.

Exercise: Try for your own benefit to sit down and honestly and truthfully answer those questions to find unbiased meaning and genuine motivation behind the change.

This will form a foundation for a potential move, a container which will create meaning, value significance and longevity of your next chapter.

  1. Why the current job is it not working? Write down the checklist, sleep and/or mediate on it for at least a week (two is always better!). Review it in a third person abstracting of self. (Byproduct: based on the findings build a guide on how to get better and areas of concern and improvement i.e., read more diverse literature (sharing my top 100 list), pick up unfamiliar subject of the interest on Coursera.org etc.)
  2. Are you exploiting Great Resignation for self-gain or sincerely looking for something different?
  3. Is your environment toxic or your work ethics, principles and self-awareness needs work? If yes, which ones? Write them down, we all can work on our ego (very safe bet!)
  4. Escapism with an easy way out, or true meaning making is missing in your life? If latter, is it really job related or there is a bigger issue at stake?
  5. Why now and how you got here in a first place? After-all you are the one who accepted an offer in the first place, what would you do differently next time? Less ambiguity on R&R perhaps, anything else?

Once you have a personal self-assessment and solid backing on the reason rather than emotional reaction to stress, burnout, and myriad of other causes for being irrationally impulsive (rightly so!), let’s move to WHAT.

Depending on the organization type (start-up vs corporation), I like to evaluate the former against these three dimensions:

DimensionWhat it really means
Skin in a GamePersonal Gain
Smoke and MirrorsSolid Product
True Meaning of CultureGreat Tribe

Being in Advertising for too long it is imperative that you join team of fantastic humans with solid product offerings and have some stake in the business to make it personal rather than 9-5 job. Some leading questions to measure these constituents:

  1. Please describe the health of the {insert company}. Growth and financial indicators (if private LLC no numbers just trajectory and grown % YoY measurement) and 3–5-year revenue projections. What is Churn, LTV metrics (if available)?
  2. What constitutes success for the potential role and {insert company} overall?
  3. How agile {insert company} really is, in terms of product diversification and adoption to remain competitive? Please outline what major pivots the {insert company} took to stay on top of the game?
  4. What is the {insert company} attrition rate? Any recent senior departures and reasons behind it? Any recent senior hires? Why?
  5. What does a 90-day plan look like? What are immediate pain points which need to be addressed? (Outside of growth, revenue)

Mantra: Stop selling fairy dust, ad/mar-tech have had enough! Find the right Tribe which is aligned with your personal virtues. Ask for meaningful stock / options to be truly involved and responsible for growth and success of the business (Exit - IPO, M&A)

Finally, it’s the HOW part. By asking the right questions to your future employer you can evaluate the “fit” for the role, your future boss character and leadership style and equally importantly an environment you will be part of.

So, what are the main questions to Ask while being interviewed? There are three main categories:

i. Vision, Mission, and Purpose

ii. Culture, Team, and Leadership

iii. Challenges, Opportunities and Strength

Every situation and job requirements are personal, and subjective. Sharing my individual favourites for each category, feel free to cherry pick some to personalize for your own interview format:

Vision - Mission - Purpose

  1. In your own words please define an evolution of the {insert company} vision and mission.
  2. Did it change in the past two years? and why? What was your influence for the change?
  3. What is the vision for driving innovation and creativity in the organization?
  4. How are new initiatives and vision communicated to the teams?
  5. How does the leadership engage the employees to be accountable to the values and mission of the organization?

Culture - Team - Leadership

  1. What does Culture mean to you? (Hopefully not one slide on PPTX; go deep till get your answer, and don’t settle for marketing/sales BS)
  2. What leadership changes are needed at {insert company}?
  3. What do you feel this leadership or otherwise role needs to be successful at to contribute to the holistic vision?
  4. How does the leadership engage the employees to be accountable to the values and mission of the {insert company}?
  5. What are your Virtues?
  6. What is your personality type?
  7. How do you like to be managed?
  8. How are business Values being different from your personal ones (if any disparity)?
  9. Do you hire against aforementioned Values? If, No – why?
  10. How is accountability propagated across the {insert company}?
  11. What personality types are the most effective under your leadership?

Challenges - Opportunities - Strength

  1. What are the top strategic initiatives at {insert company}?
  2. What are the roadblocks you are currently facing?
  3. What are the key business objectives of this role outside of profitability, growth, and new business?
  4. Based on the current {insert product, service, technology}, what are the most challenging use cases require the most help with?
  5. What is the proposed capital spending and funding to make the role effective?
  6. What are the current weaknesses of {insert product, service, technology}?
  7. Peer set analysis (SWOT, USPs) and how {insert product, service, technology} stacks against competition?
  8. What is the short- and long-term business strategy around growth goals for the {insert company}?
  9. What are the biggest challenges about leading this area of the business toward its goals?
  10. Who are the main customers? Did that change based on evolution of product/vision?

Lastly, I want to leave you with an attempt to define your next job. What is important to you should be used as matrix to measure your future ‘happy’ place, some thought starters:

  1. Is your future employer the meaning maker?
  2. Define what Purpose resonates the most with you? Sustainability, Corporate Social Responsibility and perhaps DE&I?
  3. What is the True value exchange?
  4. What unique and non-ubiquitous skills, intelligence, expertise, network do you really bring to the table? And is your worth to the business truly justifiable? Use that for negotiation and differentiation.
  5. Is the {insert company} truly egalitarian? How’s authenticity and validity of DE&I are measured?

Relevance: It is paramount to update your resume, LinkedIn is great but not enough! Your Curriculum Vitae, should be no more than 1-2 pages long and more importantly, personalized for the job your are applying for. Cull-out all unrelated experiences, jobs, achievements and ONLY focus on the role at hand. Showcase WHY you should be considered and WHY you will be effective if hired against your competence (IQ) and character (EQ + CQ).

Hope you find this helpful, and Good Luck with your next career move and personal journey!

Is the next job = your Dream job?

WHY → WHAT → HOW WHY — always start with the why. Honest, candid self-assessment is the foundation: the container which creates meaning, value, and longevity for your next chapter. STAGE 1 · WHY The Foundation Honest self-reflection — the container that creates meaning WHAT — evaluate the organization across the essay's three dimensions: Skin in a Game (personal gain), Smoke and Mirrors (a solid product), and the True Meaning of Culture (a great tribe). STAGE 2 · WHAT · THE ORGANIZATION Three dimensions to weigh Skin in a Game Smoke and Mirrors Meaning of Culture HOW — interview the future employer across three question categories: Vision, Mission and Purpose; Culture, Team and Leadership; and Challenges, Opportunities and Strength. STAGE 3 · HOW · ASK THE EMPLOYER Three categories of questions to ask Vision · Mission · Purpose Culture · Team · Leadership Challenges · Opportunities Is the next job = your Dream job?