WishkeyAI prompts for Mac

Thinking

Help me decide between options

Weighted criteria, a side-by-side comparison and a clear recommendation you can push back on.

Works with ChatGPT · Claude · Gemini  ·  Last verified October 2, 2026 with Claude

Same AI. Better ask.

Asked plainly

“Which one should I choose?”

I'd lean toward B, with a couple of conditions.

Why B fits your goal

  • Becoming a PM mostly comes down to making real product decisions: talking to users, prioritizing, shipping, and seeing what happens. On a small startup team you'll get that exposure much sooner. At a large company the scope is usually narrower and the route to PM more gated.
  • The downside is smaller than it looks. You're 29 with no dependents. If the company runs out of money, you'll be job hunting with a year or more of broad ownership on your resume, which is a strong story in PM interviews. The real cost is a stressful search, not a derailed career.
  • The lifestyle gap is big. Five office days plus about 100 minutes of commuting a day is roughly 400 hours a year, compared with mostly working from home. That likely outweighs a 15% raise in practice.

What would change my answer

  • The role itself. B only wins if the job has real product exposure or a clear path to PM. If it's a role with no contact with product decisions, the advantage shrinks. And if A is a PM role, or has a well-worn internal route into PM, A becomes much more competitive.
  • Your savings. If you don't have around six months of expenses set aside, the startup risk is more real.
  • The runway. Eighteen months is workable but not comfortable, since fundraising usually has to start 6 to 9 months before the money runs out. Ask about revenue and growth, burn rate, when they last raised, and what the plan is for the next round. How openly they answer tells you a lot.

Questions worth asking before you decide

  • At B: Is there someone senior in product who would mentor you? Would you work directly with customers and the founders?
  • At A: How many people moved into PM in the last two years, and how did they do it?

If B's answers hold up, I'd take it. The single thing most likely to flip me is a real, proven PM pathway at A.

If you tell me what the actual roles are and roughly how much runway you have personally, I can give you a sharper take.

With the Wishkey prompt

Assumptions: The commute is 50 minutes each way, neither job is a PM role today, you have no major debt or dependents, and both offers are for roles adjacent to product.

Criteria and weights

These are the five things that matter most for someone who is 29, has no kids, and wants to become a PM.

  • Path to PM (30%): This is your stated goal, so it gets the most weight.
  • Job security (20%): The startup's 18-month runway is its biggest risk.
  • Daily life (20%): Commute and flexibility affect your time and energy every week.
  • Salary (15%): The 15% gap matters, but less than the other factors.
  • Team and learning (15%): Mentorship and the people you work with shape how fast you grow.

Comparison

Scores are 1-5, where 5 is best.

Criterion (weight) A: Large company B: Startup
Path to PM (30%) 3 - Has structure and mentors, but internal moves into PM are competitive and slow 4 - Loose role boundaries let you touch product work early, if someone there actually does PM
Job security (20%) 5 - Stable employer, low risk of sudden loss 2 - With 18 months of runway, it must raise money or cut costs within about a year
Daily life (20%) 1 - Five office days plus about 100 minutes of commuting a day is roughly 380 hours a year 5 - Four remote days, so only one commute a week
Salary (15%) 5 - 15% higher and reliable 3 - Lower pay, and equity is a long shot at this runway
Team and learning (15%) 3 - Resources and a brand name, but you don't know the team yet 4 - You liked the team, though that impression comes from a small sample
Weighted total (out of 5) 3.30 3.65

B leads, but not by much. The result depends mostly on two things: how real A's PM path is, and how much a job loss would hurt you.

Deal-breakers and unknowns to check

Deal-breakers

  • Savings: If you have less than about 6 months of expenses saved, B is too risky. Stop here and take A.
  • No product exposure at B: If the role is narrow, with no customer contact, roadmap input, or PM or founder mentoring, B loses its main advantage.

Unknowns worth checking

  • B's runway: Ask the founders directly about burn, revenue, when they plan to raise, and how investors have responded so far. A good startup answers this openly, and evasiveness is a warning sign. Startups usually begin raising with 6-9 months left, so your real stability window is closer to 9-12 months.
  • B's PM path: Ask whether they would scope you toward product work in 6-12 months, and who would mentor you.
  • A's PM path: Ask how many people have moved into PM internally in the last couple of years. Check whether there is a rotation or associate PM program.
  • Remote terms at B: Check whether the 4 remote days are in writing or could change.
  • Office policy at A: Ask whether 5 office days is fixed or likely to loosen.
  • B's equity and pay: Get the actual equity terms, but value the equity at roughly zero when you compare offers.
  • Remote learning: Early-career people often learn faster in person. Think about whether remote work would slow you down.

Recommendation

Choose B, provided you have at least 6 months of savings and the founders' answers on runway and your PM path hold up.

  • Limited downside: At 29 with no dependents, the worst case is a job search in 12-18 months. By then you would have a startup story and product-adjacent experience, which PM hiring managers value.
  • A's advantages: They are mainly money and safety, and you can afford to trade some of both. Getting back about 8 hours a week is worth a lot, and you could spend some of that on PM learning like side projects, courses, or customer interviews.
  • Risk reduction: Ask B for a modest salary bump or a clear role scope, and keep your résumé and network warm.

What would make A win

  • A's PM path is real: If A has a rotation, associate PM program, or a manager who has sponsored transfers, and B's role has little product exposure, A wins 3.60 to 3.35.
  • You need stability: If you have under 6 months of savings, debt, family obligations, or plans where steady income matters (such as a mortgage application), A wins.
  • B's runway answers are shaky: This could mean no clear plan for the next raise, rising burn, or vague answers from the founders.
  • You work better in person: If remote work would leave you isolated or slow your learning, B loses much of its advantage.

Sample text · Answers by Claude Sonnet 5.5 on 2026-10-02 · Results vary by AI and model.

Sample text used
I have two job offers. A: a large company, 15% higher salary, office 5 days a week, 50-minute commute. B: a startup, remote 4 days a week, the team seemed great, but the company has about 18 months of funding left. I'm 29, no kids, and I want to grow into a product manager role.

ふつうに頼むと

“どっちを選ぶべき?”

結論から言うと、29歳・子どもなし・PM志望という条件なら、B社に傾くのが自然だと思います。ただし、決める前に確認してほしいことがいくつかあります。

B社を推す理由

  • PMに近づきやすい:スタートアップは人が少ない分、ユーザーの声を聞く、優先順位を決める、リリースまで見届けるといったPMの仕事に早く触れられます。大企業は分業が進んでいて、PM職に就くまで数年かかったり、そもそも枠が少なかったりします。
  • 年収15%の差は、時間で埋まる部分がある:通勤が片道50分なら、往復で週8時間以上です。B社は週4日リモートなので、その時間を学習や休息に使えます。
  • 失敗しても立て直しやすい時期:扶養家族がいない29歳なら、B社が厳しくなっても転職は十分できます。事業に深く関わった経験は、PM志望ならむしろ強みになります。
  • チームの雰囲気は大事な要素:成長スピードや仕事の続けやすさに直結しますし、入社後に自分で変えにくい部分でもあります。

資金18か月について

リスクではありますが、「18か月で潰れる」というより「12か月前後で次の資金調達が必要になる」と捉えるのが正確です。内定後なら、次のことを聞いても失礼になりません。

  • 現在の月次バーンと売上の伸び方
  • 次の調達の見込み(既存投資家が追加で出資する意向があるか)
  • 黒字化までの道筋
  • 数字を隠さず話してくれるか(ここで言葉を濁されるなら、かなり注意が必要です)

A社を選ぶべきなのは、こんな場合

  • A社の職種がプロダクト寄りで、社内でPMに異動するルートが具体的にある
  • 奨学金の返済や家族への仕送りなどで、収入の安定を最優先したい
  • 貯金が生活費の6か月分に届いていない
  • B社での職種がPMから遠く(営業やCSなど)、PMの経験につながりにくい

追加で教えてほしいこと

  1. 両社で任される職種は何ですか? 特にB社で、プロダクトの意思決定にどこまで関われそうですか?
  2. 貯金は生活費の何か月分ありますか?

この2点で結論が変わる可能性があります。B社の職種がPMに近く、貯金が半年分以上あるなら、B社でいいと思います。逆に、どちらかが怪しいならA社でも十分に合理的な選択です。

Wishkeyのプロンプトだと

前提: 貯金は生活費の半年分以上あり、B社の職種はPMまたはPMに近い仕事で、年収は両社とも生活に十分な水準だと仮定しています。

判断基準と比較表

基準(重み) A社(大企業) B社(スタートアップ)
PMへの近さ(30%) 3:ブランドと研修はあるが、職種が固定されやすく、PMになれるかは配属と異動次第 4:プロダクトに近く裁量も大きい。ただし、教えてくれる人がいるかは未確認
雇用・財務の安定(20%) 5:倒産や人員整理のリスクがほぼない 2:残り約18か月分の資金。実質の山場はもっと早く来る
チーム・職場環境(20%) 3:配属先が決まっておらず、良し悪しが読めない 4:雰囲気がとても良かった。ただし面接時の印象と、資金が厳しくなった後の姿は別物
年収(15%) 4:+15%。積み上がると効くが、生活が一変する差ではない 3:相対的に低い。ストックオプションの価値はほぼ期待できない
働き方・通勤(15%) 2:週5出社で往復約100分。週8時間強、年400時間超が通勤に消える 5:週4リモート。時間と体力を学習や副業に回せる
重み付き合計(5点満点) 3.40 3.60

差は小さく、重みの置き方で逆転します。たとえば「安定」を30%、「PMへの近さ」を20%にすると、A社3.60、B社3.40になります。そのため、下の「確かめること」が実質的な決め手です。

決定的な問題点

  • B社:「18か月」は18か月の安定ではありません。 多くの会社は資金が残り6〜9か月になる前に調達を始めます。つまり山場は入社後9〜12か月ごろで、調達できなければ給与の遅れ、減給、人員整理が現実的に起こり得ます。
  • A社:PMになる道筋が約束されていません。 大企業では職種が固定されることが多く、PMへの異動は競争が激しい社内公募になりがちです。「安定しているが、目標から遠回りになる」可能性があります。
  • A社:通勤と出社の負担は毎日続きます。 年収15%増の価値が、この時間の損失に見合うかは冷静に見るべきです。

内定を承諾する前に確かめること

B社

  • 直近の調達額と時期、月間の支出、売上の伸び、次の調達の見通し(CEOやCFOに直接聞けるとよい)
  • 自分の役職は何か。PM業務に触れられるか。PMの先輩や上司はいるか
  • 給与の絶対額、遅配の有無、解雇時の条件、ストックオプションの内容

A社

  • 配属先と職種は決まっているか。プロダクト部門か
  • 社内でPMに異動した実績が、直近数年で何人いるか
  • 年収15%増に残業代が含まれていないか。リモート勤務が可能になる条件はあるか

自分自身

  • 貯金は生活費の何か月分か。奨学金や家賃などの固定費はどれくらいか
  • B社が潰れた場合、次の仕事を3〜6か月で見つけられる見込みはあるか

おすすめ:B社

理由は、あなたの目標(PM)と状況に合っているからです。29歳で扶養家族がいなければ、失敗したときの損失は回復できる範囲です。一方、スタートアップで幅広い業務に関わった経験は、PMの転職で評価されやすい資産になります。年収15%の差は、1〜2年で取り返せる程度の差です。リスクを取る余裕が最も大きい時期でもあります。

ただし、条件付きです。調達の見通しの説明に納得でき、貯金が半年分以上あり、役割がPMに近いことを確認してから承諾してください。入社後は、約9か月の時点で資金状況を確認し、悪化していれば転職活動を始められるようにしておくと、リスクを抑えられます。

A社のほうが良くなる条件

  • 貯金が半年分未満、または奨学金・仕送りなど、収入が途切れると困る事情がある
  • B社が次の調達の見通しを具体的に説明できない、または売上が伸びていないのに支出が大きい
  • B社の職種がPMから遠い(営業サポートや運用が中心など)
  • A社の配属がプロダクト部門に確定している、またはPMへの異動実績が明確にある
  • 近いうちに結婚、住宅購入、扶養などの予定があり、安定を最優先したい
  • 「大企業での経験」を経歴に加えて、将来、大手のPMを狙いたい

貯金額とB社の資金計画の2点が分かれば、判断はほぼ固まります。

サンプル文で比較 · 回答:Claude Sonnet 5.5(2026-10-02)· 結果はAIやモデルによって変わります。

使ったサンプル文
2社から内定をもらった。A社:大企業、年収が15%高い、週5日出社、通勤50分。B社:スタートアップ、週4日リモート、チームの雰囲気がとても良かったが、資金はあと18か月分ほど。私は29歳、子どもなし、将来はプロダクトマネージャーになりたい。

The prompt

Help me decide between the options below.

Choose 4–6 criteria that matter for my situation and weight them. Compare the options in a table with a 1–5 score and a one-line reason per criterion, plus a weighted total. Then point out deal-breakers and unknowns worth checking, give a clear recommendation, and say what would have to be true for another option to win. State your assumptions in one line at the top; ask questions only if you truly can't compare the options without them.

## Options and situation
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