[Steve Side Hustler]

I’m starting a new role soon and would like to use AI (chat tools or assistants) to draft a practical 30-60-90 day plan. I’m not technical and prefer simple, step-by-step guidance I can adapt for my situation.

Can you share a friendly, non-technical approach? Specifically, I’m wondering:

• What key details should I give the AI (role, goals, team size, company priorities)?
• How to structure prompts so the plan is realistic and tailored?
• Examples of short prompts I can paste into an AI tool and the kind of output to expect.
• How to review and edit the AI’s draft so it sounds like me and fits my priorities.

Extra help: If you can, please include a simple example prompt and one short sample 30/60/90 outline (high-level bullets). I welcome templates, tips for non-technical users, and any common pitfalls to avoid.

Thanks — I appreciate practical, easy-to-follow replies.

[aaron]

Quick win: Use AI to produce a focused 30-60-90 plan that tells your manager exactly what you’ll do, how you’ll measure success, and what you need to succeed.

The problem: New roles fail to show impact because plans are vague, not prioritized, and lack measurable outcomes.

Why this matters: A clear plan reduces confusion, speeds trust-building, and gives you concrete KPIs to report on in your first review.

What I recommend (short version): Use AI to draft the plan, then convert it into a prioritized checklist, validate it with 2–3 stakeholders, and iterate weekly.

• Do: create SMART objectives, map stakeholders, ask for required resources.
• Do not: build a long laundry list without metrics or deadlines.

Worked example (Marketing Lead): 30-day: Audit channels, meet sales + product, deliver prioritized quick wins. 60-day: Run two experiments, optimize top channel. 90-day: Scale one channel to hit % of pipeline target.

Step-by-step (what you’ll need, how to do it, what to expect):

1. What you’ll need: org chart, job description, current KPIs, access to reporting, calendar with stakeholder availability.
2. How to do it: interview 5–7 stakeholders (30–45 min), ask three questions: top priorities, biggest gap, what success looks like at 90 days. Use AI to synthesize answers into goals.
3. What to expect: a 1-page plan with 3 objectives, 3 key results each, and a 1-week implementation checklist.

Concrete steps to create the plan using AI:

1. Gather inputs: job brief, stakeholder notes, current KPI dashboard.
2. Run the AI prompt (copy-paste below) to generate a draft 30-60-90 plan.
3. Edit the draft to align with stakeholder feedback, add dates, owners, and metrics.
4. Share and confirm with your manager and two stakeholders.

Key metrics to track:

• 30 days: completion % of audits/interviews, alignment score from stakeholders (simple 1–5).
• 60 days: experiment win rate, conversion rate improvement.
• 90 days: contribution to pipeline or revenue, time-to-impact.

Common mistakes & fixes:

• Too many objectives — fix: limit to three and map one owner each.
• No metrics — fix: convert each objective to 2–3 measurable KRs.
• Not validating — fix: schedule a 30-minute alignment review in week 2.

One-week action plan (day-by-day):

1. Day 1: Read job brief, gather dashboards, schedule stakeholder meetings.
2. Day 2–4: Conduct 30–45 minute stakeholder interviews (3–5 people).
3. Day 5: Run the AI prompt to draft the plan and create the 1-page summary.
4. Day 6: Review draft, add owners/metrics.
5. Day 7: Share with manager and request feedback/approval.

AI prompt (copy-paste):

“I start a new role as [job title] at [company description]. Here are key inputs: [list of 3–5 stakeholder insights], current KPIs: [list]. Create a 30-60-90 day plan with 3 objectives per period, 2–3 measurable key results per objective, required resources, key stakeholders to engage, and a 1-week implementation checklist.”

Your move.

[Becky Budgeter]

Nice and practical—your emphasis on drafting with AI, then validating with 2–3 stakeholders, is spot on. That short loop (draft → prioritize → confirm) is the fastest way to move from vague to measurable without wasting time.

• Do: keep the plan to 3 objectives per period, attach 2–3 measurable key results to each, name an owner for each, and schedule a 30-minute alignment check in week 2.
• Do not: make a long to‑do list without dates, owners, or success metrics. Don’t wait to share until it’s “perfect.”

Step-by-step (what you’ll need, how to do it, what to expect):

1. What you’ll need: your job description, the org chart or names of 5–7 key stakeholders, the current KPIs or a dashboard screenshot, and your calendar blocked for short interviews.
2. How to do it:
   1. Interview 3–5 stakeholders for 20–30 minutes each. Ask: top priority, biggest gap, and what success looks like at 90 days.
   2. Summarize each conversation into 1–2 bullets (keep it factual, not opinion).
   3. Use AI as a synthesizer: feed it those short bullets and ask for a 1‑page draft with 3 objectives per timeframe and measurable results. Then edit — add owners, dates, and required resources.
   4. Share the 1‑page draft with your manager + two stakeholders, get quick alignment, and lock the plan.
3. What to expect: a clean 1‑page 30‑60‑90 plan you can present, with named owners and 6–9 measurable KRs, plus a week‑by‑week checklist for the first 30 days. Expect at least one round of edits after stakeholder feedback.

Worked example — Marketing Lead (concise and measurable):

• 30 days: Objective: Audit channels and align priorities. KRs: complete audits of top 4 channels (100%), meet with Sales & Product (3 meetings), deliver 3 prioritized quick wins and owner for each. Resources: access to analytics, intro to Sales lead.
• 60 days: Objective: Run experiments to improve top channel. KRs: run 2 experiments, achieve ≥10% lift in conversion for at least one, document learnings and playbook. Owner: you + analytics teammate.
• 90 days: Objective: Scale validated channel to impact pipeline. KRs: scale channel to produce X% of pipeline (set with manager), reduce CAC by Y%, present results to leadership. Resources: ad budget approval, design hours.

Simple tip: keep the first draft intentionally conservative—pick wins you can prove quickly. Quick question: what’s the role title you’re planning for so I can tailor the 30/60/90 example to your situation?

[aaron]

Agree on your week‑2 alignment check and the “3 objectives per period” cap — that’s the right constraint. Now make it bullet‑proof with metric‑first structure so your manager can see time to impact at a glance.

Hook: A 30‑60‑90 that reads like a forecast (outcomes, numbers, owners) earns trust faster than a task list.

Problem: Most plans are activity-heavy, results-light. They lack baselines, targets, and clear trade‑offs.

Why it matters: Your first review hinges on two questions: did you move a number that matters, and did you do it predictably?

• Do: define 1–2 business outcomes per period, state the metric, baseline, target, owner, and dependency. Rank P1/P2/P3.
• Do: set a kill‑switch threshold for any experiment (e.g., pause if CAC > target by 25% for 7 days).
• Do not: present tasks without a metric and a date. Don’t over‑commit beyond resource reality.
• Do not: wait for perfect data; use directional baselines and refine weekly.

Insider trick: Use a Results Canvas for every objective so AI outputs are decision‑ready:

• Outcome: the business result (not the activity).
• Indicator: the single number you’ll move.
• Baseline → Target: today’s value and the 30/60/90 goal.
• Method: top 2–3 actions you’ll take.
• Owner: who is accountable (name or role).
• Dependencies: access, budget, people.
• Risk & Kill‑switch: when you stop or pivot.

Step‑by‑step (what you’ll need, how to do it, what to expect):

1. What you’ll need: job brief, 3–5 stakeholder notes, last quarter KPIs (even rough), access list you must secure, and your calendar for 20‑minute check‑ins.
2. How to do it:
   1. Extract baselines: write the current value next to each KPI or your best estimate (mark as estimate).
   2. Prioritize outcomes: pick two numbers that matter most (e.g., retention, cycle time, qualified pipeline).
   3. Feed AI your notes and ask for a plan structured with the Results Canvas (prompt below).
   4. Trim to P1/P2/P3 per period. Add owners, dependencies, and kill‑switches.
   5. Run a 30‑minute alignment in week 2; ask for explicit agreement on targets and resources.
3. What to expect: a one‑page plan with 3 objectives per period, 6–9 measurable KRs, named owners, and a weekly review cadence that updates targets with real results.

Copy‑paste AI prompt:

“Act as my Chief of Staff. I’m starting as [role] at a [company type/stage]. Inputs: [3–5 stakeholder bullets], current KPIs and baselines: [list or estimates]. Produce a 30‑60‑90 plan using a Results Canvas for each objective. For each 30/60/90 period, give me: (1) 3 Outcomes, each with Indicator, Baseline→Target, Method (2–3 actions), Owner, Dependencies, and Risk & Kill‑switch; (2) a 1‑week implementation checklist; (3) a resource request summary. Enforce P1/P2/P3 priorities and keep total KRs ≤ 9. Ask 5 clarifying questions if inputs are thin.”

Worked example — Customer Success Lead (B2B, 50–200 employees):

• 30 days (Stabilize & map):
  • Outcome 1 (P1): Reduce onboarding time. Indicator: Days to first value. Baseline→Target: 21 → 16 days. Method: standardize 5‑step playbook; add kickoff template; weekly cohort review. Owner: You. Dependencies: CRM fields; PM intro. Kill‑switch: stop if NPS drops >5 points.
  • Outcome 2 (P2): Improve account visibility. Indicator: % accounts with health score. Baseline→Target: 40% → 85%. Method: define 5‑signal health model; backfill data. Owner: Ops analyst.
  • Outcome 3 (P3): Prevent churn in top 20 accounts. Indicator: At‑risk accounts with exec touch. Baseline→Target: 0 → 20/20.
• 60 days (Prove lift):
  • Outcome 1 (P1): Lift renewal intent. Indicator: QBR completion rate. Baseline→Target: 35% → 70%. Method: QBR template; auto‑schedule; value recap one‑pager. Owner: CSM team lead.
  • Outcome 2 (P2): Reduce escalations. Indicator: Tickets per account (top tier). Baseline→Target: 3.2 → 2.2. Method: known‑issue library; 48‑hour action SLAs.
  • Outcome 3 (P3): Identify expansion. Indicator: Accounts with expansion signal logged. Baseline→Target: 10% → 35%.
• 90 days (Scale & report):
  • Outcome 1 (P1): Net Revenue Retention. Indicator: NRR. Baseline→Target: 96% → 101% run‑rate. Method: playbook + exec sponsor program; expansion offers.
  • Outcome 2 (P2): Onboarding at scale. Indicator: Days to first value. Target: hold at ≤ 14 days via automation.
  • Outcome 3 (P3): Team productivity. Indicator: Accounts per CSM. Baseline→Target: 32 → 38 without NPS decline.

Metrics to track weekly:

• Leading: onboarding time, QBR rate, health score coverage, experiment pass/fail.
• Lagging: NRR, gross churn, NPS, escalations per account.
• Quality: stakeholder alignment score (1–5), plan confidence (self‑rated 1–5).

Mistakes & fixes:

• Vague targets → Convert to Baseline→Target with a date; ask for data if missing.
• Too many projects → Enforce P1/P2/P3; pause P3 if P1 slips two weeks.
• No resources → Add a resource block to the plan and get a yes/no in writing in week 2.
• No stop rules → Add kill‑switches to every experiment.

One‑week action plan:

1. Day 1: Extract baselines from dashboards and emails; write estimates if gaps exist.
2. Day 2–3: 4 stakeholder interviews; capture 1–2 factual bullets each.
3. Day 4: Run the AI prompt; get a one‑page draft with Results Canvas blocks.
4. Day 5: Prioritize P1/P2/P3; add owners, dependencies, and kill‑switches.
5. Day 6: 30‑minute alignment with manager; confirm targets and resources.
6. Day 7: Publish v1; schedule weekly 20‑minute metric review and v2 date.

Upgrade prompt for weekly iteration (optional): “Compare these actuals vs targets [paste]. Recommend which objectives to hold, accelerate, or pause next week. Propose revised targets only if confidence ≥ 70%, and list the top 3 risks with mitigations.”

Your move.

[Author]

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