VEST Career Planning Guide for Women
Define what you need from work and pursue your next role with intention
Your next step should reflect the work you want to do and the life you need to sustain. Salary matters, but so do your benefits, schedule, influence, health, and opportunities to grow. This guide helps you turn those priorities into a practical career decision and focused search.
Use it whether you are entering the workforce, returning after a pause, changing fields, pursuing a promotion, or reconsidering a role that no longer fits. A next step can be a new employer, a different team, a redesign of your current role, or a job that provides stability while you prepare for a longer-term move.
How to use this guide
Work through one section at a time. Write and revise answers as you learn. Keep the worksheets in one place and revisit your priorities before interviews and offers. The goal is to develop enough clarity to act, without waiting for certainty about your entire career.
Start here | Leave with |
Assess your experience and needs | A clear reason for your next move |
Define and test possible roles | One or two directions worth pursuing |
Build evidence and relationships | A credible story and a focused search |
Interview and evaluate offers | Questions and criteria for a sound decision |
Protect time and review progress | A manageable 30-day action plan |
If you need income soon. Run two tracks, pursue realistic near-term income while exploring your preferred direction. Give more time to the income track until the pressure eases. You do not need to make a permanent career decision to take a useful next job. Bias, uneven access to networks, caregiving demands, and financial pressure can limit choices. These tools can improve your decisions and preparation, they do not make hiring outcomes entirely yours to control.
STEP 1
Assess what you want to change. Start with your lived experience. Separate the work itself from the conditions around it. You may enjoy your field and still need a different manager, workload, or schedule. Exhaustion alone may not tell you which career direction fits.
Review three recent experiences. Choose one experience that energized you, one that drained you, and one that made you proud. Paid work, education, caregiving, community work, and business ownership can all help you recognize patterns.
Experience | What I did well | What helped or drained me |
Energizing | ||
Draining | ||
Proud |
What do people consistently rely on me to do? Include one concrete example.
Which abilities do I enjoy using, and which am I good at but tired of using?
What would I change if I stayed in my current role?
What do I want more of in an ordinary workweek? What do I want less of?
Separate needs from assumptions. Identify what you need now, what interests you, and what you believe you are supposed to want. A title, leadership role, or entrepreneurial path may be someone else’s definition of progress. More predictable hours or a lateral move can be a deliberate choice.
A need I must address now is _____________________________________________
An expectation I am ready to question is _____________________________________
Decision: Is my next step primarily about changing the work, changing the conditions, increasing income, gaining stability, or creating room to grow? Circle one or two and use them to guide the next section.
STEP 2
Define what a good role must provide. Describe the conditions you need before choosing titles or employers. Mark each item as required, preferred, or negotiable. Be specific enough to verify it later. “Flexibility” might mean a predictable 4 p.m. finish, control over start times, or two days at home. Those are different needs.
Factor | What to define | My requirement |
Pay | Minimum base pay and desired range, reliability of variable pay | |
Benefits | Health coverage and cost, retirement, paid leave, eligibility dates | |
Schedule | Hours, predictability, evenings, travel, and on-call expectations | |
Location | Commute, remote or hybrid terms, relocation | |
Contribution | Problems I want to solve and people I want to serve | |
Authority | Decisions I can make and resources I can access | |
Management | Feedback, trust, boundaries, and conflict handling | |
Growth | Skills, sponsorship, advancement, and learning time | |
Sustainability | Workload, accessibility, caregiving compatibility, stability |
Choose your priorities
My three non-negotiables are __________________________________________
My three strongest preferences are ______________________________________
I could accept this tradeoff for a defined period _____________________________
Test the tradeoff: What would it cost me in time, money, or health? How long could I sustain it? What would make it worthwhile? A higher salary does not automatically compensate for an unworkable schedule. A meaningful mission does not remove the need for adequate pay and support.
Use concrete thresholds. For example: “At least $__ in base pay, no routine weekend work, and health coverage.” Set your own limits.
STEP 3
Choose and test possible directions. Translate your strengths and priorities into one or two role hypotheses. Titles vary between employers, so look for the work, level of responsibility, and environment behind the label.
Write your target statement
“I want to use [abilities] to help [team or organization] achieve [result], in a role with [scope], while protecting [key needs].”
Example: “I want to use project coordination and relationship management to help a healthcare organization improve program delivery, with responsibility for cross-team projects and predictable weekday hours.”
Test before committing. Read several job descriptions for each direction. Identify recurring responsibilities, required credentials, and the work you would do most often. Speak with people doing the work. Ask what fills their week, what is difficult, how success is measured, and how they entered the field.
Review a realistic case, observe a public professional session, or complete a short sample project using public information. Check whether a gap is a mandatory credential, a skill you can learn, or experience you already have under another name. Buy training only when it addresses a specific, verified need.
Consider a move within your organization. If the environment is workable, explore a different team, stretch assignment, promotion, or role redesign. Ask who can authorize the change and what would be required. Agree on responsibilities, resources, pay, and a decision date before taking on a lasting expansion of work.
STEP 4
Build evidence of your contribution. Employers need to understand what you can do in the role they are trying to fill. Create an evidence bank before rewriting your résumé. Specific examples will also help people understand where to refer you and give you material for interviews.
Start your evidence bank. For each example, record the problem, your responsibility, the action you took, and the result. Make your contribution clear when the outcome belonged to a team. Use accurate numbers when available, qualitative evidence is useful too.
Role requirement | My relevant example | Result or proof |
Example: coordinate projects | Created a shared schedule across four teams | Reduced missed handoffs, documented feedback |
Translate experience honestly. If you are changing fields or returning to work, explain how your experience maps to the new role. Community leadership can demonstrate budgeting or coordination when you actually performed those tasks. Caregiving may help you recognize abilities, but you do not need to make private experiences public or present them as paid employment.
A return-to-work explanation can be brief: “I stepped away from paid work for caregiving. I’m returning now and targeting operations roles that draw on my experience in [area].”
Make your story easy to repeat
I am pursuing these roles ________________________________________________
I can contribute these abilities, supported by these examples ______________________
One gap I need to address and the smallest useful way to address it _________________
Prepare a concise résumé, an accurate professional profile, and work samples when relevant. Remove confidential employer/client information. A useful sample shows your reasoning or execution, it does not require doing substantial unpaid work for a prospective employer.
STEP 5
Find roles through several routes. Use online applications as one part of a focused search. Combine them with employer research, professional conversations, recruiters, and internal opportunities. Relationships can provide context and introductions, follow required application procedures even when someone refers you.
Build a short employer list. Start with five to ten organizations where your target work exists. Include employers you may overlook, such as universities, hospitals, local businesses, public agencies, or associations, when they fit your direction. Research the relevant team, its work, and likely needs using public information.
Employer or team | Why it fits | Role or need | Contact/next action |
Choose the route that fits the opportunity. For an advertised role, confirm the posting on the employer’s own careers page, assess fit, apply, and seek relevant context from someone familiar with the team. For an employer without a suitable opening, learn about its priorities and stay connected. A conversation may clarify future possibilities without producing an immediate job. For a recruiter, describe your target function, level, location, and essential conditions. Ask which searches they handle. Maintain other routes, a recruiter may not have a matching assignment. For an internal move, learn how transfers or promotions work and speak with someone who can explain the process before making a proposal.
Remember to make the request specific
“I’m exploring program operations roles in healthcare and education. If you know someone managing that work, would you be comfortable introducing us for a short learning conversation?”
People can help more effectively when they know what you are looking for. Update them when your direction changes. If someone offers a referral, give them the posting and two or three truthful points about your fit, leave room for them to decline.
The two search routes I will prioritize this month are _____________________________
STEP 6
Build relationships you want to sustain. Meaningful professional relationships develop through shared interests, reliable follow-through, and repeated contact. Be honest about your career goals. You can ask for help without treating every person as a means to a job.
Start with people and communities you know. Consider former colleagues, classmates, clients, neighbors, volunteer peers, and professional communities. You do not need a powerful contact list to begin. Reconnect with people whose work interests you and look for recurring settings where you can contribute within your capacity. Learn from peers and people doing the work, as well as senior leaders. Their perspectives will differ. Seek peers for advice. Over time, someone who knows your work may also become a sponsor who advocates for you when opportunities arise. Offer something relevant when you can, a useful resource, thoughtful feedback, an introduction with both people’s permission, or recognition of their work. Keep commitments and respect a no. Avoid offering unpaid labor or emotional support you cannot sustain in order to earn access.
Prepare for a learning conversation. Read enough beforehand to ask questions beyond someone’s public biography. Request 15 to 20 minutes, explain what you hope to learn, and end on time. Ask permission before requesting another introduction. Do not disguise a request for a job as a request for advice.
Useful questions:
What work takes up most of your week?
What surprised you about this role?
What separates someone who succeeds from someone who struggles?
Which experience matters most when your team hires?
What would you investigate before entering this field?
Follow through without keeping score. Send a specific thank-you and act on useful advice. A later update can explain what you tried or learned. Stay interested in their work even when no opening exists. One unanswered message does not require repeated pursuit, send one brief follow-up if appropriate, then move on.
Three people or communities I want to reconnect with, and why _____________________
A useful contribution I can make without overextending myself ______________________
STEP 7
Use clear and respectful outreach. Adapt these messages to the relationship. Mention a real connection or a specific reason for reaching out. Keep the request small and easy to answer.
Reconnect with someone you know
“Hi [Name], I’ve been thinking about our work on [project] and would love to hear how things are going. I’m exploring a move toward [role or field], especially [specific work]. If you have time for a short catch-up in the next few weeks, I’d enjoy reconnecting.”
Request a learning conversation
“Hi [Name], I came across your work on [specific topic]. I’m exploring [direction] and trying to understand [specific question]. Would you be open to a 15-minute conversation about your experience? I’m looking to learn about the work and what it requires. No problem if your schedule doesn’t allow it.”
Ask about a posted role
“Hi [Name], I’m applying for [role] on [team]. My experience with [relevant work] seems aligned with [requirement]. If you know the team, is there anything about its priorities that would help me assess fit? I’m happy to send the posting for context.”
Ask for a referral when there is a basis for it
“Based on our work together on [project], would you feel comfortable referring me for [role]? I can send my résumé and a short summary of relevant experience. I understand if you don’t know my work well enough for this role.”
Thank someone and close the loop
“Thank you for explaining [specific insight]. It helped me reconsider [decision]. I’m going to [action]. I appreciated your time and will let you know what I learn.”
Follow up once
“Hi [Name], following up on my note about [topic]. If a conversation isn’t possible, no worries. Thank you for considering it.”
My message to one person this week _______________________________________
Before sending, think if your message is this personal, truthful, and specific. Have you made the time commitment clear? Can this person decline easily?
STEP 8
Apply with a clear case for fit. Prioritize roles that meet your essential conditions and where you can make a credible contribution. You may not match every preference in a posting. Distinguish a preferred qualification from a required credential or essential capability.
Decide whether the role deserves your time
Can I meet the core responsibilities, or show a realistic path to doing so?
Does the role meet my nonnegotiables, or is there a specific question I need answered?
Can I explain why this employer and this work interest me?
Is the application effort reasonable given fit and my available time?
Tailor the evidence. Identify the three most important requirements. Make relevant experience easy to find in your résumé. Describe what you did and what changed, using the employer’s terminology where accurate. Use a simple, readable layout and follow the requested format. Do not add skills or keywords you cannot support. Use a cover letter or introductory note when requested or when it clarifies a transition. Explain the work you want to do, why the employer interests you, and one or two examples of contribution. Avoid repeating your résumé paragraph by paragraph.
Track decisions and next actions
Role and employer | Date and stage | Next action + date | What I learned |
Verify unexpected recruiter messages through an independent employer contact or official website before providing sensitive information. Share only what the hiring stage reasonably requires.
Review patterns rather than blaming yourself. If well-matched applications rarely produce conversations, review targeting and how your evidence is presented. If interviews repeatedly stall, practice your examples and ask for feedback when available. Hiring timing, budgets, and internal decisions also affect outcomes. Change one part of your approach, then observe what happens.
STEP 9
Interview to assess mutual fit. Prepare to show your contribution and investigate whether the role supports your priorities. A pleasant conversation does not establish that the workload, manager, or flexibility will work for you.
Prepare concrete examples. Practice a short introduction and examples of solving a problem, collaborating through disagreement, making a decision, and learning from a mistake. Explain the situation briefly, what you did, the result, and what you learned. Connect each example to the role rather than memorizing a speech.
Ask for evidence behind promises
What you need to learn | A question to ask |
Real responsibilities | What would I own, and what would success look like after six months? |
Manager and support | How do you set priorities when requests exceed the team’s capacity? |
Workload | What does a typical week look like? How often did evenings or weekends come up last month? |
Flexibility in practice | Which hours require availability? Can you share a recent example of a schedule adjustment? |
Authority and resources | Which decisions can this role make, and what budget or staffing supports it? |
Growth and recognition | How are advancement decisions made? What is a recent example? |
Team stability | Why is the role open, and how has the team changed over the past year? |
Ask the hiring manager about daily expectations, peers about lived experience, and HR about formal benefits and policies. Compare the answers. Request written clarification of conditions central to your decision, especially hours, location, and reporting arrangements.
Evaluate assignments and follow up. For an interview assignment, ask about expected time, evaluation criteria, and how the work will be used. Consider whether the scope is reasonable before accepting. After the interview, send a concise note connecting one discussed need to your relevant experience.
Evidence this role fits my needs ____________________________________________
Unanswered questions or conflicting answers I must resolve _______________________
STEP 10
Compare offers and discuss terms. Return to your criteria before reacting to the title or salary. Compare the offer with your current situation and other realistic options. Treat unknown conditions as unresolved; a numerical score cannot override a nonnegotiable.
Criterion | Importance 1 to 3 | Offer A fit 1 to 5 | Offer B fit 1 to 5 |
Base pay and reliability | |||
Benefits and leave | |||
Hours and flexibility | |||
Work and contribution | |||
Manager and resources | |||
Growth and stability | |||
Location and added costs |
Give importance a 1 for useful, 2 for important, or 3 for essential. Rate fit from 1 for poor to 5 for strong, based on verified information. Multiply importance by fit and add the results for each offer. Leave unknowns blank and investigate them. Use the totals to organize your thinking, not to make the decision for you.
Check the full package. Request benefit details, including employee premiums, deductibles, coverage start dates, paid leave, retirement contributions, and eligibility rules. Estimate added commuting, childcare, or relocation costs. Separate guaranteed base pay from bonuses or equity whose value is uncertain. Confirm start date, reporting line, location, and any conditions attached to the offer.
Discuss the terms that matter most
“I’m excited about the work and the contribution I could make. Based on the responsibilities and my experience in [area], I’m seeking a base salary of [amount or range]. Is there room to adjust the offer?”
For flexibility: “To make this role sustainable, I need [specific arrangement]. Could we confirm how that would work, including required availability and how changes are handled?”
The two terms I want to discuss and my reasons _______________________________
My decision deadline and questions to resolve before accepting ____________________
Ask for agreed changes in writing. If declining: “Thank you for the offer and your time. After considering the role and my current needs, I’ve decided to decline.”
You do not owe a detailed explanation of private circumstances.
STEP 11
Protect your time and take the next step. Choose a pace your current life can sustain. A smaller, consistent search can be more useful than activity that leaves you too depleted to prepare. The schedule below is an adjustable starting point, not a quota.
A sample week with three hours available
Time | Purpose |
30 minutes | Research one employer and choose the best next action |
45 minutes | Have a learning conversation or reconnect with someone |
60 minutes | Prepare one strong application/ practice for an interview |
30 minutes | Follow up and close loops with people |
15 minutes | Review lessons and schedule next week |
Replace an application block with interview preparation when needed. If you have less time, keep one research or preparation block and one relationship action. If income is urgent, direct more time toward roles that can meet your immediate needs. Choose events for their relevance and opportunities for repeated contact; you do not need to attend everything.
Your next 30 days
Week 1: Complete your assessment and criteria. Draft one or two role hypotheses and your target statement.
Week 2: Test those directions through research and conversations. Build an employer list and begin your evidence bank.
Week 3: Revise your résumé and profile. Pursue a few well-matched opportunities and continue relevant conversations.
Week 4: Review what you learned. Practice interviews, resolve unanswered questions, and adjust your target or approach.
My next action, the date I will do it, and the time I am protecting ______________________
The person I will check in with and what I want help reviewing _______________________
At my 30-day review, I will ask what I learned, what moved forward, and what needs to change. If you’re a VEST member, turn to your peers for perspective, honest feedback, and accountability as you work through your next step. Share what you’re exploring, ask about their experiences, and look for ways to support one another along the way.
If you’re not yet a VEST member, consider joining a community of women across industries and career stages who exchange knowledge, build meaningful relationships, and support each other’s progress. You don’t need to have your next move figured out to join. Explore Membership