How to Evaluate an Offer Like an Adult

"You have an offer. The number looks good. But there's more to this decision than compensation—and getting it wrong is expensive."

The Real Cost of a Bad Decision

Taking the wrong job isn't just a setback—it's a compound loss. You lose time (6-18 months before you can reasonably leave), opportunity (the roles you passed up), momentum (the gap in progression), and often, confidence.

And yet most people make this decision based on a gut feeling after a few hours of interviews. They focus on the offer letter and forget to evaluate everything else.

Let's do this properly.

The Evaluation Framework

Every job offer should be evaluated across five dimensions:

1. The Role — What will you actually be doing?
2. The Manager — Who will you be working for?
3. The Compensation — What's the total package worth?
4. The Trajectory — Where does this lead?
5. The Company — Is this the right environment?

Most people over-index on #3 and under-index on everything else. Let's go through each.

1. Evaluating the Role

The title is what they put on the offer letter. The role is what you'll actually do every day.

• What does a typical week look like in this role?
• What are the key objectives for the first 6-12 months?
• What decisions will you own? What will require approval?
• Who will you work with most closely?
• What resources (budget, headcount, tools) will you have?
• Is this role set up for success, or is it a cleanup job?

• Vague descriptions that keep shifting
• The previous person left quickly or under unclear circumstances
• The scope is too broad or too narrow for one person
• The role has been open for a long time without being filled

The test: Can you describe what success looks like in 6 months? If not, the role isn't well-defined.

2. Evaluating the Manager

Your manager has more impact on your daily experience and career trajectory than almost anything else. A great role with a bad manager is miserable. A mediocre role with a great manager can be transformative.

• What's their leadership style?
• How do they give feedback?
• What happened to their previous direct reports? (Were they promoted? Did they leave?)
• How long have they been in this role?
• What do people who've worked for them say?

• Ask directly in the interview: "How would you describe your management style?"
• Ask for backchannel references: Find people who've worked for this person and ask off the record
• Look at LinkedIn: Where did their former reports go? Are they still connected?
• Watch for signals: How do they treat you during the interview process?

• High turnover on their team
• They can't articulate their management approach
• They speak poorly of their team or past employees
• The interview process feels chaotic or disorganized (they run things)

The test: Would you trust this person to have your back when things get hard?

3. Evaluating Compensation

Most people only look at base salary. That's a mistake. Total compensation includes multiple components, each with different characteristics.

Components to consider:

| Component | Considerations | |-----------|---------------| | Base salary | Stable, taxable, what you can count on | | Bonus | Variable, often tied to company and individual performance | | Equity | Illiquid, risky, potentially high upside (or worthless) | | Sign-on bonus | One-time, often has clawback provisions | | Benefits | Health, retirement matching, PTO, parental leave | | Perks | Flexibility, WFH policy, learning budgets |

• Pre-IPO equity is worth $0 until there's a liquidity event
• What's the company's realistic path to liquidity?
• What's your strike price and what's the current 409A valuation?
• How much has the company raised and at what valuation?
• What's your percentage ownership (not just share count)?

The formula: Total annual compensation = Base + (Expected bonus × probability of hitting it) + (Equity annual vesting × probability of liquidity × expected value)

Be honest about risk. If the equity is unlikely to be worth much, don't weight it heavily in your decision.

4. Evaluating Trajectory

This job isn't just about this job. It's about where it leads.

• What role does this set you up for in 2-3 years?
• Will you learn new skills or stagnate?
• Will you build valuable relationships?
• Will this company name help you? (Brand matters for some roles)
• Is there room to grow inside this company?
• Is this a stepping stone or a destination?

The trade-off: Sometimes you take a role that's lower compensation or prestige because it positions you for something bigger. That can be smart. But be clear-eyed about whether the trajectory is real or just theoretical.

• You'll be doing exactly what you're already doing
• The company has no history of promoting from within
• The skills you'll use are becoming less valuable in the market
• It's a lateral move disguised as a promotion

5. Evaluating the Company

Culture, stability, and trajectory all matter. The right role at the wrong company is still the wrong job.

• Is the company growing, stable, or declining?
• What's the financial health? (runway for startups, profitability for established)
• What's the culture like? (Ask multiple people, not just your interviewer)
• How does this company treat employees in hard times?
• What's the reputation in the industry?

• Glassdoor (filter for recent reviews)
• Blind (anonymous employee forums)
• LinkedIn (look at tenure and departures)
• Crunchbase or SEC filings (financial data)
• Back-channel references (talk to people who've worked there)

• High attrition, especially recent
• Negative press or legal issues
• Multiple rounds of layoffs
• Leadership instability

The Decision Matrix

Create a simple scoring system. Rate each dimension 1-10 and weight them by importance to you.

| Dimension | Score (1-10) | Weight | Weighted Score | |-----------|-------------|--------|----------------| | Role | 8 | 20% | 1.6 | | Manager | 9 | 25% | 2.25 | | Compensation | 7 | 20% | 1.4 | | Trajectory | 6 | 20% | 1.2 | | Company | 7 | 15% | 1.05 | | Total | | | 7.5 |

Do this for each offer you're comparing. It forces you to think systematically instead of emotionally.

Common Mistakes

Mistake 1: Focusing Only on Salary

Mistake 2: Overvaluing Equity

Mistake 3: Ignoring the Manager

Mistake 4: Rushing the Decision

Mistake 5: Not Negotiating

What You'll Walk Away With

When you evaluate an offer properly, you get:

• A clear framework for comparing your options
• Due diligence checklist for role, manager, and company
• Compensation analysis that goes beyond base salary
• Confidence in your decision—whether you take it or not
• Negotiation leverage because you know what you actually want

The goal isn't to find the perfect job. It's to make a well-informed decision that you can commit to without second-guessing.