Expert job search advice.

How to Choose Between Job Offers

Evaluating Multiple Executive Offers

If you’re an executive in the enviable position of needing to choose between multiple job offers, you’re undoubtedly on the cusp of a significant career decision. The prospect of choosing between these offers can be both exhilarating and overwhelming. Each opportunity represents a different path, with its unique set of advantages and challenges. In this blog post, we will guide you through the art of navigating this crucial juncture in your professional journey. We’ll explore the essential factors to consider, strategic insights to leverage, and ultimately help you make an informed choice that aligns with your career goals and aspirations.

Get Your Offer In Writing Before You Choose Between Job Offers

The first crucial step when faced with multiple job offers is to secure your offer in a written format. A concrete, detailed job offer in writing eliminates any potential miscommunications and provides you with a tangible document to assess. With the offer in hand, you can carefully evaluate each aspect, identifying what elements you’re content with, where negotiation might be necessary, and which questions require answers before making your final decision. Furthermore, before accepting any offer, it’s imperative to take stock of your vested equity and benefits, including stocks, options, long-term incentives, and 401k benefits set to vest in the near future that you would forfeit by leaving your current position. Ensuring you’re compensated for what you’re leaving behind is essential. Equity, in particular, plays a pivotal role in CEO and C-suite executive compensation, offering a significant stake in the company’s success.

Evaluate Culture and People Dynamics

Evaluating multiple job offers extends beyond just the compensation and benefits packages. A crucial aspect to consider is each prospective company’s organizational culture and team dynamics. When assessing your options, consider whether you resonate with the culture and if you can envision yourself developing a trusting and collaborative relationship with the team members. Equally vital is evaluating the board to which you’ll be reporting. A harmonious rapport with board members can significantly impact your ability to lead effectively and drive the organization’s success. The organization’s dynamics and leadership play a pivotal role in determining your professional satisfaction and success.

Don’t Let Your Emotions Guide You

There is an episode of The Family Guy where the main character, Peter Griffin, gets an advertisement in the mail informing him that if he sits through a sales pitch for a timeshare, he will get a free boat.

He and the family make the trek to hear the presentation. In the end, the high-pressure salesperson lets him know that he has a choice.

He can either have the boat


He can have the mystery box

“A boats a boat. But the mystery box could be anything. It could even be a boat. You know how much we wanted one of those. We’ll take the box!”

Peter Griffin, Family Guy

“We’ll take the box (said his wife mocking him). You gave up the boat for three crappy tickets to a comedy club.”

I’ve seen job seekers “Peter Griffin” their way through job decisions.

About a year ago, I worked with a client who hired me to help him land a job at a specific CPG company. He knew the exact role that he wanted.

We crafted his resume for the “dream job”

He knew someone who worked for the company & got an opportunity to interview. His mentor went to B-school with the person who would be his potential boss & raved about what a great human he was.

He got an offer. Everything was EXACTLY what he wanted.

And then he got another call.

A start-up founder got his resume & was very interested in his background & story. The founder sold him on his vision. Told him that he had big plans for his future.

The salaries were almost the same.

The opportunities could not be more different.

He was offered everything he wanted.

Guess what he chose…. THE MYSTERY BOX.

Before he made his official decision, he wanted to run things by me. As a coach, it’s not my job to tell people WHAT to do, but I can ask questions to get to the root of a client’s why.

The client struggled to articulate what made the “mystery box” job better than the job he set out for, but my gut tells me he wanted to be WANTED. He let his emotions guide his decision-making.

Choose Between Job Offers Using a Decision Matrix

If you are prone to letting your emotions guide your decisions, consider using a decision matrix. A decision matrix, often referred to as the Pugh Method, is a powerful decision-making tool designed to help individuals navigate complex choices with clarity and precision. This method offers a structured approach to assess and compare the importance of various factors that come into play when making a decision. Whether choosing between job offers, evaluating potential business investments, or any other major life decision, a weighted decision matrix allows you to weigh each factor against one another methodically.

The ultimate goal of a Job Decision Matrix, for instance, is to unearth what genuinely matters to you in your career at a particular juncture. To streamline this process, it’s crucial to rank your objectives based on their significance to you, with the most critical ones at the top. Using a table format, like Excel or Google Sheets, with each objective as a row ordered from most to least important, adds structure to your decision-making process.

How To Compare Job Offers

You can use the worksheets the way that best suits you. You can get specific, like in this example

Current JobPotential Job #1Potential Job #2
Base Pay$225,000$280,000$245,000

Or, you could use a +/- system to assess whether a job is a good match for you. 

Current JobPotential Job #1Potential Job #2
Length of Commute++

Or, you can rank criteria where 1 = good, 2 = better and 3 = best.

Current JobPotential Job #1Potential Job #2
“Interesting” Work / Creative Work132
Challenging Work231
Opportunity for Advancement123
Chance to Contribute132
Work with Other People or Alone123
Supervise OthersN/AN/AN/A

In this example, you add the total score to arrive at a “winner”. Potential Job #1 aligns most with the criteria you determined in your dream job worksheet. 

There’s no wrong answer. This is completely subjective (meaning whatever you feel – that’s the right answer). 


Current JobPotential Job #1Potential Job #2
Base Pay
Overtime/OT Policies
Incentives/Bonuses/Profit Sharing
Relocation Expenses
Stock (Employee Stock Ownership)
Cost of Living Adjustment
Pay Raises (Annual? Merit-Based?)


Current JobPotential Job #1Potential Job #2
Health Insurance
Dental Insurance
Vision Insurance/Vision Benefits
Child Care/Dependent Care
Life/Disability Insurance
Paid & Unpaid Vacation/Time Off
Tuition Reimbursement
Company Car
Professional Memberships
Additional Perks (Free Lunches, Massages)


Current JobPotential Job #1Potential Job #2
Schedule (Set Schedule or Flexible?)
Evening/Weekends Required?
Length of Commute?
Family Friendly? (Adjust Schedule for Children’s Events?)


Current JobPotential Job #1Potential Job #2
“Interesting” / Challenging Work
Opportunity for Advancement
Chance to Contribute
Work With Other People or Alone
Supervise Others


Current JobPotential Job #1Potential Job #2
Do You Like the People?
Forward-Thinking People/Company
Company Reputation
Values in Alignment With Yours
Organizational Structure(Family-Owned vs. Corporate)
Good Environment (Do People Enjoy Working Here?)


Current JobPotential Job #1Potential Job #2
Industry Growing or Dying
Company Stability (How is the Company Doing Financially?)
Startup Company vs. Established Company
Growth in Products/Services
Diversity of Clients(Number, Type of Clients)

Journal Your Thoughts

If you are still feeling stuck, consider journaling your thoughts.

What Job Title (Position) are you targeting?

Think about the employer. Give as much detail as possible. Size, culture, location, structure. What problems are they solving as a company? Are they growing? What is their reputation like? What is their community and national reputation? Do you align with their values?

Describe the job. What would the day in and day out look like? What would a perfect day look like in this role? What would a bad day look like? Do you think there will be more good days than bad? What skills do you think you’ll learn or develop in this role? Are there opportunities for growth?

Consider your future boss. What are they doing to support their employees? What is their management style? How long have they been in a leadership role? Do they have a history of promoting internally? Are they honest?

Change what sucked. What do you want your next job to do for you that your last job didn’t do? What do you want to be different about your next job? Be careful. We’ve noticed a pattern of people swinging the pendulum too far one way or the other. 



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