Negotiating Terms of Chief Legal Officer Employment Contract

 September 2025 edition

I hope this email finds you and your family in good health. We are now in our last weeks of summer, with vacations now over or ending, Labor Day and its cook-outs and other fun associated activities, all now past us, as we look forward to Autumn and a return to our usual routines. So, for most of us, the time for the beach and ocean swimming is now past, but still September is a great time for long walks, hikes and bike rides, and later this month, apple picking and the New England fall foliage season.

These are good times for Boston Red Sox fans with long win steaks in July and August, and a winning ball club anchored by a stellar starting pithing rotation of Garret Crochet, Bryan Bello and Lucas Giolito, with Garrett Whitlock and closer Aroldis Chapman. Thus, through Labor Day, the Sox are 15 games over .500 and would make the playoffs. I have been fortunate to attend a number of thrilling Red Sox victories these last two months including two walk-offs with he Sox sporting their walk-off greens. In close games, where Alex Cora calls for his closer, it has also been fun to see the entrance of Chapman into game when the Sox do a video tribute to the late Luis Tiant who passed away last October. Here is footage, with the title “Aroldis Chapman pays tribute to Luis Tiant and Celia Cruz upon entering the ballgame (Google translate from Spanish), credit to and posted by Yuni Sport. https://www.youtube.com/watch?v=Cy7bJXjV8Q4

Meanwhile, the Patriots after going 2–1 in pre-season games, will have their first real test this Sunday when the Las Vegas Raiders travel to Foxboro. With a new season springs new hope. After a 4–13 record last year, it would be stretch for the Patriots to reach .500 or to make the playoffs. But with new coach Mike Vrabel, a graduate of the Patriots Glory years, and returning offensive play caller Josh McDaniels who will no doubt aid the development of second-year quarterback Drake Maye chances for a better season seem enhanced. Plus, the Patriots used free agency and the draft to bolster the line of scrimmage, while adding key veterans including among receivers. So, fingers crossed for the opener Sunday and better season to follow.

As for Newsletter items, item #1 provides a link to an article of mine, published six days ago in CEOWORLD magazine designed for attorneys in private practice or in the public sector or already in house for a company, on key terms to seek and for which to negotiate if you are offered the position of Chief Legal Officer (CLO). This newsletter also has links, in items #3 and #4, to two other earlier articles of mine, one published by the IVYEXEC career advancement site, on terms to seek in C-level and senior executive job offers, and the second published in CEOWORLD magazine, on using your “ace in the hole” in C-level executive contract negotiations, including job offers, severance and consulting contracts. There is also a special offer as item #5. I hope some of these items might be of benefit… and my best wishes to all for the rest of September!

1. Negotiating Terms of Chief Legal Officer Employment Contract

Are you an attorney in private practice or in the public sector? or are you already in house counsel for a company? and … are you now considering or already received an offer to be Chief Legal Officer (CLO) in your current company or a different company? The CLO role will likely be a big step-up for you to a role likely much bigger than the role you have had. The CLO plays a pivotal role in protecting the company and guiding it forward. My new article, published last Thursday in CEOWORLD magazine, discusses the elevated status of CLO over that of General Counsel or other in house roles and then goes on to discuss that and the key areas every CLO should consider including your negotiations over your executive agreement terms. Read the Article Here

2. Work with CEOs, C-Suite and Senior Executives, exclusively.

Robert Adelson is an attorney specialized in the representation of CEOs, C-level and senior executives. He no longer represents companies or employers. Learn about Robert Adelson’s work with CEOs, C-level and senior executives to advise on and improve job offers, employment contracts, stock, RSUs, options, bonuses and other executive compensation matters, plus advice and aid on issues of wrongful termination, severance, exit terms, retention, change of control, other executive issues and more … More Details Here

3. Key Terms to Negotiate in your next Executive Job Offer

Are you actively considering new CEO, C-level or senior executive position? Have you received a job offer? Are you now or will you shortly be negotiating the terms of your executive job offer or employment contract? My article published by IVYEXEC career advancement site, in October 2023. explores the key terms that are negotiable and the kinds of things to seek as you negotiate your next executive employment job offer. Read the Article Here

4. Using Your Ace in the Hole in Executive Contract Negotiations

Have you ever considered keeping and using an ace in the hole in your executive contract negotiations? My article published a year ago in late August 2024 by CEOWORLD magazine discusses just that: how keeping and using an ace in the hole can help you in negotiations over executive contacts, including job offers, employment agreements, separation agreements and contracts for consulting. Read the Article Here

5. 9/2025 Offer: Good until Sept, 30th

This 4-week value-packed offer, is as a way to get introduced to my law work: an Executive Employment Job Offer Law Diagnostic — this offer is good through 9/30/25. More Details Here

It’s always a pleasure to get back in touch with you and other clients, friends, and colleagues. I hope the links and information provided will be useful to you and that there will be an opportunity for me to work with you on legal matters in the near future.

Let’s keep in touch!

Best regards,

Rob

Robert Adelson

*Adelson & Associates, LLC
Executive Employment Attorney
101 Federal Street, 19th Floor
Boston, MA 02110
(617) 204–5601 Law Firm
(617) 204–5602 Direct
(617) 204–5604 Fax
Email: rob@attorneyadelson.com
Website: www.executiveemploymentattorney.com
LinkedIn: https://www.linkedin.com/in/robert-adelson-b8a1557/
Blog: https://robadelson.wordpress.com/
X: @AttorneyAdelson

Note on Adelson & Associates, LLC:* Robert A. Adelson is the Principal of Adelson & Associates, LLC. For fifteen (15) years, from October 2004 through December 2019, Robert Adelson practiced law and referred legal work to associates of his, trusted and experienced colleagues, as a partner of Engel & Schultz, LLP. In December 2019, the lead partners of the firm announced they would go into semi-retirement, go their separate ways, and the office lease would expire in January 2020. In response, Robert Adelson formed Adelson & Associates, LLC in December 2019 and commenced the new firm’s operations on January 1, 2020, with the new firm taking over, on that date and going forward, all current Robert Adelson clients, matters and operations, as well as all referral of legal work to associates of Robert Adelson. Since 1/1/2020, the firm’s offices have been and remain at 101 Federal Street, 19th Floor, across the street from the pre-2020 offices at One Federal Street, 21st Floor, in Boston’s Financial District.

Keeping and Using Your Ace in the Hole in Negotiating Your C-level Executive Contract

 On Friday August 30, 2024, CEOWORLD magazine published an article I wrote titled, “Keeping and Using Your Ace in the Hole in Negotiating Your C-level Executive Contract.”

The new article is designed for CEOs, C-level and senior executives and those executives  who aspire to the C-suite.  This article discusses how, based on my experience representing C-suite executives, that by holding back a little – keeping an ace in the hole, as they say – you will create a sense of anticipation, increase your value in the eyes of the company, and ultimately enhance chances of achieving your desired executive contract terms.

The article goes on to discuss how we’ve applied this strategy of ascertaining and then using this “Ace in the Whole” strategy in three different types of executing contracting situations –

• Job Offer / Employment Agreement  – For example, you might outline a new approach to optimizing operational efficiency or a plan to expand into new markets. However, make it clear that these strategies are just the beginning. Let the company know that you have other strategies and ideas in your pocket, that could be deployed for the benefit of the company, if you are hired and take the position.

• Termination / Separation Agreement – in severance negotiations, part of your leverage would come from release potential claims, but other leverage may come from your knowledge, experience and contacts, and your potential use to the company in post-termination paid transition services and consulting. Here you might suggest three particular assignments for yourself that address particular gaps created by your separation…. But again not telling, even suggesting you envision several other impactful assignments, not to be discussed unless and until the company commits to reasonable severance terms.   

• Independent Consulting / Consulting between positions –  In this further application of the “Ace in the Hole” strategy, you may hold back on consulting for others and particular needs and requests, until after you’ve established yourself with the company with whom you’ve started consulting, and you could also hold off on moving to a fulltime C-level position (if offered) until the company reaches terms you seek.

I am a fan of Country Music.  So, both this executive contract strategy and the impetus to write this article drew inspiration from the great song by the Country Music singer, the legendary George Strait and  his song ,  “Ace in the Hole”.  The lyrics –

You’ve got to have an ace in the hole

A little secret that nobody knows

Life is a gamble, a game we all play

But you need to save something for a rainy day

You’ve got to learn to play your cards right

If you expect to win in life

Don’t put it all on the line for just one roll

You’ve got to have an ace in the hole

If you’re headed down a one way street

And you’re not sure it’s the way you wanna go

In money or love or all the above

Have a little more than what you show

When life deals out a surprise

Have a few surprises of your own

No matter what you do, no matter where you go

You’ve got to have an ace in the hole

Source for lyrics:  https://genius.com/George-strait-ace-in-the-hole-lyrics 

Video:   https://www.youtube.com/watch?v=eK854RfHFAc

To see my full CEOWORLD magazine. article, go to LINK: https://ceoworld.biz/2024/08/30/keeping-and-using-your-ace-in-the-hole-in-negotiating-your-c-level-executive-contract/

Or on my website at  https://www.executiveemploymentattorney.com/keeping-and-using-your-ace-in-the-hole-in-negotiating-your-c-level-executive-contract/

This was my 47th  article published in CEOWORLD since 2016.  Previously, the editor advised that I can use “Featured in the CEOWORLD magazine” and the CEOWORLD “Logo” on my website and add CEOWORLD magazine in my LinkedIn profile’s “Experience Section” as an “Opinion Columnist.” and authority in the field.  

On its own initiative, CEOWORLD magazine created on their website a library of Robert Adelson published articles.   You can peruse this library and/or read as many of my 44 published articles as you wish.  See https://ceoworld.biz/author/robert-adelson/

With more than 12.4+ million-page views, CEOWORLD magazine is the world’s leading business magazine written strictly for CEOs, CFOs, CIOs, senior management executives, business leaders, and high net worth individuals worldwide. https://www.linkedin.com/company/ceomagazine/

It is my hope this new article will be beneficial to CEOs, C-level executives, VPs and other senior executives and those aspire to C-suite positions to use this “Ace-in-the-Hole” strategy in your own negotiations over important executive contracts in the course of your career.

If you or any colleague of yours has a need in this area, please do reach out to me –  rob@attorneyadelson.com or call 617-875-8665.