Interview with Sally Whitehead: "Stand out by being part of the business rather than apart from the business"

how i contract interview May 01, 2023

We have had the great pleasure to interview Sally Whitehead, the former Global Senior Director, Commercial Contracts & Legal Operations at Sophos, as part of our How I Contract interview series. This interview is gold for lawyers and professionals who are starting out their careers in-house and are looking for day-to-day tips on how they can excel at their jobs.

Dive in! 

Sally, thank you for doing this interview! Let’s start by getting to know you a little bit more. Can you tell us a story about what brought you to this specific career path? How long have you been working with contracts?

Thank you so much for the invitation to be interviewed! :) 

My journey was a non-traditional one of sorts. I grew up in the north, in a rural village of only 50 people; without electricity or running water for my formative years; and education in a one-room school of just 14 kids and one teacher for all grades 1-7.

I learned that to expand beyond the available horizons meant taking chances, being willing to try new things and go to new places, and grabbing hold of opportunities whenever they presented themselves.

Working at a software startup in my early twenties, I created one of those opportunities when I identified high spend with various outside law firms and offered to do initial contract reviews to reduce those costs.  Showing a savings of tens of thousands of dollars a quarter made for a slam-dunk pitch for a contracts manager role. Over my two-plus decades in contract management and legal operations, that story has repeated itself for me many times: 

  • Step 1: identify a problem for the business; 
  • Step 2: demonstrate a viable solution to that problem showcasing my skills; 
  • Step 3: profit ;)

Let’s move to the topic we all love — contracts. What should you do on day one of working with contracts? What shouldn’t you do?

Breathe. On day one no one expects you to know everything. Each role plans for ramp-up time for a new employee. So don’t panic. Ask questions. Organize your thoughts and identify where you need help and then ask for that help. As a bonus move, document and share your own ramp-up plan of what you’ll focus on in the first 30/60/90 days and then validate that with your manager and team. You’ll get them invested in your success and ensure you’re all trying to steer the boat in the same direction.

For the first 30 days plan, I’d suggest identifying what resources are available to you. Is there a template library? A knowledge base of approved clauses? A group of other legal professionals you can workshop ideas with? How does the team organize their work? What tips does each team member have for you?

Don’t silo yourself away and try to go it alone. And don’t try to hide mistakes. Almost everything can be fixed if you raise it up quickly and engage others to assist.

What mistakes should new contract lawyers and professionals avoid when working with contracts? 

This isn’t ‘Wolf of Wall Street’ ;)  Don’t treat the legal professionals on the other side of the negotiation as your opponent. Win them over to the idea of working together to create a sensible document that moves the business goals of both your companies forward in a timely manner.  That’s your win.

If you build those relationships and reap the rewards of honest communication during the negotiation, you’ll build a better contract. Meanwhile, the likelihood of having to fall back on the legal language of the contract to protect you via the courts will be dramatically reduced. And isn’t that our purpose in these roles: risk reduction?

What is your favorite contract management tip? Why?

Build a legal operations team. 

Data-driven decisions are the best decisions. Legal data is hidden in contracts. Don’t let all that work by you and other legal professionals be filed away after the negotiation ends. Make it exponentially more valued by your company. Mine it for useful data that can be used by other departments to consolidate vendor spend, reduce time and friction on day-to-day processes, and even advocate for additional legal department roles. A legal operations team can do this for you — they aren’t just for e-billing work.

What is your favorite time management tip when working with contracts?

Add explanatory comments to your redlines and then summarize those in the cover note in the email.  And let me tell you why it’s worth your time to take that extra step: that email is what will be forwarded around the company on the other side of the negotiation and is a tool to help you close out protracted discussions (only the contract negotiator is likely to actually open the attached document and view embedded comments).  

A summary note showing how many clauses you marked ‘AGREED,” with a one-sentence note on the remaining issues, is leverage. The business leader on the other side will see progress and can press for closure with you: reducing cycles of redlining, freeing up your time, and progressing both companies’ goals.

What advice do you have for dealing with difficult counterparties?

Take the high road, and stay calm and rational. And include more people on the call.  

Have your sales or procurement rep join you and ask for their counterparts from the negotiating counterparty to join as well.  

Discuss the clause in question at a high level in the context of the real business relationship and likely outcomes rather than a word-by-word negotiation. Plan with your sales/procurement rep how to bring the business parties around to your point of view and leverage them to calm the difficult person on the call.  

Make sure you have a reasonable compromise to present (are you the difficult one?).  

And know when to walk away — and agree that beforehand with the rest of your sales/procurement team.

Can you name one thing every contract lawyer or professional should do every day to get better at contracts?

Top tip: make sure you subscribe to How To Contract!  Keeping your knowledge fresh, not only on negotiating positions but also on what is reasonable in the current market & industry you are working in.  

Follow thought leaders on LinkedIn in your areas of focus and take time each week to read items in your feed.  

And block time in your calendar to learn about the technology tools available to you at your workplace. You’ll see me hit this point a few times in my answers today.

What advice would you give to your younger self when you started working with contracts?

Enjoy every day! 

I have the fondest memories of my time negotiating contracts in those early days. There was a great team vibe with the sales team and their leaders, an openness to learn how Legal was important in the process; there was passion, humour, and great outcomes for all of us at the end of the day. I worked long hours and had great fun doing it.

What advice would you give to contract lawyers and professionals working in a team?

Help your teammates. Everyone has different areas they excel in and others where they could use a helping hand. Even me, even you. And everyone will have moments in their life where they need support. Pitch in without complaint and receive help with gratitude when it’s your turn.  Life is messy and everyone ends up at the center of that ring of support at some point.

Have you ever felt imposter syndrome when working on contracts? How have you been dealing with it?

Everyone I’ve ever met knows something I don’t. I find great joy in finding that in conversations and in team discussions.  

For me, building resources of knowledge with everyone contributing helps to turn imposter syndrome on its head so that instead of people feeling lesser than and isolated, everyone has an opportunity to feel equal and contributory, supported with a tool that fills the gaps they may feel they have.

What advice do you have for managing the stress and work demands that come with working on contracts?

No one can do it all.  Everyone is overwhelmed. It’s not just you.

And I have a few suggestions that I’ve found most helpful for myself and my teams over the years:

  • Identify what is most important to support the company and department goals and focus on those items. Work with your manager to prioritize to ensure what you have determined is the most important aligns with their thoughts - that two-way communication is vital.
  • Use. Technology. Tools. Don’t be too busy to learn to be less busy. The time investment you make to learn automation skills and the technology platforms available in your company will reduce your stress on a logarithmic scale. 
  • Show your work. Use metrics to show how many contracts are reviewed, for what areas of the business, and in support of what company goals. That information will not only show your value, but allow you to request additional headcount as you can show the increase of work over time (or get approval for funding allocation for ALSPs for spikes in work at the end of quarter). If your company doesn’t do this already for the group, do it for your own work and share it with your manager. You may be the spark that creates it for your department. Bonus move: keep a running list of your accomplishments each week for yourself to visualize your own progress, and also to leverage when it comes time for your annual review. You’ll forget what you did 6 months ago, and that list will make completing your review faster and easier for you, and your review faster and easier for your manager (increasing the likelihood of positive outcomes).
  • Block your calendar. If you wait for time to be available it will rarely happen. Plan for learning time (see second bullet above), block 15-30 minute spaces between each meeting to ensure you (and others in the meeting) have enough time to write down action items, and *block out time to do actual focused work*.  If you do not plan for this yourself, those spaces in your calendar will be filled by others with their own priorities rather than those you and your manager are working towards.

And at the end of the day, to reference a Stoic belief mixed with the ubiquitous business ‘20,00-foot view’, take a step back and remember this little planet we inhabit in the arm of a spiral galaxy, one of the trillions upon trillions, in a small section of the universe. Maybe the day’s problems aren’t so big after all?

What should contract lawyers and professionals do to stand out?

Stand out by being part of the business rather than apart from the business. 

Treat other departments as teammates in the same game and not as difficulties preventing the perfect risk reduction you’d like to attain. 

  • Take time to learn about the products and services your company sells and your contract work supports. 
  • Understand the current business goals of your company and celebrate completed contracts & deals with the wider department teams. 
  • Join the team calls of the other departments you work with and be a trusted advisor when they have questions and an eager student of the new-to-you information they share. 
  • Demonstrate with metrics and dashboards how your work in the Legal Dept is a helping hand in that overall company success. 
  • TEST your own processes: submit a contract for review acting as a Sales person; try to set up a new vendor; send out NDA without access to Legal-only sites. What is your experience when you do?
    • Is it easy to find the information on how to send a request to Legal? 
    • Is there a simple intake form to fill out? 
    • Are there too many questions on the intake form?  
    • How long and how many steps does it take? 
    • Are there regular status updates so you know what is happening with your request?
    • What frustrated you during your tests and what could you simplify for a better experience for those coming to Legal for help?

What interview question would you like to be asked and how would you answer it? 

Ah! Great question! Similar to the one I always ask my oncologist at the end of an appointment: “If you were me and self-advocating in this position, what question didn’t I ask that you would have asked?”  

How about: “What is one of your favourite or most used aphorisms and why do you find it so insightful or useful in your workday?” 

For me, that would be ‘let not the perfect be the enemy of the good.’  

Having spent decades in the software industry, I see incredible value in ‘ship and iterate’ versus ‘perfection paralysis.’ It is so important to get a draft out for feedback, and to finalize at an acceptable risk balance, rather than endlessly cycling and tweaking. We work at the speed of business and the perfect contract is usually not attainable. 

Nor is the perfect process. Start with something and try it. Does it make a slight improvement in how you and your team work?  Great!  That’s a success! Now build on it for the next incremental improvement.

Who do you think we should interview next? Why?

Sanchita Deora.  A senior contracts manager I have been incredibly impressed with.  She has worked in-house in a variety of roles, has a strong understanding of her employer’s business needs, and balances her skills as an exceptional peer mentor along with her remote studies for her Master of Law at Harvard.

Thank you very much, Sally!


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